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2,4-Dichlorophenol structure

2,4-Dichlorophenol
  • CAS：120-83-2
  • MW:162.997
  • MF：C6H4Cl2O
2,4-Dichlorophenol, with the chemical formula C6H4Cl2O and CAS registry number 120-83-2, is a compound known for its use as a disinfectant and pesticide. This colorless crystalline solid is characterized by its two chlorine atoms attached to the phenol ring. It is commonly used in the production of herbicides, fungicides, and wood preservatives. 2,4-Dichlorophenol has been studied for its potential toxic effects on humans and the environment. It is an important compound in the field of environmental science and toxicology, contributing to the understanding of chemical pollutants and their impact on ecosystems.
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1. Names and Identifiers
1.1 Name
2,4-Dichlorophenol
1.2 Synonyms
1,3-DICHLORO-4-HYDROXYBENZENE; 1-Hydroxy-2,4-dichlorobenzene; 2, 4-Dichlorophenol; 2,4,6- TRIFLUORO -DL-PHENYLALANINE; 2,4,6-TRIFLUORO-DL-PHENYLALANINE; 2,4-Cl-Ph-OH; 2,4-DCP; 2,4-Dichloropheno; 2,4-dichloro-pheno; 2,4-di-chlorophenol; 2,4-dichloro-Phenol; 2,4-dichlorophenol solution; 2,4-DichlorophenolForSynthesis; 2,4-Dichlorphenol; 2,4-dlchlorophenol; 4,6-dichlorophenol; DICHLOROPHENOL(2,4-); DL-2,4,6-Trifluoro-Phe-OH; EINECS 204-429-6; Isobac; MFCD00002169; Phenol, 2,4-dichloro-; rcrawastenumberu081;
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1.3 CAS No.
120-83-2
1.4 CID
8449
1.5 EINECS
204-429-6
1.6 Molecular Formula
C6H4Cl2O
1.7 Inchi
InChI=1S/C6H4Cl2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H
1.8 InChkey
HFZWRUODUSTPEG-UHFFFAOYSA-N
1.9 Canonical Smiles
C1=CC(=C(C=C1Cl)Cl)O
1.10 Isomers Smiles
C1=CC(=C(C=C1Cl)Cl)O
2. Properties
2.1 Vapour pressure
5.6 (vs air)
2.2 Solubility
methanol: soluble1g in 10ml
2.3 VaporDensity
5.6 (vs air)
2.4 AnalyticLaboratory Methods
EPA Method 8250: Gas Chromatography/Mass Spectrometry for Semivolatile Organics, Packed Column Technique. This gas chromatography/mass spectrometry method is used to determine the concentration of semivolatile organic compounds in extracts prepared from all types of solid waste matrices, soils, and ground water;. The practical quantitation limit for determining an individual compound is approximately 1 mg/kg (wet weight) for soil/sediment samples, 1-200 mg/kg for wastes, and 10 ug/l for ground water; samples. This method is applicable to quantify most neutral, acidic, and basic organic compounds that are soluble in methylene chloride;, including the title compound, and capable of being eluted without derivatization as sharp peaks from a gas chromatographic packed column. For base/neutral compound detection, a 2 m by 2 mm ID stainless or glass column packed with 3% SP-2250-DB on 100/120 mesh Supelcoport or equivalent is used. For acid compound detection, a 2 m by 2 mm ID glass column packed with 1% SP-1240-DA on 100/120 mesh Supelcoport or equivalent is used. A representative sample is collected in a glass container equipped with a Teflon-lined cap. Care is taken to avoid sample contact with any plastic. Under the prescribed conditions, 2,4-dichlorophenol; has a detection limit of 2.7 ug/l, a range for the average recovery of four measurements of 52.5-121.7 ug/l, and a limit for the standard deviation of 26.4 ug/l.
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2.5 Appearance
2,4-dichlorophenol is a colorless crystalline solid with a medicinal odor. Melting point 45°C. Sinks in water. Strong irritant to tissues; toxic by ingestion.
2.6 AutoIgnition
500°C
2.7 Storage
Ambient temperatures.
2.8 Carcinogenicity
In mammalian cells in vitro 2,4-DCP producedchromosomal aberrations and inducedunscheduled DNA synthesis; it was negativefor sister chromatid exchange in vivo and wasmostly negative in bacterial assays.Oral exposure of pregnant rats to750mg/kg/day for 10 gestational days inducedslightly decreased fetal weight, delayed ossificationof sternal and vertebral arches, and someearly embryonic deaths.10 Maternal deaths alsooccurred at this dose, indicating that 2,4-DCPwas not selectively toxic to embryos or fetuses.No effects were noted in dams or offspringexposed at 375mg/kg/day.A threshold limit value (TLV) has not beenestablished for 2,4-dichlorophenol.
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2.9 Chemical Properties
white to beige crystalline solid
2.10 Color/Form
COLORLESS CRYSTALS OR NEEDLES
Hexagonal needles from benzene
White ... solid
Pale yellow solid
2.11 Decomposition
When heated to decomposition ... it emits highly toxic fumes of /hydrogen chloride;/.
2.12 Heat of Vaporization
13,230.4 cal/mole
2.13 Odor
Strong medicinal
2.14 Odor Threshold
Odor detection in water;: 2.10X10-1 ppm (chemically pure)
2.15 Physical
2,4-DICHLOROPHENOL; is a colorless crystalline solid with a medicinal odor. Melting point 45°C. Sinks in water;. Strong irritant to tissues; toxic by ingestion.
2.16 pKa
pK1:7.85 (25°C)
2.17 Water Solubility
H2O: 4.5 g/L (20 oC);Slightly soluble
2.18 Spectral Properties
MAX ABSORPTION (0.1 N NaOH): 304 NM (LOG E= 3.50); SADTLER REFERENCE NUMBER: 1315 (IR, PRISM)
MASS: 68941 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 1439 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
IR: 1320 (Coblentz Society Spectral Collection)
UV: 9786 (Sadtler Research Laboratories Spectral Collection)
Raman: 1041 (Sadtler Research Laboratories Spectral Collection)
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2.19 Stability
Stable under normal temperatures and pressures.
2.20 StorageTemp
2-8°C
3. Use and Manufacturing
3.1 Definition
ChEBI: A dichlorophenol that is phenol carrying chloro substituents at positions 2 and 4.
3.2 Description
2,4-Dichlorophenol (CAS 120-83-2) is a white crystalline solid with a molecular formula of C6H4Cl2O. It has a melting point of 42-44 degrees Celsius and a boiling point of 214 degrees Celsius. This chemical is sparingly soluble in water, with a solubility of 0.9 grams per liter at 25 degrees Celsius. It is also soluble in organic solvents such as ethanol and acetone.

2,4-Dichlorophenol has a distinct odor and is toxic if ingested, inhaled, or absorbed through the skin. It is a corrosive substance and can cause severe burns. This chemical is flammable and may release toxic fumes when heated or exposed to fire. It is important to handle and store it with caution.

Applicable Fields
Water Treatment: 2,4-Dichlorophenol is used as a biocide in water treatment processes. It acts as a disinfectant, killing bacteria and other microorganisms present in water. The mechanism of action involves disrupting the cellular membranes of these organisms, leading to their death.

Agriculture: In agriculture, 2,4-Dichlorophenol is used as a herbicide. It is effective in controlling broadleaf weeds in crops such as corn, wheat, and soybeans. The mechanism of action involves disrupting the growth and development of the weeds, ultimately leading to their death.

Storage Conditions
Store in a cool, dry place.
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3.3 GHS Classification
Signal: Danger
GHS Hazard Statements
H302: Harmful if swallowed [Warning Acute toxicity, oral]
H311: Toxic in contact with skin [Danger Acute toxicity, dermal]
H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes
P260, P264, P270, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P361, P363, P391, P405, and P501
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3.4 Methods of Manufacturing
... Industrially by chlorination of phenol; with chlorine; gas in a melt in cast-iron; reactors. The isomer distribution in the product may be adjusted to market demands by the chlorination level and by recycling various intermediates. The yield, based on chlorine; and phenol;, is greater than 95%. /Mono-, Di-, and Trichlorophenols with No Chlorine; in a Meta Position/
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3.5 Potential Exposure
2,4-Dichlorophenol is a commerciallyproduced substituted phenol used in the manufactureof industrial and agricultural products; in synthesis ofpharmaceuticals. As an intermediate in the chemical industry, 2,4-DCP is utilized as the feedstock for the manufacture of 2,4-dichlorophenoxyacetic acid (2,4-D), and 2,4-Dderivatives (germicides, soil sterilants, etc.); certain methylcompounds used in mothproofing, antiseptics and seeddisinfectants. 2,4-DCP is also reacted with benzene sulfonylchloride to produce miticides or further chlorinated topentachlorophenol, a wood preservative. It is thus a widelyused pesticide intermediate. The only group expected to beat risk for high exposure to 2,4-DCP is industrial workersinvolved in the manufacturing or handling of 2,4-DCPand 2,4-D
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3.6 Purification Methods
Crystallise it from pet ether (b 30-40o). Purify it also by repeated zone melting, using a P2O5 guard tube to exclude moisture. It is very hygroscopic when dry. [Beilstein 6 IV 885.]
3.7 Shipping
UN2020 Chlorophenols, solid, Hazard Class:6.1; Labels: 6.1-Poisonous materials
3.8 Usage
2,4-Dichlorophenol is a chlorinated derivative of phenol and is used as an intermediate for the preparation of herbicide 2,4-dichlorophenoxyacetic acid (D435680).
4. Safety and Handling
4.1 Octanol/Water Partition Coefficient
log Kow = 3.06
4.2 Other Preventative Measures
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Keep material out of water sources and sewers; Build dikes to contain flow as necessary; Keep upwind; Avoid breathing vapors or dusts; Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Trichlorophenol/
Immediately wash contaminated areas of skin with concentrated soap solution. Contaminated gloves, clothing, shoes should be removed without delay and disposed by incineration.
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4.3 Cleanup Methods
Activated carbon is a good method for removing chlorophenols from water. Competitive adsorption occurs between chlorophenols & humic substances present in nearly all municipal water supplies. This competition decr the capacity of carbon for chlorophenols. /Chlorophenols/
Land Spill: Dig a pit, pond, lagoon, or holding area /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner/ to contain liquid or solid material. Cover solids with plastic sheet to prevent dissolving in rain or fire fighting water. /Trichlorophenol/
Water Spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved, apply activated carbon at ten times the spilled amount in region of 10 ppm or greater concentration. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Trichlorophenol/
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4.4 DisposalMethods
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U081, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids.
The following wastewater treatment technologies have been investigated for 2,4-dichlorophenol: biological treatment, solvent extraction, and resin adsorption.
Dissolve in a combustible solvent and incinerate in a furnace equipped with afterburner and scrubber. Recommendable method: Incineration. Not recommendable method: Discharge to sewer. Peer-review: Incinerate at high temp. PCDDs may be formed. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
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4.5 DOT Emergency Guidelines
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Chlorophenols, liquid; Chlorophenols,solid/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Chlorophenols, liquid; Chlorophenols,solid/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Chlorophenols, liquid; Chlorophenols,solid/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Chlorophenols, liquid; Chlorophenols,solid/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Evacuation: ... Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /Chlorophenols, liquid; Chlorophenols,solid/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire: Small fires: Dry chemical, CO2 or water spray. Large fires: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. /Chlorophenols, liquid; Chlorophenols,solid/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. /Chlorophenols, liquid; Chlorophenols,solid/
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Chlorophenols, liquid; Chlorophenols,solid/
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4.6 Fire Fighting Procedures
Alcohol foam, foam, carbon dioxide, dry chemical.
Cool exposed containers with water.
Wear goggles, self-contained breathing apparatus, and rubber overclothing (including gown); /when fighting a fire involving 2,4-Dichlorophenol/
Extinguish fire using agent suitable for type of surrounding fire. Material itself does not burn or burns with difficulty. /Trichlorophenol/
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4.7 FirePotential
Combustible when exposed to heat or flame.
Behavior in fire: Solid melts and burns.
May accumulate static electrical charges, and may cause ignition of its vapors.
4.8 Safety Profile
Suspected carcinogen with experimental carcinogenic and teratogenic data. Poison by intraperitoneal route. Moderately toxic by ingestion and subcutaneous routes. An experimental teratogen. Mutation data reported. Combustible when exposed to heat or flame. Can react vigorously with oxidizing materials. To fight fre, use alcohol foam, foam, CO2, dry chemical. When heated to decomposition, or on contact with acid or acid fumes, it emits hghly toxic fumes of Cl-. See also CHLOROPHENOLS.
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4.9 Incompatibilities
Incompatible with oxidizers (chlorates,nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases,strong acids, oxoacids, and epoxides. Contact with acids oracid fumes causes decomposition releasing poisonouschlorine gas. Incompatible with caustics, acid anhydrides;acid chlorides. Quickly corrodes aluminum; slowlycorrodes zinc, tin, brass, bronze, copper and its alloys. Mayaccumulate static electrical charges, and may cause ignitionof its vapors.
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4.10 Protective Equipment and Clothing
Wear boots, protective gloves, and goggles. /Trichlorophenol/
/Wear/ approved dust respirator for toxic dusts; Protective clothing to prevent contact with skin. /Trichlorophenol/
4.11 Reactivities and Incompatibilities
... Can react vigorously with oxidizing materials.
... On contact with acid or acid fumes, it emits highly toxic fumes of /hydrogen chloride/.
Quickly corrodes aluminum; slowly corrodes zinc, tin, brass, bronze, copper and its alloys.
4.12 Skin, Eye, and Respiratory Irritations
Skin or eye contact can cause irritation and burns. Inhalation can cause resp irritation, coughing and wheezing.
Solid or dust will burn the skin and eyes.
4.13 Safety

Safety Information of 2,4-Dichlorophenol (CAS NO.120-83-2):
Hazard Codes: TToxic,NDangerous,FFlammable
Risk Statements:?22-24-34-51/53-39/23/24/25-23/24/25-11???
R22:Harmful if swallowed.?
R24:Toxic in contact with skin.?
R34:Causes burns.?
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R39:Danger of very serious irreversible effects.?
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.?
R11:Highly flammable.
Safety Statements: 26-36/37/39-45-61-36/37-16
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.?
S36/37:Wear suitable protective clothing and gloves.?
S16:Keep away from sources of ignition.
RIDADR: UN 2928 6.1/PG 2
WGK Germany: 3
RTECS: SK8575000
HazardClass: 6.1
PackingGroup: III
HS Code: 29081000

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4.14 Specification

?2,4-Dichlorophenol , its CAS NO. is 120-83-2, the synonyms are 1-Hydroxy-2,4-dichlorobenzene ; 2,4-DCP ; 2,4-Dichlorohydroxybenzene ; Phenol, 2,4-dichloro- .?

4.15 Toxicity
Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo oral 2gm/kg (2000mg/kg) ? Antibiotics Annual. Vol. 7, Pg. 321, 1959/1960.
mammal (species unspecified) LD50 oral 464mg/kg (464mg/kg) ? Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(10), Pg. 16, 1980.
mammal (species unspecified) LD50 skin 790mg/kg (790mg/kg) ? Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(10), Pg. 16, 1980.
mouse LD50 intraperitoneal 153mg/kg (153mg/kg) ? Journal of Medicinal Chemistry. Vol. 18, Pg. 868, 1975.
mouse LD50 oral 1276mg/kg (1276mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Fundamental and Applied Toxicology. Vol. 5, Pg. 478, 1985.
rabbit LDLo skin 3160mg/kg (3160mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

LUNGS, THORAX, OR RESPIRATION: PULMONARY EMBOLI

LIVER: OTHER CHANGES		 National Technical Information Service. Vol. OTS0534822,
rat LD50 intraperitoneal 430mg/kg (430mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 British Journal of Pharmacology and Chemotherapy. Vol. 13, Pg. 20, 1958.
rat LD50 oral 47mg/kg (47mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: OTHER CHANGES		 National Technical Information Service. Vol. OTS0534822,
rat LD50 subcutaneous 1730mg/kg (1730mg/kg) ? Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 2, Pg. 76, 1943.
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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 3

Skin corrosion, Category 1B

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H302 Harmful if swallowed

H311 Toxic in contact with skin

H314 Causes severe skin burns and eye damage

H411 Toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P273 Avoid release to the environment.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

P321 Specific treatment (see ... on this label).

P361+P364 Take off immediately all contaminated clothing and wash it before reuse.

P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower].

P363 Wash contaminated clothing before reuse.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P310 Immediately call a POISON CENTER/doctor/\u2026

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P391 Collect spillage.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
13C NMR : in CDCl3  
13C NMR : Predict  
1H NMR : 90 MHz in CDCl3  
1H NMR : Predict  
Predict 1H proton NMR  
IR : CCl4 solution  
IR : KBr disc  
IR : nujol mull  
Raman : 4880 A,100M,powder  
Mass  
Mass spectrum (electron ionization)  
7. Synthesis Route
120-83-2Total: 95 Synthesis Route
 
95-57-8
95-57-8 35 Suppliers
 
120-83-2
120-83-2 160 Suppliers
 
94-75-7
94-75-7 298 Suppliers
 
120-83-2
120-83-2 160 Suppliers
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8. Precursor and Product
precursor:
88-06-2
88-06-2
69-72-7
69-72-7
58-90-2
58-90-2
94-75-7
94-75-7
95-57-8
95-57-8
product:
120-82-1
120-82-1
90-60-8
90-60-8
50-84-0
50-84-0
554-00-7
554-00-7
609-89-2
609-89-2
94-75-7
94-75-7
95-57-8
95-57-8
106-48-9
106-48-9
697-91-6
697-91-6
97-18-7
97-18-7
9. Computed Properties
10.Other Information
Merck
14,3072
BRN
742467
Chemical Properties
white to beige crystalline solid
Chemical Properties
2,4-DCP is a colorless crystalline solid with a characteristic odor
Physical properties
Colorless to yellow crystals with a sweet, musty, or medicinal odor. At 40 °C, the average odor threshold concentration and the lowest concentration at which an odor was detected were 29 and 5.4 μg/L, respectively. Similarly, at 25 °C, the average taste threshold concentration and the lowest concentration at which a taste was detected were 2.5 and 0.98 μg/L, respectively (Young et al., 1996).
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Uses
2,4-Dichlorophenol is a chlorinated derivative of phenol and is used as an intermediate for the preparation of herbicide 2,4-dichlorophenoxyacetic acid (D435680).
Uses
Intermediate in production of herbicidal chlorophenoxy acids such as 2,4- dichlorophenoxyacetic acid
Definition
ChEBI: A dichlorophenol that is phenol carrying chloro substituents at positions 2 and 4.
Synthesis Reference(s)
Synthetic Communications, 20, p. 2991, 1990 DOI: 10.1080/00397919008051517
General Description
Colorless crystalline solid with a medicinal odor. Melting point 45°C. Sinks in water. Strong irritant to tissues; toxic by ingestion.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
2,4-Dichlorophenol can react vigorously with oxidizing agents. Can also react with acids or acid fumes. Incompatible with acid chlorides and acid anhydrides.
Health Hazard
Tremors, convulsions, shortness of breath, inhibition of respiratory system.
Safety Profile
Suspected carcinogen with experimental carcinogenic and teratogenic data. Poison by intraperitoneal route. Moderately toxic by ingestion and subcutaneous routes. An experimental teratogen. Mutation data reported. Combustible when exposed to heat or flame. Can react vigorously with oxidizing materials. To fight fre, use alcohol foam, foam, CO2, dry chemical. When heated to decomposition, or on contact with acid or acid fumes, it emits hghly toxic fumes of Cl-. See also CHLOROPHENOLS.
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Potential Exposure
2,4-Dichlorophenol is a commercially produced substituted phenol used in the manufacture of industrial and agricultural products; in synthesis of pharmaceuticals. As an intermediate in the chemical industry, 2,4-DCP is utilized as the feedstock for the manufacture of 2,4-dichlorophenoxyacetic acid (2,4-D), and 2,4-D derivatives (germicides, soil sterilants, etc.); certain methyl compounds used in mothproofing, antiseptics and seed disinfectants. 2,4-DCP is also reacted with benzene sulfonyl chloride to produce miticides or further chlorinated to pentachlorophenol, a wood preservative. It is thus a widely used pesticide intermediate. The only group expected to be at risk for high exposure to 2,4-DCP is industrial workers involved in the manufacturing or handling of 2,4-DCP and 2,4-D
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Carcinogenicity
In mammalian cells in vitro 2,4-DCP produced chromosomal aberrations and induced unscheduled DNA synthesis; it was negative for sister chromatid exchange in vivo and was mostly negative in bacterial assays.
Oral exposure of pregnant rats to 750mg/kg/day for 10 gestational days induced slightly decreased fetal weight, delayed ossification of sternal and vertebral arches, and some early embryonic deaths.10 Maternal deaths also occurred at this dose, indicating that 2,4-DCP was not selectively toxic to embryos or fetuses. No effects were noted in dams or offspring exposed at 375mg/kg/day.
A threshold limit value (TLV) has not been established for 2,4-dichlorophenol.
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Environmental fate
Biological. In activated sludge, 2.8% mineralized to carbon dioxide after 5 d (Freitag et al., 1985). In freshwater lake sediments, anaerobic reductive dechlorination produced 4-chlorophenol (Kohring et al., 1989). Chloroperoxidase, a fungal enzyme isolated from Caldariomyces fumago, converted 9 to 12% of 2,4-dichlorophenol to 2,4,6-trichlorophenol (Wannstedt et al., 1990). When 2,4-dichlorophenol was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, significant biodegradation with rapid adaptation was observed. At concentrations of 5 and 10 mg/L, 100 and 99% biodegradation, respectively, were observed after 7 d (Tabak et al., 1981). In activated sludge inoculum, 98.0% COD removal was achieved. The average rate of biodegradation was 10.5 mg COD/g?h (Pitter, 1976).
Surface Water. Hoigné and Bader (1983) reported 2,4-dichlorophenol reacts with ozone at a rate constant of <1,500/M?sec at the pH range of 1.5 to 3.0.
Groundwater. Nielsen et al. (1996) studied the degradation of 2,4-dichlorophenol in a shallow, glaciofluvial, unconfined sandy aquifer in Jutland, Denmark. As part of the in situ microcosm study, a cylinder that was open at the bottom and screened at the top was installed through a cased borehole approximately 5 m below grade. Five liters of water was aerated with atmospheric air to ensure aerobic conditions were maintained. Groundwater was analyzed weekly for approximately 3 months to determine 2,4-dichlorophenol concentrations with time. The experimentally determined first-order biodegradation rate constant and corresponding half-life were 0.20/d and 3.47 d, respectively.
Photolytic. In distilled water, photolysis occurs at a slower rate than in estuarine waters containing humic substances. Photolysis products identified in distilled water were the three isomers of chlorocyclopentadienic acid. The following half-lives were reported for 2,4- dichlorophenol in estuarine water exposed to sunlight and microbes: 0.6 and 2.0 h during summer (24 °C) and winter (10 °C), respectively; in distilled water: 0.8 and 3.0 h during summer and winter, respectively; in poisoned estuarine water: 0.7 and 2.0 h during summer and winter, respectively (Hwang et al., 1986). When titanium dioxide suspended in an aqueous solution was irradiated with UV light (λ = 365 nm), 2,4-dichlorophenol was converted to carbon dioxide at a significant rate (Matthews, 1986). An aqueous solution containing hydrogen peroxide and irradiated by UV light (λ = 296 nm) converted 2,4-dichlorophenol to chlorohydroquinone and 1,4- dihydroquinone (Moza et al., 1988). A carbon dioxide yield of 50.4% was achieved when 2,4- dichlorophenol adsorbed on silica gel was irradiated with UV light (λ >290 nm) for 17 h (Freitag et al., 1985).
Chemical/Physical. 2,4-Dichlorophenol will not hydrolyze to any reasonable extent (Kollig, 1993). Reported second-order rate constants for the reaction of 2,4-dichlorophenol and singlet oxygen in water at 292 K: 7 x 106/M?sec at pH 5.5, 2 x 106/M?sec at pH 6, 1.0 x 105/M?sec at pH 6.65, 1.5 x 106/M?sec at pH 7.0, 7.6 x 105/M?sec at pH 7.9, 1.20 x 104/M?sec at pH 9.0 to 9.6. At pH 8, the half-life of 2,4-dichlorophenol is 62 h (Scully and Hoigné, 1987). In an aqueous phosphate buffer at 27 °C, 2,4-dichlorophenol reacted with singlet oxygen at a rate of 5.1 x 106/M?sec (Tratnyek and Hoigné, 1991). At neutral pH, 2,4-dichlorophenol was completely oxidized by potassium permanganate (2.0 mg/L) after 15 min (quoted, Verschueren, 1983).
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Shipping
UN2020 Chlorophenols, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials
Purification Methods
Crystallise it from pet ether (b 30-40o). Purify it also by repeated zone melting, using a P2O5 guard tube to exclude moisture. It is very hygroscopic when dry. [Beilstein 6 IV 885.]
Incompatibilities
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides. Contact with acids or acid fumes causes decomposition releasing poisonous chlorine gas. Incompatible with caustics, acid anhydrides; acid chlorides. Quickly corrodes aluminum; slowly corrodes zinc, tin, brass, bronze, copper and its alloys. May accumulate static electrical charges, and may cause ignition of its vapors.
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Waste Disposal
Dissolve in a combustible solvent and incinerate in a furnace equipped with afterburner and scrubber. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≧100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal
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Storage features
Fireproof. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing. Separated from strong oxidants and food and feedstuffs. Ventilation along the floor.
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12. Related Questions
Can 2,4-Dichlorophenol be used in agriculture?2,4-Dichlorophenol was relatively stable in terms of pricing in March and can be considered for use in many industries, especially in agriculture. It is said to be used for the production of insectici..
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