Encyclopedia / Chloride / Organic Intermediate / Pharmaceutical Intermediates

2,3-Dichlorobenzyl chloride

CAS：3290-01-5
MW:195.467
MF：C7H5Cl3

2,3-Dichlorobenzyl chloride, with the chemical formula C7H5Cl3 and CAS registry number 3290-01-5, is a compound known for its applications in various chemical processes. This colorless liquid, also referred to as 2,3-dichlorophenyl chloride, is characterized by its two chlorine atoms attached to a benzene ring. It is commonly used as a starting material in the synthesis of various pharmaceuticals and agrochemicals. 2,3-Dichlorobenzyl chloride is also used as a reagent in organic synthesis, offering a versatile platform for the introduction of chlorine atoms into different molecules. It is important to handle this compound with caution, as it is toxic and can cause irritation to the skin, eyes, and respiratory system. Overall, 2,3-Dichlorobenzyl chloride plays a significant role in the field of chemistry and serves as a valuable building block for the development of new compounds.

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Realated Product Infomation

1. Names and Identifiers

1.1 Name: 2,3-Dichlorobenzyl chloride

1.2 Synonyms: 1,2-Dichloro-3-(chloromethyl)benzene; 2,3-Dichloro-1-(chloromethyl)benzene; 2,3-Dichlorobenzyl chloride; Benzene, 1,2-dichloro-3-(chloromethyl)-; Toluene, a,2,3-trichloro- (7CI,8CI); Toluene, α,2,3-trichloro-;

1.3 CAS No.: 3290-01-5

1.4 CID: 76790

1.5 EINECS: 221-947-8

1.6 Molecular Formula: C7H5Cl3

1.7 Inchi: InChI=1S/C7H5Cl3/c8-4-5-2-1-3-6(9)7(5)10/h1-3H,4H2

1.8 InChkey: AIPJZPPOFWCJRC-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=C(C(=C1)Cl)Cl)CCl

1.10 Isomers Smiles: C1=CC(=C(C(=C1)Cl)Cl)CCl

2. Properties

2.1 Appearance: Clear colorless liquid

2.2 Chemical Properties: clear colorless liquid 2,3-Dichlorobenzyl chlorideSupplier

2.3 Color/Form: COLORLESS LIQUID

2.4 Odor: Penetrating odor

2.5 Water Solubility: soluble in alcohol, ether, acetone. Slightly soluble in heptane. Insoluble in water.

3. Use and Manufacturing

3.1 Description

2,3-Dichlorobenzyl chloride, with the chemical formula C7H5Cl3, has the CAS number 3290-01-5. It appears as a colorless to pale yellow liquid with a strong, pungent odor. The basic structure of 2,3-Dichlorobenzyl chloride consists of two chlorine atoms and one benzyl group attached to a carbon atom. This compound is insoluble in water. 2,3-Dichlorobenzyl chloride is a highly reactive compound and should be handled with caution. It may cause irritation to the skin, eyes, and respiratory system. Ingestion or inhalation of this chemical can lead to serious health effects. It is important to use appropriate protective measures when working with 2,3-Dichlorobenzyl chloride. Proper ventilation and personal protective equipment should be used to minimize exposure to this compound.

Applicable Fields

Disinfectant: 2,3-Dichlorobenzyl chloride is commonly used as a disinfectant in various applications. Its purpose in this field involves its ability to kill or inhibit the growth of microorganisms. The mechanism of action of 2,3-Dichlorobenzyl chloride as a disinfectant is based on its ability to disrupt the cell membranes of microorganisms, leading to their death or inactivation.

Chemical Synthesis: This compound is also used in chemical synthesis processes. It can be used as a starting material or intermediate in the production of various chemicals. The mechanism of action in chemical synthesis depends on the specific reaction and the role of 2,3-Dichlorobenzyl chloride in that reaction.

Storage

Conditions: Store in a cool and dry place.

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3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 24 companies from 2 notifications to the ECHA C&L Inventory.

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501

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3.3 Methods of Manufacturing: 2,4- and 3,4-dichlorobenzyl chloride are manufactured by side-chain chlorination of the appropriate chlorotoluene. 3,4-Dichlorobenzyl chloride containing some 2,3-dichlorobenzyl chloride is produced by the chloromethylation of o-dichlorobenzene in oleum solution.

4. Safety and Handling

4.1 Other Preventative Measures: The manufacturing process is designed so that a local exhaust ventilation system (i.e. suction hosing) controls emissions in the workplace during product drumming, catalyst addition, and emissions which may arise through accidental release.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

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4.2 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

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4.3 Reactivities and Incompatibilities: Contamination with metals in the presence of moisture may cause rapid decomposition, liberating heat, hydrogen chloride, and hydrogen which can result in explosive pressure build-up in closed systems.

4.4 Safety: Hazard Note:
Hazard Codes:
    C: Corrosive
Risk Statements about 2,3-Dichlorobenzyl chloride (3290-01-5):
    R22 Harmful if swallowed.
    R34 Causes burns.
Safety Statements about 2,3-Dichlorobenzyl chloride (3290-01-5):
    S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
    S45 In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
    S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin corrosion, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H314 Causes severe skin burns and eye damage
Precautionary statement(s)
Prevention	P260 Do not breathe dust/fume/gas/mist/vapours/spray. P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	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 P321 Specific treatment (see ... on this label). P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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

1H NMR : 400 MHz in CDCl3

IR : liquid film

Mass

7. Synthesis Route

3290-01-5Total: 5 Synthesis Route

608-27-5 66 Suppliers

3290-01-5 48 Suppliers

100-44-7 176 Suppliers

104-83-6 134 Suppliers

611-19-8 191 Suppliers

3290-01-5 48 Suppliers

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8. Precursor and Product

precursor:

608-27-5

6334-18-5

100-44-7

38594-42-2

product:

3218-45-9

9. Computed Properties

Molecular Weight：195.467g/mol
Molecular Formula：C₇H₅Cl₃
Compound Is Canonicalized：True
Exact Mass：3.6
XLogP3-AA：193.945683
Monoisotopic Mass：193.945683
Complexity：105
Rotatable Bond Count：1
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：0
Topological Polar Surface Area：0
Heavy Atom Count：：10
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADcYBgAAAGAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGAIAAAAADAOAGGAwAIAAAACAAiBCAAACAAAgBQAIikAAAogIICKBExCAIAAggAAIiAcAgAAOAAAAIAABAAQAAABAAAIACAAAAAAAAA==

10.Other Information

Disposal Methods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

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Special Reports: ITC/USEPA; Information Review #354 (Draft) Tri & Dichlorobenzyl Chlorides (1983)

Personal Protective Equipment: For line and vessel entry without decontamination and for accidents, maintenance and operational personnel employ full face and respiratory protection. In addition, all personnel carry disposable mouth bite respirators for emergency escape.

Preventive Measures: The manufacturing process is designed so that a local exhaust ventilation system (i.e. suction hosing) controls emissions in the workplace during product drumming, catalyst addition, and emissions which may arise through accidental release.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

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Populations At Special Risk: /Individuals who suffer from/ skin, liver, kidney, or chronic respiratory disease, will be at an increased risk if they are exposed to chlorobenzenes. /Chlorobenzenes/

Pollution Sources: Dichlorobenzyl chloride's production and use as an intermediate for organic chemicals, pharmaceuticals, and dyes, and as an insecticide(1) may result in its release to the environment through various waste streams(SRC).

Environmental Fate: TERRESTRIAL FATE: Dichlorobenzyl chloride is expected to hydrolyze in moist soils(SRC) based upon the rapid hydrolysis of the structurally similar benzyl chloride; at pH 7 and 25 °C the hydrolysis half-life is approx 15 hours(1). Volatilization, adsorption, and biodegradation are not expected to be important fate processes in moist soils because of hydrolysis(SRC). Dichlorobenzyl chloride is not expected to volatilize from dry soil surfaces based upon estimated vapor pressure for the six isomers ranging from 0.024 to 0.033 mm Hg(SRC), determined from a fragment constant method(2).|AQUATIC FATE: Dichlorobenzyl chloride is expected to hydrolyze in aquatic environments(SRC) based upon the rapid hydrolysis of the structurally similar benzyl chloride; at pH 7 and 25 °C the hydrolysis half-life is approx 15 hours(1). Volatilization from water surfaces, adsorption to suspended solids and sediments, biodegradation, and bioconcentration are not expected to be an important fate process in aquatic systems for the parent compound because of rapid rate of hydrolysis(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dichlorobenzyl chloride, which has estimated vapor pressures for the six isomers ranging from 0.024 to 0.033 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dichlorobenzyl chloride is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); estimated half-lives for this reaction in air range from 12 to 21 days for the six isomers(3,SRC).

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Abiotic Degradation: Rate constants, estimated using a structure estimation method(1), for the vapor-phase reaction of the six isomers of dichlorobenzyl chloride with photochemically-produced hydroxyl radicals range from 7.8X10-13 to 1.4X10-12 cu cm/molecule-sec at 25 °C(SRC). These rate constants correspond to atmospheric half-lives ranging from 12 to 21 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Hydrolysis is expected to be an important removal process(SRC), based upon a reported hydrolysis half-life of 15 hours at 25 °C and pH 7 for the structural analog benzyl chloride(2).

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Bioconcentration: Based upon the rapid hydrolysis of the structurally similar benzyl chloride in aqueous environments(1), bioconcentration of dichlorobenzyl chloride in aquatic organisms is not expected to be an important fate process(SRC).

Mobility: Using a structure estimation method based on molecular connectivity indices(1), the Koc for dichlorobenzyl chloride can be estimated to be about 1,400(SRC). According to a classification scheme(2), this estimated Koc value suggests that dichlorobenzyl chloride is expected to have low mobility in soil(SRC). Hydrolysis of dichlorobenzyl chloride is expected in moist soils(SRC), based upon a reported hydrolysis half-life of 15 hours for the structural analog benzyl chloride(3).

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Volatilization: Based upon the rapid hydrolysis of the structurally similar benzyl chloride in aqueous environments(1), volatilization of dichlorobenzyl chloride from water and moist soil surfaces is not expected to be an important fate process(SRC). Dichlorobenzyl chloride is not expected to volatilize from dry soil surfaces based upon estimated vapor pressure for the six isomers ranging from 0.024 to 0.033 mm Hg(SRC), determined from a fragment constant method(2).

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Human Exposure: Occupational exposure to dichlorobenzyl chloride may occur through inhalation and dermal contact with this compound at workplaces where dichlorobenzyl chloride is produced or used. (SRC)

Production: Stauffer produces less than 300,000 lb annually.

Manufacturing Info: Benzene, dichloro(chloromethyl)-: INACTIVE|Monsanto and Tenneco reported in 1983 that they no longer manufacture the compound therefore Stauffer may be the sole domestic producer of dichlorobenzyl chloride.|Manufactured in a batch type process involving 2 distinct chlorination and fractionation steps carried out in closed vessels.

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