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p-Tolualdehyde structure

p-Tolualdehyde
  • CAS：104-87-0
  • MW:120.14900
  • MF：C8H8O

p-Tolualdehyde, with the chemical formula C8H8O and CAS registry number 104-87-0, is a compound commonly used in organic synthesis and industrial applications. Also known as 4-Methylbenzaldehyde, it is a colorless liquid with a characteristic almond-like odor. p-Tolualdehyde is utilized in the production of fragrances, dyes, and pharmaceuticals, as well as in the manufacturing of plastics and resins, in perfumes, flavoring agent. Its aromatic properties make it a valuable intermediate in the synthesis of various organic compounds. This compound has been studied for its reactivity in numerous chemical reactions, contributing to the development of synthetic methodologies and materials science.

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1. Names and Identifiers
1.1 Name
p-Tolualdehyde
1.2 Synonyms
4-Formyltoluene, p-Tolualdehyde; 4-Methylbenzaldehyde; 4-Methyl-Benzaldehyde; 4-METHYLBENZALDEHYDE FOR SYNTHESIS; 4-METHYLPIPERIDINE FOR SYNTHESIS; 4-Tolualdehyde; 4-Toluylaldehyde; Benzaldehyde, 4-methyl-; EINECS 203-246-9; MFCD00006954; NSC 2224; para-Methylbenzaldehyde; para-Tolualdehyde; para-Toluyl aldehyde; p-Formyltoluene; p-Methyl benzaldehyde; p-Methylbenzaldehyde; PTAL; p-Toluic aldehyde; p-Toluylaldehyde; p-Tolylaldehyde;
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1.3 CAS No.
104-87-0
1.4 CID
7725
1.5 EINECS
203-246-9
1.6 Molecular Formula
C8H8O
1.7 Inchi
InChI=1S/C8H8O/c1-7-2-4-8(6-9)5-3-7/h2-6H,1H3
1.8 InChkey
FXLOVSHXALFLKQ-UHFFFAOYSA-N
1.9 Canonical Smiles
CC1=CC=C(C=C1)C=O
1.10 Isomers Smiles
CC1=CC=C(C=C1)C=O
2. Properties
2.1 Solubility
0.25 g/L (25 oC)
2.2 Appearance
Clear colorless to yellow Liquid
2.3 Storage
Air Sensitive. Store under Argon. Ambient temperatures.
2.4 Chemical Properties
clear colorless to pale yellow liquid
2.5 Color/Form
COLORLESS LIQUID
2.6 Odor
Floral odor
2.7 Water Solubility
water: soluble 0.25 g/L at 25°C
2.8 Spectral Properties
SADTLER REF NUMBER: 21549 (IR, PRISM); INDEX OF REFRACTION: 1.5454 AT 20 DEG C
MAX ABSORPTION (HEXANE): 251 NM (LOG E= 4.18); 257 NM (LOG E= 4.10); 279 NM (LOG E= 3.08); 284 NM (LOG E= 3.00)
Index of refraction: 1.5454 at 20 deg C
IR: 6182 (Coblentz Society Spectral Collection)
UV: 15952 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 6900 (Sadtler Research Laboratories Spectral Collection)
MASS: 69763 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 4815 (National Bureau of Standards)
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2.9 Stability
Stable under normal temperatures and pressures.
2.10 StorageTemp
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
3. Use and Manufacturing
3.1 Definition
ChEBI: A tolualdehyde compound with the methyl substituent at the 4-position.
3.2 Description

Liquid


4-Methylbenzaldehyde is a simple aromatic aldehyde. It is commercially available, but may be prepared from the Friedel-Crafts formylation of toluene with carbon monoxide and hydrogen chloride under Gattermann-Koch conditions:. 4-Methylbenzaldehyde has a cherry-like scent similar to benzaldehyde.


Liquid


P-tolualdehyde is a tolualdehyde compound with the methyl substituent at the 4-position. It has a role as a plant metabolite.

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3.3 Methods of Manufacturing
It is derived from the oxidation of p-xylene.
3.4 Purification Methods
Steam distil the aldehyde, dry it with CaSO4, then fractionally distil it. [Beilstein 7 IV 672.] p-Tolualdehyde Preparation Products And Raw materials Preparation Products
3.5 Usage

In perfumes, pharmaceutical & dyestuff intermediate, flavoring agent.

4. Safety and Handling
4.1 Octanol/Water Partition Coefficient
log Kow = 2.26 (est)
4.2 Other Preventative Measures
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.
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4.3 DisposalMethods
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.
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4.4 Formulations/Preparations
Grades: Technical; Pure.
4.5 Protective Equipment and Clothing
The low molecular weight aldehydes, the halogenated aliphatic aldehydes, and the unsaturated aldehydes are particularly irritating. /Aldehydes/
4.6 Skin, Eye, and Respiratory Irritations
The low molecular weight aldehydes, the halogenated aliphatic aldehydes, and the unsaturated aldehydes are particularly irritating. /Aldehydes/
4.7 Safety

A poison by intraperitoneal. Moderately toxic by ingestion and inhalation. A skin irritant. A combustible liquid. When heated to decomposition it emits acrid smoke and irritating vapors.
The Hazard Codes:?? Xn
The Risk Statements information:
26:? Very Toxic by inhalation?
36/37/38:? Irritating to eyes, respiratory system and skin?
36/38:? Irritating to eyes and skin?
The Safety Statements information:
26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
36:? Wear suitable protective clothing?
37/39:? Wear suitable gloves and eye/face protection?

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4.8 Sensitive
Air Sensitive
4.9 Specification

?p-Tolualdehyde , its cas register number is 104-87-0. It also can be called 4-Methylbenzaldehyde ; 4-Toluylaldehyde ; and Benzaldehyde, 4-methyl- . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition, p-Tolualdehyde (CAS NO.104-87-0) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, strong reducing agents, strong bases, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: carbon monoxide, carbon dioxide.

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4.10 Toxicity
1. ???

skn-rbt 500?mg MOD

 ??? NTIS** ?? National Technical Information Service . (Springfield, VA 22161)(Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0533443 .
2. ???

eye-rbt 100?mg MOD

 ??? NTIS** ?? National Technical Information Service . (Springfield, VA 22161)(Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0533443 .
3. ???

orl-rat LD50:1600?mg/kg

 ??? NTIS** ?? National Technical Information Service . (Springfield, VA 22161)(Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0533443 .
4. ???

ihl-rat LC :>2200?mg/m3

 ??? NTIS** ?? National Technical Information Service . (Springfield, VA 22161)(Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0533443 .
5. ???

ipr-rat LD50:800?mg/kg

 ??? NTIS** ?? National Technical Information Service . (Springfield, VA 22161)(Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0533443 .
6. ???

orl-mus LD50:3200?mg/kg

 ??? NTIS** ?? National Technical Information Service . (Springfield, VA 22161)(Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0533443 .
7. ???

ipr-mus LD50:400?mg/kg

 ??? NTIS** ?? National Technical Information Service . (Springfield, VA 22161)(Formerly U.S. Clearinghouse for Scientific and Technical Information) OTS0533443 .
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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302 Harmful if swallowed

H319 Causes serious eye irritation
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.

Response

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

P330 Rinse mouth.

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

P337+P313 If eye irritation persists: Get medical advice/attention.

Storage

none

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 : 90 MHz in CDCl3  
Predict 1H proton NMR  
IR : liquid film  
Raman : 4880 A,200 M,liquid  
Mass  
7. Synthesis Route
104-87-0Total: 292 Synthesis Route
 
99-75-2
99-75-2 96 Suppliers
 
104-87-0
104-87-0 222 Suppliers
 
94-08-6
94-08-6 88 Suppliers
 
104-87-0
104-87-0 222 Suppliers
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8. Precursor and Product
precursor:
95-63-6
95-63-6
622-96-8
622-96-8
98-88-4
98-88-4
104-85-8
104-85-8
589-18-4
589-18-4
106-42-3
106-42-3
99-75-2
99-75-2
94-08-6
94-08-6
99-94-5
99-94-5
104-82-5
104-82-5
product:
100-21-0
100-21-0
619-55-6
619-55-6
99-04-7
99-04-7
589-18-4
589-18-4
105-13-5
105-13-5
99-75-2
99-75-2
94-08-6
94-08-6
99-94-5
99-94-5
104-81-4
104-81-4
104-82-5
104-82-5
9. Computed Properties
10.Other Information
Usage
p-Tolualdehyde is used as an intermediate for the synthesis of pharmaceuticals, dyes perfumes and agrochemicals. It is also used as a fixative of flavorings. It is also used as an important organic intermediates, used for spices, triphenylmethane dye synthesis, etc.
Storage Conditions
It is derived from the oxidation of p-xylene.
Henrys Law Constant
Henry's Law constant = 1.74X10-5 atm-cu m/mol at 25 °C (est)
Experimental Properties
Liquid Molar Volume = 0.119047 cu m/kmol|Hydroxyl radical reaction rate constant = 1./87X10-11 cu cm/molec-sec at 25 °C (est)
Disposal Methods
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.
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Preventive Measures
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.
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Environmental Concentrations
4-Methylbenzaldehyde was measured in tire wear particles and brake lining particles at concns of 2.3 and 0.30 ug/g sample, respectively, and was not detected in samples of road dust particles(1).
Natural Pollution Sources
4-Methylbenzaldehyde was detected in raw earth almonds (Cyperus esculentus L.)(1).
Pollution Sources
4-Methylbenzaldehyde's production and use in perfumes, as a pharmaceutical and dyestuff intermediate, and as a flavoring agent(1) may result in its release to the environment through various waste streams(SRC). Exhaust from outboard motors(2), automobiles and trucks(3), and emissions from fireplaces(4) contain 4-methylbenzaldehyde.
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Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 62(SRC), determined from a water solubility of 2,270 mg/L(2) and a regression-derived equation(3), indicates that 4-methylbenzaldehyde is expected to have high mobility in soil(SRC). Volatilization of 4-methylbenzaldehyde from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.7X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.25 mm Hg(4), and its water solubility(2). 4-Methylbenzaldehyde is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Based on limited information, 4-methylbenzaldehyde is expected to biodegrade in soil(SRC). A Pseudomonas strain was able to utilize 4-methylbenzaldehyde as the sole carbon source(5); a yeast strain grown with both this compound and either sucrose or pyruvate biodegraded 4-methylbenzaldehyde to the respective aromatic carbinol or alcohol(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 62(SRC), determined from a water solubility of 2,270 mg/L(2) and a regression-derived equation(3), indicates that 4-methylbenzaldehyde is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.7X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.25 mm Hg(4), and its water solubility(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.4 and 21 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 8(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Based on limited data, biodegradation of 4-methylbenzaldehyde will take place in water(SRC). A Pseudomonas strain was able to utilize 4-methylbenzaldehyde as the sole carbon source(6); a yeast strain grown with both this compound and either sucrose or pyruvate biodegraded 4-methylbenzaldehyde to the respective aromatic carbinol or alcohol(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-methylbenzaldehyde, which has a vapor pressure of 0.25 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 4-methylbenzaldehyde is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 21 hrs(SRC), calculated from its rate constant of 1.8X10-11 cu cm/molecule-sec at 25 °C(3). The reactivity of 4-methylbenzaldehyde (1 ppm) with NOx (0.5 ppm) in light was measured in a smog chamber as 1.78 ppb/min(4). 4-Methylbenzaldehyde contains chromophores that absorb at wavelengths >290 nm(5) and therefore may be susceptible to direct photolysis by sunlight(SRC).
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Abiotic Degradation
The rate constant for the vapor-phase reaction of 4-methylbenzaldehyde with photochemically-produced hydroxyl radicals has been measured as 1.8X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 21 hrs at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). The reactivity of 4-methylbenzaldehyde was measured using the smog chamber method where the aldehyde is irradiated in a mixture with nitric oxide and air; the reactivity of 1 ppm of 4-methylbenzaldehyde with 0.5 ppm of NOx was measured as 1.78 ppb/min(2). 4-Methylbenzaldehyde is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). 4-Methylbenzaldehyde contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).
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Bioconcentration
An estimated BCF of 8 was calculated in fish for 4-methylbenzaldehyde(SRC), using a water solubility of 2,270 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Mobility
The Koc of 4-methylbenzaldehyde is estimated as 62(SRC), using a water solubility of 2,270 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 4-methylbenzaldehyde is expected to have high mobility in soil.
Volatilization
The Henry's Law constant for 4-methylbenzaldehyde is estimated as 1.7X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.25 mm Hg(1), and water solubility, 2270 mg/L(2). This Henry's Law constant indicates that 4-methylbenzaldehyde is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 2.4 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 21 days(SRC). 4-Methylbenzaldehyde's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 4-Methylbenzaldehyde is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
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Food Survey Values
4-Methylbenzaldehyde is a constituent of coffee aroma(1), roasted filberts(2), roasted earth almonds (Cyperus esculentus L.)(3). 4-Methylbenzaldehyde was detected in a Spanish type paprika oleoresin at 1.3 mg/kg(4).
Human Exposure
NIOSH (NOES Survey 1981-1983) has statistically estimated that 12,495 workers (8505 of these were female) were potentially exposed to 4-methylbenzaldehyde in the US(1). Occupational exposure to 4-methylbenzaldehyde may occur through inhalation and dermal contact with this compound at workplaces where 4-methylbenzaldehyde is produced or used. Monitoring data and use information indicate that the general population may be exposed to 4-methylbenzaldehyde via inhalation of ambient air, ingestion of food and dermal contact with this compound(SRC).
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Metabolism
Aromatic aldehydes are oxidized in vivo almost entirely to corresponding acid. Thus, in rabbits, p-tolualdehyde is converted to p-toluic acid which has been detected in urine as the ester glucuronide.|p-Tolualdehyde was oxidized to p-toluic acid by resting cells of pseudomonas aeruginosa. Perillaldehyde dehydrogenase, isolated from soil pseudomonad, catalyzed the oxidn of m- & p-tolualdehyde but not o-tolualdehyde.|Aldehydes are readily oxidized to organic acids. Oxidation of aldehydes is catalyzed by aldehyde dehydrogenase, which has been found in the brain, erythrocytes, liver, kidney, heart, and placenta. /Aldehydes/|... The detoxification of aldehydes can be seen to proceed basically via two routes: (1) an oxidation to yield readily metabolized acids; (2) inactivation by reaction with sulfhydryl groups, particularly glutathione. Under conditions that either deplete glutathione levels, or that result in an inhibition of aldehyde dehydrogenase (for example, Antabuse treatment), the acute and chronic effects of aldehyde toxicity might be more fully expressed. /Aldehydes/|For more Metabolism/Metabolites (Complete) data for 4-METHYLBENZALDEHYDE (7 total), please visit the HSDB record page.
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Antidote
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aldehydes and Related Compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Aggressive airway management may be necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Anticipate seizures and treat if necessary ... . Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aldehydes and Related Compounds/|/SRP:/ Advanced treatment: Consider Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Intubation should be considered at the first sign of upper airway obstruction caused by edema. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aldehydes and Related Compounds/
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Human Toxicity Excerpts
/SIGNS AND SYMPTOMS/ The mucus membranes of the nasal and oral passages and the upper respiratory tract are affected, producing a burning sensation, ... bronchial constriction, choking, and coughing. The eyes tear, and a burning sensation is noted on the skin of the face. /Aldehydes/|/SIGNS AND SYMPTOMS/ No evidence of skin sensitization was found in volunteers treated with dilute solutions. /Tolualdehydes/
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Mesh Entry Terms
4-methylbenzaldehyde
Production
(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS|(1981) PROBABLY GREATER THAN 4.54X10+6 GRAMS|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5377]
Formulations
Grades: Technical; Pure.
Manufacturing Info
All other basic organic chemical manufacturing|Benzaldehyde, 4-methyl-: ACTIVE
Use Classification
Food additives -> Flavoring Agents
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12. Related Questions
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13. Realated Product Infomation
 
1. Names and Identifiers
2. Properties
3. Use and Manufacturing
4. Safety and Handling
5. Msds
6. NMR Spectrum
7. Synthesis Route
8. Precursor and Product
9. Computational chemical data
10. Other Information
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13. Realated Product Infomation
 
 
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