2-Methylbenzaldehyde
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2-Methylbenzaldehyde
structure -
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CAS No:
529-20-4
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Formula:
C8H8O
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Chemical Name:
2-Methylbenzaldehyde
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Synonyms:
Benzaldehyde,2-methyl-;o-Tolualdehyde;2-Methylbenzaldehyde;o-Methylbenzaldehyde;o-Toluic aldehyde;o-Tolylaldehyde;2-Tolualdehyde;2-Formyltoluene;NSC 103152
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CAS No:
Description
2-Methylbenzaldehyde is an endogenous metabolite.
O-tolualdehyde is a clear liquid. (NTP, 1992)|Solid
O-tolualdehyde is a clear liquid. (NTP, 1992)|O-tolualdehyde is a tolualdehyde compound with the methyl substituent at the 2-position. It has a role as a plant metabolite.
2-Methylbenzaldehyde Basic Attributes
120.15
120.15
605841
208-452-2
Q7E5H6W6BG
103152
DTXSID1022051
Liquid
29122900
Characteristics
17.1
2.1
Clear colorless to yellow Liquid
1.0342 g/cm3 @ Temp: 20 °C
<25 °C
200 °C
153 °F
1.558
H2O: slightly soluble
Store below +30°C.
0.335 mm Hg at 25 deg C (est)
Henry's Law constant = 1.48X10-5 atm-cu m/mol at 25 °C (est)
Specific gravity: 1.0386 at 19 °C/4 °C|Hydroxyl radical reaction rate constant = 1.87X10-11 cu cm/molec-sec at 25 °C (est)
Insoluble in water.
Aldehydes
O-TOLUALDEHYDE is incompatible with strong bases and strong reducing agents. It is also incompatible with strong oxidizers. It may react with ketones, sulfuric acid, nitric acid, caustics and ammonia. (NTP, 1992).
Safety Information
AIR SENSITIVE
1993
3
22-37/38-41-36/38
26-39-37/39
Xn,Xi
Irritant
Stable under normal temperatures and pressures.
P261-P273-P280-P305 + P351 + P338
H302-H315-H318-H335-H412
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.
This chemical is combustible. (NTP, 1992)
|Warning|H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|Aggregated GHS information provided by 263 companies from 1 notifications to the ECHA C&L Inventory.
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures, and keep it away from oxidizing materials. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
2-Methylbenzaldehyde has been identified in exhaust gases from gasoline engines, diesel engines and in diesel blowby(1). 2-Methylbenzaldehyde was found in highway tunnels in Tuscarora; light duty trucks emitted 0.023 mg/km traveled or 0.335 mg/L fuel used, heavy duty trucks emitted 0.305 mg/km traveled or 0.962 mg/L fuel used(2). 2-Methylbenzaldehyde was not detected in the emissions of gasoline powered motor vehicles with catalyst equipped engines but was measured at 45,000 ug/km for non-catalyst equipped engines(3). Fine aerosol emission rates of 2-methylbenzaldehyde from heavy-duty diesel trucks, noncatalyst-equipped, and catalyst-equipped automobiles were 15.2, 2.8, and 5.0 ug/km, respectively(4). 2-Methylbenzaldehyde was not detected in road dust particles collected from paved streets in a residential area of Pasadena, CA in May 1988, was detected in brake lining particles at a concn of 0.48 ug/g of particle sample and in tire wear particles at a concn of 4.1 ug/g of particle sample(5). Operation of a four-stroke outboard motor resulted in the exhaust emission of 2.9 mg/10 min of 2-methylbenzaldehyde into the water(6). 2-Methylbenzaldehyde was detected at 1.87 ug/cu m in the effluent of an incineration plant in Germany(7). 2-Methylbenzaldehyde was detected in the emissions of cookstoves in China using wheat crop residue, wood, kerosene, and liquid propane gas at concns of 5.2, 10.2, 9.3, and 20.8 mg/kg, respectively(8).
URBAN/SUBURBAN: 2-Methylbenzaldehyde, analyzed in Athens, Greece, June to December 2000, was detected at Patission Street at concns of 1.2-5.9 ug/cu m(1). 2-Methylbenzaldehyde was detected in air from San Paulo, Brazil at 0.032-0.131 ppb in samples taken July 1988(2). 2-Methylbenzaldehyde was detected in Santiago, Chile atmospheric samples at <0.08-0.22 ppbv in Nov 2003(3).|RURAL/REMOTE: 2-Methylbenzaldehyde, analyzed outside of Athens, Greece, June to December 2000, was not detected at Likovrisi(1). 2-Methylbenzaldehyde was identified in forest air collected in the Southern Black Forest, Germany, at unreported concentrations(2). 2-Methylbenzaldehyde was detected, not quantified in a forest in Tsukuba, Japan in samples taken April 1985(3).|SOURCE DOMINATED: A field monitoring study along a highway in Raleigh, NC in May 1983 detected 2-methylbenzaldehyde levels of 0.00-1.56 ppb; the primary source of the 2-methylbenzaldehyde was considered to be exhaust from cars and trucks(1).
Toxicity
IDENTIFICATION AND USE: 2-Methylbenzaldehyde is a liquid. It is slightly soluble in water; soluble in carbon tetrachloride, ethanol, ethyl ether, AND benzene, and very soluble in acetone. No information could be located on its useS. HUMAN EXPOSURE AND TOXICITY: No evidence of skin sensitization was found in volunteers treated with dilute solutions. Monitoring and effluent data indicate that the general population may be exposed to this chemical by inhalation of ambient air, and ingestion of certain foods. ANIMAL STUDIES: Tolualdehyde was a skin irritant in rabbits. Sensitization reactions have been reported in guinea pigs. In rats, the acute oral and dermal toxicity were low. In rats, the pituitary gland weight was reduced following repeated oral administration .There was no evidence of mutagenicity in Salmonela typhimurium bacterial tests.
2-Methylbenzaldehyde was detected at trace amounts in garlic(1).
2-Methylbenzaldehyde presence in exhaust emissions(1-5), in brake lining and tire wear particles(6), incineration plant effluent(7) and in the emissions of cookstoves using various fuel sources(8) may result in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 54(SRC), determined from a structure estimation method(2), indicates that 2-methylbenzaldehyde is expected to have high mobility in soil(SRC). Volatilization of 2-methylbenzaldehyde from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.0X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). 2-Methylbenzaldehyde is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.34 mm Hg(SRC), determined from a fragment constant method(4). A yeast strain grown with both 2-methylbenzaldehyde and either sucrose or pyruvate biodegraded 2-methylbenzaldehyde to small amounts of the respective aromatic alcohol(5). The yeast strain grown with 2-methylbenzaldehyde and pyruvate degraded 2-methylbenzaldehyde to its respective carbinol(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 54(SRC), determined from a structure estimation method(2), indicates that 2-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 3.0X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1.5 and 14 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 30(SRC), from its log Kow of 2.26(6) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). 2-Methylbenzaldehyde is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). A yeast strain grown with both 2-methylbenzaldehyde and either sucrose or pyruvate biodegraded 2-methylbenzaldehyde to small amounts of the respective aromatic alcohol(7). The yeast strain grown with 2-methylbenzaldehyde and pyruvate degraded 2-methylbenzaldehyde to its respective carbinol(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-methylbenzaldehyde, which has an estimated vapor pressure of 0.34 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-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). 2-Methylbenzaldehyde has a maximum absorbance wavelength of 280 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of 2-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 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Methylbenzaldehyde is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2-Methylbenzaldehyde has a maximum absorbance wavelength of 280 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 30 was calculated in fish for 2-methylbenzaldehyde(SRC), using a log Kow of 2.26(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2-methylbenzaldehyde can be estimated to be 54(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-methylbenzaldehyde is expected to have high mobility in soil.
The Henry's Law constant for 2-methylbenzaldehyde is estimated as 3.0X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-methylbenzaldehyde is expected to volatilize from water surfaces(2). 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)(2) is estimated as 1.5 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)(2) is estimated as 14 days(SRC). 2-Methylbenzaldehyde's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 2-Methylbenzaldehyde is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.34 mm Hg(SRC), determined from a fragment constant method(3).
Monitoring and effluent data indicate that the general population may be exposed to 2-methylbenzaldehyde via inhalation of ambient air and ingestion of certain foods. (SRC)
Drug Information
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/
SYMPTOMS: Symptoms of exposure to this compound may include irritation. ACUTE/CHRONIC HAZARDS: This compound may be harmful by inhalation, ingestion or skin absorption. It may cause irritation. When heated to decomposition it emits toxic fumes of carbon monoxide and carbon dioxide. (NTP, 1992)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
/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/
/SIGNS AND SYMPTOMS/ No evidence of skin sensitization was found in volunteers treated with dilute solutions. /Tolualdehydes/
2-methylbenzaldehyde
2-Methylbenzaldehyde Use and Manufacturing
2-Methylbenzaldehyde can be produced by partial oxidation of o-xylene, e.g., in acetic acid with cobalt salts as catalysts and bromine compounds as promoters. It can also be obtained from 2-methylbenzyl chloride by gas-phase oxidation at 350-450 °C in the presence of AL2O3-V2O5 catalysts. In the Sommelet reaction, 2-methylbenzyl chloride reacts with hexamethylenetetramine to form 2-methylbenzaldehyde. This reaction can also use industrial chlorination mixtures containing small amounts of highly chlorinated products in addition to 2-methylbenzyl chloride and unreacted o-xylene.|Prepared by reacting nitropropane with o-xylyl bromide in the presence of sodium ethanoate.
Used as an intermediate in organic synthesis
Food additives -> Flavoring Agents
Flavoring Agents
Computed Properties
Molecular Weight:120.15
XLogP3:2.1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:120.057514874
Monoisotopic Mass:120.057514874
Topological Polar Surface Area:17.1
Heavy Atom Count:9
Complexity:98.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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