Carbamic acid, methyl ester

75.06660

75.07

209-939-2

9WFX634X2T

3054

2811

DTXSID8020834

WHITE CRYSTALS|NEEDLES

2924199090

52.32000

-0.7

Methyl carbamate appears as white crystals. (NTP, 1992)

1.1361 g/cm³ @ Temp: 56 °C

52-54 °C

177 °C

93ºC

1.41 (55ºC)

H2O: 700 g/L (20 ºC)

Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.

Freely sublimes at room temperature|These compounds are all hydrolyzed using 5 M sodium hydroxide solution, although the reaction times vary. Methyl carbamate is hydrolyzed to methanol and carbamic acid and urethane /ethyl carbamate/ is hydrolyzed to ethanol and carbamic acid. ... Carbamic acid decomposes to carbon dioxide and ammonia ... In all cases destruction is greater than 99% and good accountances are obtained for the products ... .

Water soluble.

Carbamates

METHYL CARBAMATE is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

NONH for all modes of transport

3

R40

S36/37

FC2450000

Xn

Freely sublimes even at room temperature.

P281-P305 + P351 + P338

H319-H351

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.

This intermediate /N-carbomethoxymethylimino phosphoryl chloride/ (or its ethyl homolog), produced during prepn of phosphoryl dichloride isocyanate from interaction of phosphorus pentachloride & methyl (or ethyl) carbamate, is unstable. Its decomposition to the required product may be violent or explosive unless moderated by the presence of a halogenated solvent.

DHHS/NTP; Toxicology & Carcinogenesis Studies of Methyl Carbamate in F344/N Rats and B6C3F1 Mice Technical Report Series No. 328 (1987) NIH Publication No. 88-2584

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

|Warning|H315 (76.19%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 652 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: 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. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. 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. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces 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 material under ambient temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Male CF-1 mice were treated with urethane (0, 0.5, 1.0, 1.5, and 2 g/kg; ip) and 18 hr later hepatic metallothionein concentrations were determined with the cadmium hemoglobin radioassay. Urethane (1 g/kg and higher) significantly increase hepatic metallothionein levels, resulting in a 14 fold increase after 2 g/kg. Time course experiments indicated that metallothionein levels were increased significantly at 6 hr after administration of urethane (1.5 g/kg) and reached a maximum between 12 and 24 hr. Gel filtration, anion exchange chromatography, and UV spectral analysis were used to characterize the protein induced by urethane. Pretreatment with actinomycin-D prevented induction of metallothionein by urethane. Administration of equimolar dosages (20 mmol/kg) of urethane, N-hydroxyurethane, and methyl carbamate indicated that urethane and N-hydroxyurethane induce metallothionein but that methyl carbamate does not. Metallothionein induction was also not observed with (pentobarbital and phenobarbital). Urethane induces hepatic metallothionein but this effect is not related to its anesthetic action, nor is it a common property of all carbamates.

LD50 MICE ORAL 6200 MG/KG

... 2 yr studies of methyl carbamate were conducted by administering 0, 100, or 200 mg/kg methyl carbamate in distilled water by gavage, 5 days per week for 103 weeks, to groups of 50 F344/N rats of each sex for 103 weeks. Groups of 50 B6C3F1 mice of each sex were administered 0, 500, or 1,000 mg/kg methyl carbamate on the same schedule. Additional groups of 30 rats of each sex were administered 0 or 400 mg/kg methyl carbamate, and additional groups of 30 mice of each sex were administered 0 or 1,000 mg/kg methyl carbamate in distilled water by gavage, 5 days per week. ... Conclusions: Under the conditions of these ... 2 yr gavage studies, there was clear evidence of carcinogenic activity for male and female F344/N rats given methyl carbamate as indicated by incr incidences of hepatocellular neoplastic nodules and hepatocellular carcinomas. There was no evidence of carcinogenic activity for male and female B6C3F1 mice given methyl carbamate at doses of 500 or 1,000 mg/kg. ...

METHYL CARBAMATE HAS BEEN ISOLATED FROM 4 SALSOLA SPECIES...

Methyl carbamate's production and use as an intermediate in the manufacture of dimethylol methyl carbamate-based resins(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 10(SRC), determined from a measured log Kow of -0.66(2) and a recommended regression-derived equation(3), indicates that methyl carbamate is expected to have very high mobility in soil(SRC). However, methyl carbamate was determined to adsorb onto the clay mineral montmorillonite(4). Volatilization of methyl carbamate will not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 4.0X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Hydrolysis of methyl carbamate in moist soils may be catalyzed by adsorption to Na+, Mg2+, Al3+, and Cu2+ montmorillonites(4,SRC). Biodegradation of methyl carbamate in soil may be important(SRC), based on its biodegradation in river and seawater(6).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 10(SRC), determined from a measured log Kow of -0.66(2) and a recommended regression-derived equation(3), indicates that methyl carbamate is not expected to adsorb to suspended solids and sediment in water(SRC). Methyl carbamate is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 4.0X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF value of 0.19(3,SRC), from a measured log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). Methyl carbamate was degraded 19 and 18% in river and seawater, respectively, over a three day period(6). Purely aliphatic carbamates are expected to be resistant to hydrolysis under environmental conditions(7); hydrolysis half-lives of 3300 and 330 years at pH values of 7 and 8, respectively, were estimated for methyl carbamate(8,SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl carbamate, which has an estimated vapor pressure of 0.56 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl carbamate 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 about 4.8 days(3,SRC).

The rate constant for the vapor-phase reaction of methyl carbamate with photochemically-produced hydroxyl radicals has been estimated as 3.4X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 4.8 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Purely aliphatic carbamates are expected to be resistant to hydrolysis under environmental conditions(2). A base-catalyzed second-order rate constant of 6.6X10-5 L/mol-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 3300 and 330 years at pH values of 7 and 8, respectively(3,SRC). Hydrolysis in moist soils may be catalyzed by adsorption to Na+, Mg2+, Al3+, and Cu2+ montmorillonites(4,SRC).

An estimated BCF value of 0.19 was calculated for methyl carbamate(SRC), using a measured log Kow of -0.66(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

The Koc of methyl carbamate is estimated as approximately 10(SRC), using a measured log Kow of -0.66(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that methyl carbamate is expected to have very high mobility in soil(SRC). Methyl carbamate adsorbs on Na+, Mg2+, Al3+, and Cu2+ montmorillonites which catalyze the hydrolysis of methyl carbamate when equilibrated at room temperature and 100% relative humidity(4).

The Henry's Law constant for methyl carbamate is estimated as 4.0X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that methyl carbamate will be essentially nonvolatile from water surfaces(2,SRC). Methyl carbamate's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces is not expected to occur(SRC).

Methyl carbamate was detected in trace amounts in red and white wines, sherry, whisky, and Armagnac(1). Methyl carbamate was detected in fruit brandy from France and Austria at an average concentration of 28 and 9 ug/kg, respectively(1). Methyl carbamate was detected in various breads, light toast, and dark toast at an average concentration of 3.0, 2.2, and 2.7 ug/kg, respectively(1). Trace levels, 1 to 4 ug/kg, of methyl carbamate were detected in various yogurt samples(1). Soy sauce samples contained minute amounts, 0.1 to 1.1 ug/kg, of methyl carbamate(1).

Occupational exposure to methyl carbamate may occur through inhalation and dermal contact with this compound at workplaces where methyl carbamate is produced or used. Limited monitoring data indicate the general population may be exposed to methyl carbamate via inhalation of ambient air and ingestion of food. (SRC)

RATS INJECTED IP WITH METHYL CARBAMATE...EXCRETED...CARBAMATE...IN URINE...|DNA BINDING OF...(14)C-METHYL CARBAMATE LABELED IN METHYL GROUP HAS BEEN INVESTIGATED IN MOUSE LIVER & KIDNEY. ... INCORP OF (3)H-METHYL CARBAMATE INTO LIVER-CELL RNA HAS BEEN EXAMINED IN MICE...

SYMPTOMS: Overexposure to this compound may cause narcosis. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of nitrogen oxides. (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. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. 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. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

For immediate first aid: Ensure that adequate decontamination has been carried out. If victim is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask as trained. Perform CPR if 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 victim quiet and maintain normal body temperature. Obtain medical attention. /Esters and related compounds/|For basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... Monitor for shock and treat if necessary ... For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline 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 ... . /Esters and related compounds/

carbamic acid, methyl ester

PROBABLY 100% AS A CHEM INT FOR DIMETHYLOL METHYL CARBAMATE-BASED RESINS AS A DURABLE-PRESS FABRIC FINISH (1976)

Adhesive manufacturing|Carbamic acid, methyl ester: ACTIVE

COLORIMETRIC METHODS HAVE BEEN USED TO DETERMINE METHYL CARBAMATE IN AIR @ SENSITIVITY OF 20 UG/L (BABINA, 1975, GIG I SANIT, 7, 76-77). THIN-LAYER & CHROMATOGRAPHIC METHODS...ALSO USED FOR ITS DETERMINATION (KARAWYA ET AL, 1972, PHYTOCHEMISTRY, 11, 441-442; KNAPPE & ROHDEWALD, 1966, Z ANALYT CHEM, 217, 110-113).|METHODS FOR CHROMATOGRAPHIC ANALYSIS OF CARBAMATES, INCL ALKYL CARBAMATES HAVE BEEN REVIEWED (FISHBEIN & ZIELINSKI, CHROMAT REV, 9, 37-101, 1967). GAS CHROMATOGRAPHIC METHOD...FOR DETECTION OF UG AMT OF METHYL CARBAMATE IN MIXT OF ALKYL CARBAMATES...(NERY R, ANALYST, 94, 130-135 (1969)).