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Methyl carbamate

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Name

Methyl carbamate

EINECS 209-939-2
CAS No. 598-55-0 Density 1.092 g/cm3
PSA 52.32000 LogP 0.41180
Solubility 700 g/L (20 °C) in water Melting Point 56-58 °C(lit.)
Formula C2H5NO2 Boiling Point 178.7 °C at 760 mmHg
Molecular Weight 75.0672 Flash Point 105.2 °C
Transport Information N/A Appearance white adhering crystals
Safety 26-36/37-22 Risk Codes 36-40
Molecular Structure Molecular Structure of 598-55-0 (Methyl carbamate) Hazard Symbols HarmfulXn
Synonyms

Methylurethane;NSC 3054;Urethylane;

Article Data 88

Methyl carbamate Synthetic route

67-56-1

methanol

598-55-0

methyl carbamate

Conditions
ConditionsYield
With alumina supported titanium dioxide-bismuth oxide metal oxide catalyst at 120℃; for 8h; Sealed tube;99.41%
Stage #1: methanol; urea at 30℃; for 20h; Autoclave;
Stage #2: With carbon dioxide; 6O4P(3-)*5Ni(2+)*5Ca(2+)*2F(1-) at 160℃; under 4500.45 Torr; for 6h; Temperature; Concentration;
98.9%
With silica supported titanium dioxide at 160℃; under 17251.7 Torr; for 8h; Temperature; Pressure; Inert atmosphere;98%
616-38-6

carbonic acid dimethyl ester

598-55-0

methyl carbamate

Conditions
ConditionsYield
With Na-ZnO-ZrO2 / γ-Al2O3 at 180℃; for 6h; Temperature; Reagent/catalyst; Autoclave;98.8%
80284-00-0

C9H10N2O6S

A

598-55-0

methyl carbamate

B

ammonium salt of N-nitro-p-toluenesulfamide

Conditions
ConditionsYield
With ammonia In diethyl ether for 0.0833333h;A 78%
B 92%
67-56-1

methanol

70678-13-6

1,2-bis(1-isocyanato-1-methylethyl)diazene

A

112700-85-3

5,5-dimethyl-Δ1-1,2,4-triazolin-3-one

B

598-55-0

methyl carbamate

C

2-methoxy-2-methoxycarbonylaminopropane

D

[1-(1-Methoxycarbonylamino-1-methyl-ethylazo)-1-methyl-ethyl]-carbamic acid methyl ester

Conditions
ConditionsYield
for 2h; Product distribution; Mechanism; Heating; other alcohols; var. reaction time; var. temperatures;A 90%
B n/a
C n/a
D n/a
for 2h; Heating; Yield given. Yields of byproduct given;
671-50-1

methyl aziridine-1-carboxylate

A

151-56-4

ethyleneimine

B

598-55-0

methyl carbamate

Conditions
ConditionsYield
With ammonia In ethanol at 18 - 25℃; for 24h;A n/a
B 90%
67-56-1

methanol

A

598-55-0

methyl carbamate

B

616-38-6

carbonic acid dimethyl ester

Conditions
ConditionsYield
at 179.84℃; for 10h;A 84.8%
B 6.5%
With zinc/aluminum mixed oxide at 179.84℃; for 10h; Reagent/catalyst; Autoclave;A 55.1%
B 36.5%
calcined La(NO3)3x6H2O at 170℃; under 14821 Torr; for 4h; Product distribution / selectivity; Autoclave; Inert atmosphere;A 41.2%
B 53.4%
With Zn/Ca-catalyst at 179.84℃; for 10h;A 50.5%
B 41.2%
With Ga2O3/CeO2-Al2O3 at 110℃; for 5h;
67-56-1

methanol

590-28-3

potassium cyanate

598-55-0

methyl carbamate

Conditions
ConditionsYield
With para-dodecylbenzenesulfonic acid In neat (no solvent) at 60℃; for 0.5h; Green chemistry;80%
With DBSA at 60℃; for 1h;
79-22-1

methyl chloroformate

598-55-0

methyl carbamate

Conditions
ConditionsYield
With triethylamine In methanol; dichloromethane; ethyl acetate78%
With ammonia; benzene
With potassium hydrogencarbonate In water
67-56-1

methanol

2911-21-9

2,4-dioxo-6-methyl-3,4-dihydro-2H-1,3-oxazine

A

105-45-3

acetoacetic acid methyl ester

B

598-55-0

methyl carbamate

Conditions
ConditionsYield
With triethylamine for 24h; Heating;A 70%
B 15%
4651-91-6

3-cyano-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene

79-22-1

methyl chloroformate

598-55-0

methyl carbamate

Conditions
ConditionsYield
With sodium hydrogencarbonate In butanone66%

Methyl carbamate Specification

The Methyl carbamate, with the CAS registry number 598-55-0 and EINECS registry number 209-939-2, is also known as Methoxyformamide. And the molecular formula of this chemical is C2H5NO2. It is a carbamate ester with th apperance of white adhering crystals. What's more, it is used by the textile industry to manufacture resins to be applied on polyester/cotton blend fabrics as durable-press finishes. And it is also used as intermediate in the pharmaceuticals and Pesticide industry. In addition, it is used as selective solvent for dutrex.

The physical properties of Methyl carbamate are as following: (1)ACD/LogP: -0.68; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.68; (4)ACD/LogD (pH 7.4): -0.68; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 10.15; (8)ACD/KOC (pH 7.4): 10.15; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 29.54 Å2; (13)Index of Refraction: 1.399; (14)Molar Refractivity: 16.62 cm3; (15)Molar Volume: 68.7 cm3; (16)Polarizability: 6.59×10-24cm3; (17)Surface Tension: 33.6 dyne/cm; (18)Density: 1.092 g/cm3; (19)Flash Point: 105.2 °C; (20)Enthalpy of Vaporization: 41.5 kJ/mol; (21)Boiling Point: 178.7 °C at 760 mmHg; (22)Vapour Pressure: 0.976 mmHg at 25°C.

Preparation of Methyl carbamate: Heat methyl alcohol to boil, and add urea with stirring. Reflux for 30 hours, and leach for 2 times with boiling sherwood oil. Collect the 175-177 °C distillates after fractionation, and the distillates are the desired product. The yield is about 75%.
1. ClCOOCH3 + 2NH3 → NH2COOCH3
2. NH2CONH2 + CH3OH → NH2COOCH3 + NH3

You should be cautious while dealing with this chemical. It irritates eyes, and there's limited evidence of a carcinogenic effect about this chemical. Therefore, you had better take the following instructions: Do not breathe dust; Wear suitable protective clothing and gloves, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)N
(2)InChI: InChI=1/C2H5NO2/c1-5-2(3)4/h1H3,(H2,3,4)
(3)InChIKey: GTCAXTIRRLKXRU-UHFFFAOYAJ

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 6200mg/kg (6200mg/kg)   National Toxicology Program Technical Report Series. Vol. NTP-TR-328, Pg. 1987,
mouse LD50 subcutaneous 4450mg/kg (4450mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Australian Journal of Experimental Biology and Medical Science. Vol. 45, Pg. 507, 1967.
mouse LDLo intraperitoneal 200mg/kg (200mg/kg)   Toxicology and Applied Pharmacology. Vol. 23, Pg. 288, 1972.
quail LD50 oral 21mg/kg (21mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Ecotoxicology and Environmental Safety. Vol. 8, Pg. 551, 1984.
rabbit LD50 skin > 2gm/kg (2000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 161, 1992.
rat LD50 oral 2500mg/kg (2500mg/kg)   National Toxicology Program Technical Report Series. Vol. NTP-TR-328, Pg. 1987,

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