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Urethane

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Name

Urethane

EINECS 200-123-1
CAS No. 51-79-6 Density 1.045 g/cm3
PSA 52.32000 LogP 0.80190
Solubility slightly soluble Melting Point 48-50 °C(lit.)
Formula C3H7NO2 Boiling Point 184 °C at 760 mmHg
Molecular Weight 89.0941 Flash Point 97.2 °C
Transport Information N/A Appearance COA
Safety 53-45-99 Risk Codes 45
Molecular Structure Molecular Structure of 51-79-6 (Urethane) Hazard Symbols ToxicT
Synonyms

Ethylaminoformate;Ethyl carbamate;Ethylurethane;Leucethane;O-Ethylurethane;Pracarbamine;

Article Data 185

Urethane Synthetic route

110-82-7

cyclohexane

66121-61-7

N,O-bistrimethylsilyl-N-(ethoxycarbonyl)hydroxylamine

A

107-46-0

Hexamethyldisiloxane

B

1541-19-1

ethyl N-cyclohexylcarbamate

C

51-79-6

urethane

Conditions
ConditionsYield
at 100℃; for 25h;A 100%
B 80%
C 8%
at 45℃; for 58h; Irradiation;A 75%
B 45%
C 55%
64-17-5

ethanol

51-79-6

urethane

Conditions
ConditionsYield
With alumina supported chromium oxide-nickel oxide-bismuth oxide trimetal oxide catalyst at 90℃; for 12h; Sealed tube;99.1%
at 179.84℃; for 7h; Autoclave;90%
75934-53-1

ethyl-N-(carboethoxy)-N-nitrocarbamate

A

62258-40-6

N-nitrouretahne ammonium salt

B

51-79-6

urethane

Conditions
ConditionsYield
With ammonia In acetonitrile for 0.0833333h;A 99%
B 0.15 g

trichloroethoxycarbonyl chloride

51-79-6

urethane

Conditions
ConditionsYield
sodium hydrogencarbonate96%
24482-75-5

Dichloronitroacetic acid ethyl ester

51-79-6

urethane

Conditions
ConditionsYield
With ammonium hydroxide for 48h; Ambient temperature;91%
64-17-5

ethanol

917-61-3

sodium isocyanate

51-79-6

urethane

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane at -2 - 2℃; for 6h;90%
With perchloric acid on silica gel at 20℃; for 0.75h;73%
60-29-7

diethyl ether

2746-25-0

p-Methoxybenzyl bromide

51-79-6

urethane

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide; Petroleum ether; benzene90%

(Z,E)-N2-(ethoxycarbonyl)-N1-methyl-N1-octylformamidine

A

36600-01-8

N-methyl-N-octylformamide

B

51-79-6

urethane

Conditions
ConditionsYield
With acetic acid In 1,4-dioxane at 20℃; for 1h;A 89%
B n/a

1-Ethoxycarbonylamino-2,4,6-trimethyl-pyridinium; perchlorate

A

108-75-8

2,4,6-trimethyl-pyridine

B

C11H16N2O2

C

51-79-6

urethane

Conditions
ConditionsYield
With tetraethylammonium perchlorate In acetonitrile preparative electrolyse, - 2.3 V;A 87%
B n/a
C n/a

2Rh(1+)*4CO*2NCO(1-)=[Rh(CO)2NCO]2

A

hexarhodium hexadecacarbonyl

B

51-79-6

urethane

Conditions
ConditionsYield
With ethanol; carbon monoxide In ethanol to degassed ethanol educt added with stirring while CO bubled through for 15 h; product filtered off, washed with ethanol and hexane, dried in vac.; elem. anal.;A 85%
B n/a

Urethane Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1974,p. 111.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Urethane Standards and Recommendations

DFG MAK: Animal Carcinogen, Suspected Human Carcinogen

Urethane Specification

The Urethane with CAS registry number of 51-79-6 is also called Carbamic acid, ethylester. Its EINECS registry number is 200-123-1. The IUPAC name is ethyl carbamate. In addition, the molecular formula is C3H7NO2 and the molecular weight is 89.09. It is a kind of white crystalline powder. And it is incompatible with strong acids, strong bases and strong oxidizing agents.

Physical properties about this chemical are: (1)ACD/LogP: -0.15; (2)ACD/LogD (pH 5.5): -0.15; (3)ACD/LogD (pH 7.4): -0.15; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 19.74; (7)ACD/KOC (pH 7.4): 19.74; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 29.54 Å2; (12)Index of Refraction: 1.413; (13)Molar Refractivity: 21.25 cm3; (14)Molar Volume: 85.2 cm3; (15)Polarizability: 8.42 ×10-24cm3; (16)Surface Tension: 33.6 dyne/cm; (17)Density: 1.045 g/cm3; (18)Flash Point: 97.2 °C; (19)Enthalpy of Vaporization: 42.03 kJ/mol; (20)Boiling Point: 184 °C at 760 mmHg; (21)Vapour Pressure: 0.748 mmHg at 25°C.

Preparation of Urethane: it can be prepared by urea nitrate, ethanol and sodium nitrite in the presence of sulfuric acid. This reaction is a kind of esterification reaction. Then go through the operation of distillation, crystallization and drying to get the products. In addition, it can be prepared by ethanol and cyanic acid;sodium cyanate. This reaction will need reagent HCl and solvent CH2Cl2. The reaction time is 6 hours at reaction temperature of -2 - 2 °C. The yield is about 90%.

Urethane can be prepared by ethanol and cyanic acid;sodium cyanate.

Uses of Urethane: this chemical can be used as intermediates for medicine, pesticides and perfume. And it is used for biochemical research and the production of sleeping pills and tranquilizers. Moreover, it can be used as fungicides, cosolvent of injection and colorants in dyeing industry. In addition, it can be used to get isocyanatophosphoric acid-dichloride. This reaction will need reagent PCl5 and solvent CH2Cl2. The reaction time is 4 hours by heating. The yield is about 65%.

Urethane can be used to get isocyanatophosphoric acid-dichloride

When you are using this chemical, please be cautious about it as the following:
This chemical may cause cancer. Avoid exposure-obtain special instructions before use. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). In addition, you should keep container in a well-ventilated place.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCC)N
(2)InChI: InChI=1/C3H7NO2/c1-2-6-3(4)5/h2H2,1H3,(H2,4,5)
(3)InChIKey: JOYRKODLDBILNP-UHFFFAOYAY

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LDLo oral 2188mg/kg (2188mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
guinea pig LDLo intraarterial 800mg/kg (800mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 131, Pg. 171, 1928.
guinea pig LDLo intravenous 800mg/kg (800mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 131, Pg. 171, 1928.
mouse LD50 intraperitoneal 1539mg/kg (1539mg/kg)   Progress in Mutation Research. Vol. 1, Pg. 682, 1981.
mouse LD50 intravenous 500mg/kg (500mg/kg)   Acta Pharmaceutica Jugoslavica. Vol. 5, Pg. 43, 1955.
mouse LD50 oral 2500mg/kg (2500mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 9, Pg. 595, 1959.
mouse LD50 subcutaneous 1750mg/kg (1750mg/kg)   Gann. Japanese Journal of Cancer Research. Vol. 63, Pg. 731, 1972.
mouse LD50 unreported 2gm/kg (2000mg/kg)   British Journal of Cancer. Vol. 6, Pg. 160, 1952.
mouse LDLo parenteral 1gm/kg (1000mg/kg) GASTROINTESTINAL: PERITONITIS Progress Report for Contract No. PH-43-63-1132, Submitted to the National Cancer Institute by Scientific Associates, Inc. Vol. PH-43-62-483,
pigeon LDLo oral 800mg/kg (800mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
rabbit LDLo intravenous 2gm/kg (2000mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 272, 1973.
rat LD50 intramuscular 1400mg/kg (1400mg/kg)   Zeitschrift fuer Krebsforschung und Klinische Onkologie. Vol. 84, Pg. 227, 1975.
rat LD50 intraperitoneal 1500mg/kg (1500mg/kg)   Cancer Research. Vol. 26, Pg. 1448, 1966.
rat LD50 oral 1809mg/kg (1809mg/kg)   Cancer Letters Vol. 57, Pg. 37, 1991.
rat LDLo subcutaneous 1800mg/kg (1800mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 182, Pg. 348, 1936.

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