Urethane

Base Information

• Chemical Name: Urethane
• CAS No.: 51-79-6
• Deprecated CAS: 121382-27-2
• Molecular Formula: C3H7NO2
• Molecular Weight: 89.0941
• Hs Code.: 29241990
• European Community (EC) Number: 200-123-1
• ICSC Number: 0314
• NSC Number: 758452,746
• UN Number: 3077
• UNII: 3IN71E75Z5
• DSSTox Substance ID: DTXSID9021427
• Nikkaji Number: J2.306J
• Wikipedia: Ethyl_carbamate
• Wikidata: Q422884
• NCI Thesaurus Code: C920
• RXCUI: 1420982
• Metabolomics Workbench ID: 44760
• ChEMBL ID: CHEMBL462547
• Mol file: 51-79-6.mol

Synonyms:Carbamate, Ethyl;Ethyl Carbamate;Urethan;Urethane

Chemical Property of Urethane

Chemical Property:

• Appearance/Colour: COA
• Vapor Pressure: 10 mm Hg ( 77.8 °C)
• Melting Point: 48-50 °C(lit.)
• Refractive Index: 1.413
• Boiling Point: 184 °C at 760 mmHg
• PKA: 13.58±0.50(Predicted)
• Flash Point: 97.2 °C
• PSA: 52.32000
• Density: 1.045 g/cm³
• LogP: 0.80190
• Storage Temp.: Room temperature.
• Solubility.: slightly soluble
• Water Solubility.: slightly soluble
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 89.047678466
• Heavy Atom Count: 6
• Complexity: 52.8

Purity/Quality:

99% ^*data from raw suppliers

Urethane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-22
• Safety Statements: 53-45-99

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Carbamic Acid Esters
• Canonical SMILES: CCOC(=O)N
• Recent NIPH Clinical Trials: Verification of the face pillows for patients maintaining a prone position after vitrectomy to distribute pressure and relieve distress.
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.
• Effects of Short Term Exposure: The substance may cause effects on the nervous system. Exposure could cause lowering of consciousness.
• Effects of Long Term Exposure: This substance is probably carcinogenic to humans.
• Description: Ethyl carbamate occurs as colourless or white columnar crystals or granular powder. It is very soluble in water. With heat, ethyl carbamate undergoes decomposition and emits toxic fumes of carbon monoxide, carbon dioxide, and nitrogen oxides. Ethyl carbamate is used as an intermediate in the synthesis of a number of chemical products, for example, pharmaceuticals, in biochemical research and medicine, and as a solubiliser and co-solvent for pesticides and fumigants. Prior to World War II, ethyl carbamate saw relatively heavy use in the treatment of multiple myeloma before it was found to be toxic, carcinogenic, and largely ineffective. However, due to U.S. FDA regulations, ethyl carbamate has been withdrawn from pharmaceutical use. However, small quantities of ethyl carbamate are also used in laboratories as an anaesthetic for animals.
• Uses: The primary use of urethane has been as a chemical intermediate in preparation of amino resins (IARC 1974). The process involves a reaction with formaldehyde to give hydroxymethyl derivatives that are used as cross-linking agents in permanent-press textile treatments designed to impart wash-and-wear properties to fabrics. Urethane isalso used as a solubilizer and co-solvent in the manufacture of pesticides, fumigants, and cosmetics, as an intermediate in the manufacture of pharmaceuticals, and in biochemical research (HSDB 2009). Urethane was formerly used as an active ingredient in drugs prescribed for the treatment of neoplastic diseases, as a sclerosing solution for varicose veins, as a hypnotic, and as a topical bactericide. It is also used in veterinary medicine as an anesthetic (IARC 1974). Urethane is produced naturally during many fermentation processes(Zimmerli and Schlatter 1991). Naturally occurring contaminant in fermented foods, particularly wine, stone-fruit brandies, and bread. This substance is reasonably anticipated to be a human carcinogen. Intermediate in organic synthesis. In the preparation and modification of amino resins. As solvent, solubilizer and cosolvent for various organic materials. Animal anesthetic in laboratory procedures.

Technology Process of Urethane

There total 244 articles about Urethane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

oxalic acid diethyl ester (95-92-1) + urea (57-13-6) → Ethyl oxamate (617-36-7) + urethane (51-79-6)

Guidance literature:

With di(n-butyl)tin oxide; at 140 ℃; for 12h; Inert atmosphere;

DOI:10.1002/aoc.1629

Reference yield: 26.0%

N-fluoro-N-methylurethan (21298-14-6) → Ethyl N-methylcarbamate (105-40-8) + N,N'-methanediyl-bis-carbamic acid diethyl ester (3693-53-6) + ethyl (((ethoxycarbonyl)amino)methyl)(methyl)carbamate (90498-82-1) + urethane (51-79-6)

Guidance literature:

In acetonitrile; for 4h; electrochemical reduction;

Reference yield: 22.0%

4bH,13bH-bis[1,3]dioxolo[4,5-g;4',5'-g'][1,2,4,5]tetrazino[1,6-c;4,3-c']diquinazoline-5,14-dicarboxylic acid diethyl ester (58277-22-8,62418-38-6) → 2-formylamino-4,5-methylenedioxybenzaldehyde (77850-69-2) + urethane (51-79-6) + ethylhydrazine carboxylate (4114-31-2) + 7-Butyl-7H-[1,3]dioxolo[4,5-g]quinazolin-8-one (68358-39-4)

Guidance literature:

In various solvent(s); for 100h; Irradiation;

upstream raw materials:

diethyl imidocarbonate

carbamoyl azide

ethanol

ethoxycarbonylisocyanate

Downstream raw materials:

2,3,4,5,6,7-Hexahydro-1H-benzimidazol-2-on

(2-phenyl-quinoline-4-carbonyl)-carbamic acid ethyl ester

propionylcarbamic acid ethyl ester

4,5-dimethyl-3H-oxazol-2-one

Refernces

• 1、 Vishnyakova et al.. "-". . . Retrieved 1971.
• 2、 Pudovik,Krepysheva,Kharitonov,Pudovik. "Reactions of trimethylsilyl isocyanate with alcohols and phenols". . p. 325 - 326. Retrieved 2001.
• 3、 -. "Preparation method of carbamate". Paragraph 0041; 0045-0047. . Retrieved 2020/09/23.
• 4、 Sardarian, Ali Reza,Dindarloo Inaloo, Iman,Zangiabadi, Milad. "An Fe3O4@SiO2/Schiff base/Cu(ii) complex as an efficient recyclable magnetic nanocatalyst for selective mono: N-arylation of primary O-alkyl thiocarbamates and primary O-alkyl carbamates with aryl halides and arylboronic acids". . p. 8557 - 8565. Retrieved 2019/06/14.