N-Hydroxyurethane

Base Information

• Chemical Name: N-Hydroxyurethane
• CAS No.: 589-41-3
• Molecular Formula: C3H7 N O3
• Molecular Weight: 105.093
• Hs Code.: 2924199090
• European Community (EC) Number: 209-648-0
• NSC Number: 83629,71045
• UNII: QWI3C4ASI7
• DSSTox Substance ID: DTXSID20207635
• Nikkaji Number: J1.640C
• Wikidata: Q72482141
• ChEMBL ID: CHEMBL153081
• Mol file: 589-41-3.mol

Synonyms:ethyl N-hydroxycarbamate;hydroxycarbamic acid ethyl ester;N-hydroxyurethane

Chemical Property of N-Hydroxyurethane

Chemical Property:

• Vapor Pressure: 0.00268mmHg at 25°C
• Refractive Index: n20/D 1.445(lit.)
• Boiling Point: 113-116 ºC (3 mmHg)
• PKA: 9.30±0.23(Predicted)
• Flash Point: >110 ºC
• PSA: 58.56000
• Density: 1.196g/cm³
• LogP: 0.51260
• Storage Temp.: −20°C
• Solubility.: Diethyl Ether, Dimethyl Sulfoxide, Water
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 105.042593085
• Heavy Atom Count: 7
• Complexity: 63.2

Purity/Quality:

98%,99%, ^*data from raw suppliers

Hydroxyurethane ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)NO
• Uses: Hydroxyurethane is a metabolite of carcinogenic Urethane (U825300). Reactant involved in:Synthesis of molecules used for intermolecular Sharpless aminohydroxylation reactionsIntermolecular ortho-C-H amidation of anilidesCinchona alkaloid-catalyzed asymmetric cycloadditionAllylic arylation Metabolite of carcinogenic Urethane (U825300).

Technology Process of N-Hydroxyurethane

There total 6 articles about N-Hydroxyurethane 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: 96.0%

chloroformic acid ethyl ester (541-41-3) → ethyl N-hydroxylcarbamate (589-41-3)

Guidance literature:

With hydroxylamine hydrochloride; potassium carbonate; In tetrahydrofuran; at 20 ℃; for 48h;

Reference yield:

ethanol (64-17-5) + 1,1'-carbonyldiimidazole (530-62-1) → ethyl N-hydroxylcarbamate (589-41-3)

Guidance literature:

ethanol; 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 0 - 20 ℃; for 1h; Inert atmosphere; Schlenk technique;

With 1H-imidazole; hydroxylamine hydrochloride; In tetrahydrofuran; at 0 - 20 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.6b02724

Reference yield:

Diethyl carbonate (105-58-8,76619-83-5) → ethyl N-hydroxylcarbamate (589-41-3)

Guidance literature:

With sodium hyponitrite; ethanol;

upstream raw materials:

chloroformic acid ethyl ester

Diethyl carbonate

hydroxylamine

ethanol

Downstream raw materials:

N-benzyloxycarbamic acid ethyl ester

N-benzyloxy-N-benzylcarbamic acid ethyl ester

N-(ethoxycarbonyl)isoxazolidine

N-<2-Nitro-4-cyan-phenoxy>-urethan

Refernces

• 1、 Ma, Nuannuan,Li, Peihe,Wang, Zheng,Dai, Qipu,Hu, Changwen. "Synthesis of indoles from aroyloxycarbamates with alkynes: Via decarboxylation/cyclization". supporting information. p. 2421 - 2426. Retrieved 2018/04/12.
• 2、 Li, Peihe,Ma, Nuannuan,Li, Jikun,Wang, Zheng,Dai, Qipu,Hu, Changwen. "Regioselective Synthesis of 2-Vinylanilines Using O-aroyloxycarba-mates by Sequential Decarboxylation/Amination/Heck Reaction". . p. 8251 - 8257. Retrieved 2017/08/14.