589-41-3

Basic information

• Product Name: N-Hydroxyurethane
• Synonyms: ETHYL HYDROXYCARBAMATE;ETHYL N-HYDROXYCARBAMATE;HYDROXYCARBAMIC ACID ETHYL ESTER;Ethylester kyseliny N-hydroxykarbaminove;Ethyl Hydroxycarbamate Hydroxycarbamic Acid Ethyl Ester;N-Hydroxyurethane;ethylesterkyselinyn-hydroxykarbaminove;hydroxy-carbamicaciethylester
• CAS NO: 589-41-3
• Molecular Formula: C₃H₇NO₃
• Molecular Weight: 105.09
• EINECS: 209-648-0
• Product Categories: Aliphatics;Hydroxylamines;Hydroxylamines (N-Substituted);Amines;Mutagenesis Research Chemicals
• Mol File: 589-41-3.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 113-116 °C3 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.3895 (rough estimate)
• Vapor Pressure: 0.00268mmHg at 25°C
• Refractive Index: n20/D 1.445(lit.)
• Storage Temp.: −20°C
• Solubility: Diethyl Ether, Dimethyl Sulfoxide, Water
• PKA: 9.30±0.23(Predicted)
• BRN: 1747529
• CAS DataBase Reference: N-Hydroxyurethane(CAS DataBase Reference)
• NIST Chemistry Reference: N-Hydroxyurethane(589-41-3)
• EPA Substance Registry System: N-Hydroxyurethane(589-41-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 2
• RTECS: FB1750000
• Hazardous Substances Data: 589-41-3(Hazardous Substances Data)

Usage

Description

N-Hydroxyurethane, also known as Urethane, is a metabolite of the carcinogenic compound Urethane (U825300). It plays a significant role in various chemical reactions and has potential applications in the synthesis of molecules and drug development.

Uses

Used in Chemical Synthesis:
N-Hydroxyurethane is used as a reactant in the synthesis of molecules used for intermolecular Sharpless aminohydroxylation reactions, intermolecular ortho-C-H amidation of anilides, cinchona alkaloid-catalyzed asymmetric cycloaddition, and allylic arylation. Its involvement in these reactions contributes to the development of new compounds and molecules with potential applications in various industries.
Used in Drug Development:
As a metabolite of carcinogenic Urethane (U825300), N-Hydroxyurethane may have potential applications in drug development, particularly in the study of its metabolic pathways and the development of drugs targeting these pathways. Further research is needed to explore its potential uses in this field.

Biochem/physiol Actions

N-Hydroxyurethane causes the chromosomal fragmentation at millimolar concentrations and cell toxicity in cultured normal human leukocytes.

InChI:InChI=1/C3H7NO3/c1-2-7-3(5)4-6/h6H,2H2,1H3,(H,4,5)

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 105-58-8 Diethyl carbonate 
• 7803-49-8 hydroxylamine 
• 64-17-5 ethanol 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 5618-62-2 O-isobutylhydroxylamine 
• 51-79-6 urethane 
• 5555-72-6 N-benzyloxycarbamic acid ethyl ester 
• 1867-23-8 N-benzyloxy-N-benzylcarbamic acid ethyl ester 
• 54020-55-2 N-(ethoxycarbonyl)isoxazolidine 
• 6919-62-6 ethyl N-methoxy-N-methylcarbamate 
• 13278-89-2 N-<5-chlor-2-nitro-phenoxy>-urethan 
• 92765-13-4 N-(2,4,6-Trinitrophenoxy)-urethan 
• 13516-41-1 N-<2-Nitro-4-cyan-phenoxy>-urethan 
• 13278-86-9 4,6-Dinitro-O,O'-bis-aethoxyxcarbonylamino-resorcin 
• 15308-35-7 N-(3,4-Dichlor-benzyloxy)-carbamidsaeure-ethylester 
• 52245-10-0 N-Carboethoxy-O-2,4,6-trimethylbenzylhydroxylamin 
• 5555-70-4 N-(4-Chlor-benzyloxy)-carbaminsaeure-ethylester 
• 5553-48-0 N-(4-Methyl-benzyl)-N-(4-methyl-benzyloxy)-carbamidsaeure-ethylester 

Relevant articles and documents

An Effective Method for the Synthesis of 1,3-Dihydro-2H-indazoles via N-N Bond Formation

The [4+1] cycloaddition reaction of bifunctional amino reagents has been achieved with in situ formed aza-ortho-quinone methides. Specifically, N-(tosyloxy)carbamates were used as an N1 synthon and bifunctional amino reagents for this transformation, which provides a metal-free, catalyst-free, and oxidant-free strategy to form nitrogen-nitrogen bonds. (Figure presented.).

Regioselective Synthesis of 2-Vinylanilines Using O-aroyloxycarba-mates by Sequential Decarboxylation/Amination/Heck Reaction

A new sequential approach for 2-vinylanilines utilizing aryl carboxylic acids as stable, inexpensive and widely available arylating reagents is described. Employing a Pd-POVs catalyst system, this protocol is not only overcoming the restriction barrier of decarboxylative coupling to ortho-substituted substrates, but also provides site-special to create new C(sp2)-N and C(sp2)-C(sp2) bonds. Mechanistic experiments suggest the cleavage of C(sp2)-COOH gives priority to C(sp2)-X bond in this reaction.

Palladium-Catalyzed Decarboxylative Synthesis of Arylamines

A novel approach has been developed for the synthesis of arylamines via the palladium-catalyzed intramolecular decarboxylative coupling (IDC) of aroyloxycarbamates, obtained in situ by reacting aryl carboxylic acids with hydroxycarbamates. The reaction offers facile access to structurally diverse arylamines with the site-specific formation of the C(sp2)-N bond under mild conditions.