N-CYANOACETYLURETHANE Chemical Properties

Melting point:

167-169 °C (lit.)

Boiling point:

280.35°C (rough estimate)

Density 

1.197

refractive index 

1.5010 (estimate)

storage temp. 

2-8°C

solubility 

DMSO, Methanol

form 

Solid

pka

3.46±0.10(Predicted)

color 

Pale Yellow

InChI

InChI=1S/C6H8N2O3/c1-2-11-6(10)8-5(9)3-4-7/h2-3H2,1H3,(H,8,9,10)

InChIKey

HSOGVWWWGVFXGF-UHFFFAOYSA-N

SMILES

C(OCC)(=O)NC(CC#N)=O

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

EZ3480000

HazardClass 

IRRITANT

HS Code 

2926907090

MSDS

• Language:English Provider:SigmaAldrich

N-CYANOACETYLURETHANE Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

N-Cyanoacetylurethane is used in the synthesis of inhibitors targetting the PDZ domain of PICK1, which is a potential target for brain ischemia, pain and addiction illnesses. Also it is used in the synthesis of cathespin K inhibitors.

Reactions

N-Cyanoacetylurethane has multiple reactivity and can participate in diazotization reactions and coordinate reactions with metal complexes.

Synthesis

2-Cyanoacetic acid was reacted with ethyl carbamate, DMF and phosphorus oxychloride, and finally extracted with ethyl acetate to obtain N-Cyanoacetylurethane.

References

[1] Patent: WO2014/190199, 2014, A1. Location in patent: Paragraph 00250
[2] Patent: WO2016/81522, 2016, A1. Location in patent: Paragraph 00284; 00285; 00290
[3] Organic and Biomolecular Chemistry, 2010, vol. 8, # 19, p. 4281 - 4288
[4] Patent: US2013/252958, 2013, A1. Location in patent: Paragraph 0094
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 13011 - 13015

N-CYANOACETYLURETHANE(6629-04-5)Related Product Information

• N-CYANOACETYLURETHANE
• Urethane
• ETHYL N-(2-CYANO-2-[2-(2,6-DIFLUOROPHENYL)HYDRAZONO]ACETYL)CARBAMATE
• ETHYL N-(2-CYANO-3-ETHOXYACRYLOYL)CARBAMATE
• ETHYL N-(2-CYANO-2-(2-[3-(TRIFLUOROMETHYL)PHENYL]HYDRAZONO)ACETYL)CARBAMATE
• ACETYLURETHANE
• ETHYL N-(2-CYANO-3-[2-(2,4-DICHLOROPHENYL)HYDRAZINO]ACRYLOYL)CARBAMATE
• ETHYL N-[2-CYANO-3-(2,4-DICHLOROANILINO)ACRYLOYL]CARBAMATE
• ETHYL N-(2-[2-(3-CHLOROPHENYL)HYDRAZONO]-2-CYANOACETYL)CARBAMATE
• ETHYL N-[2-CYANO-3-(4-METHOXYANILINO)ACRYLOYL]CARBAMATE
• ETHYL N-(2-CYANO-2-[2-(3-METHOXYPHENYL)HYDRAZONO]ACETYL)CARBAMATE
• ETHYL N-(3-ANILINO-2-CYANOACRYLOYL)CARBAMATE
• ETHYL N-[2-CYANO-3-(METHOXYIMINO)PROPANOYL]CARBAMATE
• ETHYL N-[3-(4-ACETYLANILINO)-2-CYANOACRYLOYL]CARBAMATE
• ETHYL N-[2-CYANO-3-(CYANOAMINO)ACRYLOYL]CARBAMATE
• ETHYL N-[2-CYANO-3-(3-PYRIDINYLAMINO)ACRYLOYL]CARBAMATE
• ETHYL N-(3-[(2-([3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]AMINO)ETHYL)IMINO]-2-CYANOPROPANOYL)CARBAMATE
• ETHYL N-(3-([(4-CHLOROBENZYL)OXY]IMINO)-2-CYANOPROPANOYL)CARBAMATE