Ethyl cyanoglyoxylate-2-oxime Chemical Properties

Melting point:

130-132 °C (lit.)

Boiling point:

259.65°C (rough estimate)

Density 

1.4801 (rough estimate)

refractive index 

1.5090 (estimate)

storage temp. 

Store at +2°C to +8°C.

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

6.18±0.10(Predicted)

color 

Off-White

BRN 

774783

InChI

InChI=1S/C5H6N2O3/c1-2-10-5(8)4(3-6)7-9/h9H,2H2,1H3

InChIKey

LCFXLZAXGXOXAP-QPJJXVBHSA-N

SMILES

C(OCC)(=O)C(C#N)=NO

CAS DataBase Reference

3849-21-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22

Safety Statements 

22-24/25-36/37

RIDADR 

3276

WGK Germany 

3

F 

10

Hazard Note 

Irritant

HS Code 

2928 00 90

HazardClass 

6.1

PackingGroup 

III

MSDS

• Language:English Provider:Ethyl cyanoglyoxylate-2-oxime
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

Ethyl cyanoglyoxylate-2-oxime Usage And Synthesis

Chemical Properties

light yellow crystals or chunks

Uses

A non-explosive alternative to HOBt.

Uses

This product is a non-explosive alternative to HOBt or HOAt, and allows high peptide coupling rates at low racemization when applied in combination with carbodiimides.

reaction suitability

reaction type: Coupling Reactions

Synthesis

Example 1: Preparation of ethyl 2-oxime cyanoacetate To a suspension of ethyl cyanoacetate (1.0 kg, 8.84 mol) and sodium nitrite (0.735 kg, 10.65 mol) in water (0.80 L) was slowly added acetic acid (0.70 kg, 11.66 mol), and the reaction temperature was controlled to be in the range of 0-50°C. The reaction temperature was slowly raised to 23-27 °C over a period of 1 h and the reaction mixture was continuously stirred at this temperature for 1 h. The reaction temperature was then adjusted to the temperature of the reaction mixture. After confirming complete consumption of ethyl cyanoacetate by TLC or GC monitoring, the reaction mixture was extracted with ethyl acetate (5 x 1.5 L). The organic layers were combined and washed sequentially with 10% sodium bicarbonate solution (2 x 1.25 L) and saturated brine (1.25 L). The organic layer was dried over anhydrous sodium sulfate and filtered through a hyflow bed. The solvent was removed by distillation under reduced pressure at 40-45 °C. The resulting solid was stirred with cyclohexane (3.0 L) at 25-30 °C for 30 min, filtered and dried in vacuum at 40-45 °C to give ethyl 2-oxime cyanoacetate 1.14 kg (91.2% yield) with 99.82% HPLC purity.

References

[1] Chemistry - A European Journal, 2015, vol. 21, # 16, p. 6090 - 6099
[2] Synthesis, 1999, # 1, p. 46 - 48
[3] Patent: WO2010/140168, 2010, A1. Location in patent: Page/Page column 14
[4] PLoS ONE, 2014, vol. 9, # 10,
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 553 - 557

Ethyl cyanoglyoxylate-2-oxime(3849-21-6)Related Product Information

• Glyoxylic acid
• Ethyl glyoxalate
• 3-Hydroxypropionitrile
• ammonium propionate
• Cyanoacetic acid
• Ethyl cyanoglyoxylate-2-oxime
• FORMOXIME
• AURORA KA-6208
• Acetaldoxime
• Ethyl cyanoacetate
• Methyl cyanoacetate
• Acetone oxime
• 3-Methoxypropionitrile
• 3-Ethoxypropionitrile