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Ethyl cyanoglyoxylate-2-oxime

CAS No.
3849-21-6
Chemical Name:
Ethyl cyanoglyoxylate-2-oxime
Synonyms
Oxyma Pure;OxiMa;ETHYL (HYDROXYIMINO)CYANOACETATE;ethyl (2E)-2-cyano-2-hydroxyimino-acetate;Oxima Pure;Oxyma Pure Novabiochem;ETHYL ISONITROSOCYANOACETATE;ETHYL CYANOGLYOXALATE-2-OXIME;Cyano-hydroxyiMino-acetic acid ethyl ester (OxyMa);cyanogL
CBNumber:
CB6234638
Molecular Formula:
C5H6N2O3
Molecular Weight:
142.11
MDL Number:
MFCD00002112
MOL File:
3849-21-6.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-06-24 13:15:37
Product description Number Pack Size Price
Oxyma Pure Novabiochem? 8.51086 25g $43.5
Oxyma Pure Novabiochem? 8.51086 100g $127
Oxyma Pure Novabiochem® 8.51086 250 g $232
Oxyma Pure Novabiochem® 8.51086 500 g $408
Oxyma Pure Novabiochem® 8.51086 5 kg $3070
More product size

Ethyl cyanoglyoxylate-2-oxime 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
Major Application peptide synthesis
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)
FDA UNII 2PHR89MH6P
UNSPSC Code 12352126
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  Skull and Crossbones (GHS06)
GHS06
Signal word  Warning
Hazard statements  H301
Precautionary statements  P264-P270-P301+P310a-P321-P405-P501a
PPE Eyeshields, Gloves, type N95 (US)
Hazard Codes  Xn,Xi
Risk Statements  20/21/22
Safety Statements  22-24/25-36/37
RIDADR  3276
WGK Germany  3
10
Hazard Note  Irritant
HS Code  2928 00 90
HazardClass  6.1
PackingGroup  III
Storage Class 11 - Combustible Solids
REACH Registrations Active
NFPA 704
1
2 0

Ethyl cyanoglyoxylate-2-oxime price More Price(93)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.51086 Oxyma Pure Novabiochem? 3849-21-6 25g $43.5 2026-04-30 Buy
Sigma-Aldrich 8.51086 Oxyma Pure Novabiochem? 3849-21-6 100g $127 2026-04-30 Buy
Sigma-Aldrich 8.51086 Oxyma Pure Novabiochem® 3849-21-6 250 g $232 2026-04-30 Buy
Sigma-Aldrich 8.51086 Oxyma Pure Novabiochem® 3849-21-6 500 g $408 2026-04-30 Buy
Sigma-Aldrich 8.51086 Oxyma Pure Novabiochem® 3849-21-6 5 kg $3070 2026-04-30 Buy
Product number Packaging Price Buy
8.51086 25g $43.5 Buy
8.51086 100g $127 Buy
8.51086 250 g $232 Buy
8.51086 500 g $408 Buy
8.51086 5 kg $3070 Buy

Ethyl cyanoglyoxylate-2-oxime Chemical Properties,Uses,Production

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

Ethyl cyanoacetate

105-56-6

Ethyl cyanoglyoxylate-2-oxime

3849-21-6

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

105-56-6
3849-21-6
Synthesis of Ethyl cyanoglyoxylate-2-oxime from Ethyl cyanoacetate
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View Lastest Price from Ethyl cyanoglyoxylate-2-oxime manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Ethyl cyanoglyoxylate-2-oxime pictures 2026-08-06 Ethyl cyanoglyoxylate-2-oxime
3849-21-6
1kg 0.99 20tons HANGZHOU HAILAN CHEMICAL CO.,LTD.
Ethyl cyanoglyoxylate-2-oxime pictures 2026-06-30 Ethyl cyanoglyoxylate-2-oxime
3849-21-6
1kg 98% 1000kg Shaanxi Dideu New Materials Co. Ltd
Ethyl cyanoglyoxylate-2-oxime pictures 2025-04-04 Ethyl cyanoglyoxylate-2-oxime
3849-21-6
1KG 98% 1ton Henan Aochuang Chemical Co.,Ltd.
ETHYL 2-(HYDROXYIMINO)-3-NITRILOPROPANOATE ETHYL 2-(HYDROXYIMINO) CYANOACETATE ETHYL ISONITROSOCYANOACETATE ETHYL OXIMINOCYANOACETATE ETHYL CYANOGLYOXYLATE-2-OXIME ETHYL CYANOGLYOXYLATE OXIME ETHYL CYANO(HYDROXYIMINO)-ACETATE TIMTEC-BB SBB007937 Ethyl (hydroxyimino)cyanoacetate 97% (2E)-2-cyano-2-hydroximino-acetic acid ethyl ester (2E)-2-cyano-2-hydroxyiminoacetic acid ethyl ester 2-BroMo-4'-chloroacetophenone, 99%+ 2-cyano-2-hydroximino-acetic acid ethyl ester Acetic acid, cyano(hydroxyimino)-, ethyl ester ethyl (2E)-2-cyano-2-hydroxyiminoacetate ethyl (2E)-2-cyano-2-hydroxyimino-ethanoate Ethyl (hydroxyimino)cyano ethyl 2-cyano-2-hydroxyimino-ethanoate NSC 42116 Ethyl (2E)-cyano(hydroxyimino)acetate Ethyl cyanoglyoxalate 2-oxime, Ethyl cyano(isonitroso)acetate, Oxyma Ethyl Cyanoglyoxalate Oxime Ethyl[Hydroximino]Cyanoacetate Ethyl cyanoglyoxalate-2-oxime, Ethyl isonitrosocyanoacetate Oximinocyanoaceticacidethylester Ethylcyanoglyoxylate-2-oxime=Ethyloximinocyanoacetate isonitrosocyanoacetic acid ethyl ester Ethyl2-cyano-2-oximinoacetate Ethyl cyanoximidoacetate 2-Ethyloximinocyanocaetate Ethyl 2-cyano-2-hydroxyiminoacetate 2-Cyano-2-(hydroxyimino)acetic acid ethyl ester Cyano(hydroxyimino)acetic acid ethyl ester Ethyl cyanoglyoxylate-2-oxime,97% (Z)-ethyl 2-cyano-2-(hydroxyimino)acetate Cyano(hydroxyimino)acetic Acid Ethyl Ester Ethyl Cyanoglyoxalate Oxime Oxyma OxyMa Pure, Ethyl 2-cyano-2-(hydroxyiMino)acetate Acetic acid, 2-cyano-2-(hydroxyiMino)-, ethyl ester Ethyl cyano(hydroxyimino)acetate, Ethyl cyanoglyoxalate-2-oxime, Ethyl isonitrosocyanoacetate Ethyl cyanoglyoxalate-2-oxime, Ethyl isonitrosocyanoacetate, Oxyma ate-2-oxime EthylCyano(hydroxyimino)acetate> OXYMA PURE 25 G OXYMA PURE 100 G cyanogL (E)-Ethyl 2-cyano-2-(hydroxyimino) acetate (Oxyma) Ethyl 2-cyano-2-(hydroxyimino)acetate, Oxyma pure (E)-Ethyl 2-cyano-2-(hydroxyimino) acetate (OxymaPure) Ethyl cyanoglyoxylate-2-oxime (Oxyma) OxymaPure [Ethyl (hydroxyimino)cyanoacetate] Cymoxanil Impurity 18 Cyano-hydroxyiMino-acetic acid ethyl ester (OxyMa) ethyl (2E)-2-cyano-2-hydroxyimino-acetate ETHYL (HYDROXYIMINO)CYANOACETATE ETHYL CYANOGLYOXALATE-2-OXIME Oxima Pure OxiMa Oxyma Pure Novabiochem