ChemicalBook > CAS DataBase List > Ethyl cyanoglyoxylate-2-oxime

Ethyl cyanoglyoxylate-2-oxime

Product Name
Ethyl cyanoglyoxylate-2-oxime
CAS No.
3849-21-6
Chemical Name
Ethyl cyanoglyoxylate-2-oxime
Synonyms
Oxyma Pure;ETHYL (HYDROXYIMINO)CYANOACETATE;OxiMa;ETHYL ISONITROSOCYANOACETATE;cyanogL;NSC 42116;ate-2-oxime;OXYMA PURE 25 G;OXYMA PURE 100 G;TIMTEC-BB SBB007937
CBNumber
CB6234638
Molecular Formula
C5H6N2O3
Formula Weight
142.11
MOL File
3849-21-6.mol
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Ethyl cyanoglyoxylate-2-oxime Property

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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P321Specific treatment (see … on this label).

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.51086
Product name
Oxyma Pure
Purity
Novabiochem?
Packaging
25g
Price
$40.9
Updated
2025/07/31
Sigma-Aldrich
Product number
8.51086
Product name
Oxyma Pure
Purity
Novabiochem?
Packaging
100g
Price
$119
Updated
2025/07/31
Sigma-Aldrich
Product number
8.51086
Product name
Oxyma Pure
Purity
Novabiochem<SUP>&#174;</SUP>
Packaging
250 g
Price
$218
Updated
2025/07/31
Sigma-Aldrich
Product number
8.51086
Product name
Oxyma Pure
Purity
Novabiochem<SUP>&#174;</SUP>
Packaging
250 g
Price
$218
Updated
2025/07/31
Sigma-Aldrich
Product number
8.51086
Product name
Oxyma Pure
Purity
Novabiochem<SUP>&#174;</SUP>
Packaging
500 g
Price
$383
Updated
2025/07/31
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Ethyl cyanoglyoxylate-2-oxime Chemical Properties,Usage,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

105-56-6

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

Ethyl cyanoglyoxylate-2-oxime Preparation Products And Raw materials

Raw materials

Preparation Products

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Ethyl cyanoglyoxylate-2-oxime Suppliers

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View Lastest Price from Ethyl cyanoglyoxylate-2-oxime manufacturers

Henan Aochuang Chemical Co.,Ltd.
Product
Ethyl cyanoglyoxylate-2-oxime 3849-21-6
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1ton
Release date
2022-09-26
Shaanxi Dideu Medichem Co. Ltd
Product
Ethyl cyanoglyoxylate-2-oxime 3849-21-6
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20T
Release date
2024-08-13
Zhuozhou Wenxi import and Export Co., Ltd
Product
Ethyl (hydroxyimino)cyanoacetate 3849-21-6
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10

3849-21-6, Ethyl cyanoglyoxylate-2-oximeRelated Search:

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

  • ETHYL 2-(HYDROXYIMINO)-3-NITRILOPROPANOATE
  • ETHYL 2-(HYDROXYIMINO) CYANOACETATE
  • ETHYL ISONITROSOCYANOACETATE
  • ETHYL (HYDROXYIMINO)CYANOACETATE
  • ETHYL OXIMINOCYANOACETATE
  • ETHYL CYANOGLYOXALATE-2-OXIME
  • 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-acetate
  • 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
  • Oxyma Pure Novabiochem
  • 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
  • Oxyma Pure
  • Cyano(hydroxyimino)acetic Acid Ethyl Ester Ethyl Cyanoglyoxalate Oxime Oxyma
  • Cyano-hydroxyiMino-acetic acid ethyl ester (OxyMa)
  • OxyMa Pure, Ethyl 2-cyano-2-(hydroxyiMino)acetate
  • OxiMa
  • 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&gt
  • 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]
  • 3849-21-6