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Ethyl 2-cyano-2-(hydroxyimino)acetate, Ethyl cyanohydroxyiminoacetate, oxyma, 3849-21-6, SRCE-001

Ethyl 2-cyano-2-(hydroxyimino)acetate, Oxyma, Ethyl cyanohydroxyiminoacetate, 3849-21-6

Research Chemicalsoxyma

SKU: SRCO-001

₹1,200.00 – ₹75,000.00

Name: Oxyma, Ethyl 2-cyano-2-(hydroxyimino)acetate

CAT NO.:SRC0-001

CAS No.: 3849-21-6

Description
Datasheet
Additional information

Description

Oxyma

Chemical Name	Ethyl cyanohydroxyiminoacetate
Catalog Number	SRC0-001
Synonyms	Ethyl 2-cyano-2-(hydroxyimino)acetate
CAS Number	3849-21-6
Molecular Formula	C5H6N2O3
Molecular Weight	142.11
Appearance	White to Off-White Solid
Melting Point	130-132 °C
Shipping & Storage Information	Storage2-8°C Shipping: Free Shipping at Room Temperature in INDIA, may vary elsewhere, Stability: Datasheet
Solubility	Chloroform, DMSO, Methanol, ethyl acetate, water
Stability	Unstable in Solution, Very Hygroscopic
Category	Reagent in synthesis
Description &Applications	it is the oxime of ethyl cyanoacetate and finds use as an additive for carbodiimides, such as dicyclohexylcarbodiimide (DCC) in peptide synthesis. It acts as a neutralizing reagent for the basicity or nucleophilicity of the DCC due to its pronounced acidity (pKa 4.60) and suppresses base catalyzed side reactions, in particular racemization
References	Subirós-Funosas, R.; Prohens, R.; Barbas, R.; El-Faham, A.; Albericio, F. (2009), “Oxyma: An efficient additive for peptide synthesis to replace the benzotriazole-based HOBt and HOAt with a lower risk of explosion”, Chem. Eur. J., vol. 15, no. 37, pp. 9394–9403, doi:10.1002/chem.200900614, PMID 19575348 Conrad, M.; Schulze, A. (1909), “Über Nitroso-cyanessigsäure-Derivate”, Chem. Ber. (in German), vol. 42, no. 1, pp. 735–742, doi:10.1002/cber.190904201117 Albericio, F.; Subirós-Funosas, R. (2012). “Ethyl 2-Cyano-2-(hydroxyimino)acetate”. Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01377. ISBN 978-0471936237. US 5166394, Breipohl, G. & König, W., “Coupling reagent for peptide synthesis”, published 1992-11-2, assigned to Hoechst AG Subirós-Funosas, R.; Khattab, S.N.; Nieto-Rodriguez, L.; El-Faham, A.; Albericio, F. (2013), “Advances in acylation methodologies enabled by Oxyma-based reagents”, Aldrichimica Acta, vol. 46, no. 1, pp. 21–41

In the organic synthesis and peptide synthesis, the development of efficient coupling agents is crucial for the synthesis of complex molecules. It has emerged as a versatile and potent linker in peptide and organic synthesis. Its unique properties make it an invaluable tool for researchers and chemists working in thoactive compound creation.

Role in Peptide Synthesis: Peptides are essential biomolecules that play vital roles in various physiological processes. They are often synthesized using solid-phase peptide synthesis (SPPS), which involves linking amino acids together step-by-step. In this process, coupling agents are necessary to facilitate the reaction between the carboxyl group of one amino acid and the amino group of another. It has proven to be a highly effective coupling reagent in this context.

It enhances the efficiency of peptide coupling reactions by several mechanisms:

Activation of Carboxyl Groups: it assists in activating carboxyl groups, making them more susceptible to nucleophilic attack by amino groups. This activation step increases the overall reaction rate.
Improved Steric Accessibility: The hydroxyimino group in it enhances the steric accessibility of the carboxyl group, allowing for better alignment and interaction with the amino group.
Suppression of Epimerization: it has been shown to suppress racemization and epimerization during peptide coupling reactions, leading to the formation of desired peptide sequences with higher purity.
Compatibility: it is compatible with a wide range of solvents and reaction conditions, providing chemists with flexibility in their experimental setups.

Applications Beyond Peptide Synthesis: it is prominently known for its role in peptide synthesis, its utility extends beyond this realm. It has been employed in various organic reactions, including esterifications, amidations, and other coupling reactions. It has demonstrated its potential in promoting reactions that involve carboxyl activation, making it a valuable tool in diverse synthetic endeavors.