Cyano-hydroxyimino-acetic acid methyl ester

Base Information

• Chemical Name: Cyano-hydroxyimino-acetic acid methyl ester
• CAS No.: 61295-92-9
• Molecular Formula: C₄H₄N₂O₃
• Molecular Weight: 128.087
• Hs Code.: 2928000090
• European Community (EC) Number: 653-749-6
• NSC Number: 158573
• DSSTox Substance ID: DTXSID90425920
• Nikkaji Number: J3.593.286K
• Mol file: 61295-92-9.mol

Synonyms:61295-92-9;Cyano-hydroxyimino-acetic acid methyl ester;methyl (2E)-2-cyano-2-hydroxyiminoacetate;127745-39-5;(E)-(METHYL CYANO(HYDROXYIMINO)FORMATE);Acetic acid, 2-cyano-2-(hydroxyiMino)-, Methyl ester;methyl 2-cyano-2-(hydroxyimino)acetate;Methyl (2E)-cyano(hydroxyimino)ethanoate;(E)-methyl 2-cyano-2-(hydroxyimino)acetate;Acetic acid, cyanohydroxyimino-, methyl ester;SCHEMBL9780919;DTXSID90425920;ZTUBRMAHOKWHCL-ZZXKWVIFSA-N;NSC158573;STL449604;AKOS001073871;NSC-158573;methyl 2-cyano-2-(hydroxyimino)-acetate;Methyl (2E)-cyano(hydroxyimino)ethanoate #;Methyl (E)-2-cyano-2-(hydroxyimino)acetate;EN300-06757;J3.593.286K;A934038;(Z)-2-Cyano-2-(hydroxyimino)acetic acid methyl ester;F1905-7130

Chemical Property of Cyano-hydroxyimino-acetic acid methyl ester

Chemical Property:

• Vapor Pressure: 0.00834mmHg at 25°C
• Boiling Point: 236.8°C at 760 mmHg
• Flash Point: 97°C
• PSA: 82.68000
• Density: 1.3g/cm³
• LogP: -0.48682
• Solubility.: Acetone, Chloroform, Dichloromethane, DMSO, Methanol
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 128.02219199
• Heavy Atom Count: 9
• Complexity: 187

Purity/Quality:

99%min ^*data from raw suppliers

Methyl2-Cyano-2-oximinoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(=NO)C#N
• Isomeric SMILES: COC(=O)/C(=N/O)/C#N
• Uses: Methyl 2-Cyano-2-oximinoacetate is an intermediate in synthesizing 2-Cyano-2-(methoxyimino)acetic Acid (C989423), which is a cyano-oxime derivative used as a fungicide.

Technology Process of Cyano-hydroxyimino-acetic acid methyl ester

There total 3 articles about Cyano-hydroxyimino-acetic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

methyl 2-cyanoacetate (105-34-0) → methyl 2-cyano-2-hydroxyiminoacetate (61295-92-9,127745-39-5)

Guidance literature:

With sodium hydroxide; water; acetic acid; sodium nitrite; for 3h; Ambient temperature;

DOI:10.1055/s-1999-3669

Reference yield:

ethyl 2-cyanoacetate (105-56-6) → methyl 2-cyano-2-hydroxyiminoacetate (61295-92-9,127745-39-5)

Guidance literature:

With potassium ethoxide; at 0 ℃;

Reference yield:

methyl 2-cyanoacetate (105-34-0) + isopentyl nitrite (110-46-3) → methyl 2-cyano-2-hydroxyiminoacetate (61295-92-9,127745-39-5)

Guidance literature:

With methanol; sodium methylate;

upstream raw materials:

methyl 2-cyanoacetate

isopentyl nitrite

ethyl 2-cyanoacetate

Downstream raw materials:

amino-2 cyano-2 acetate de methyle

methyl O-acetylisonitrosocyanoacetate

3,5-dimethyl-1H-pyrrole-2-carbonitrile

methyl 3,5-dimethyl-1H-pyrrole-2-carboxylate

Refernces

• 1、 Johnson, Eric C.,Miller, Christopher W.,Orlicki, Joshua A.,Sabatini, Jesse J.,Sausa, Rosario C.. "A Safer Synthesis of the Explosive Precursors 4-Aminofurazan-3-Carboxylic Acid and its Ethyl Ester Derivative". . p. 599 - 603. Retrieved 2020/04/20.
• 2、 Hung, Truong Ngoc,ádám, Adél,Varga, Gábor,Dudás, Csilla,Kele, Zoltán,Sipos, Pál,Pálinkó, István. "Thionation of a cyanoxime derivative to form the sulphur-containing derivative, a novel ligand for complexation with transitional metal ions". . p. 475 - 478. Retrieved 2017/02/23.