3849-20-5

Basic information

• Product Name: 2-Cyano-2-oximinoacetamide
• Synonyms: 2-Cyano-2-oximinoacetamide;2-Hydroximino-2-cyanoacetamide;2-cyano-2-(hydroxyimino)acetamide;(2Z)-2-Cyano-2-(hydroxyimino)acetamide
• CAS NO: 3849-20-5
• Molecular Formula: C₃H₃N₃O₂
• Molecular Weight: 113.07482
• Mol File: 3849-20-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 183 °C (decomp)
• Boiling Point: 321.5 °C at 760 mmHg
• Flash Point: 148.3 °C
• Appearance: /
• Density: 1.54 g/cm³
• Vapor Pressure: 2.37E-05mmHg at 25°C
• Refractive Index: 1.596
• PKA: 7.96±0.10(Predicted)
• CAS DataBase Reference: 2-Cyano-2-oximinoacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyano-2-oximinoacetamide(3849-20-5)
• EPA Substance Registry System: 2-Cyano-2-oximinoacetamide(3849-20-5)

Safety Data

• Hazardous Substances Data: 3849-20-5(Hazardous Substances Data)

Usage

General Description

2-Cyano-2-oximinoacetamide is a chemical compound with the molecular formula C4H5N3O2. It is a white to light yellow crystalline powder with a molecular weight of 127.10 g/mol. 2-Cyano-2-oximinoacetamide is used in organic synthesis as a building block for the preparation of various compounds. It can also be used as a reagent in chemical reactions, particularly in the formation of heterocyclic compounds. Additionally, it has potential pharmaceutical applications and is being studied for its antibacterial and antiviral properties. 2-Cyano-2-oximinoacetamide should be handled and stored with care, as it is considered a hazardous material and may cause irritation to the skin and eyes upon contact.

InChI:InChI=1/C3H3N3O2/c4-1-2(6-8)3(5)7/h8H,(H2,5,7)/b6-2+

Upstream product

• 97925-39-8 nitromalononitrile 
• 107-91-5 cyanoacetic acid amide 
• 64-17-5 ethanol 

Downstream Products

• 6719-21-7 2-Amino-2-cyanoacetamide 
• 475-08-1 cyano-nitro-acetic acid amide 
• 57967-17-6 C₆H₉N₃O₂ 
• 57967-16-5 C₆H₉N₃O₂ 
• 57967-21-2 C₉H₁₃N₃O₂ 
• 57967-29-0 C₁₀H₈BrN₃O₂ 
• 57967-30-3 C₁₀H₈FN₃O₂ 
• 57967-31-4 Cyan(phenacyloxyimino)acetamid 
• 57967-33-6 C₁₂H₁₃N₃O₃ 
• 57967-34-7 C₁₁H₁₀BrN₃O₃ 
• 57967-32-5 C₁₁H₈ClN₃O₃ 
• 57967-28-9 2-Cyano-2-[(E)-2-cyano-benzyloxyimino]-acetamide 
• 93270-67-8 1-(p-tolyl)-5-aminoimidazole-4-carboxamide 
• 93270-68-9 5-amino-1-(p-chlorophenyl)imidazole-4-carboxamide 

Relevant articles and documents

The synthesis of (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetic acid

The objective was to synthesize (Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2- ethoxyiminoacetic acid (the side chain for Ceftaroline fosamil). Oximation and alkylation were used on cyanoacetamide to get 2-cyano-2-hydroxyiminoacetamide, which became 2-ethyoxyiminopropanedinitrile through reaction with phosphorus oxychloride, and then aminolysis to get 2-ethoxyiminopropanedinitrile, which became 2-ethoxyimion-2-(5-amino-1,2,4 thiadiazol-3-yl) acetonitrile by brominating and with KSCN, followed by hydrolysis to get (Z)-2-(5-Amino-1,2,4- thiadiazol-3-yl)-2-ethoxyiminoacetic acid.

Preparation method of 3-aminofurazan-4-methanamide

The invention discloses a preparation method of 3-aminofurazan-4-methanamide. The method comprises the following steps: cyanoacetamide is subjected to nitrosation and isomerization to prepare 2-oximido cyanoacetamide, 2-oximido cyanoacetamide and hydroxylamine hydrochloride and organic base are subjected to a reaction to prepare an amidoxime intermediate which is 2-oximido-3-amidoxime acetamide, and the 2-oximido-3-amidoxime acetamide is subjected to a closed loop reaction under effect of thionyl chloride to generate a target product 3-aminofurazan-4-methanamide. The method has the advantagesof simple process flow, easily available raw material, and high product yield, and is suitable for industrial product, and is the novel synthetic method for 3-aminofurazan-4-methanamide.

Synthesis process of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid

The invention relates to a synthesis process of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid. With cyanoacetamide serving as a starting material, 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid is obtained through a hydroxyl oximation reaction, a methylation reaction, a cyclization reaction, a nitrile hydrolysis reaction and the like. Particularly, due to the fact that hydroxyapatite is added in the fifth step to serve as a catalyst, the yield of the intermediate product 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetonitrile and the total yield of the final product 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid can be effectively increased, and compared with the total yield not exceeding 9% in the prior art, the total yield of the technical scheme reaches 13% or so and is substantially increased; cost is lowered; industrial large-scale application is facilitated.