Cyanoacetic acid

Base Information

• Chemical Name: Cyanoacetic acid
• CAS No.: 372-09-8
• Molecular Formula: C3H3NO2
• Molecular Weight: 85.0623
• Hs Code.: 2926 90 70
• European Community (EC) Number: 206-743-9
• NSC Number: 5571
• UN Number: 1759
• UNII: QZT550H2Y9
• DSSTox Substance ID: DTXSID0027149
• Nikkaji Number: J2.581J
• Wikipedia: Cyanoacetic_acid
• Wikidata: Q1146963
• Metabolomics Workbench ID: 57948
• ChEMBL ID: CHEMBL3185860
• Mol file: 372-09-8.mol

Synonyms:cyanoacetic acid;cyanoacetic acid, copper (+2) salt

Chemical Property of Cyanoacetic acid

Chemical Property:

• Appearance/Colour: yellow-brown liquid with an unpleasant odor
• Vapor Pressure: 0.1 mm Hg ( 100 °C)
• Melting Point: 65 °C
• Refractive Index: 1.3764 (estimate)
• Boiling Point: 318.5 °C at 760 mmHg
• PKA: 2.45(at 25℃)
• Flash Point: 107.8 °C
• PSA: 61.09000
• Density: 1.287 g/cm³
• LogP: -0.01532
• Storage Temp.: Store at 0-5°C
• Sensitive.: Hygroscopic
• Solubility.: H2O: soluble50mg/mL, clear, colorless to very faintly yellow
• Water Solubility.: 1000 g/L (20 ºC)
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 85.016378338
• Heavy Atom Count: 6
• Complexity: 98.6
• Transport DOT Label: Corrosive

Purity/Quality:

99% ^*data from raw suppliers

Cyanoacetic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 22-31-34-52/53-20/22
• Safety Statements: 26-36/37/39-45-61-20

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(C#N)C(=O)O
• Description: Cyanoacetic acid is an organic compound. It is a white, hygroscopic solid. The compound contains two functional groups, a nitrile (C≡N) and a carboxylic acid. It is a precursor to cyanoacrylates, components of adhesives.Cyanoacetic acid is used in pharmaceutical industry for producing vitamin B6 and caffeine. It is also used in making dyes, agricultural chemicals, and in the synthesis of phenylacetic acid esters. It acts as a precursor cyanoacrylates viz. ethyl cyanoacrylate.
• Uses: Cyanoacetic acid was used in the synthesis of N-piperidine-cyanacetamide and N-morpholyl-cyanacetamide. It was also used in the preparation of a panchromatic dye for dye-sensitized solar cells. Synthesis of intermediates; manufacture of barbital. Cyanoacetic acid is used in pharmaceutical industry for producing vitamin B6 and caffeine. It is also used in making dyes, agricultural chemicals, and in the synthesis of phenylacetic acid esters. It acts as a precursor cyanoacrylates viz. ethyl cyanoacrylate.

Technology Process of Cyanoacetic acid

There total 52 articles about Cyanoacetic acid 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: 100.0%

potassium cyanide + bromoacetic acid (79-08-3) → cyanoacetic acid (372-09-8)

Guidance literature:

With sodium hydrogencarbonate; In water; at 20 - 80 ℃; for 16h;

DOI:10.1002/chem.201805077

Reference yield: 99.0%

L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) → cyanoacetic acid (372-09-8)

Guidance literature:

With sodium hydroxide; trichloroisocyanuric acid; at 25 ℃; for 1h;

DOI:10.1055/s-2004-830896

Reference yield: 87.0%

malononitrile (109-77-3) → cyanoacetic acid (372-09-8)

Guidance literature:

With potassium phosphate buffer; nitrilase from Alcaligenes faecalis ATCC₈₇₅₀; at 30 ℃; for 51h; pH=7.3;

DOI:10.1021/jf048827q

upstream raw materials:

hydroxyimino-succinic acid

2-cyano-3-amino-3-phenyl acrylic acid ethyl ester

sodium ethanolate

potassium cyanide

Downstream raw materials:

cinnamic nitrile

(Z)-cinnamonitrile

3-phenylglutaronitrile

2-cyano-3-phenylacrylic acid

Refernces

• 1、 Veghini,Shul'pina,Strelkova,Shul'pin. "Hydrogen peroxide oxidation of 2-cyanoethanol catalyzed by metal complexes". . p. 167 - 170. Retrieved 2006.
• 2、 Al-Mallah, Khawla,Stedman, Geoffrey. "Kinetics of the Deamination of Amides by Nitrous Acid". . p. 670 - 671. Retrieved 1998.
• 3、 Bhat, Khursheed Ahmad,Bhat, Mohsin Ahmad,Bhat, Sajad Ahmad,Ingole, Pravin P.,Manzoor Bhat, Zahid,Pandit, Sarwar Ahmad,Rather, Mudasir Ahmad,Rehman, Shakeel U.,Sofi, Feroz Ahmad,Thotiyl, Musthafa Ottakam. "Surface active ionic liquid assisted metal-free electrocatalytic-carboxylation in aqueous phase: A sustainable approach for CO2utilization paired with electro-detoxification of halocarbons". . p. 9992 - 10005. Retrieved 2021/12/24.
• 4、 Guo, Ying,Xue, Qiang,Cui, Kangping,Zhang, Jia,Wang, Hui,Zhang, Huanzhen,Yuan, Fang,Chen, Honghan. "Study on the degradation mechanism and pathway of benzene dye intermediate 4-methoxy-2-nitroaniline: Via multiple methods in Fenton oxidation process". . p. 10764 - 10775. Retrieved 2018/03/26.