Sodium cyanoacetate

Base Information

• Chemical Name: Sodium cyanoacetate
• CAS No.: 1071-36-9
• Molecular Formula: C3H3 N O2 . Na
• Molecular Weight: 107.044
• Hs Code.: 29269095
• European Community (EC) Number: 213-991-1
• DSSTox Substance ID: DTXSID30147912
• Nikkaji Number: J21.848K
• Mol file: 1071-36-9.mol

Synonyms:Sodium cyanoacetate;sodium 2-cyanoacetate;1071-36-9;sodium;2-cyanoacetate;EINECS 213-991-1;starbld0026790;C3H2NNaO2;C3H3NO2.Na;Cyanoacetic acid sodium salt;C3-H3-N-O2.Na;SCHEMBL2027652;DTXSID30147912;MFCD00067028;Sodium 2-cyanoacetate(White to off-white);CS-0187634;D70707

Chemical Property of Sodium cyanoacetate

Chemical Property:

• Appearance/Colour: clear yellow to brown solution
• Vapor Pressure: 7.55E-05mmHg at 25°C
• Boiling Point: 318.5°Cat760mmHg
• Flash Point: 107.8°C
• PSA: 63.92000
• Density: g/cm³
• LogP: -1.35002
• Storage Temp.: Inert atmosphere,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 106.99832259
• Heavy Atom Count: 7
• Complexity: 103

Purity/Quality:

98%,99%, ^*data from raw suppliers

Sodium2-cyanoacetate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C#N)C(=O)[O-].[Na+]

Technology Process of Sodium cyanoacetate

There total 4 articles about Sodium cyanoacetate 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%

cyanoacetic acid (372-09-8) → sodium cyanoacetate (1071-36-9)

Guidance literature:

With sodium t-butanolate; In ethanol; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201006763

Reference yield: 93.0%

ethyl 2-cyanoacetate (105-56-6) → sodium cyanoacetate (1071-36-9)

Guidance literature:

With sodium hydroxide; In ethanol; at 20 ℃; for 2h; Large scale;

Reference yield: 85.0%

L-aspartic acid monosodium salt (3792-50-5) → sodium cyanoacetate (1071-36-9)

Guidance literature:

With ammonium bromide; In water; Electrochemical reaction;

DOI:10.1002/ejoc.201403112

upstream raw materials:

cyanoacetic acid

L-aspartic acid monosodium salt

ethyl 2-cyanoacetate

Downstream raw materials:

3t-(3-methoxy-4-benzyloxy-phenyl)-2-cyano-acrylic acid

1,5-di(o-carboxyphenyl)-3-cyanoformazane

2-cyano-3-phenylacrylic acid

2-phenylsuccinic acid

Refernces

Synthesis of α-Aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates

10.1002/anie.201006763

This study aims to develop a new synthetic strategy for the preparation of a-aryl nitriles, which are valuable intermediates for various chemical syntheses and have biological activities. This study introduces a palladium-catalyzed decarboxylative coupling reaction involving readily available cyanoacetates and aryl halides or triflates. Sodium cyanoacetate (NaOOCCN) is the main reactant to carry out the decarboxylative coupling. It provides the nitrile group in the final product. The palladium catalyst plays a crucial role in promoting the decarboxylation process, while the ligand helps in optimizing the reaction conditions. The study concluded that this new method has several advantages over the traditional methods, such as good selectivity for monoarylation, tolerance to various functional groups, and the ability to use a variety of aryl halides and triflates as substrates. In addition, the concept of decarboxylative coupling is extended to carbonyl compounds, providing an alternative method for the synthesis of a-aryl esters. This work not only expands the scope of catalytic decarboxylative coupling reactions but also shows practical benefits in terms of reagent accessibility and reaction scope.