Methyl cyanoacetate

Base Information

• Chemical Name: Methyl cyanoacetate
• CAS No.: 105-34-0
• Molecular Formula: C4H5NO2
• Molecular Weight: 99.0892
• Hs Code.: 29269095
• European Community (EC) Number: 203-288-8
• NSC Number: 68507,3113
• UNII: A28RI36V30
• DSSTox Substance ID: DTXSID8033649
• Nikkaji Number: J4.029K
• Wikidata: Q22829041
• Metabolomics Workbench ID: 57973
• ChEMBL ID: CHEMBL1532013
• Mol file: 105-34-0.mol

Synonyms:METHYL CYANOACETATE;Methyl 2-cyanoacetate;105-34-0;Cyanoacetic acid methyl ester;Methyl cyanoethanoate;Acetic acid, cyano-, methyl ester;MethylCyanoacetate;USAF KF-22;C4H5NO2;Methylester kyseliny kyanoctove;Malonic methyl ester nitrile;methyl cyano acetate;NSC 3113;EINECS 203-288-8;Acetic acid, 2-cyano-, methyl ester;Methylester kyseliny kyanoctove [Czech];BRN 0773945;Cyanoacetic acid, methyl ester;UNII-A28RI36V30;AI3-05599;MLS002177808;2-cyanoacetic acid methyl ester;DTXSID8033649;CHEBI:51928;2-cyanoacetic acid, methyl ester;A28RI36V30;NSC-3113;NSC-68507;SMR001261799;EC 203-288-8;WLN: NC1VO1;3-Methoxy-3-oxopropanenitrile;methylcyanacetate;methylcyanoacetat-;methyl-cyanoacetate;methyl-cyano-acetate;MFCD00001939;Cyanoacetic acid methyl;methyl 2-cyanoethanoate;starbld0016244;NCCH2CO2CH3;Methyl cyanoacetate, 99%;cid_7747;(Methoxycarbonyl)acetonitrile;cyano acetic acid methyl ester;cyano-acetic acid methyl ester;CHEMBL1532013;DTXCID6013649;BDBM74253;2-Cyano-acetic acid methyl ester;NSC3113;METHYL .ALPHA.-CYANOACETATE;BCP25864;NSC68507;STR01166;Tox21_200938;Acetic acid, 2-yano-, methyl ester;STL146530;AKOS000118973;CS-W016657;J4.029K;NCGC00090994-01;NCGC00090994-02;NCGC00258492-01;BP-13327;CAS-105-34-0;FT-0624127;EN300-19214;Methyl cyanoacetate, purum, >=99.0% (GC);D77797;J-001390;Q22829041;F0001-0103

Chemical Property of Methyl cyanoacetate

Chemical Property:

• Appearance/Colour: clear colorless to very slighlty yellow liquid
• Vapor Pressure: 0.2 mm Hg ( 20 °C)
• Melting Point: -13 °C
• Refractive Index: n20/D 1.417(lit.)
• Boiling Point: 140.3 °C at 760 mmHg
• PKA: 2.75±0.10(Predicted)
• Flash Point: 42.7 °C
• PSA: 50.09000
• Density: 1.123 g/cm³
• LogP: 0.07308
• Storage Temp.: Store below +30°C.
• Sensitive.: Light Sensitive
• Solubility.: 54g/l
• Water Solubility.: 54 g/L (20 ºC)
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 99.032028402
• Heavy Atom Count: 7
• Complexity: 110

Purity/Quality:

99% ^*data from raw suppliers

Methyl cyanoacetate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: COC(=O)CC#N
• Description: Methyl cyanoacetate is the intermediate product in pharmaceutical organic synthesis as well as in the synthesis of some biologically active compounds used in agriculture. It may be used in the synthesis of various 1,2,5-tricarbonyl compounds. It is often used as a nucleophile in the electrochemical oxidation of catechols. Methyl Cyanoacetate is also a reagent in the synthesis of Methyl 2-Amino-4-trifluoromethylthiophene-3-carboxylate; a compound used in the synthesis of DPP-IV inhibitors for treating type-2 diabetes. In addition, it is an intermediate in the preparation of α-cyanoacrylate, malononitrile, and 1,1-cyclohexanediacetic acid dyes. It is used as UV absorber or stabilizer, intermediate for pharmaceuticals. It may be used in the synthesis of various 1,2,5-tricarbonyl compounds.
• Uses: pharmaceutical intermediate Methyl cyanoacetate is an intermediate in the preparation of α-cyanoacrylate, malononitrile, 1,1-cyclohexanediacetic acid dye. It is used as UV absorber or stabiliser, intermediate for pharmaceuticals. It may be used in the synthesis of various 1,2,5-tricarbonyl compounds.

Technology Process of Methyl cyanoacetate

There total 24 articles about Methyl 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%

methanol (67-56-1) + cyanoacetic acid (372-09-8) → methyl 2-cyanoacetate (105-34-0)

Guidance literature:

With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1055/s-1980-29116

Reference yield: 97.0%

isocyanoacetic acid methyl ester (39687-95-1) → methyl 2-cyanoacetate (105-34-0)

Guidance literature:

at 520 - 550 ℃; under 0.01 Torr;

Reference yield: 96.2%

methyl chloroacetate (96-34-4) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → methyl 2-cyanoacetate (105-34-0)

Guidance literature:

at 70 ℃; for 2.5h; Temperature;

upstream raw materials:

methanol

sodium cyanoacetate

sodium cyanide

methyl chloroacetate

Downstream raw materials:

2-cyano-2-cyclohex-1-enyl-butyric acid methyl ester

3-cyano-2-hydroxy-2-phenyl-succinic acid dimethyl ester

methyl (E)-2-cyano-3-(2-furyl)-2-propenoate

3-(4-ethoxycarbonyl-3,5-dimethyl-pyrrol-2-yl)-3-oxo-propionic acid methyl ester

Refernces

• 1、 Motokura, Ken,Fujita, Noriaki,Mori, Kohsuke,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi. "An acidic layered clay is combined with a basic layered clay for one-pot sequential reactions". . p. 9674 - 9675. Retrieved 2005.
• 2、 ?ebular, Klara,Bo?i?, Bojan ?.,Stavber, Stojan. "1,3-Dibromo-5,5-dimethylhydantoin as a Precatalyst for Activation of Carbonyl Functionality". . . Retrieved 2019.
• 3、 Raber et al.. "-". . p. 1149,1150. Retrieved 1979.
• 4、 Jayachitra,Yasmeen,Srinivasa Rao,Ralte, Samuel L.,Srinivasan,Singh. "Borontrifluoride etherate promoted one-pot conversion of nitriles to esters". . p. 3461 - 3466. Retrieved 2003.
• 5、 Srinivasan,Rao, K. Srinivasa,Jayachitra,Ralte, Samuel L.. "Iron(III) chloride-promoted direct conversion of aryl/alkyl cyanides to esters". . p. 2883 - 2886. Retrieved 2006.
• 6、 Haidekker, Mark A.,Brady, Thomas P.,Chalian, Sevag H.,Akers, Walter,Lichlyter, Darcy,Theodorakis, Emmanuel A.. "Hydrophilic molecular rotor derivatives - Synthesis and characterization". . p. 274 - 289. Retrieved 2004.
• 7、 Cook,A.F.,Moffatt,J.G.. "-". . p. 740 - 746. Retrieved 1968.
• 8、 -. "BTK Inhibitors and uses thereof". Paragraph 1771-1776. . Retrieved 2020/05/02.