Methyl 1-cyanocyclohexanecarboxylate

Base Information

• Chemical Name: Methyl 1-cyanocyclohexanecarboxylate
• CAS No.: 58920-80-2
• Molecular Formula: C9H13NO2
• Molecular Weight: 167.208
• Hs Code.: 2926909090
• European Community (EC) Number: 889-386-7
• DSSTox Substance ID: DTXSID60457879
• Nikkaji Number: J2.024.517D
• Wikidata: Q72489576
• Mol file: 58920-80-2.mol

Synonyms:methyl 1-cyanocyclohexanecarboxylate;58920-80-2;Methyl 1-cyanocyclohexane-1-carboxylate;SCHEMBL14859472;DTXSID60457879;methyl1-cyanocyclohexanecarboxylate;PVFHKRCUWUPRFA-UHFFFAOYSA-N;MFCD09030934;AKOS005072206;DC-0840;SB13856;ETHYL3-(4-FORMYLPHENYL)PROPANOATE;CS-0252076;FT-0680931;1-Cyanocyclohexanecarboxylic acid methyl ester;EN300-58900;V10156;1-cyano-cyclohexane-1-carboxylic acid methyl ester;J-521758;1-CYANO-CYCLOHEXANECARBOXYLIC ACIDMETHYL ESTER

Chemical Property of Methyl 1-cyanocyclohexanecarboxylate

Chemical Property:

• Vapor Pressure: 0.00952mmHg at 25°C
• Refractive Index: 1.467
• Boiling Point: 264.8 °C at 760 mmHg
• Flash Point: 118.6 °C
• PSA: 50.09000
• Density: 1.06 g/cm³
• LogP: 1.63348
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 167.094628657
• Heavy Atom Count: 12
• Complexity: 220

Purity/Quality:

98%min ^*data from raw suppliers

methyl1-cyanocyclohexanecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1(CCCCC1)C#N

Technology Process of Methyl 1-cyanocyclohexanecarboxylate

There total 13 articles about Methyl 1-cyanocyclohexanecarboxylate 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: 96.0%

methyl cyanoformate (17640-15-2) + 1-(phenylsulfinyl)cyclohexanecarbonitrile (1360557-39-6) → methyl 1-cyanocyclohexane-1-carboxylate (58920-80-2)

Guidance literature:

1-(phenylsulfinyl)cyclohexanecarbonitrile; With isopropylmagnesium chloride; In tetrahydrofuran; at -78 ℃; for 0.0833333h;

methyl cyanoformate; With benzyl bromide; In tetrahydrofuran; at -78 - 20 ℃; for 2h; Reagent/catalyst; chemoselective reaction;

DOI:10.1021/acs.orglett.5b02481

Reference yield: 96.0%

methyl cyanoformate (17640-15-2) + cyclohexane carbonitrile (766-05-2) → methyl 1-cyanocyclohexane-1-carboxylate (58920-80-2)

Guidance literature:

cyclohexane carbonitrile; With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃; for 1h;

With magnesium bromide; In tetrahydrofuran; for 0.25h;

methyl cyanoformate; With benzyl bromide; In tetrahydrofuran; at -78 - 20 ℃; for 2h; Reagent/catalyst; chemoselective reaction;

DOI:10.1021/acs.orglett.5b02481

Reference yield: 92.0%

methyl cyanoformate (17640-15-2) + 1-(pyridin-2-ylthio)cyclohexanecarbonitrile (1510799-28-6) → methyl 1-cyanocyclohexane-1-carboxylate (58920-80-2)

Guidance literature:

With n-butyllithium; dibutylmagnesium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2h;

DOI:10.1021/ol403020s

upstream raw materials:

Methyl N-(1-cyanocyclohexyl)-diazoformiat

1,5-dibromo-pentane

methyl 2-cyanoacetate

methyl cyanoformate

Downstream raw materials:

(1-(aminomethyl)cyclohexyl)methanol

methyl 1-(aminomethyl)cyclohexanecarboxylate

Boc-Aib-β^2,2Ac₆c-OMe

Refernces

• 1、 Yang, Xun,Nath, Dinesh,Fleming, Fraser F.. "Chemoselective Alkylations with N- and C-Metalated Nitriles". . p. 4906 - 4909. Retrieved 2015/10/12.
• 2、 Nath, Dinesh,Skilbeck, Melanie C.,Coldham, Iain,Fleming, Fraser F.. "Arylthio-metal exchange of α-arylthioalkanenitriles". . p. 62 - 65. Retrieved 2014/01/23.