Cyclohexenecarbonitrile

Base Information

• Chemical Name: Cyclohexenecarbonitrile
• CAS No.: 1855-63-6
• Deprecated CAS: 108031-42-1,33292-55-6
• Molecular Formula: C7H9N
• Molecular Weight: 107.155
• Hs Code.: 2926909090
• European Community (EC) Number: 217-454-2
• NSC Number: 177484
• UNII: J2E8HV5A42
• DSSTox Substance ID: DTXSID101015401
• Nikkaji Number: J199.671A
• Wikidata: Q81993889
• Mol file: 1855-63-6.mol

Synonyms:1855-63-6;Cyclohexene-1-carbonitrile;1-Cyanocyclohexene;Cyclohexenecarbonitrile;cyclohex-1-enecarbonitrile;1-Cyclohexenecarbonitrile;1-Cyclohexene-1-carbonitrile;Cyanocyclohexene;1-Cyclohexenyl cyanide;1-Cyano-1-cyclohexene;cyclohex-1-ene-1-carbonitrile;J2E8HV5A42;27456-25-3;EINECS 217-454-2;NSC 177484;NSC-177484;Cyclohexen-1-carbonitrile;1-cyclohexene carbonitrile;cyclohex-1-ene carbonitrile;UNII-J2E8HV5A42;SCHEMBL153189;DTXSID101015401;4-Amino-2,6-difluoro-benzonitrile;AMY16356;BCP21551;MFCD00013772;NSC177484;AKOS005166897;Cyclohexene-1-carbonitrile, >=97.0%;C3191;CS-0155409;FT-0607664;EN300-40341;D89547;J-011905

Chemical Property of Cyclohexenecarbonitrile

Chemical Property:

• Vapor Pressure: 0.481mmHg at 25°C
• Refractive Index: n20/D 1.482(lit.)
• Boiling Point: 192.7 °C at 760 mmHg
• Flash Point: 69.9 °C
• PSA: 23.79000
• Density: 0.95 g/cm³
• LogP: 2.01038
• Water Solubility.: Not miscible in water.
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 107.073499291
• Heavy Atom Count: 8
• Complexity: 147

Purity/Quality:

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

1-Cyclohexene-1-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(=CC1)C#N
• Uses: 1-Cyclohexene-1-carbonitrile has been used in the preparation of cyclohexene-1-carboxylic acid.

Technology Process of Cyclohexenecarbonitrile

There total 43 articles about Cyclohexenecarbonitrile 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: 93.0%

2-phenylseleno-cyclohexanecarbonitrile (83990-78-7) → cyclohex-1-enecarbonitrile (1855-63-6)

Guidance literature:

With dihydrogen peroxide; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1039/c39820000871

Reference yield: 92.0%

1-chlorocyclohexene (930-66-5) + potassium cyanide (151-50-8) → cyclohex-1-enecarbonitrile (1855-63-6)

Guidance literature:

With dibromobis(triphenylphosphine)nickel(II); triphenylphosphine; zinc; In N,N-dimethyl-formamide; at 50 ℃; for 16h;

DOI:10.1246/bcsj.68.3137

Reference yield: 85.0%

1-bromocyclohex-1-ene (2044-08-8) + potassium cyanide (151-50-8) → cyclohex-1-enecarbonitrile (1855-63-6)

Guidance literature:

With potassium hydroxide; water; hydrogen; at 45 ℃; for 4.5h;

DOI:10.1246/bcsj.56.649

upstream raw materials:

1-hydroxy-1-cyclohexanecarbonitrile

1-methyl-4-nitrosobenzene

cyclohex-2-enecarbonitrile

(+/-)-cis-2-chloro-cyclohexanecarbonitrile

Downstream raw materials:

(+/-)-trans-2-[2]pyridylmethyl-cyclohexanecarbonitrile

6-Pyridin-4-yl-cyclohex-1-enecarbonitrile

2-Chloro-cyclohexanecarboximidic acid methyl ester; hydrochloride

N-methyl-1-cyclohexene-1-carboxamide

Refernces

• 1、 Funabiki, Takuzo,Kishi, Hirohito,Sato, Yoshihiro,Yoshida, Satohiro. "Cyanation of 1-Halocycloalkenes Catalyzed by Tetracyanocobaltate(I). Convenient Synthesis of 1-Cyanocycloalkenes". . p. 649 - 650. Retrieved 1983.
• 2、 Chen, Yifeng,Romaire, Justin P.,Newhouse, Timothy R.. "Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles". supporting information. p. 5875 - 5878. Retrieved 2015/05/27.
• 3、 Banaag, April R.,Berger, Gideon O.,Dhoro, Francis,Delos Santos, Derrick B.,Dixon, Darryl D.,Mitchell, James P.,Tokeshi, Bradley K.,Tius, Marcus A.. "Tandem alkylation-cyclization process via an O,C-dianion". . p. 3419 - 3428. Retrieved 2007/10/03.