3-Cyclohexene-1-carbonitrile

Base Information

• Chemical Name: 3-Cyclohexene-1-carbonitrile
• CAS No.: 100-45-8
• Molecular Formula: C7H9 N
• Molecular Weight: 107.155
• Hs Code.: 2926909090
• European Community (EC) Number: 623-115-3
• NSC Number: 7407
• UNII: D65GN9AVCH
• DSSTox Substance ID: DTXSID70861706
• Nikkaji Number: J34.008A
• Wikidata: Q22079568
• Mol file: 100-45-8.mol

Synonyms:3-Cyclohexene-1-carbonitrile;100-45-8;4-Cyano-1-cyclohexene;4-Cyanocyclohexene;cyclohex-3-enecarbonitrile;3-Cyclohexenecarbonitrile;3-Cyclohexenyl cyanide;1-Cyano-3-cyclohexene;cyclohex-3-ene-1-carbonitrile;Cyclohex-3-enenitrile;3-Cyklohexenylkyanid;3-Cyklohexenylkyanid [Czech];NSC 7407;UNII-D65GN9AVCH;D65GN9AVCH;BRN 0636074;AI3-08635;NSC-7407;4-09-00-00116 (Beilstein Handbook Reference);4-Cyanocyclohexene-1;1,2,5,6-Tetrahydrobenzonitrile;NSC7407;Tetrahydrobenzonitrile;4-Cyclohexenecarbonitrile;WLN: L6UTJ DCN;SCHEMBL167234;1,2,3,6-Tetrahydrobenzonitrile;DTXSID70861706;MFCD00013778;AKOS006229199;AS-47878;LS-57405;FT-0618302;(+/-)-3-CYCLOHEXENE-1-CARBONITRILE;F16653;Q22079568

Chemical Property of 3-Cyclohexene-1-carbonitrile

Chemical Property:

• Vapor Pressure: 0.317mmHg at 25°C
• Refractive Index: 1.4720-1.4750
• Boiling Point: 200.9°Cat760mmHg
• Flash Point: 65.8°C
• PSA: 23.79000
• Density: 0.94g/cm³
• LogP: 1.86628
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 107.073499291
• Heavy Atom Count: 8
• Complexity: 138

Purity/Quality:

97% ^*data from raw suppliers

4-Cyano-1-cyclohexene ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC(CC=C1)C#N

Technology Process of 3-Cyclohexene-1-carbonitrile

There total 7 articles about 3-Cyclohexene-1-carbonitrile 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%

3-Cyclohexene-1-carboxaldehyde (100-50-5,61746-36-9) → 3-cyclohexene-1-carbonitrile (100-45-8)

Guidance literature:

With bismuth(lll) trifluoromethanesulfonate; acetylhydroxamic acid; In acetonitrile; for 16h; Reflux;

DOI:10.1016/j.tetlet.2012.04.057

Reference yield: 96.0%

3-cyclohexene-1-carboxaldehyde oxime (57606-87-8,57606-88-9,84049-09-2,112710-09-5,112710-10-8,4736-13-4) → 3-cyclohexene-1-carbonitrile (100-45-8)

Guidance literature:

With bismuth(lll) trifluoromethanesulfonate; In acetonitrile; for 8h; Reflux;

DOI:10.1016/j.tetlet.2012.04.057

Reference yield: 94.0%

→ 3-cyclohexene-1-carbonitrile (100-45-8)

Guidance literature:

With ammonium acetate; acetic acid; N-(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)acetamide tetrafluoroborate; at 70 ℃; for 12h; Inert atmosphere;

upstream raw materials:

buta-1,3-diene

acrylonitrile

3-cyclohexene-1-carboxaldehyde oxime

3-Cyclohexene-1-carboxaldehyde

Downstream raw materials:

benzonitrile

1-(3-iodopyridin-4-yl)cyclohex-3-enecarbonitrile

dimethyl 3-(3-cyclohexenyl)-1,4-dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridine-6,6-dicarboxylate

4-cyanocyclohexanone

Refernces

• 1、 Sun, Daolai,Sato, Fumiya,Yamada, Yasuhiro,Sato, Satoshi. "Solvent-free Diels-Alder reaction in a closed batch system". . p. 276 - 282. Retrieved 2013.
• 2、 Janz,Duncan. "-". . p. 5389,5390. Retrieved 1953.
• 3、 Betke, Tobias,Rommelmann, Philipp,Oike, Keiko,Asano, Yasuhisa,Gr?ger, Harald. "Cyanide-Free and Broadly Applicable Enantioselective Synthetic Platform for Chiral Nitriles through a Biocatalytic Approach". supporting information. p. 12361 - 12366. Retrieved 2017/09/06.
• 4、 Kim, Myeong Jin,Mun, Junyoung,Kim, Jinho. "Oxoammonium salt-mediated oxidative nitriles synthesis from aldehydes with ammonium acetate". supporting information. p. 4695 - 4698. Retrieved 2017/11/17.