1-Cyclohexene-1-acetonitrile

Base Information

• Chemical Name: 1-Cyclohexene-1-acetonitrile
• CAS No.: 6975-71-9
• Molecular Formula: C8H11N
• Molecular Weight: 121.182
• Hs Code.: 29269090
• European Community (EC) Number: 230-235-6
• NSC Number: 21642
• UNII: F7P4K7ULM7
• DSSTox Substance ID: DTXSID1064536
• Nikkaji Number: J81.312E
• Wikidata: Q72459774
• Mol file: 6975-71-9.mol

Synonyms:6975-71-9;1-Cyclohexenylacetonitrile;1-Cyclohexene-1-acetonitrile;2-(cyclohex-1-en-1-yl)acetonitrile;Cyclohexenylacetonitrile;2-(cyclohexen-1-yl)acetonitrile;cyclohex-1-enyl-acetonitrile;1-Cyclohexen-1-ylacetonitrile;F7P4K7ULM7;EINECS 230-235-6;NSC 21642;NSC-21642;AI3-04979;1-Cyclohexeneacetonitrile;NSC21642;1-cyclohexenacetonitrile;2-Cyclohexenylacetonitrile;UNII-F7P4K7ULM7;Cyclohex-1-ene-1-acetonitrile;SCHEMBL1003717;Cyclohex-1-en-1-ylacetonitrile;DTXSID1064536;2-(1-cyclohexenyl)-acetonitrile;1-Cyclohexenylacetonitrile, 92%;MFCD00001566;AKOS004115243;AB00143;CS-0204899;FT-0636324;EN300-72661;N11908;W-104593;Z1150307002

Chemical Property of 1-Cyclohexene-1-acetonitrile

Chemical Property:

• Appearance/Colour: Clear yellow to orange liquid
• Vapor Pressure: 0.147mmHg at 25°C
• Refractive Index: n20/D 1.478(lit.)
• Boiling Point: 215.6 °C at 760 mmHg
• Flash Point: 83.9 °C
• PSA: 23.79000
• Density: 0.941 g/cm³
• LogP: 2.40048
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 121.089149355
• Heavy Atom Count: 9
• Complexity: 159

Purity/Quality:

99% ^*data from raw suppliers

1-Cyclohexenylacetonitrile 92% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-27-36/37/39-36/37-60-9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCC(=CC1)CC#N
• General Description: 1-Cyclohexene-1-acetonitrile (also known as 1-Cyclohexen-1-ylacetonitrile or 2-(1-Cyclohexenyl)acetonitrile) is an unsaturated nitrile where the double bond is not conjugated with the nitrile group. Studies on its chemoselective hydrogenation indicate that such structural features—where the C=C bond is distant from the C≡N group—favor higher selectivity for unsaturated amines. Additionally, the use of Cr-doped Raney cobalt catalysts enhances this selectivity, whereas Raney nickel tends to hydrogenate the C=C bond more readily, reducing chemoselectivity. The compound's reactivity aligns with the broader trend that non-conjugated double bonds and increased substitution near the C=C bond improve selectivity in hydrogenation reactions.

Technology Process of 1-Cyclohexene-1-acetonitrile

There total 14 articles about 1-Cyclohexene-1-acetonitrile 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: 95.0%

2-(1-cyclohexenyl)ethylamine (3399-73-3) → 1-cyclohexenylacetonitrile (6975-71-9)

Guidance literature:

With nickel(II) sulphate; sodium hydroxide; dipotassium peroxodisulfate; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1246/bcsj.63.301

Reference yield: 85.0%

(+/-)-2-(7-oxabicyclo[4.1.0]heptyl)ethanenitrile (29625-35-2) → 1-cyclohexenylacetonitrile (6975-71-9)

Guidance literature:

With sodium iodide; tin(ll) chloride; In ethanol; for 0.05h; Reflux; Green chemistry;

DOI:10.1055/s-0034-1378821

Reference yield:

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + cyanoacetic acid (372-09-8) → 1-cyclohexenylacetonitrile (6975-71-9)

Guidance literature:

With piperidine; at 105 ℃;

upstream raw materials:

2-cyclohexylideneacetonitrile

sodium ethanolate

ethyl 2-cyano-2-cyclohexylideneacetate

2-cyano-2-cyclohexylideneacetic acid

Downstream raw materials:

1-cyclohexenylacetone

2-cyclohexylideneacetonitrile

ethyl 2-(1-cyclohexenyl)acetate

1-cyclohexenylacetic acid

Refernces

Structure-selectivity relationship in the chemoselective hydrogenation of unsaturated nitriles

10.1016/j.jcat.2005.06.011

The research investigates the structure-selectivity relationship in the chemoselective hydrogenation of various unsaturated nitriles using different catalysts. The purpose of the study was to understand how the molecular structure of substrates influences the selectivity for unsaturated amines and to explore the scope and limitations of this type of hydrogenation. The researchers used several unsaturated nitriles, including cinnamonitrile, cyclohex-1-enyl-acetonitrile, acrylonitrile, 3,3-dimethyl-acrylonitrile, geranylnitrile, and 2- and 3-pentenenitrile, which were hydrogenated over Cr-doped Raney cobalt and nickel, as well as their undoped equivalents. The conclusions drawn from the study were that the position of the double bond relative to the nitrile group and the substitution of the double bond are crucial factors in determining the chemoselectivity for unsaturated amines. The highest selectivities were obtained when the double bond was not conjugated with the nitrile group, and the further the C=C bond was from the C≡N group, the higher the selectivity. Additionally, the presence of more substituents at the C=C bond increased the selectivity for unsaturated amines. The study also highlighted the suitability of Raney cobalt, especially Cr-doped Raney cobalt, for the chemoselective hydrogenation of unsaturated nitriles, while Raney nickel catalysts were found to be less selective due to their higher activity in C=C bond hydrogenation.