Cyclohexanecarbonitrile

Base Information

• Chemical Name: Cyclohexanecarbonitrile
• CAS No.: 766-05-2
• Molecular Formula: C7H11N
• Molecular Weight: 109.171
• Hs Code.: 2926907090
• European Community (EC) Number: 212-157-4
• NSC Number: 17557
• DSSTox Substance ID: DTXSID30227400
• Nikkaji Number: J154.041F
• Wikidata: Q72459565
• Mol file: 766-05-2.mol

Synonyms:cyanocyclohexane

Chemical Property of Cyclohexanecarbonitrile

Chemical Property:

• Vapor Pressure: 0.335mmHg at 25°C
• Melting Point: 11 °C(lit.)
• Refractive Index: n20/D 1.4505(lit.)
• Boiling Point: 199.8 °C at 760 mmHg
• Flash Point: 68.8 °C
• PSA: 23.79000
• Density: 0.91 g/cm³
• LogP: 2.09028
• Storage Temp.: Store below +30°C.
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 109.089149355
• Heavy Atom Count: 8
• Complexity: 103

Purity/Quality:

99% ^*data from raw suppliers

Cyclohexanecarbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 24/25-36/37/38-23/24/25
• Safety Statements: 36/37-45-36/37/39-26-23

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)C#N
• General Description: Cyclohexanecarbonitrile, also known as cyanocyclohexane or cyclohexyl cyanide, is a nitrile compound that exhibits distinct coordination preferences when metalated with Li, Mg, or Cu cations. The study reveals that magnesiated cyclohexanecarbonitrile tends to favor C-metalation, contrasting with its N-metalation preference in arylacetonitriles, highlighting the influence of the carbon scaffold on coordination behavior. This demonstrates Cyclohexanecarbonitrile's role in understanding the structural and electronic factors governing metal-nitrogen versus metal-carbon interactions in nitrile chemistry.

Technology Process of Cyclohexanecarbonitrile

There total 119 articles about Cyclohexanecarbonitrile 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: 100.0%

cyclohexanecarbaldoxime (4715-11-1) → cyclohexane carbonitrile (766-05-2)

Guidance literature:

With nickel(II) chloride dihydrate; In acetonitrile; at 80 ℃; Molecular sieve; Inert atmosphere;

DOI:10.1055/s-0030-1260119

Reference yield: 97.0%

cyclohexylmethylamine (3218-02-8) → cyclohexane carbonitrile (766-05-2)

Guidance literature:

With pyridine; Oxone; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; Pyridine hydrobromide; In dichloromethane; at 20 ℃; for 12h; Green chemistry;

DOI:10.1002/chem.201600549

Reference yield: 95.0%

cyclohexylmethyl alcohol (100-49-2) → cyclohexane carbonitrile (766-05-2)

Guidance literature:

With ammonia; at 210 ℃; Inert atmosphere;

DOI:10.1039/c8cy01799a

upstream raw materials:

cyclohex-1-enecarbonitrile

toluene-4-sulfonamide

Cyclohexanecarboxylic acid

cyclohexylcarboxamide

Downstream raw materials:

methyl cyclohexanecarboximidate hydrochloride

N-phenylcyclohexanecarboximidamide

3-(5-cyclohexyl-1H-[1,2,4]triazol-3-yl)-naphthalen-2-ol

3-cyclohexyl-5-phenyl-1H-[1,2,4]triazole

Refernces

Metalated nitriles: N- and C-coordination preferences of Li, Mg, and Cu cations

10.1039/c3cc41703d

The research aims to investigate the coordination preferences of lithium (Li), magnesium (Mg), and copper (Cu) cations with nitriles, focusing on whether these metals preferentially coordinate to the nitrogen (N-metalation) or carbon (C-metalation) atoms in nitriles. The study used a series of metalated arylacetonitriles and cyclohexanecarbonitriles to analyze the influence of the carbon scaffold and the nature of the metal on the preference for N- or C-metalation through 13C NMR analyses. The chemicals used in the process include phenylacetonitrile, cyclohexanecarbonitrile, and various metalating agents such as BuLi, i-PrMgCl, CuI, and Me2CuLi. The research concluded that lithium and magnesium preferentially coordinate to the nitrile nitrogen in arylacetonitriles, while copper favors C-metalation. The study also found that the carbon scaffold can significantly influence the coordination preferences, with magnesiated nitriles showing a preference for N-metalation with arylacetonitriles and C-metalation with cyclohexanecarbonitrile. These findings underscore the complex nature of metalated nitriles and their structural identity, which is intimately tied to the metal cation and the nature of the substituents on the nucleophilic carbon.

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