27634-88-4

Basic information

• Product Name: BENZONITRILE, 4-CYCLOHEXYL-
• Synonyms: BENZONITRILE, 4-CYCLOHEXYL-
• CAS NO: 27634-88-4
• Molecular Formula: C₁₃H₁₅N
• Molecular Weight: 185.26
• Mol File: 27634-88-4.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 314.1±21.0 °C(Predicted)
• Appearance: /
• Density: 1.02±0.1 g/cm3(Predicted)
• CAS DataBase Reference: BENZONITRILE, 4-CYCLOHEXYL-(CAS DataBase Reference)
• NIST Chemistry Reference: BENZONITRILE, 4-CYCLOHEXYL-(27634-88-4)
• EPA Substance Registry System: BENZONITRILE, 4-CYCLOHEXYL-(27634-88-4)

Safety Data

• Hazardous Substances Data: 27634-88-4(Hazardous Substances Data)

Upstream product

• 85418-99-1 4-cyclohexylaniline hydrochloride 
• 623-26-7 terephthalonitrile 
• 108-91-8 cyclohexylamine 
• 108-85-0 1-bromocyclohexane 
• 131379-14-1 4-cyanophenylzinc bromide 
• 58992-27-1 cyclohexyltrimethylgermane 
• 623-00-7 4-bromobenzenecarbonitrile 
• 695-12-5 vinylcyclohexane 
• 626-62-0 Cyclohexyl iodide 
• 3058-39-7 4-iodobenzonitrile 
• 126812-30-4 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate 
• 110-83-8 cyclohexene 
• 623-03-0 4-Cyanochlorobenzene 
• 256390-55-3 cyclohexylzinc chloride 

Downstream Products

• 121193-16-6 4-cyclohexyl-benzoyl chloride 
• 27634-87-3 4-cyclohexyl-benzoic acid amide 
• 20029-52-1 4-cyclohexylbenzoic acid 

Relevant articles and documents

Alkyl-GeMe3: Neutral Metalloid Radical Precursors upon Visible-Light Photocatalysis

Single-electron transfer (SET) oxidation of ionic hypervalent complexes, in particular alkyltrifluoroborates (Alkyl-BF3?) and alkylbis(catecholato)silicates (Alkyl-Si(cat)2?), have contributed substantially to alkyl radical generation compared to alkali or alkaline earth organometallics because of their excellent activity–stability balance. Herein, another proposal is reported by using neutral metalloid compounds, Alkyl-GeMe3, as radical precursors. Alkyl-GeMe3 shows comparable activity to that of Alkyl-BF3? and Alkyl-Si(cat)2? in radical addition reactions. Moreover, Alkyl-GeMe3 is the first successful group 14 tetraalkyl nucleophile in nickel-catalyzed cross-coupling. Meanwhile, the neutral nature of these organogermanes offset the limitation of ionic precursors in purification and derivatization. A preliminary mechanism study suggests that an alkyl radical is generated from a tetraalkylgermane radical cation with the assistance of a nucleophile, which may also result in the development of more non-ionic alkyl radical precursors with a metalloid center.

Micelle enabled C(sp2)-C(sp3) cross-electrophile coupling in waterviasynergistic nickel and copper catalysis

A robust and sustainable C(sp2)-C(sp3) cross-electrophile coupling was developedvianickel/copper synergistic catalysis under micellar conditions. This protocol provided a general method to access alkylated arenes with good to excellent yields on a very large scale.

Photoactive electron donor-acceptor complex platform for Ni-mediated C(sp3)-C(sp2) bond formation

A dual photochemical/nickel-mediated decarboxylative strategy for the assembly of C(sp3)-C(sp2) linkages is disclosed. Under light irradiation at 390 nm, commercially available and inexpensive Hantzsch ester (HE) functions as a potent organic photoreductant to deliver catalytically active Ni(0) species through single-electron transfer (SET) manifolds. As part of its dual role, the Hantzsch ester effects a decarboxylative-based radical generation through electron donor-acceptor (EDA) complex activation. This homogeneous, net-reductive platform bypasses the need for exogenous photocatalysts, stoichiometric metal reductants, and additives. Under this cross-electrophile paradigm, the coupling of diverse C(sp3)-centered radical architectures (including primary, secondary, stabilized benzylic, α-oxy, and α-amino systems) with (hetero)aryl bromides has been accomplished. The protocol proceeds under mild reaction conditions in the presence of sensitive functional groups and pharmaceutically relevant cores.