33235-14-2

Basic information

• Product Name: 1-methyl-3-oxocyclohexanecarbonitrile
• Synonyms: 1-methyl-3-oxocyclohexanecarbonitrile;3-Cyano-3-methylcyclohexanone
• CAS NO: 33235-14-2
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.17904
• Mol File: 33235-14-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 152 °C(Press: 19 Torr)
• Appearance: /
• Density: 1.02±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1-methyl-3-oxocyclohexanecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-3-oxocyclohexanecarbonitrile(33235-14-2)
• EPA Substance Registry System: 1-methyl-3-oxocyclohexanecarbonitrile(33235-14-2)

Safety Data

• Hazardous Substances Data: 33235-14-2(Hazardous Substances Data)

Usage

Physical state

Colorless to pale yellow liquid at room temperature

Functional groups

Nitrile (carbon-nitrogen triple bond) and ketone (carbonyl group)

Uses

Building block in the synthesis of pharmaceuticals and other organic compounds

Safety precautions

Can cause irritation to skin and eyes, may be harmful if swallowed or inhaled, proper protective equipment and safety protocols should be followed.

Upstream product

• 1193-18-6 3-methylcyclohexen-2-one 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 5804-85-3 diethylaluminium cyanide 
• 31883-98-4 3-methylcyclohex-3-en-1-one 
• 7677-24-9 trimethylsilyl cyanide 
• 1084693-44-6 C₁₄H₂₅NOSi 
• 119072-55-8 tert-butylisonitrile 
• 151-50-8 potassium cyanide 

Downstream Products

• 1143-97-1 Cyano-[3-cyano-3-methyl-cyclohex-(E)-ylidene]-acetic acid ethyl ester 
• 92871-64-2 3-(2,4-dinitro-phenylhydrazono)-1-methyl-cyclohexanecarboxylic acid methyl ester 
• 7356-04-9 ethyl (RS)-1-methyl-3-oxocyclohexanecarboxylate 
• 1202411-64-0 ethyl 3-benzylamino-1-methylcyclohexanecarboxylate 
• 56294-21-4 methyl 1-methyl-3-oxo-4-cyclohexenecarboxylate 
• 55833-75-5 1-methyl-5-oxocyclohexa-3-ene carboxylic acid 
• 1142-41-2 dimethyl ester of cis-1,3-dimethylcyclohexane-1,3-dicarboxylic acid 
• 1135-56-4 1,3-Dimethylcyclohexan-1,3-dicarbonsaeure 
• 94390-45-1 Acetic acid (R)-3-hydroxymethyl-1-methyl-cyclohex-3-enylmethyl ester 
• 94390-44-0 Acetic acid (R)-3-hydroxymethyl-1-methyl-cyclohex-2-enylmethyl ester 
• 94390-41-7 (S)-3-hydroxymethyl-3-methylcyclohexanone 
• 94390-40-6 (R)-3-hydroxymethyl-3-methylcyclohexanone 
• 94390-49-5 ((R)-3-Benzenesulfonylmethyl-3-methyl-cyclohex-1-enylmethoxy)-tert-butyl-dimethyl-silane 
• 94390-48-4 Acetic acid (R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-1-methyl-cyclohex-2-enylmethyl ester 

Relevant articles and documents

A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters

The generation of carbon-centered radicals from air-sensitive organoboron compounds through nucleohomolytic substitution at boron is a general method to generate non-functionalized and functionalized radicals. Due to their reduced Lewis acidity, alkylboronic pinacol esters are not suitable substrates. We report their in situ conversion into alkylboronic catechol esters by boron-transesterification with a substoichiometric amount of catechol methyl borate combined with an array of radical chain processes. This simple one-pot radical-chain deboronative method enables the conversion of pinacol boronic esters into iodides, bromides, chlorides, and thioethers. The process is also suitable the formation of nitriles and allylated compounds through C?C bond formation using sulfonyl radical traps. The power of combining radical and classical boron chemistry is illustrated with a modular 5-membered ring formation using a combination of three-component coupling and protodeboronative cyclization.

Deboronative cyanation of potassium alkyltrifluoroborates: Via photoredox catalysis

A photoredox catalytic method was developed for the direct cyanation of alkyltrifluoroborates. This reaction provides a new and useful transformation of the easily available alkyltrifluoroborates. The photocatalytic reaction can tolerate a variety of functional groups with mild reaction conditions. Mechanistic investigations are consistent with the present reaction following a radical pathway.

Catalytic conjugate addition of cyanide to enones: Cooperative catalysis of Ni(0) and Gd(OTf)

An efficient, synthetically useful catalytic cunjugate addition of cyanide to enones was developed using cooperative catalysis of Ni(0) and Gd(OTf) 3. The co-catalyst, Gd(OTf)3, dramatically accelerated the reaction. The substrate sc