107485-34-7

Basic information

• Product Name: (S)-2-HYDROXY-2-CYCLOHEXYLACETONITRILE
• Synonyms: (S)-2-HYDROXY-2-CYCLOHEXYLACETONITRILE
• CAS NO: 107485-34-7
• Molecular Formula: C₈H₁₃NO
• Molecular Weight: 139.19
• Mol File: 107485-34-7.mol
• Article Data: 83

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-2-HYDROXY-2-CYCLOHEXYLACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-HYDROXY-2-CYCLOHEXYLACETONITRILE(107485-34-7)
• EPA Substance Registry System: (S)-2-HYDROXY-2-CYCLOHEXYLACETONITRILE(107485-34-7)

Safety Data

• Hazardous Substances Data: 107485-34-7(Hazardous Substances Data)

Usage

General Description

"(S)-2-Hydroxy-2-cyclohexylacetonitrile is a chemical compound with the molecular formula C8H13NO. It is also known by its synonyms like (S)-Benzylidenecyclohexane nitrile glycol, which indicates its structure, consisting of a cyclohexyl ring and a nitrile group. It is most commonly known for its role in chemical synthesis as an ingredient or intermediate in the production of other chemicals. The specific properties of this compound, such as its stereospecificity (indicated by the "(S)" in its name) and the presence of the hydroxy and nitrile groups, make it suitable for use in synthetic reactions where these features are beneficial. However, like many chemicals, appropriate safety measures should be taken when handling (S)-2-Hydroxy-2-cyclohexylacetonitrile due to its potential hazards.

Upstream product

• 74-90-8 hydrogen cyanide 
• 2043-61-0 cyclohexanecarbaldehyde 
• 143-33-9 sodium cyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 151-50-8 potassium cyanide 
• 134863-85-7 2-cyclohexyl-2-(trimethylsilyloxy)acetonitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 4435-18-1 2-cyclohexylideneacetonitrile 
• 613-90-1 benzoyl cyanide 
• 108-24-7 acetic anhydride 
• 773837-37-9 sodium cyanide 
• 4746-48-9 2-hydroxy-2,2-diphenylacetonitrile 
• 98-89-5 Cyclohexanecarboxylic acid 
• 26565-45-7 C₁₃H₂₆O₂Si 

Downstream Products

• 57230-08-7 1-amino-2-cyclohexylethan-2-ol 
• 40651-95-4 2-amino-2-cyclohexylacetonitrile 
• 125849-99-2 3,5-Dichloro-6-cyclohexyl-[1,4]oxazin-2-one 
• 4957-67-9 2-cyclohexyl-2-hydroxyethanoic acid N-t-butylamide 
• 4442-94-8 2-cyclohexyl-2-hydroxyacetic acid 
• 716362-15-1 benzyl 2-cyclohexyl-2-hydroxyethanoate 
• 887642-20-8 benzyl 2-cyclohexyl-2-ketoethanoate 
• 4354-49-8 2-cyclohexyl-2-oxoethanoic acid 
• 862461-50-5 3-(4-chlorophenyl)-5-cyclohexyloxazolidin-2,4-dione 
• 752235-31-7 3-benzyloxy-5-cyclohexyl-oxazolidin-2,4-dione 
• 3193-02-0 (+/-)-2-cyclohexyl-2-hydroxy-2-(3-thienyl)ethanoic acid 
• 16199-74-9 (+/-)-2-cyclohexyl-2-(3-thienyl)ethanoic acid 
• 81560-74-9 N-(tert-butyl)-2-cyclohexyl-2-oxoacetamide 
• 40652-42-4 N-Cyclohexylidenemethyl-formamide 

Relevant articles and documents

CO2-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions**

Thermodynamic and kinetic control of a chemical process is the key to access desired products and states. Changes are made when a desired product is not accessible; one may manipulate the reaction with additional reagents, catalysts and/or protecting groups. Here we report the use of carbon dioxide to accelerate cyanohydrin synthesis under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN. Under inert atmosphere, the reaction is essentially not operative due to the unfavored equilibrium. The utility of CO2-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani–Fischer synthesis under neutral conditions. This protocol offers an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atmospheric pressure of CO2.

Enantioconvergent Cu-Catalyzed Radical C-N Coupling of Racemic Secondary Alkyl Halides to Access α-Chiral Primary Amines

α-Chiral alkyl primary amines are virtually universal synthetic precursors for all other α-chiral N-containing compounds ubiquitous in biological, pharmaceutical, and material sciences. The enantioselective amination of common alkyl halides with ammonia is appealing for potential rapid access to α-chiral primary amines, but has hitherto remained rare due to the multifaceted difficulties in using ammonia and the underdeveloped C(sp3)-N coupling. Here we demonstrate sulfoximines as excellent ammonia surrogates for enantioconvergent radical C-N coupling with diverse racemic secondary alkyl halides (>60 examples) by copper catalysis under mild thermal conditions. The reaction efficiently provides highly enantioenrichedN-alkyl sulfoximines (up to 99% yield and >99% ee) featuring secondary benzyl, propargyl, α-carbonyl alkyl, and α-cyano alkyl stereocenters. In addition, we have converted the masked α-chiral primary amines thus obtained to various synthetic building blocks, ligands, and drugs possessing α-chiral N-functionalities, such as carbamate, carboxylamide, secondary and tertiary amine, and oxazoline, with commonly seen α-substitution patterns. These results shine light on the potential of enantioconvergent radical cross-coupling as a general chiral carbon-heteroatom formation strategy.

Visible-Light-Driven N-Heterocyclic Carbene Catalyzed γ- and ?-Alkylation with Alkyl Radicals

The merging of photoredox catalysis and N-heterocyclic carbene (NHC) catalysis for γ- and ?-alkylation of enals with alkyl radicals was developed. The alkylation reaction of γ-oxidized enals with alkyl halides worked well for the synthesis γ-multisubstituted-α,β-unsaturated esters, including those with challenging vicinal all-carbon quaternary centers. The synthesis of ?-multisubstituted-α,β-γ,δ-diunsaturated esters by an unprecedented NHC-catalyzed ?-functionalization was also established.