28937-48-6

Usage

InChI:InChI=1/C10H9NO/c1-10(9(7-11)12-10)8-5-3-2-4-6-8/h2-6,9H,1H3

Upstream product

• 107-14-2 chloroacetonitrile 
• 98-86-2 acetophenone 

Downstream Products

• 51776-04-6 3-Hydroxy-2-(1-hydroxy-1-phenyl-ethyl)-3-phenyl-butyronitrile 
• 31508-44-8 2-phenylpropionic acid methyl ester 
• 62115-08-6 Acetic acid (E)-1-cyano-2-phenyl-propenyl ester 
• 81860-77-7 2-phenyl-1-(piperidin-1-yl)propan-1-one 
• 79205-65-5 3-fluoro 3-methylphenylalanine 
• 79205-61-1 2-Amino-3-fluoro-3-phenyl-butyronitrile 
• 79205-56-4 3-fluoro-2-hydroxy-3-phenylbutanonitrile 
• 34713-70-7 2-Phenylpropanal 
• 81436-71-7 (4R,5R)-2,2,5-Trimethyl-5-phenyl-[1,3]dioxolane-4-carbonitrile 
• 81436-71-7 (4S,5R)-2,2,5-Trimethyl-5-phenyl-[1,3]dioxolane-4-carbonitrile 
• 74548-68-8 Acetic acid 2-chloro-1-cyano-2-phenyl-propyl ester 
• 89278-00-2 2-(1-nitronaphthalen-2-yl)acetonitrile 
• 72301-67-8 4-Nitro-1-naphthaleneacetonitrile 
• 98-86-2 acetophenone 

Relevant academic research and scientific papers

Indium(I) bromide-mediated bromocyanomethylation of carbonyl compounds

Bromocyanomethylation of a variety of carbonyl compounds to produce the corresponding 2-bromo-3-hydroxynitriles has been achieved in moderate to good yields by the action of dibromoacetonitrile and indium(I) bromide. Moderate diastereoselectivity was observed. Exclusive mono-coupling at the carbonyl group was found with 1,2-diketones and α-haloketones. (C) 2000 Elsevier Science Ltd.

Two-phase Darzens Condensation Reaction with Octopus Compounds as a Catalyst

The octopus compound, readily derived from hexakis(mercaptomethyl)benzene and 1-chloro-3,6,9-triozadecane, was effectively employed as a catalyst in the two-phase Darzens condensation of carbonyl compounds with chloroacetonitrile to afford the correspondi

Expedient synthesis of glycidonitriles by darzens condensation of α-halogenonitriles with aldehydes and ketones

Chloroacetonitrile (1), α-halogenopropionitriles 4, and α-chlorophenylacetonitrile (6) react with aldehydes 2a,b,h-o and ketones 2c-g,p-t in the presence of solid NaOH in THF or DME, without any added catalyst, affording substituted glycidonitriles 3a-t, 5a, c-g,r,s and 7a,b,i,j,u,v, respectively (Darzens condensation). The glycidonitriles 3a-h, prepared from 1 and carbonyl compounds 2a-h, are obtained in high yields, exceeding those reported in the literature (Table 5). Expedient results of the reactions studied are due to increased reactivity of anions with Na+ as counterion in ethereal solvents. Investigation of the concentration of NaOH and the carbanion of diphenylacetonitrile in selected solvents reveals that ethereal solvents may increase the solubility of the anions participating in Darzens condensation.

REACTION OF 4-SUBSTITUTED BENZALDEHYDES AND ACETOPHENONES WITH CHLOROACETONITRILE

Under conditions of phase-transfer catalysis or in homogeneous solution of potassium tert-butoxide the title compounds give stereoisomeric mixtures of substituted 2,3-epoxy nitriles III and IV.Alkaline hydrolysis of epoxy nitriles IV afforded the corresponding 2-arylpropanals in low yields.On treatment with methanol and potassium carbonate, epoxy nitriles III and IV were converted into epoxy esters in good yields.

NEW SYNTHETIC ROUTES TO β-FLUORO β-PHENYLLACTIC ACID DERIVATIVES AND Β-FLUOROCYANOHYDRINS

Alkyl phenyl 2,3-epoxycarboxylates from the well-known Darzens glycidic esters synthesis react under very mild conditions with pyridinium-poly-hydrogen fluoride to give corresponding 3-fluoro 3-phenyllactates in almost quantitative yields with a high regio and stereoselectivity.This method can be applied succesfully to other flycidic derivatives: glycidoamides, glycidonitriles, glycidoiminoesters...The spectrometric properties (IR, NMR) are presented.