15657-96-2

Usage

Physical state

Colorless to yellow liquid

Odor

Fruity

Primary uses

Chemical intermediate in production of pharmaceuticals, agrochemicals, and other organic compounds

Secondary uses

Solvent and reagent in organic synthesis

Importance

Versatile building block for the synthesis of a wide range of compounds, valuable in chemical manufacturing industry

Safety concerns

Toxic if ingested or inhaled, may cause skin and eye irritation, should be handled with care and in accordance with proper safety protocols.

Upstream product

• 463-51-4 Ketene 
• 78-97-7 2-hydroxy-propionitrile 
• 5912-58-3 1-chloroethyl acetate 
• 143-33-9 sodium cyanide 
• 542-10-9 ethylidene diacetate 
• 151-50-8 potassium cyanide 
• 75-36-5 acetyl chloride 
• 108-05-4 vinyl acetate 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 74-90-8 hydrogen cyanide 
• 38939-83-2 2-acetoxypropionyl chloride 
• 122-78-1 phenylacetaldehyde 
• 75-07-0 acetaldehyde 
• 107-13-1 acrylonitrile 

Downstream Products

• 74-90-8 hydrogen cyanide 
• 75-07-0 acetaldehyde 
• 64-19-7 acetic acid 
• 107-13-1 acrylonitrile 
• 56955-19-2 ethyl 2-(2-oxo-1-cyano-2-ethoxyethylidene)-cyclohexanecarboxylate 
• 869719-14-2 1-cyano-4-oxo-2,6-diphenyl-cyclohexanecarboxylic acid methyl ester 
• 302-72-7 rac-Ala-OH 
• 78-97-7 2-hydroxy-propionitrile 

Relevant academic research and scientific papers

Hydroacetoxylation of olefins with acetic acid genetated in situ from vinyl acetate in the presence of ruthenium complexes

Ruthenium complexes catalyze the decomposition of vinyl acetate releasing the acetic acid and its subsequent addition to linear and cyclic olefins.

The chemistry of acylals. 3. Cyanohydrin esters from acylals with cyanide reagents

(equation presented) When treated with KCN in DMSO at room temperature, acylals from aliphatic aldehydes gave the corresponding cyanohydrin esters in good to excellent yields. Acylals from aromatic aldehydes were less reactive and gave several byproducts in addition to fair yields of cyanohydrin under the same conditions. Trimethylsilyl cyanide mixed with titanium(IV) chloride afforded cyanohydrin esters in good to excellent yields from both aliphatic and aromatic aldehydes.

Asymmetric hydrocyanation of olefins catalyzed by chiral diphosphite-nickel complexes

Chiral aryl diphosphite ligands derived from binaphthol were found to be effective in the nickel-catalyzed hydrocyanation of a variety of olefins. Enantioselective hydrocyanations of styrene, 4-substituted styrenes and norbornene were achieved with excell

Processes for producing alpha -cyanohydrin esters and alpha -hydroxy acids

In the presence of a metal catalyst such as a samarium compound, an enol ester compound shown by the formula (1) is reacted with a carbonyl compound shown by the formula (3) and a cyanogenation agent to produce an alpha -cyanohydrin ester shown by the formula (4): wherein R1, R7, and R8 are the same or different from each other, each representing a non-reactive atom or a non-reactive organic group; R2, R3, and R4 are the same or different from each other, each representing a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. By hydrolyzing the obtained compound, the corresponding alpha -hydroxy acid or a salt thereof can be obtained. According to the above processes, an alpha -cyanohydrin ester and an alpha -hydroxy acid can be obtained in high yields.

DABCO-Mediated Synthesis and Biological Activity of Cyanihydrin Esters

Cyanohydrin esters 1-31 have been prepared from α-ketonitriles and aldehydes using DABCO (1,4-diazabicyclooctane) as nucleophilic acylation catalyst.The modofied piperonal 8 was found to inhibit the formation of thromboxane synthetase.

Asymmetric hydrolysis of 1-Cyanoalkyl Acetates

Microorganisms that enantioselectively hydrolyze 1-cyanoalkyl acetates (aldehyde cyanohydrin) were screened.Candida tropicalis was found to be the best.The enzyme system of this strain catalyzed the enantioselective hydrolysis of (S)-isomers, leaving behind the (R)-acetates.The optical purities of recovered acetates were high as measured by 1H-NMR analysis in the presence of a chiral shift reagent.

Benzoxazinones et acyloxynitriles via des acyliminophosphorannes

Ph3P=NSiMe3 reacts with acetyl and p-tolyl salicylic acid chlorides to afford the corresponding benzoxazinones: This new reaction allows the first preparation of the compound in which R1=Me, since the formation of the dimer, only provided by the unique route previously described, can be avoided.In contrast, o-acyl derivatives of lactic acid chlorides react with Ph3P=NSiMe3 to give the corresponding nitriles and not the expected oxazolones, as previously described.

Process for the manufacture of cyanohydrin acylates of aldehydes

Cyanohydrin acylates of aldehydes are manufactured by reacting aldehydes with aqueous solutions of cyanides and organic acid chlorides or anhydrides in the molar ratio of aldehyde:cyanide:acid chloride or anhydride of 1:1:1 with deviations of at most only about 10%, optionally in the presence of an inert organic solvent immiscible with water in a one-stage process. The process products are intermediates mainly in the fields of pharmaceuticals and plant protection.