75599-81-4

Basic information

• Product Name: α-acetoxy-2-(4-methylphenyl)acetonitrile
• Synonyms: α-acetoxy-2-(4-methylphenyl)acetonitrile
• CAS NO: 75599-81-4
• Molecular Weight: 189.214
• Mol File: 75599-81-4.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: α-acetoxy-2-(4-methylphenyl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: α-acetoxy-2-(4-methylphenyl)acetonitrile(75599-81-4)
• EPA Substance Registry System: α-acetoxy-2-(4-methylphenyl)acetonitrile(75599-81-4)

Safety Data

• Hazardous Substances Data: 75599-81-4(Hazardous Substances Data)

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 108-24-7 acetic anhydride 
• 104-87-0 4-methyl-benzaldehyde 
• 631-57-2 Acetyl cyanide 
• 143-33-9 sodium cyanide 
• 2929-93-3 p-tolylmethylenediacetate 
• 4815-10-5 2-hydroxy-2-(4-methylphenyl)acetonitrile 

Downstream Products

• 53360-85-3 2-amino-1-(4-methylphenyl)ethanol 
• 1228319-58-1 N-[2-acetoxy-3-(4-methylphenyl)-2-propen-1-ylidene]-3,5-diphenyl-2-furanamine 
• 10017-04-6 2-hydroxy-2-p-tolylacetonitrile 
• 4815-10-5 (S)-2-hydroxy(4-methylphenyl)acetonitrile 
• 119904-34-6 (R)-(-)-1-cyano-1-(4-methylphenyl)methyl acetate 
• 589-18-4 4-Methylbenzyl alcohol 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 75920-45-5 (+/-)-2-(4'-methylphenyl)-propionitrile 

Relevant articles and documents

3-Methyl-6-methylene-3-nitrocyclohexa-1,4-diene and (4-methyl-4- nitrocyclohexa-2,5-dienylidene)acetonitrile, intermediates in the rearomatizations of 1,4-dimethyl-4-nitrocyclohexa-2,5-dienyl acetate and (1-acetoxy-4-methyl-4-nitrocyclohexa-2,5-dienyl)acetonitrile

4-Methyl-4-nitro-1-trimethylsilylmethyl- (1e) and 4-methyl-4-nitro-1- cyanomethyl-cyclohexa-2,5-dienol (1c) in acidified acetic anhydride give 3-methyl-6-methylene-3-nitrocyclohexa-1,4-diene (3a) and (4-methyl-4- nitrocyclohexa-2,5-dienylidene)acetonitrile (3c), respectively.

High-Throughput Preparation of Optically Active Cyanohydrins Mediated by Lipases

Cyanohydrins are versatile compounds with high applicability in organic synthesis; they are used as starting materials for the synthesis of other chemical targets with high industrial added value. Lipase-mediated kinetic resolution reactions are a promising route for the synthesis of optically active cyanohydrins. These reactions can be carried out through the acylation of cyanohydrins or the deacylation of cyanohydrin esters, with different biocatalysts and under different reaction conditions. Unfortunately, depending on the substrate structure, long reaction times can be required to achieve suitable enantiomeric excesses. In this context, we present a high-throughput protocol for the production of optically active cyanohydrins in continuous-flow mode. The products were obtained with moderate to good enantioselectivity (E values from 8 up to >200) and with productivity values from 2.4 to 8.7 times higher in continuous-flow mode than in batch mode. Moreover, the reaction times were reduced from hours in batch mode to minutes in continuous-flow mode.

A simple separation method for (S)-hydroxynitrile lyase from cassava and its application in asymmetric cyanohydrination

Using an acetone precipitation method, crude (S)-hydroxynitrile lyase [(S)-MeHNL] was separated from Munihot esculenta (cassava) leaves, and used directly as biocatalyst to catalyze asymmetric cyanohydrination and produce cyanohydrins with enantiomeric purities (≥90% ee) significantly greater than those previously reported. The use of a water/i-Pr2O system with an enzyme, NaCN, and appropriate amounts of acetic acid is crucial in improving the stereoselectivity of cyanohydrin formation by minimizing the non-enzymatic reaction and the racemization of the chiral products. The proposed isolation method for crude (S)-MeHNL has a high value because of its simplicity, and low cost as well as the high activity of the crude (S)-MeHNL.