4355-46-8

Basic information

• Product Name: 2-amino-2-phenylpropanenitrile
• Synonyms: 2-amino-2-phenylpropanenitrile
• CAS NO: 4355-46-8
• Molecular Formula: C₉H₁₀N₂
• Molecular Weight: 146.1891
• Mol File: 4355-46-8.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-amino-2-phenylpropanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-2-phenylpropanenitrile(4355-46-8)
• EPA Substance Registry System: 2-amino-2-phenylpropanenitrile(4355-46-8)

Safety Data

• Hazardous Substances Data: 4355-46-8(Hazardous Substances Data)

Usage

Physical appearance

White to off-white powder

Main usage

Intermediate in pharmaceutical production and organic synthesis

Specific applications

Synthesis of anti-inflammatory drugs
Synthesis of anti-asthmatic medications

Versatility

Participates in a wide range of chemical reactions

Value

Valued as a versatile building block in organic chemistry

Utility

Useful starting material for preparing complex organic molecules

Upstream product

• 98-86-2 acetophenone 
• 618-36-0 rac-methylbenzylamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 74-90-8 hydrogen cyanide 
• 151-50-8 potassium cyanide 
• 20102-12-9 2-hydroxy-2-phenylpropionitrile 

Downstream Products

• 5083-00-1 2-Acetamino-2-methyl-phenylessigsaeure-nitril 
• 565-07-1 2-amino-2-phenylpropanoic acid 
• 65-85-0 benzoic acid 
• 19196-63-5 DL-α-methylphenylglycine amide 
• 81512-12-1 α-[(4-methoxyphenyl)amino]-α-methylbenzeneacetonitrile 
• 13398-26-0 (S)-2-methyl-2-phenylglycine 
• 29738-09-8 (R)-2-amino-2-phenylpropanoic acid 
• 1617545-79-5 2-[6-(3-chloro-phenyl)-pyrazin-2-ylamino]-2-phenyl-propan-1-ol 
• 1617545-95-5 2-(6-chloro-pyrazin-2-ylamino)-2-phenyl-propan-1-ol 
• 90642-81-2 (R,S)-2-amino-2-phenylpropan-1-ol 
• 1381803-89-9 C₁₇H₁₆N₂O 
• 1381802-78-3 4-amino-5-methyl-3,5-diphenyl-1H-pyrrol-2(5H)-one 
• 6843-49-8 5-methyl-5-phenylimidazolidin-2,4-dione 
• 166538-41-6 2-(4-Nitrobenzoylamino)-2-phenylpropanamide 

Relevant articles and documents

Titanium-Catalyzed Cyano-Borrowing Reaction for the Direct Amination of Cyanohydrins with Ammonia

α-Aminonitrile was an important building block in natural products and key intermedia in organic chemistry. Herein, the direct amination of cyanohydrins with the partner of ammonia to synthesis N-unprotected α-aminonitriles is developed. The reaction proceeds via titanium-catalyzed cyano-borrowing reaction, which features high atom economy and simple operation. A broad range of ketone or aldehyde cyanohydrins was tolerated with ammonia, and the N-unprotected α-aminonitriles were synthesis with moderate to high yields under mild reaction conditions.

New enzymatic methods for the synthesis of primary α-aminonitriles and unnatural α-amino acids by oxidative cyanation of primary amines with d-amino acid oxidase from porcine kidney

Oxidation of amino groups in amines or amino acids activates the sp3 Cα-H bond to form imines, making the alpha carbon atom a preferable target for nucleophilic reagents such as cyanide. Therefore, we focused on the oxidase reaction for the production of primary α-aminonitriles via imines. d-Amino acid oxidase from porcine kidney (pkDAO) and l-amino acid oxidase from Crotalus atrox catalyzed the synthesis of 2-amino-2-cyano-3-phenylpropanoic acid from phenylalanine and potassium cyanide (KCN). Mutant pkDAO (Y228L/R283G) catalyzed the synthesis of racemic-2-methyl-2-phenylglycinonitrile from (R)-α-methylbenzylamine and KCN. Based on these results, we developed a new cascade reaction for the synthesis of unnatural α-amino acids from primary amines using mutant pkDAO and nitrilase AY487533. This is the first report of the enzymatic synthesis of primary α-aminonitriles and unnatural α-amino acids. These methods will contribute widely to the synthesis of primary α-aminonitriles and unnatural α-amino acids in aqueous systems.

Process for the preparation of (schiff bases of)alpha-alkyl-alpha-amino acid amides

Process for the preparation of a Schiff base of an α-alkyl-α-amino acid amide and an aldehyde, wherein the corresponding α-aminonitrile is contacted with a base and the aldehyde and wherein it is ensured that the reagents are in good contact. The Schiff base obtained may be further hydrolysed to form the α-alkyl-α-amino acid amide and the aldehyde. Preferably a substituted or unsubstituted benzaldehyde is used as the aldehyde. The reaction is preferably carried out in a practically homogeneously mixed phase obtained by using a solvent, for example methanol or ethanol. Preferably NaOH or KOH is used as the base.