42456-26-8

Basic information

• Product Name: 2-amino-2-(4-methoxyphenyl)acetonitrile
• Synonyms: 2-amino-2-(4-methoxyphenyl)acetonitrile
• CAS NO: 42456-26-8
• Molecular Weight: 162.191
• Mol File: 42456-26-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-amino-2-(4-methoxyphenyl)acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-2-(4-methoxyphenyl)acetonitrile(42456-26-8)
• EPA Substance Registry System: 2-amino-2-(4-methoxyphenyl)acetonitrile(42456-26-8)

Safety Data

• Hazardous Substances Data: 42456-26-8(Hazardous Substances Data)

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 2393-23-9 4-methoxy-benzylamine 
• 123-11-5 4-methoxy-benzaldehyde 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 33646-40-1 4-methoxymandelonitrile 
• 773837-37-9 sodium cyanide 

Downstream Products

• 6324-01-2 p-hydroxyphenylglycine 
• 6617-78-3 5-(4-methoxyphenyl)imidazolidone-2,4-dione 
• 56463-62-8 1-[4-amino-5-(4-methoxy-phenyl)-2-methyl-pyrrol-3-yl]-ethanone 
• 60093-45-0 D-p-methoxyphenylglycine nitrile 
• 5550-46-9 2-Amino-2-(4-methoxy-phenyl)-acetamide; hydrochloride 
• 2540-53-6 2-(4-methoxyphenyl)glycine 
• 24593-48-4 (2S)-2-amino-2-(4-methoxyphenyl)acetic acid 
• 24593-49-5 D-(-)-2-(4-methoxyphenyl)glycine 
• 75561-85-2 1-[4-amino-5-(4-methoxy-phenyl)-pyrrol-3-yl]-ethanone 
• 67412-96-8 D-(-)-4-methoxyphenylglycine amide 

Relevant articles and documents

Facile Access to 1,4-Disubstituted Pyrrolo[1,2- a ]pyrazines from α-Aminoacetonitriles

An efficient and practical synthetic protocol for the synthesis of 1,4-disubstituted pyrrolo[1,2- a ]pyrazine derivatives is described that originates from α-substituted pyrroloacetonitriles which, in turn, are readily available from aryl and alkyl aldehydes. The α-pyrroloacetonitriles were subjected to a Friedel-Crafts acylation with methyl chlorooxoacetate followed by reduction of the nitrile group under Pd-catalyzed hydrogenation conditions and finally aromatization with DDQ leading to the desired pyrrolo[1,2- a ]pyrazine derivatives. This method was generalized and successfully applied to various aryl, heteroaryl, and alkyl substrates. The developed protocol provides direct and convenient access to 1,4-disubstituted ring systems in moderate to good overall yields (51-68percent) without the need for purification of the intermediates. Further functionalization via the stepwise halogenation (bromination, iodination) and nitration was also demonstrated. In addition, the potential of the ester functionality for elaboration was demonstrated by manipulating into heterocyclic ring systems, exemplified by conversion into benzoxazole derivatives.

A Sustainable, Semi-Continuous Flow Synthesis of Hydantoins

Hydantoins are an important class of heterocycles with applications in pharmacy, agriculture, and as intermediates in organic synthesis. Traditional synthetic procedures to access hydantoins are target oriented with multiple synthetic steps and often use reagents that are not commercially available or sustainable. Herein, an efficient process is described for accessing hydantoins starting from commercially available amines using consecutive gas–liquid transformations (oxygen, carbon dioxide). This semi-continuous process produced ten benzylic/aliphatic hydantoins in good overall yields (52–84 %).

Development of a new α-aminonitrile synthesis

α-Aminonitriles are prepared upon reaction of aryl carboxaldehydes with LiHMDS and acetone cyanohydrin. This new method provides a general route to the synthesis of various substituted α-aminoarylacetonitriles in high yield and purity, and avoids the use of the highly toxic cyanide salts.