133474-07-4

Basic information

• Product Name: 2-Aziridinecarboxamide,3-phenyl-,trans-(9CI)
• Synonyms: 2-Aziridinecarboxamide,3-phenyl-,trans-(9CI)
• CAS NO: 133474-07-4
• Molecular Formula: C₉H₁₀N₂O
• Molecular Weight: 162.19
• Product Categories: AMIDE
• Mol File: 133474-07-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Aziridinecarboxamide,3-phenyl-,trans-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aziridinecarboxamide,3-phenyl-,trans-(9CI)(133474-07-4)
• EPA Substance Registry System: 2-Aziridinecarboxamide,3-phenyl-,trans-(9CI)(133474-07-4)

Safety Data

• Hazardous Substances Data: 133474-07-4(Hazardous Substances Data)

Upstream product

• 14737-94-1 methyl 2-chloro-3-phenylprop-2(Z)-enoate 
• 19922-81-7 2,3-dibromo-3-phenyl-propionic acid amide 
• 64300-27-2 cis-(+/-)-3-phenylaziridine-2-carbonitrile 
• 621-79-4 cinnamamide 
• 114703-28-5 3-bromo-1,1,2-trichloro-3-phenylpropene 
• 88286-26-4 α,β-dibromocinnamonitrile 

Downstream Products

• 79559-53-8 threo-2-amino-3-fluoro-3-phenylpropionic acid amide 
• 863311-93-7 2-(4-chloro-[1,2,3]-dithiazol-5-ylideneamino)-3-phenylacrylamide 
• 75197-99-8 threo-3-Fluorophenylaniline isopropyl ester 
• 57362-93-3 threo-DL-β-fluorophenylalanine 

Relevant articles and documents

Enantiopure trans -3-arylaziridine-2-carboxamides: Preparation by bacterial hydrolysis and ring-openings toward enantiopure, unnatural D -α-amino acids

Several racemic trans-3-arylaziridine-2-carboxamides were prepared and then resolved by Rhodococcus rhodochrous IFO 15564-catalyzed hydrolysis. The resulting enantiopure (2R,3S)-3-arylaziridine-2-carboxamides are adequate substrates to undergo fully stereoselective nucleophilic ring-openings at the C-3 ring position to finally yield enantiopure, unnatural d-α- aminocarboxylic acids. Experimental evidence is provided that suggests the fate of the (2S,3R)-3-arylaziridine-2-carboxylic acids concomitantly formed during the resolution processes. In this context, the similar bacterial resolution of racemic 1-arylaziridine-2-carboxamides and -carbonitriles, previously investigated by our research group, has been partially re-examined.

Synthesis of α-Halocinnamate Esters via Solvolytic Rearrangement of Trichloroallyl Alcohols

Aryl trichlorovinyl ketones undergo regioselective reduction to the corresponding carbinols with sodium borohydride in alcoholic solvents and are transformed to the (Z)-α-chlorocinnamate ester derivatives via an acid-catalyzed allylic rearrangement.Micharl addition of ammonia to these ester derivatives affords cis- and/or trans-aziridine amides.The facile rearrangement allows the synthesis of d,l-phenylalanine derived from perchloroethylene and toluene.

Reaction of Hydrogen Fluoride in Pyridine Solution with cis-Cyano-2- and cis-Amido-2-aziridines. Preparation of β-Fluoro-α-amino Acids and Esters by Means of Acidic Hydrolysis and Alcoholysis of β-Fluoro-α-Amino Nitriles and/or β-Fluoro-α-Amino Acid Amide

The addition of hydrogen fluoride generated from pyridinium poly(hydrogen fluoride) (i.e.Olah's reagent) to some cis-2-cyano- and cis-2-amido-aziridines has been examined.The reaction led to fluoroamine derivatives which upon acidic hydrolysis and alcohol