120990-00-3

Basic information

• Product Name: (R)-(E)-(+)-4-phenyl-3-buten-2-yl azide
• Synonyms: (R)-(E)-(+)-4-phenyl-3-buten-2-yl azide
• CAS NO: 120990-00-3
• Molecular Weight: 173.217
• Mol File: 120990-00-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (R)-(E)-(+)-4-phenyl-3-buten-2-yl azide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(E)-(+)-4-phenyl-3-buten-2-yl azide(120990-00-3)
• EPA Substance Registry System: (R)-(E)-(+)-4-phenyl-3-buten-2-yl azide(120990-00-3)

Safety Data

• Hazardous Substances Data: 120990-00-3(Hazardous Substances Data)

Upstream product

• 84519-63-1 (R,E)-4-phenyl-3-buten-2-yl acetate 
• 14371-10-9 (E)-3-phenylpropenal 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 32644-22-7 1-methyl-3-phenylallene 
• 98-80-6 phenylboronic acid 

Downstream Products

• 100-52-7 benzaldehyde 
• 147860-04-6 (R)-α-azidopropionic aldehyde 
• 233672-89-4 3-phenyl-1-methyl-prop-2-en-1-azide 
• 57066-11-2 (R)-(+)-N-<(E)-4-phenyl-3-buten-2-yl>benzamide 
• 57066-11-2 (S)-N-<(E)-4-phenyl-3-buten-2-yl>benzamide 
• 51773-65-0 (R)-(E)-(+)-4-phenyl-3-buten-2-ylamine 
• 51616-91-2 (-)-(S,E)-4-Phenylbut-3-en-2-ylamin 

Relevant articles and documents

Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes

The gold-catalyzed enantioselective hydroazidation and hydroamination reactions of allenes are presented herein. ADC gold(I) catalysts derived from BINAM were critical for achieving high levels of enantioselectivity in both transformations. The sense of enantioinduction is reversed for the two different nucleophiles, allowing access to both enantiomers of the corresponding allylic amines using the same catalyst enantiomer. Chiral allylic azides and amines are obtained by enantioselective hydroazidation and hydroamination of allenes catalyzed by acyclic diaminocarbene gold(I) catalysts derived from BINAM. The sense of enantioinduction is reversed for the two different nucleophiles, allowing easy access to both enantiomers with a single catalyst enantiomer.

Palladium(0)-Catalyzed Azidation of Allyl Esters. Selective Synthesis of Allyl Azides, Primary Allylamines, and Related Compounds

Palladium(0)-catalyzed reaction of allyl esters such as phosphates, carbonates, and carboxylates with sodium azide gives allyl azides.The azidation proceeds with retention of configuration at the allylic carbon.Optically active (R)-(E)-(+)-4-phenyl-3-buten-2-yl azide (19) is obtained from (R)-(E)-(+)-4-phenyl-3-buten-2-yl acetate (18) stereoselectively.Sequential substitution of (Z)-4-acetoxy-2-buten-1-yl diethyl phosphate (24) with nucleophiles and subsequently azide ion gives (E)-4-substituted-2-buten-1-yl azides 27.The reaction of allyl azides with triphenylphosphine gives iminotriphenylphosphoranes, which are versatile synthetic intermediates of primary allylamines, N-allylamines, and N-allylamides.Treatment of allyl azides with triphenylphosphine and subsequently with aqueous ammonium solution gives primary allylamines.Other synthetic applications of allyl azides are also described.