7477-20-5

Basic information

• Product Name: 1,3,4-TRIPHENYL-2-AZETIDINONE
• Synonyms: 1,3,4-TRIPHENYL-2-AZETIDINONE;1,3,4-triphenylazetidin-2-one
• CAS NO: 7477-20-5
• Molecular Formula: C₂₁H₁₇NO
• Molecular Weight: 299.3658
• Mol File: 7477-20-5.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 512.7°Cat760mmHg
• Flash Point: 247.4°C
• Appearance: /
• Density: 1.192g/cm³
• Vapor Pressure: 1.26E-10mmHg at 25°C
• Refractive Index: 1.643
• PKA: -1.07±0.60(Predicted)
• CAS DataBase Reference: 1,3,4-TRIPHENYL-2-AZETIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4-TRIPHENYL-2-AZETIDINONE(7477-20-5)
• EPA Substance Registry System: 1,3,4-TRIPHENYL-2-AZETIDINONE(7477-20-5)

Safety Data

• Hazardous Substances Data: 7477-20-5(Hazardous Substances Data)

Usage

Appearance

White to off-white crystalline solid

Usage

Building block in organic synthesis and pharmaceutical research

Structural feature

Unique four-membered ring (azetidinone)

Role in synthesis

Key intermediate in the synthesis of various pharmaceuticals and biologically active compounds

Potential applications

Antineoplastic and antitumor agent

InChI:InChI=1/C21H17NO/c23-21-19(16-10-4-1-5-11-16)20(17-12-6-2-7-13-17)22(21)18-14-8-3-9-15-18/h1-15,19-20H

Upstream product

• 31491-21-1 2-phenyl-1,1-bis(trimethylsilyloxy)ethene 
• 538-51-2 benzylidene phenylamine 
• 101-97-3 Ethyl 2-phenylethanoate 
• 33993-35-0 cis-benzylideneaniline 
• 536-74-3 phenylacetylene 
• 201024-81-9 C,N-diphenylnitrone 
• 1137-96-8 N-(benzylidene)aniline N-oxide 
• 103-80-0 phenylacetyl chloride 
• 201230-82-2 carbon monoxide 
• 100-44-7 benzyl chloride 
• 100-52-7 benzaldehyde 
• 62-53-3 aniline 
• 103-82-2 phenylacetic acid 
• 3282-32-4 2-diazo-acetophenone 

Downstream Products

• 3210-15-9 N-phenyl-2,3-diphenylpropanamide 
• 73308-42-6 N-benzyl-N-phenyl-2-phenylacetamide 
• 538-51-2 benzylidene phenylamine 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 54746-64-4 N,2,3-triphenylacrylamide 

Relevant articles and documents

CuFe2O4nanoparticles catalyze the reaction of alkynes and nitrones for the synthesis of 2-azetidinones

CuFe2O4 nanoparticles acted as a highly efficient heterogeneous catalyst in the reaction of alkynes and nitrones (Kinugasa reaction) for the synthesis of various 2-azetidinones. In all cases, the reactions proceeded conveniently under mild conditions with good-to-excellent yields and with a wide range of functional-group tolerance. The catalyst could be separated readily using an external magnet. This journal is

A Revised Mechanism for the Kinugasa Reaction

Detailed kinetic analysis for the Cu(I)-catalyzed Kinugasa reaction forming β-lactams has revealed an anomalous overall zero-order reaction profile, due to opposing positive and negative orders in nitrone and alkyne, respectively. Furthermore, the reaction displays a second-order dependence on the catalyst, confirming the critical involvement of a postulated bis-Cu complex. Finally, reaction progress analysis of multiple byproducts has allowed a new mechanism, involving a common ketene intermediate to be delineated. Our results demonstrate that β-lactam synthesis through the Kinugasa reaction proceeds via a cascade involving (3 + 2) cycloaddition, (3 + 2) cycloreversion, and finally (2 + 2) cycloaddition. Our new mechanistic understanding has resulted in optimized reaction conditions to dramatically improve the yield of the target β-lactams and provides the first consistent mechanistic model to account for the formation of all common byproducts of the Kinugasa reaction.

Carbocation catalyzed carboxylic acid activation in Staudinger reaction for stereoselective synthesis of β-lactams

A novel strategy to synthesize stereoselective β-lactams has been disclosed via cyclopropenium-ion-catalyzed reaction of substituted acetic acids with aldimines under mild conditions. Products are formed in high yields (86–95%) and good diastereoselectivi