33474-61-2

Basic information

• Product Name: TRANS-2,3-DIPHENYL-1-PHTHALIMIDO- AZIRDINE
• Synonyms: TRANS-2,3-DIPHENYL-1-PHTHALIMIDO- AZIRDINE;trans-2,3-Diphenyl-1-phthalimidoaziridine;trans-N-(2,3-diphenylaziridin-1-yl)phthalimide
• CAS NO: 33474-61-2
• Molecular Formula: C₂₂H₁₆N₂O₂
• Molecular Weight: 340.37464
• EINECS: 251-537-4
• Mol File: 33474-61-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 174-176 °C
• Boiling Point: 513.9°Cat760mmHg
• Flash Point: 231.7°C
• Appearance: /
• Density: 1.367g/cm³
• Vapor Pressure: 1.13E-10mmHg at 25°C
• Refractive Index: 1.711
• CAS DataBase Reference: TRANS-2,3-DIPHENYL-1-PHTHALIMIDO- AZIRDINE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-2,3-DIPHENYL-1-PHTHALIMIDO- AZIRDINE(33474-61-2)
• EPA Substance Registry System: TRANS-2,3-DIPHENYL-1-PHTHALIMIDO- AZIRDINE(33474-61-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 33474-61-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C22H16N2O2/c25-21-17-13-7-8-14-18(17)22(26)24(21)23-19(15-9-3-1-4-10-15)20(23)16-11-5-2-6-12-16/h1-14,19-20H

Upstream product

• 103-30-0 (E)-1,2-diphenyl-ethene 
• 1875-48-5 N-aminophthalamide 
• 37802-08-7 1a-acetyl-1-phthalimidoamino-1a,6b-dihydro-1H-benzofuro<2,3-b>azirine 
• 100-52-7 benzaldehyde 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 645-49-8 cis-stilben 

Downstream Products

• 28161-60-6 trans-1-amino-2,3-diphenylaziridine 
• 1370658-50-6 N-[(E)-1-(benzylideneamino)benzyl]phthalimide 
• 134340-44-6 (1-Benzyl-piperidin-4-ylidene)-((2S,3S)-2,3-diphenyl-aziridin-1-yl)-amine 
• 134340-43-5 (1,4-Dioxa-spiro[4.5]dec-8-ylidene)-((2S,3S)-2,3-diphenyl-aziridin-1-yl)-amine 
• 134340-42-4 ((2S,3S)-2,3-Diphenyl-aziridin-1-yl)-[1-methyl-3-phenyl-prop-(E)-ylidene]-amine 
• 134340-41-3 (4-tert-Butyl-cyclohexylidene)-((2S,3S)-2,3-diphenyl-aziridin-1-yl)-amine 
• 134340-45-7 ((2S,3S)-2,3-Diphenyl-aziridin-1-yl)-non-(E)-ylidene-amine 

Relevant articles and documents

Thermal rearrangement of 2,3-diaryl-1-phthalimidoaziridines

2,3-Diaryl-1-phthalimidoaziridines and 2,3-diaryl-1-phthalimidoaziridine-2-carbonitriles were found to readily undergo thermal rearrangement into imines via 1,2-migration of the phthalimido group and accompanying C-C bond cleavage. Isomerization proceeds regioselectively with preferable migration to the electron-deficient carbon atom. Interestingly, this reaction was found to predominate even in the presence of dipolarophiles.

Aryl iodide mediated aziridination of alkenes

(Chemical Equation Presented) Aryl iodide mediated aziridination of a variety of alkenes with N-aminophthalimide under mild conditions (m-CPBA, K 2CO3, CH2Cl2, 25°C) was achieved in moderate to good yields (up to 94%). By recovering the aryl iodide, a recyclable system is developed with product yield over 79% attained for the aziridination of trans-1,2-diphenylethylene.

Lithium Aluminum Hydride Reduction of N-Aziridinylimines to Hydrocarbons

The hydride reduction of ketone and aldehyde N-aziridinylimines is reported.Unlike most other hydrazone reductions, the reaction proceeds at room temperature under non-acidic conditions, providing an unusually mild carbonyl-to-methylene conversion.