696-18-4

Basic information

• Product Name: 1-phenylaziridine
• Synonyms: 1-phenylaziridine
• CAS NO: 696-18-4
• Molecular Formula: C₈H₉N
• Molecular Weight: 119.16376
• EINECS: 211-789-8
• Mol File: 696-18-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 195.3°C at 760 mmHg
• Flash Point: 64.4°C
• Appearance: /
• Density: 1.098g/cm³
• Vapor Pressure: 0.422mmHg at 25°C
• Refractive Index: 1.602
• CAS DataBase Reference: 1-phenylaziridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenylaziridine(696-18-4)
• EPA Substance Registry System: 1-phenylaziridine(696-18-4)

Safety Data

• Hazardous Substances Data: 696-18-4(Hazardous Substances Data)

Usage

General Description

1-Phenylaziridine, also known as phenylaziridine or 2-phenylaziridine, is an organic compound with the molecular formula C8H9N. It is a cyclic amine with a three-membered aziridine ring that contains a phenyl group attached to the nitrogen atom. 1-Phenylaziridine is a colorless liquid at room temperature and is highly reactive due to the strain in the aziridine ring. It is primarily used as a building block in organic synthesis, where it serves as a versatile precursor for various pharmaceuticals, agrochemicals, and other fine chemicals. Additionally, 1-phenylaziridine is also used as a reagent in the synthesis of chiral ligands and catalysts for asymmetric catalysis. However, it is important to handle and use 1-phenylaziridine with caution due to its potential health hazards and irritant properties.

InChI:InChI=1/C8H9N/c1-2-4-8(5-3-1)9-6-7-9/h1-5H,6-7H2

Upstream product

• 42059-30-3 1-azido-2-iodoethane 
• 873-51-8 phenylborondichloride 
• 699-11-6 N-phenyl-2-bromoethylamine 
• 122-98-5 2-Anilinoethanol 
• 41210-94-0 2-hydroxylethylphenylamine hydrochloride 
• 115011-74-0 N-phenyloxazolidin-5-one 
• 103-01-5 N-Phenylglycine 
• 20503-92-8 3-phenyl-oxazolidine 
• 874-78-2 N-(2-chloroethyl)aniline hydrochloride 
• 1005-66-9 N-(β-bromoethyl)aniline hydrobromide 
• 935-06-8 N-(2-chloroethyl)aniline 

Downstream Products

• 80865-94-7 N-<2-(Methylthio)ethyl>aniline 
• 703-56-0 N-phenyl-2-oxazolidinone 
• 613-39-8 1,4-diphenyl-piperazine 
• 80865-98-1 N-<1-phenyl-3-(phenylamino)propyl>aniline 
• 23099-29-8 4,4-Dimethyl-1-phenylaminopentan-3-ol 
• 62750-11-2 ethyl 3-phenylaminopropionate 
• 103-69-5 N-ethyl-N-phenylamine 
• 208394-99-4 N-phenylaziridine-dicarbonyl-η(5)-cyclopentadienyl-manganese(I) 
• 174261-98-4 N-(4'-chlorobiphenyl-4-carbonyl)-2(R)-phenyl-aziridine 
• 5679-75-4 (Z)-N-(3-phenyloxazolidin-2-ylidene)benzenamine 
• 728-24-5 1,3-diphenyl-2-imidazolidone 
• 6200-49-3 3-phenyl-2-phenylimino-1,3-thiazolidine 
• 36916-67-3 (2-chloro-ethyl)-(3-phenyl-thiazolidin-2-ylidene)-amine 
• 22258-76-0 N-(2-benzothiazol-2-ylsulfanyl-ethyl)-aniline 

Relevant articles and documents

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Formation of azomethine ylids by thermolysis of oxazolidines. Study of the reaction in solution and in the gaseous phase

Thermolysis of oxazolidines leads to azomethine ylids via cycloreversion.In the liquid phase, these intermediates then give 1-3 dipolar cycloaddition; in the gaseous phase, they lead to aziridines.With an alkyl group in position 2, we observed also the formation of enamines.The effect of substituents on both the cycloreversion reaction and the evolution of azomethine ylids was studied.The mechanism of the process tautomerism aziridine -> azomethine ylid -> enamine is discussed.Keywords - azomethine ylids / oxazolidines / cycloreversion / aziridines / enamines / tautomerism

Organoboranes for synthesis. Reaction of organoboranes with representative organic azides. A general stereospecific synthesis of secondary amines and N-substituted aziridines

Reaction of trialkylboranes with organic azides in refluxing xylene, followed by hydrolysis, leads to good yields of secondary amines. This reaction is highly dependent on the steric effects around both boron and the azide moiety. The reaction becomes much slower when the steric bulk of one of the reagents is increased and fails when both are hindered. The dialkylchloroboranes are more reactive than trialkylboranes and provide better yields of the desired secondary amines with a11 azides tested. The alkyldichloroboranes react with organic azides at temperatures between room temperature and 60°C and produce excellent yields of secondary amines. Furthermore, the stereochemistry of the original carbon-boron bond is retained. The mechanism of these reactions is discussed and the reaction applied to the synthesis of N-alkyl- and N-arylaziridines.