7654-06-0

Basic information

• Product Name: 3-phenyl-2H-azirene
• Synonyms: 2H-azirine, 3-phenyl-; 3-Phenyl-2H-azirene; 3-Phenyl-2H-azirine
• CAS NO: 7654-06-0
• Molecular Formula: C₈H₇N
• Molecular Weight: 117.1479
• Mol File: 7654-06-0.mol

Chemical Properties

• Boiling Point: 190.1°C at 760 mmHg
• Flash Point: 60.1°C
• Density: 1.07g/cm³
• Vapor Pressure: 0.765mmHg at 25°C
• Refractive Index: 1.603
• CAS DataBase Reference: 3-phenyl-2H-azirene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-2H-azirene(7654-06-0)
• EPA Substance Registry System: 3-phenyl-2H-azirene(7654-06-0)

Safety Data

• Hazardous Substances Data: 7654-06-0(Hazardous Substances Data)

Upstream product

• 16717-64-9 1-azidostyrene 
• 1199-01-5 2-phenylazlactone 
• 100-42-5 styrene 
• 4098-17-3 1-(1-azido-2-iodoethyl)benzene 
• 1147550-11-5 ammonium thiocyanate 
• 16722-99-9 β-azidostyrene 
• 613-91-2 acetophenone oxime 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 29847-04-9 1-(1-azido-2-bromoethyl)benzene 
• 1923-01-9 trimethyl(1-phenylvinyl)silane 

Downstream Products

• 41414-81-7 2-phenyl-2-(2-phenyl-[1,3]dithian-2-yl)-aziridine 
• 36879-73-9 4-phenyl-5-p-tolyl-2,5-dihydro-oxazole 
• 36879-74-0 4-phenyl-5-propyl-2,5-dihydro-oxazole 
• 4190-14-1 N-(2-oxo-2-phenylethyl)benzamide 
• 33893-01-5 2,4-dibenzhydrylidene-6-phenyl-3,5-dioxa-1-aza-bicyclo[4.1.0]heptane 
• 60794-55-0 (5-phenyl-thiazol-2-yl)-pyridin-2-yl-amine 
• 37005-14-4 3,3,3',3'-tetramethyl-2,2'-(6-phenyl-3,5-dioxa-1-aza-bicyclo[4.1.0]heptane-2,4-diylidene)-bis-butyronitrile 
• 36879-85-3 4-phenyl-2H-oxazol-5-one 
• 66785-82-8 9a,20-diphenyl-5,6,9,9a,15,16-hexahydro-8H-naphtho[1,2-b]naphtho[2',1':5,6][1,4,3]oxathiazino[2,3-g][1,4,5,8]oxathiadiazecine 7,7,17,17-tetraoxide 
• 43154-01-4 (RS)-2,4-diphenyl-4-((SR)-2-phenyl-aziridin-2-yl)-4H-oxazol-5-one 
• 36879-72-8 4,5-diphenyl-3-oxazoline 
• 86947-71-9 3-Methyl-1,6-diphenyl-3a,4-dihydro-1H-1,2,5-triaza-6a-phospha-pentalene 
• 31594-51-1 2-phenyl-4-cyano-Δ¹-pyrroline 
• 106762-05-4 2-phenyl-3-cyano-Δ¹-pyrroline 

Relevant articles and documents

AZIRIDINE-AZIRINE TRANSFORMATION BY 1,2-ELIMINATION via AN AZIRIDINYL CARBANION INTERMEDIATE

Desilylation of aziridine (5) by treatment with cesium fluoride in dry dimethylformamide in the presence of benzaldehyde followed by oxidation with manganese dioxide gives the benzoylaziridine (11) in 80percent yield: in the absence of benzaldehyde, the presumed aziridinyl carbanion intermediate (9) gives the aziridine (7) (58percent).

Ni-Catalyzed Redox-Neutral Ring-Opening/Radical Addition/Ring-Closing Cascade of Cycloketone Oxime Esters and Vinyl Azides

A nickel-catalyzed iminyl radical-triggered C-C bond cleavage/radical addition/cyclization cascade of oxime esters and vinyl azides is described. This protocol enables rapid access to the cyanoalkylated 3,4-dihydro-2H-pyrroles and phenanthridines in good

Copper-Catalyzed Sulfonyl Azide-Alkyne Cycloaddition Reactions: Simultaneous Generation and Trapping of Copper-Triazoles and -Ketenimines for the Synthesis of Triazolopyrimidines

First simultaneous generation and utilization of both copper-triazole and -ketenimine intermediates in copper-catalyzed sulfonyl azide-alkyne cycloaddition reactions is achieved for the one-pot synthesis of triazolopyrimidines via a novel copper-catalyzed

Carbamoyl Anion Addition to Azirines

The addition of carbamoyl anions to azirines affords synthetically useful 2-aziridinyl amide building blocks. The reaction scope was explored with respect to both formamide and azirine, and the addition was found to be highly diastereoselective. A one-pot conversion of a ketoxime to an aziridinyl amide was demonstrated. The method was employed to incorporate an aziridine residue into a dipeptide segment.

Copper-Catalyzed Ring-Expansion Cascade of Azirines with Alkynes: Synthesis of Multisubstituted Pyridines at Room Temperature

The first intermolecular ring-expansion cascade of azirines with alkynes for the synthesis of pyridines, enabled by a copper/triethylamine catalytic system via simultaneous generation and utilization of yne-enamine and skipped-yne-imine intermediates, is reported. Experimental as well as computational mechanistic studies revealed that the role of triethylamine is crucial in deciding the reaction pathway toward the pyridine products. This process offers a novel, one-step, direct, and practical strategy for the rapid construction of highly substituted pyridines under exceedingly mild conditions, and an installed alkyne functionality.

A general strategy to optimize the performance of aza-BODIPY-based probes for enhanced photoacoustic properties

In this chapter, we describe a generalizable strategy to obtain a high PA output platform that is optimized for ratiometric imaging. Our approach entails conformationally restricting pendant aryl rings on the aza-BODIPY core to enhance orbital overlap which consequently increases the extinction coefficient. This strategy can potentially be applied to other dye platforms to enhance their signal intensity. We provide detailed protocols for the synthesis, in vitro characterization, and in vivo application.

Copper-catalyzed [2+3]-annulation of N-H imines with vinyl azides: Access to polyaryl 2: H -imidazoles

A practical method for the synthesis of 2H-imidazoles via a [2+3] annulation of N-H imines with vinyl azides using a copper catalyst is developed. In this conversion, environmentally friendly oxygen is used as the sole oxidant and N2 and H2O are the only by-products. The catalytic transformation, operating under mild conditions, is operationally simple and is considered as a readily available catalytic system having good substrate and functional compatibility with high atom-efficiency without the need for additional ligands or additives.

Synthesis of Isoquinoline Derivatives via Palladium-Catalyzed C?H/C?N Bond Activation of N-Acyl Hydrazones with α-Substituted Vinyl Azides

A palladium-catalyzed cyclization of N-acetyl hydrazones with vinyl azides has been developed. Various substituted isoquinolines, including diverse fused isoquinolines can be prepared via this protocol in moderate to good yields. Mechanistic studies suggest that α-substituted vinyl azide serves as an internal nitrogen source. Also, C?H bond activation and C?N bond cleavage have been realized using hydrazone as directing group. (Figure presented.).

Self-Catalyzed Rapid Synthesis of N-Acylated/ N-Formylated α-Aminoketones and N-Hydroxymethylated Formamides from 3-Aryl-2 H-Azirines and 2-Me/Ph-3-Aryl-2 H-Azirines

A rapid and effective method has been established for the synthesis of N-acylated α-aminoketone derivatives by the reaction of 3-aryl-2H-azirines and highly substituted 2-Me/Ph-3-aryl-2H-azirines with various carboxylic acids under ambient air within 10 min at room temperature. N-Trifluoroacetylated α-aminoketones with different substituents have been reported in the presence of trifluoroacetic acid. This protocol is equally effective to synthesize N-formylated α-aminoketone and N-hydroxymethylated formamide derivatives.

Bonded- A nd discreted-Lindqvist hexatungstate-based copper hybrids as heterogeneous catalysts for the one-pot synthesis of 2-phenylquinoxalines: Via 2-haloanilines with vinyl azides or 3-phenyl-2 H-azirines

One bonded- A nd one discreted-Lindqvist hexatungstate-based copper hybrids (Cu-POMs) ([Cu2(O)OH (phen)2]2[W6O19]?6H2O (1) and [Cu2(phen)4Cl] [HW6O19]?2H2O (2) (phen = 1,10-phenanthroline)) were controllably synthesized and routinely characterized. Cu-POM