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

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

Downstream Products

• 41414-81-7 2-phenyl-2-(2-phenyl-[1,3]dithian-2-yl)-aziridine 
• 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 
• 31594-55-5 2-phenyl-4-carbomethoxy-Δ¹-pyrroline 
• 101402-44-2 2-phenyl-3-carbomethoxy-Δ¹-pyrroline 
• 31594-54-4 2-phenyl-4-carbomethoxy-4-methyl-Δ¹-pyrroline 
• 31594-53-3 2-phenyl-3-carbomethoxy-3-methyl-Δ¹-pyrroline 
• 52179-69-8 methyl 2-phenyl-1H-pyrrole-3-carboxylate 

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.

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.

Efficient Far-Red/Near-IR Absorbing BODIPY Photocages by Blocking Unproductive Conical Intersections

Photocages are light-sensitive chemical protecting groups that give investigators control over activation of biomolecules using targeted light irradiation. A compelling application of far-red/near-IR absorbing photocages is their potential for deep tissue activation of biomolecules and phototherapeutics. Toward this goal, we recently reported BODIPY photocages that absorb near-IR light. However, these photocages have reduced photorelease efficiencies compared to shorter-wavelength absorbing photocages, which has hindered their application. Because photochemistry is a zero-sum competition of rates, improvement of the quantum yield of a photoreaction can be achieved either by making the desired photoreaction more efficient or by hobbling competitive decay channels. This latter strategy of inhibiting unproductive decay channels was pursued to improve the release efficiency of long-wavelength absorbing BODIPY photocages by synthesizing structures that block access to unproductive singlet internal conversion conical intersections, which have recently been located for simple BODIPY structures from excited state dynamic simulations. This strategy led to the synthesis of new conformationally restrained boron-methylated BODIPY photocages that absorb light strongly around 700 nm. In the best case, a photocage was identified with an extinction coefficient of 124000 M-1 cm-1, a quantum yield of photorelease of 3.8%, and an overall quantum efficiency of 4650 M-1 cm-1 at 680 nm. This derivative has a quantum efficiency that is 50-fold higher than the best known BODIPY photocages absorbing >600 nm, validating the effectiveness of a strategy for designing efficient photoreactions by thwarting competitive excited state decay channels. Furthermore, 1,7-diaryl substitutions were found to improve the quantum yields of photorelease by excited state participation and blocking ion pair recombination by internal nucleophilic trapping. No cellular toxicity (trypan blue exclusion) was observed at 20 μM, and photoactivation was demonstrated in HeLa cells using red light.

Mono-iodine substituted BODIPY compound and preparation method and application thereof

The invention belongs to the field of drug synthesis, relates to a BODIPY compound shown as a general formula (I), in particular to a mono-iodine substituted BODIPY compound and a preparation method and application thereof in pharmacy. Tests show that the