16483-98-0

Basic information

• Product Name: 2,3-Diphenyl-2H-azirine
• Synonyms: 2,3-Diphenyl-2H-azirine
• CAS NO: 16483-98-0
• Molecular Formula: C₁₄H₁₁N
• Molecular Weight: 193.2438
• Mol File: 16483-98-0.mol

Chemical Properties

• Boiling Point: 323.1°Cat760mmHg
• Flash Point: 141.3°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 0.000506mmHg at 25°C
• Refractive Index: 1.623
• PKA: 3.16±0.40(Predicted)
• CAS DataBase Reference: 2,3-Diphenyl-2H-azirine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Diphenyl-2H-azirine(16483-98-0)
• EPA Substance Registry System: 2,3-Diphenyl-2H-azirine(16483-98-0)

Safety Data

• Hazardous Substances Data: 16483-98-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,3-Diphenyl-2H-azirine is used as a reactive intermediate in organic synthesis for the preparation of various compounds. Its high reactivity allows for the formation of new chemical bonds and the synthesis of complex organic molecules.
Used in Chemical Research:
In the field of chemical research, 2,3-Diphenyl-2H-azirine is used to study the reactivity of aziridines and their potential applications in chemical reactions. Researchers investigate its behavior in different reaction conditions to understand its properties and explore new synthetic pathways.
Used in Pharmaceutical Industry:
2,3-Diphenyl-2H-azirine may be used as a building block or intermediate in the synthesis of pharmaceutical compounds. Its unique reactivity can be harnessed to create novel drug molecules with potential therapeutic applications.
Used in Material Science:
In material science, 2,3-Diphenyl-2H-azirine can be utilized in the development of new materials with specific properties. Its reactivity can contribute to the formation of polymers, coatings, or other materials with desired characteristics for various applications.

InChI:InChI=1/C14H11N/c1-3-7-11(8-4-1)13-14(15-13)12-9-5-2-6-10-12/h1-10,13H

Upstream product

• 5162-99-2 2,3-Diphenylthiirene 1,1-dioxide 
• 61588-68-9 N-(4,5-diphenyl-[1,2,3]triazol-1-yl)-benzamide 
• 61588-70-3 N-(4,5-diphenyl-1H-[1,2,3]triazol-1-yl)-4-methyl-benzamide 
• 451-40-1 phenyl benzyl ketone 
• 33785-81-8 1,2-diphenylethan-1-one N,N-dimethylhydrazone 
• 33777-82-1 N'-[1,2-Diphenyl-eth-(E)-ylidene]-N,N,N-trimethyl-hydrazinium; iodide 
• 4098-15-1 (1-azido-2-iodoethane-1,2-diyl)dibenzene 
• 140-29-4 phenylacetonitrile 
• 98-80-6 phenylboronic acid 
• 19690-01-8 1,2-diphenylethanone O-acetyl oxime 
• 588-59-0 stilbene 
• 61795-22-0 (1-azidoethene-1,2-diyl)dibenzene 
• 952-06-7 deoxybenzoin oxime 
• 103-30-0 (E)-1,2-diphenyl-ethene 

Downstream Products

• 2818-82-8 2-methyl-4,5-diphenyl-1H-imidazole 
• 261171-05-5 (E)-3-azido-1,2,3-triphenyl-1-propene 
• 1369425-94-4 C₂₈H₂₂N₂ 
• 1369425-93-3 C₂₈H₂₂N₂ 
• 100-47-0 benzonitrile 
• 185623-84-1 (1E,3Z)-1,3,4-triphenyl-2-aza-1,3-butadiene 
• 17799-61-0 3,4-dimethyl-2,5-diphenyl-1H-pyrrole 
• 74065-55-7 2,5-diphenyl-pyrrole-3,4-dicarboxylic acid 
• 93325-15-6 2,5-diphenyl-pyrrole-3-carboxylic acid 
• 13901-70-7 dimethyl 2,5-diphenyl-1H-pyrrole-3,4-dicarboxylate 
• 66092-09-9 diethyl 2,5-diphenyl-1H-pyrrole-3,4-dicarboxylate 
• 1629159-61-0 methyl 4-benzoyl-2,5-diphenyl-1H-pyrrole-3-carboxylate 
• 13901-74-1 methyl 2,5-diphenyl-1H-pyrrole-3-carboxylate 
• 65474-26-2 ethyl 2,5-diphenyl-1H-pyrrole-3-carboxylate 

Relevant articles and documents

Visible-Light-Promoted [3 + 2] Cycloaddition of 2H-Azirines with Quinones: Access to Substituted Benzo[f]isoindole-4,9-diones

A visible-light-promoteded [3 + 2] cycloaddition reaction of 2H-azirines with quinones has been developed under mild reaction conditions. The reaction provides a general and efficient strategy for the synthesis of the benzo[f]isoindole-4,9-diones scaffold

A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach

The reported flow-batch approach enables the easy preparation of 2H-azirines and their stereoselective transformation into highly functionalized NH-aziridines, starting from vinyl azides and organolithium compounds. The protocol has been developed using c

Harnessing in Situ Radical Oxygenation: Copper-Catalyzed Interrupted Azirine-Alkyne Ring-Expansion Reaction for the Synthesis of Pyrrolones

Here we report a novel interrupted azirine-alkyne ring-expansion reaction with molecular oxygen for the direct synthesis of highly functionalized pyrrolones enabled by copper catalysis. Mechanistic investigations indicate that the present three-component reaction proceeds via two copper-catalyzed sequential reactions, an azirine-ring-opening alkynylation and an amine-directed radical oxygenation, leading to the formation of interesting pyrrolone structures under mild conditions.

Copper-Catalyzed Three-Component Carboboronation of Allenes Using Highly Strained Cyclic Ketimines as Electrophiles

A diastereoselective copper and NHC-ligand-catalyzed three-component difunctionalization of allenes with bis(pinacolato)diboron and 2H-azirines to afford borylated allylaziridines is described. The reaction exhibits complete diastereoselectivity and good yields, and the further chlorination of the corresponding borylated products was also performed. It is believed that the high ring-strain force of 2H-azirines facilitates the reaction. More chemical transformations of borylated allylaziridines are also reported.

Photocatalytic Approach for Construction of 5,6-Dihydroimidazo[2,1- A[isoquinolines and Their Luminescent Properties

A visible-light-driven photoredox reaction of tetrahydroisoquinoline with 2H-azirines is described. 4,7-Bis(4-methoxyphenyl)benzo[c][1,2,5]thiadiazole, a benzothiadiazole (BTD) derived fluorophore, is used as an organic photoredox catalyst, and the reacti

Zinc-Enabled Annulation of Trifluorodiazoethane with 2 H-Azirines to Construct Trifluoromethyl Pyrazolines, Pyrazoles, and Pyridazines

A diethylzinc-promoted unconventional annulation reaction of 2,2,2-trifluorodiazoethane with 2H-azirines is described. This transformation involves two [3 + 2] cycloaddition steps and one dinitrogen extrusion process in one pot, thus giving a broad array

A Domino Approach for the Synthesis of 4-Carboxamide Oxazolines from Azirines

A regio- and diastereoselective ring-expansion reaction of N-acylaziridines is described for the synthesis of 4-carboxamide oxazolines using InCl3. A domino Ugi-Joullié/ring-expansion reaction of arylphenylazirines, isocyanides, and carboxylic

A copper-catalyzed insertion of sulfur dioxide: Via radical coupling

A copper-catalyzed three-component reaction of O-acyl oximes, DABCO·(SO2)2, and 2H-azirines under mild conditions has been achieved. This protocol provides an efficient route for the construction of various tetrasubstituted β-sulfonyl N-unprotected enamines in moderate to good yields with excellent stereoselectivity and regioselectivity. Notably, this method represents a rare example of 2H-azirines as useful synthons for β-functionalized N-unprotected enamines. Preliminary mechanistic studies indicate that the reaction proceeds through coupling of a sulfonyl radical and α-carbon radical via copper-catalyzed ring-opening C-C bond cleavage of O-acyl oxime and C-N bond cleavage of 2H-azirine with the insertion of sulfur dioxide.

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.

General Synthesis of Tri-Carbo-Substituted N2-Aryl-1,2,3-triazoles via Cu-Catalyzed Annulation of Azirines with Aryldiazonium Salts

The general synthesis of fully substituted N2-aryl-1,2,3-triazoles is hitherto challenging compared with that of the N1-aryl counterparts. Herein, we describe a Cu-catalyzed annulation reaction of azirines and aryldiazonium salts. This regiospecific metho