18709-45-0

Basic information

• Product Name: 2-Phenyl-3H-azirine-3-carboxylic acid methyl ester
• Synonyms: 2-Phenyl-3H-azirine-3-carboxylic acid methyl ester;3-Phenyl-2H-azirine-2-carboxylic acid methyl ester;Methyl 3-Phenyl-2H-azirine-2-carboxylate
• CAS NO: 18709-45-0
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• Mol File: 18709-45-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 262.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.21±0.1 g/cm3(Predicted)
• PKA: 1.68±0.40(Predicted)
• CAS DataBase Reference: 2-Phenyl-3H-azirine-3-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenyl-3H-azirine-3-carboxylic acid methyl ester(18709-45-0)
• EPA Substance Registry System: 2-Phenyl-3H-azirine-3-carboxylic acid methyl ester(18709-45-0)

Safety Data

• Hazardous Substances Data: 18709-45-0(Hazardous Substances Data)

Usage

General Description

2-Phenyl-3H-azirine-3-carboxylic acid methyl ester is a compound with the molecular formula C11H9NO2. It is a methyl ester derivative of 2-phenyl-3H-azirine-3-carboxylic acid, which is a cyclic organic compound with a reactive three-membered ring containing nitrogen. This chemical is used in organic synthesis and medicinal chemistry as a reagent and intermediate for the synthesis of various compounds. It is also used as a building block for the preparation of pharmaceuticals and biologically active molecules. Additionally, it can be employed as a starting material for the production of agrochemicals and other fine chemicals.

Upstream product

• 127053-48-9 rac Methyl (2R^*,3S^*)-3-phenyl-1H-aziridine-2-carboxylate 
• 67-56-1 methanol 
• 70272-01-4 methyl 3-amino-3-phenylacrylate 
• 3356-89-6 3-phenyl-5-chloroisoxazole 
• 1076-59-1 3-phenyl-4H-isoxazol-5-one 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 367967-56-4 methyl 2-bromo-3-phenyl-2H-azirine-2-carboxylate 
• 18803-02-6 5-methoxy-3-phenylisoxazole 
• 140429-60-3 methyl 1-chloro-trans-3-phenylaziridine-2-carboxylate 

Downstream Products

• 89649-16-1 3-Phenyl-7a-pyrrolidin-1-yl-3a,4,5,6,7,7a-hexahydro-1H-indole-2-carboxylic acid methyl ester 
• 163061-47-0 (S)-(+)-2-carbomethoxy-3-phenyl-2H-azirine 

Relevant articles and documents

A novel approach to 5: H -pyrazino[2,3- b] indoles via annulation of 3-diazoindolin-2-imines with 2 H -azirines or 5-alkoxyisoxazoles under Rh(II) catalysis

A novel one-step method for the preparation of 5H-pyrazino[2,3-b]indoles with different substitution patterns in all rings of the tricyclic system via the Rh2(OAc)4-catalyzed reaction of 2H-azirines with 3-diazoindolin-2-imines is reported. Alkyl 5H-pyrazino[2,3-b]indole-3-carboxylates were also prepared by a one-pot procedure from synthetic equivalents of alkyl 2H-azirine-2-carboxylates, 5-alkoxyisoxazoles. The reactions provide the first examples of the use of Rh(ii) catalysis for intermolecular annulations with 2H-azirines and isoxazoles.

Nucleophile-Induced Rearrangement of 2 H-Azirine-2-carbonyl Azides to 2-(1 H-Tetrazol-1-yl)acetic Acid Derivatives

2H-Azirine-2-carbonyl azides undergo a rearrangement into derivatives of 2-(1H-tetrazol-1-yl)acetic acid when interacting with O- and S-nucleophiles at room temperature. The reaction is catalyzed by tertiary amines or hydrazoic acid. The reaction with primary alcohols and phenols gives alkyl/aryl 2-(1H-tetrazol-1-yl)acetates. Thiophenols react with 2H-azirine-2-carbonyl azides to afford S-aryl 2-(1H-tetrazol-1-yl)ethanethioates. The mechanism of the nucleophile-induced rearrangement of 2H-azirine-2-carbonyl azides is discussed on the basis of DFT calculations as well as kinetic and 15N labeling experiments.

An Azirine Strategy for the Synthesis of Alkyl 4-Amino-5-(trifluoromethyl)-1 H -pyrrole-2-carboxylates

1-(3,3,3-Trifluoro-2,2-dihydroxypropyl)pyridin-1-ium bromide serves as a trifluoromethyl-containing building block for the preparation of trifluoromethyl-substituted aminopyrroles based on the 2 H -azirine ring expansion strategy. The primary products, 3-