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

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

Uses

Used in Organic Synthesis:
2-Phenyl-3H-azirine-3-carboxylic acid methyl ester is used as a reagent in organic synthesis for the preparation of various compounds. Its unique structure and reactivity make it a valuable component in creating complex organic molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-Phenyl-3H-azirine-3-carboxylic acid methyl ester is employed as an intermediate for the synthesis of pharmaceuticals and biologically active molecules. Its properties allow for the development of new drugs and therapeutic agents.
Used in Pharmaceutical Production:
2-Phenyl-3H-azirine-3-carboxylic acid methyl ester is used as a building block in the preparation of pharmaceuticals. Its incorporation into drug molecules can contribute to the discovery of novel treatments and medications.
Used in Agrochemical Production:
2-Phenyl-3H-azirine-3-carboxylic acid methyl ester is also utilized as a starting material for the production of agrochemicals. Its application in this industry aids in the development of new pesticides, herbicides, and other agricultural chemicals to improve crop protection and yield.
Used in the Production of Fine Chemicals:
2-Phenyl-3H-azirine-3-carboxylic acid methyl ester is employed in the synthesis of fine chemicals, which are high-purity, specialized chemicals used in various industries, including research, pharmaceuticals, and cosmetics. Its versatility and reactivity contribute to the creation of high-quality specialty products.

Upstream product

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

• 89649-15-0 3-Phenyl-6a-pyrrolidin-1-yl-1,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrole-2-carboxylic acid methyl ester 
• 89649-16-1 3-Phenyl-7a-pyrrolidin-1-yl-3a,4,5,6,7,7a-hexahydro-1H-indole-2-carboxylic acid methyl ester 
• 25755-94-6 methyl 2,5-diphenyloxazole-4-carboxylate 
• 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.

A new hypervalent iodine(iii/v) oxidant and its application to the synthesis of 2: H -azirines

The reaction of o-nitroiodobenzene and mCPBA in acetic acid was found to afford a novel hypervalent iodine compound, in the structure of which both iodine(iii) and iodine(v) moieties coexist. The nitro groups at the ortho phenyl positions were found to be crucial in stabilizing this uncommon structure. This novel hypervalent iodine(iii/v) oxidant is proved to be effective in realizing the synthesis of 2-unsubstitued 2H-azirines via intramolecular oxidative azirination, which could not be efficiently achieved by the existing known hypervalent iodine reagents.

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-

Metal-Catalyzed Isomerization of 5-Heteroatom-Substituted Isoxazoles as a New Route to 2-Halo-2 H -azirines

A convenient gram-scale method for the preparation of 2-halo-2 H -azirine-2-carboxylic acid esters, thioesters and amides via metal-catalyzed isomerization of 5-heteroatom-substituted 4-haloisoxazoles is developed. The formation of the esters and amides is efficiently catalyzed by Rh 2 (Piv) 4, while FeCl 2 ·4H 2 O is the catalyst of choice for the synthesis of the thioesters. In addition, rhodium catalysis is successfully applied in the synthesis of azirine-2-carboxylates from non-halogenated 5-alkoxyisoxazoles.

Photocycloaddition of aromatic and aliphatic aldehydes to isoxazoles: Cycloaddition reactivity and stability studies

The first photocycloadditions of aromatic and aliphatic aldehydes to methylated isoxazoles are reported. The reactions lead solely to the exo-adducts with high regio- and diastereoselectivities. Ring methylation of the isoxazole substrates is crucial for high conversions and product stability. The 6-arylated bicyclic oxetanes 9a-9c were characterized by X-ray structure analyses and showed the highest thermal stabilities. All oxetanes formed from isoxazoles were highly acid-sensitive and also thermally unstable. Cleavage to the original substrates is dominant and the isoxazole derived oxetanes show type T photochromism.

Exploiting the chemistry of strained rings: Synthesis of indoles via domino reaction of aryl iodides with 2 H-azirines

(Equation Presented). The highly strained 2H-azirine ring system has been the source of considerable theoretical and synthetic work. The reaction of these strained heterocycles with transition metals has been documented to give rise to ring opening and subsequent formation of varied heterocycles. An interesting domino reaction is described wherein the strained bicyclic alkene, norbornene, mediates the reaction of 2H-azirines with aryl iodides under palladium catalysis to provide indole or polycyclic dihydroimidazole heterocycles.

Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates

The dehalogenation of 2-halo-3-phenyl-2H-azirine-2-carboxylates is described. Using sodium borohydride and tributyltin hydride 3-phenyl-2H-azirine-2-carboxylates were obtained in moderate yields. The synthesis of a new 2-bromo-2H-azirines with a chiral au

Iron dichloride induced isomerization or reductive cleavage of isoxazoles: A facile synthesis of 2-carboxy-azirines

5-Alkoxy-isoxazoles and N,N-disubstituted-5-isoxazolamines were found to isomerize to azirine derivatives by the use of iron dichloride as catalyst. On the contrary 5-alkyl- and 5-aryl-isoxazoles in the presence of the same salt, undergo reductive cleavage to enaminoketones. A common reaction intermediate is proposed.

Conversion of aziridine-2-carboxylic esters into 2H-azirine-2-carboxylic esters

Aziridine-2-carboxylic esters 1 were converted into 2H-azirine-2-carboxylic esters 4 in two steps.Treatment of 1 with tert-butyl hypochlorite in ether gave smooth N-chlorination.Reaction of N-chloroaziridines 2 with 1,8-diazabicycloundec-7-ene (DBU