169889-24-1

Basic information

• Product Name: 2H-Azirine-2-carboxylicacid,3-propyl-,methylester,(R)-(9CI)
• Synonyms: 2H-Azirine-2-carboxylicacid,3-propyl-,methylester,(R)-(9CI)
• CAS NO: 169889-24-1
• Molecular Formula: C7H11NO2
• Molecular Weight: 141.17
• Product Categories: CARBOXYLICESTER
• Mol File: 169889-24-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 184.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.14±0.1 g/cm3(Predicted)
• PKA: 2.78±0.40(Predicted)
• CAS DataBase Reference: 2H-Azirine-2-carboxylicacid,3-propyl-,methylester,(R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Azirine-2-carboxylicacid,3-propyl-,methylester,(R)-(9CI)(169889-24-1)
• EPA Substance Registry System: 2H-Azirine-2-carboxylicacid,3-propyl-,methylester,(R)-(9CI)(169889-24-1)

Safety Data

• Hazardous Substances Data: 169889-24-1(Hazardous Substances Data)

Usage

Heterocyclic ring

Contains one nitrogen atom and two carbon atoms

Use

Organic synthesis, starting material for pharmaceuticals and agrochemicals, building block for fine chemicals

Stereochemical configuration

(R)-(9CI) designation indicates specific stereochemistry at chiral center

Applications

Diverse applications in chemical and pharmaceutical industries

Upstream product

• 30414-54-1 methyl 3-oxohexanoate 
• 948292-48-6 3-(4-bromophenyl)-1H-pyrazole-5-carboxylic acid ethyl ester 
• 127127-37-1 Methyl (2R,3S)-(-)-3-propylaziridine-2-carboxylate 
• 497237-96-4 methyl (2S,3S)-1-[(S)-4-methylbenzenesulfinyl]-3-propylaziridine-2-carboxylate 
• 497238-02-5 methyl (2S,3S)-3-propylaziridine-2-carboxylate 

Downstream Products

• 497238-06-9 methyl (2S,3R)-3-methyl-3-propylaziridine-2-carboxylate 

Relevant articles and documents

Organocatalyzed nucleophilic addition of pyrazoles to 2: H -azirines: Asymmetric synthesis of 3,3-disubstituted aziridines and kinetic resolution of racemic 2 H -azirines

The first organocatalytic asymmetric nucleophilic addition of arylpyrazoles to 2H-azirines and kinetic resolution of racemic 2H-azirines have been realized. Chiral aziridines were obtained with up to 98% yields and up to 99.9% ee. Meanwhile, simply changing the ratio of reactants, optically active 2H-azirines were recovered in good yields with excellent enantioselectivities.

Convenient synthesis of optically active 2H-azirine-2-carboxylic esters by Swern oxidation of aziridine-2-carboxylic esters

The synthesis of optically active 2H-azirine-2-carboxylic esters was achieved by Swern oxidation of the corresponding aziridine-carboxylic esters. For both trans and cis aziridine esters this oxidation gives a regioselective introduction of the double bond which is not in conjugation with the ester function. The methyl ester of ent-Azirinomycin was prepared in this manner.