516031

Methyl (S)-(−)-N-Z-aziridine-2-carboxylate

96%

• Synonym(s): (2S)-1,2-Aziridinedicarboxylic acid 2-methyl 1-(phenylmethyl) ester, (S)-N-Cbz-aziridine-2-carboxylic acid methyl ester, 1-Benzyl 2-methyl (S)-(−)-1,2-aziridinedicarboxylate, Methyl (S)-N-Cbz-aziridine-2-carboxylate
• Empirical Formula (Hill Notation): C₁₂H₁₃NO₄
• CAS Number: 104597-98-0
• Molecular Weight: 235.24
• MDL number: MFCD06799020
• UNSPSC Code: 12352005
• PubChem Substance ID: 24873860
• NACRES: NA.22

Properties

• assay: 96%
• optical activity: [α]20/D −25°, c = 1 in toluene
• refractive index: n20/D 1.519 (lit.)
• bp: 160-165 °C/2 mmHg (lit.)
• density: 1.19 g/mL at 25 °C (lit.)
• functional group: ester; phenyl
• SMILES string: COC(=O)C1CN1C(=O)OCc2ccccc2
• InChI: 1S/C12H13NO4/c1-16-11(14)10-7-13(10)12(15)17-8-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3/t10-,13?/m0/s1
• InChI key: GTZJUBQWCWZING-NKUHCKNESA-N

Description

General description

Methyl (S)-(−)-N-Z-aziridine-2-carboxylate is commonly used as an electrophilic aziridination reagent in organic synthesis. It is a chiral bicyclic lactam reagent that can be used for the synthesis of chiral aziridines from alkenes. The reagent is particularly useful in the synthesis of chiral building blocks.

Application

Methyl (S)-(−)-N-Z-aziridine-2-carboxylate can be used as a reactant in the total synthesis of α-C-mannosyltryptophan (C-Man-Trp), a naturally occurring C-glycosylamino acid. It is also used in the preparation of optically active aziridine derivatives.

Safety Information

• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves