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516031

Sigma-Aldrich

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

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About This Item

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

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.)

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

Related Categories

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

Certificates of Analysis (COA)

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