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Merck
CN

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

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About This Item

Empirical Formula (Hill Notation):
C12H13NO4
CAS Number:
104597-98-0
Molecular Weight:
235.24
NACRES:
NA.22
PubChem Substance ID:
24873860
UNSPSC Code:
12352005
MDL number:
MFCD06799020

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Product Name

Methyl (S)-(−)-N-Z-aziridine-2-carboxylate, 96%

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

SMILES string

COC(=O)C1CN1C(=O)OCc2ccccc2

InChI key

GTZJUBQWCWZING-NKUHCKNESA-N

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

Quality Level

200

Related Categories

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.

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.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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Certificates of Analysis (COA)

Lot/Batch Number
0000254864
0000254864
0000142125
0000141059
0000132149

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