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Sigma-Aldrich

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

96%

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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:
Molecular Weight:
235.24
MDL number:
PubChem Substance ID:
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

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This Item
79257839230877970
bp

160-165 °C/2 mmHg (lit.)

bp

-

bp

-

bp

55-56 °C/2.5 mmHg (lit.)

density

1.19 g/mL at 25 °C (lit.)

density

1.072 g/mL at 25 °C

density

-

density

1.045 g/mL at 20 °C (lit.)

refractive index

n20/D 1.519 (lit.)

refractive index

n20/D 1.452

refractive index

-

refractive index

n20/D 1.513, n20/D 1.5145 (lit.)

optical activity

[α]20/D −25°, c = 1 in toluene

optical activity

-

optical activity

[α]24/D −63.0°, c = 2.5 in methanol

optical activity

[α]20/D −10.5±0.5°, neat

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.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves


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