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:
Molecular Weight:
235.24
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Assay:
96%
Quality Level
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
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves
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Global Trade Item Number
| SKU | GTIN |
|---|---|
| 516031-5G | 04061837727672 |