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516031

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

Name: Methyl (<I>S</I>)-(−)-<I>N</I>-Z-aziridine-2-carboxylate
Brand: ALDRICH

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

Chiral Catalysts & Ligands

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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

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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