tert-Butyl diazoacetate

Name: <I>tert</I>-Butyl diazoacetate
Brand: ALDRICH

Synonym(s):

(tert-Butoxycarbonyl)diazomethane, 1,1-Dimethylethyl diazoacetate, 2-Diazoacetic acid tert-butyl ester, 2-Diazonio-1-[(2-methylpropan-2-yl)oxy]ethenolate, Diazoacetic acid 1,1-dimethylethyl ester, tert-Butyl α-diazoacetate

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About This Item

Linear Formula:

N₂CHCO₂C(CH₃)₃

CAS Number:

35059-50-8

Molecular Weight:

142.16

NACRES:

NA.22

PubChem Substance ID:

24871716

UNSPSC Code:

12352108

MDL number:

MFCD01318409

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Properties

impurities

≤15% dichloromethane

Quality Level

100

refractive index

n20/D 1.453 (lit.)

bp

51-53 °C/12 mmHg (lit.)

density

1.026 g/mL at 25 °C (lit.)

functional group

ester

storage temp.

2-8°C

SMILES string

CC(C)(C)OC(=O)C=[N+]=[N-]

InChI

1S/C6H10N2O2/c1-6(2,3)10-5(9)4-8-7/h4H,1-3H3

InChI key

JBVSBLLOZVDAAZ-UHFFFAOYSA-N

Description

General description

tert-Butyl diazoacetate can be used for numerous organic transformations, including cyclopropanation, insertion, and aziridine-forming reactions.

Application

tert-Butyl diazoacetate may be used for the preparation of tert-butyl 2-(4-chlorophenyl)cyclopropane-1-carboxylate with high enantioselectivity and trans-cis selectivity via cyclopropanation with 4-chlorostyrene in the presence of a chiral (salen)cobalt(III) bromide complex as a catalyst.

It is a key starting material in the total synthesis of manzacidin A. It can also be used in the synthesis of diastero- and enantioselective synthesis of 2-vinylcyclopropa[b]indolines from 2-vinylindoles.

New Diazoacetate Formulations