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480754

tert-Butyl diazoacetate

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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impurities

≤15% dichloromethane

Quality Segment

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

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

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Flam. Liq. 3 - Repr. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

109.4 °F - closed cup

flash_point_c

43 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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