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166804

Sigma-Aldrich

Dibenzyl azodicarboxylate

technical grade, 90%

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Linear Formula:
C6H5CH2OCON=NCOOCH2C6H5
CAS Number:
Molecular Weight:
298.29
Beilstein/REAXYS Number:
2298734
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

grade

technical grade

Quality Level

assay

90%

form

solid

mp

43-47 °C (lit.)

storage temp.

2-8°C

SMILES string

O=C(OCc1ccccc1)\N=N\C(=O)OCc2ccccc2

InChI

1S/C16H14N2O4/c19-15(21-11-13-7-3-1-4-8-13)17-18-16(20)22-12-14-9-5-2-6-10-14/h1-10H,11-12H2/b18-17+

InChI key

IRJKSAIGIYODAN-ISLYRVAYSA-N

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1 of 4

This Item
22554112305611625
Dibenzyl azodicarboxylate technical grade, 90%

166804

Dibenzyl azodicarboxylate

Diisopropyl azodicarboxylate 98%

225541

Diisopropyl azodicarboxylate

4-(2-Aminoethyl)aniline 97%

123056

4-(2-Aminoethyl)aniline

Di-tert-butyl azodicarboxylate purum, ≥98.0% (GC)

11625

Di-tert-butyl azodicarboxylate

mp

43-47 °C (lit.)

mp

-

mp

28-31 °C (lit.)

mp

89-92 °C (lit.)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

form

solid

form

liquid

form

-

form

solid

grade

technical grade

grade

-

grade

-

grade

-

General description

Dibenzyl azodicarboxylate undergoes[4+2] cycloaddition reaction with glycal to yield 2-aminoglycosides.

Application

Dibenzyl azodicarboxylate was used as electrophilic reagent in the synthesis of C-glycosyl α-amino acids via proline-catalyzed α-amination of C-glycosylalkyl aldehydes. It was used in enantioselective synthesis of optically active pyrazolidine derivatives.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Andrea Nuzzi et al.
Organic letters, 10(20), 4485-4488 (2008-09-16)
Non-natural axially and equatorially linked C-glycosyl alpha-amino acids (glycines, alanines, and CH2-serine isosteres) with either S or R alpha-configuration were prepared by D- and L-proline-catalyzed (de >95%) alpha-amination of C-glycosylalkyl aldehydes using dibenzyl azodicarboxylate as the electrophilic reagent.
Shengming Ma et al.
Organic letters, 6(13), 2193-2196 (2004-06-18)
[reaction: see text] Optically active pyrazolidine derivatives have been constructed by the Cu- and Pd-catalyzed asymmetric one-pot tandem addition-cyclization reaction of 2-(2',3'-dienyl)-beta-ketoesters, organic halides, and dibenzyl azodicarboxylate. The absolute configurations of the final products depend on the structure of the
[4+ 2] Cycloaddition reaction of dibenzyl azodicarboxylate and glycals.
Leblanc Y, et al.
Journal of the American Chemical Society, 111(8), 2995-3000 (1989)

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