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Sigma-Aldrich

Dibenzyl azodicarboxylate

technical grade, 90%

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About This Item

Linear Formula:
C6H5CH2OCON=NCOOCH2C6H5
CAS Number:
2449-05-0
Molecular Weight:
298.29
Beilstein:
2298734
EC Number:
219-508-0
MDL number:
MFCD00016737
UNSPSC Code:
12352100
PubChem Substance ID:
24850186
NACRES:
NA.22

grade

technical grade

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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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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

A96606

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Diamide

Sigma-Aldrich

D3648

Diamide

[4+ 2] Cycloaddition reaction of dibenzyl azodicarboxylate and glycals.
Leblanc Y, et al.
Journal of the American Chemical Society, 111(8), 2995-3000 (1989)
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
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.

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