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166804

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)

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[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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