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680850

Di-(4-chlorobenzyl)azodicarboxylate

Name: Di-(4-chlorobenzyl)azodicarboxylate
Brand: ALDRICH

97%

Synonym(s):

Bis(4-chlorobenzyl)azodicarboxylate, DCAD

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About This Item

Empirical Formula (Hill Notation):

C₁₆H₁₂Cl₂N₂O₄

CAS Number:

916320-82-6

Molecular Weight:

367.18

NACRES:

NA.22

PubChem Substance ID:

24885598

UNSPSC Code:

12352101

MDL number:

MFCD27995640

Assay:

97%

Form:

solid

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Properties

Quality Segment

200

assay

97%

form

solid

mp

108-112 °C

functional group

azo, chloro

SMILES string

O=C(/N=N\C(OCC1=CC=C(Cl)C=C1)=O)OCC2=CC=C(Cl)C=C2

InChI

1S/C16H12Cl2N2O4/c17-13-5-1-11(2-6-13)9-23-15(21)19-20-16(22)24-10-12-3-7-14(18)8-4-12/h1-8H,9-10H2/b20-19-

InChI key

UIFGGABIJBWRMG-VXPUYCOJSA-N

Description

General description

Learn More at the Professor and Product Portal of Professor Bruce Lipshutz.

Application

Di-(4-chlorobenzyl)azodicarboxylate (DCAD) is a novel, stable, solid alternative to DEAD and DIAD for a variety of Mitsunobu couplings giving a readily separable hydrazine byproduct that can be recycled.

Reactant for preparation of:

Amino thioesters via guanidine-catalyzed biomimetic enantioselective decarboxylative Mannich and amination reactions of malonic acid half thioesters
Hydroacylation reaction of aldehydes in Ionic liquid (IL) medium
DCAD (di-p-chlorobenzyl azodicarboxylate) for Mitsunobu coupling reactions

pictograms

GHS07

signalword

Warning

hcodes

H317

pcodes

P280

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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