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680850

Di-(4-chlorobenzyl)azodicarboxylate

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
MDL number:
MFCD27995640
UNSPSC Code:
12352101
PubChem Substance ID:
24885598
NACRES:
NA.22

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Quality Level

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

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This Item
238902111902135992
Di-(4-chlorobenzyl)azodicarboxylate 97%

Sigma-Aldrich

680850

Di-(4-chlorobenzyl)azodicarboxylate

2-(Trimethylsilyl)ethoxymethyl chloride technical grade

Sigma-Aldrich

238902

2-(Trimethylsilyl)ethoxymethyl chloride

4-Chlorobenzoyl chloride 99%

Sigma-Aldrich

111902

4-Chlorobenzoyl chloride

Di-tert-butyl azodicarboxylate 98%

Sigma-Aldrich

135992

Di-tert-butyl azodicarboxylate

assay

97%

assay

-

assay

99%

assay

98%

mp

108-112 °C

mp

-

mp

11-14 °C (lit.)

mp

89-92 °C (lit.)

form

solid

form

liquid

form

-

form

solid

functional group

azo

functional group

chloro, ether

functional group

acyl chloride, chloro

functional group

azo

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.[1]
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

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

pcodes

P280

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000425458
0000425458
0000253849
0000213649
0000204324

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Kyohei Ishida et al.
Animal science journal = Nihon chikusan Gakkaiho, 89(1), 132-139 (2017-09-16)
Lowering dietary cation-anion differences (DCAD) can enhance responsiveness to Ca-homeostatic hormones and increase Ca availability, which might have potential to activate a Ca-dependent protease, calpain, and to enhance postmortem myofibrillar proteolysis. In this study, we investigated the effects of DCAD
M R Wilkens et al.
Journal of animal physiology and animal nutrition, 100(1), 156-166 (2015-02-04)
The concept of feeding anionic salts in late gestation is widely used to prevent milk fever in dairy cows. While the effects of these diets on renal Ca excretion and tissue responsiveness towards parathyroid hormone have clearly been demonstrated, data
Vivian F Su et al.
BMC developmental biology, 7, 43-43 (2007-05-09)
The Hedgehog (Hh) family of secreted growth factors are morphogens that act in development to direct growth and patterning. Mutations in human Hh and other Hh pathway components have been linked to human diseases. Analysis of Hh distribution during development
J E P Santos et al.
Journal of dairy science, 102(3), 2134-2154 (2019-01-08)
The objectives were to use meta-analytic methods to determine the effects of changes in dietary cation-anion difference (DCAD) prepartum on productive performance and health of dairy cows. The literature was systematically reviewed, searching randomized experiments with transition cows that manipulated
R Zimpel et al.
Journal of dairy science, 101(9), 8461-8475 (2018-07-05)
The objective was to determine if the reduction in dry matter (DM) intake of acidogenic diets is mediated by inclusion of acidogenic products, content of salts containing Cl, or changes in acid-base status. The hypothesis was that a decrease in
View All Related Papers

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Designer surfactants enable diverse transformations like Suzuki-Miyaura, Olefin Metathesis, and 1,4-Addition to Enones in water by Prof. Bruce Lipshutz.

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