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680850

Sigma-Aldrich

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

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

General description

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

Application

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
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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Precautionary Statements

P280

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000253849
0000213649
0000184533
0000184531
0000204324

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D3648

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Diethyl azodicarboxylate solution purum, ~40% in toluene (H-NMR)

Sigma-Aldrich

11627

Diethyl azodicarboxylate solution

T Amirabadi Farahani et al.
Journal of dairy science, 100(8), 6199-6217 (2017-05-30)
This experiment was conducted to compare conventional (CON; 21 d) and shortened (SH; 10 d) close-up period, and evaluate the effect of shortened close-up period combined with feeding different metabolizable protein (MP) levels on dry matter (DM) intake, metabolic status
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
Bruce H Lipshutz et al.
Organic letters, 8(22), 5069-5072 (2006-10-20)
Di-p-chlorobenzyl azodicarboxylate (DCAD) is introduced as a novel, stable, solid alternative to DEAD and DIAD for a variety of Mitsunobu couplings. DCAD/Ph(3)P-mediated reactions in CH(2)Cl(2) generate a readily separable hydrazine byproduct. [reaction: see text]
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