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255920

Sigma-Aldrich

1,1′-(Azodicarbonyl)dipiperidine

99%

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Synonym(s):
1,1′-Azobis(N,N-pentamethyleneformamide), ADD, Azodicarboxylic acid dipiperidide, NSC 356027, SR 4077
Empirical Formula (Hill Notation):
C12H20N4O2
CAS Number:
Molecular Weight:
252.31
Beilstein/REAXYS Number:
261917
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

form

solid

mp

134-136 °C (lit.)

SMILES string

O=C(\N=N\C(=O)N1CCCCC1)N2CCCCC2

InChI

1S/C12H20N4O2/c17-11(15-7-3-1-4-8-15)13-14-12(18)16-9-5-2-6-10-16/h1-10H2/b14-13+

InChI key

OQJBFFCUFALWQL-BUHFOSPRSA-N

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1 of 4

This Item
53449811590D3648
1,1′-(Azodicarbonyl)dipiperidine 99%

255920

1,1′-(Azodicarbonyl)dipiperidine

4-Piperidinopiperidine 97%

534498

4-Piperidinopiperidine

4,4′-Azobis(4-cyanovaleric acid) ≥98.0% (T)

11590

4,4′-Azobis(4-cyanovaleric acid)

Diamide

D3648

Diamide

form

solid

form

-

form

solid

form

powder

mp

134-136 °C (lit.)

mp

64-66 °C (lit.)

mp

118-125 °C (dec.) (lit.)

mp

113-115 °C

Application

Reactant for preparation of:
  • Polyfluoroalkylated tripyrazolylmethane ligands

  • (-)-Hygromycin A via Mitsunobu glycosylation
  • Optically active α,α-disubstituted amino acids via Mitsunobu reaction
  • Aza-β-lactams through [2+2] cycloaddition reactions
  • Glycosyl disulfides
  • Pyridine ether PPAR agonists
  • S-glycosyl amino acid building blocks for combinatorial neoglycopeptide synthesis
  • Histamine H3 receptor antagonists

Reactant for:
  • Mitsunobu inversion reactions
Used in a study of the copper-catalyzed addition of aryboronic acids to azodicarboxyl derivatives providing aryl-substituted hydrazides.
Widely used reagent for the Mitsunobu reaction

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Dougherty, J.M.; et al.
Tetrahedron, 61, 6218-6218 (2005)
Takeshi Uemura et al.
The Journal of organic chemistry, 70(21), 8631-8634 (2005-10-08)
The addition of arylboronic acids 1 to azodicarboxylates 2 in the presence of a catalytic amount of a copper salt under mild reaction conditions gives aryl-substituted hydrazines 3 in high yields. The reaction is tolerant of a wide variety of
M A Baker et al.
Radiation research, 113(2), 346-355 (1988-02-01)
The mechanism of radiosensitization by diazenedicarboxylic acid bis(N),N-piperidide (SR 4077), a less toxic analog of diamide, was studied using Chinese hamster ovary cells. SR 4077 gave an average SER of 1.58 for postirradiation incubations of 0.5, 1.0, or 2.0 h.
Tetrahedron Letters, 34, 1639-1639 (1993)
E A Bump et al.
International journal of radiation oncology, biology, physics, 29(2), 249-253 (1994-05-15)
To determine whether biological effects of radiation, such as apoptosis, that differ from classical clonogenic cell killing, can be modified with agents that would not be expected to modify classical clonogenic cell killing. This would expand the range of potential

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