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255920

Sigma-Aldrich

1,1′-(Azodicarbonyl)dipiperidine

99%

Sinónimos:

1,1′-Azobis(N,N-pentamethyleneformamide), ADD, Azodicarboxylic acid dipiperidide, NSC 356027, SR 4077

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About This Item

Fórmula empírica (notación de Hill):
C12H20N4O2
Número de CAS:
10465-81-3
Peso molecular:
252.31
Beilstein/REAXYS Number:
261917
MDL number:
MFCD00010111
UNSPSC Code:
12352005
PubChem Substance ID:
24855495
NACRES:
NA.22

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

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
GHS07

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

Certificados de análisis (COA)

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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
Dougherty, J.M.; et al.
Tetrahedron, 61, 6218-6218 (2005)
Tetrahedron Letters, 34, 1639-1639 (1993)
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.
Hiroki Sato et al.
Bioorganic & medicinal chemistry, 10(5), 1595-1610 (2002-03-12)
Structure--activity relationship studies of 1beta-methyl-2-[(3S,5R)-5-(4-aminomethylphenyl)pyrrolidin-3-ylthio]carbapenems, especially those pertaining to the relationship between antibacterial activity and side-chain structure were conducted. These studies suggested that the trans-(3S,5R)-5-phenylpyrrolidin-3-ylthio side-chain and the aminomethyl group at the 4-position of the phenyl ring play a key
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Reagents for the Mitsunobu Reaction

One of the most powerful and widely used carboncarbon bond forming reactions in organic synthesis is the Mitsunobu reaction.

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