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255920

Sigma-Aldrich

1,1′-(Azodicarbonyl)dipiperidine

99%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C12H20N4O2
CAS Number:
10465-81-3
Molecular Weight:
252.31
Beilstein:
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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
E A Bump et al.
International journal of radiation oncology, biology, physics, 12(8), 1533-1535 (1986-08-01)
Several analogs of the glutathione (GSH) oxidizing reagent diamide [diazenedicarboxylic acid bis(N,N'-diethylamide)] were tested as radiosensitizers of aerobic cells. In general, radiosensitization correlates with the rate of reaction with cellular reducing agents and occurs only when the reductive capacity of
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.
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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Articles

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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