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255920 Sigma-Aldrich

1,1′-(Azodicarbonyl)dipiperidine

99%

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

  • CAS Number 10465-81-3

  • Empirical Formula (Hill Notation) C12H20N4O2

  • Molecular Weight 252.31

  •  Beilstein/REAXYS Number 261917

  •  MDL number MFCD00010111

  •  PubChem Substance ID 24855495

  •  NACRES NA.22

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Properties

Related Categories C-X Bond Formation (Non-Halogen), Chemical Synthesis, Mitsunobu, Synthetic Reagents
assay   99%
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

Description

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

Packaging

5, 25 g in poly bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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.1 The Mitsunobu reaction is also useful in the preparation of other moietie...
ChemFiles Volume 4 Article 2
Keywords: Mitsunobu Reaction, Organic synthesis

Peer-Reviewed Papers
15

References

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