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705055

Sigma-Aldrich

4,4′-Azopyridine

Synonym(s):

Azobis(4-pyridine)

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About This Item

Empirical Formula (Hill Notation):
C10H8N4
CAS Number:
2632-99-7
Molecular Weight:
184.20
MDL number:
MFCD00129061
UNSPSC Code:
12352005
PubChem Substance ID:
329762502
NACRES:
NA.22

form

solid

Quality Level

100

mp

96-101 °C

SMILES string

c1cc(ccn1)N=Nc2ccncc2

InChI

1S/C10H8N4/c1-5-11-6-2-9(1)13-14-10-3-7-12-8-4-10/h1-8H

InChI key

XUPMSLUFFIXCDA-UHFFFAOYSA-N

Related Categories

General description

4,4′-Azopyridine is an aromatic heterocyclic compound used as a ligand in the formation of [HgI2(4,4′-azopyridine)]n complex.

Application

4,4′-Azopyridine can be used:
  • To prepare porous coordination polymers (PCPs) by reacting with Zn(NO3)2 and 1,4-benzenedicarboxylic acid.
  • As a reagent for the conversion of aliphatic alcohols into disulfides under Mitsunobu conditions.
  • To prepare 4,4′-azopyridine-bridged binuclear zinc(II) complexes.

Reactant for preparation of:
  • Flexible porous coordination polymers constructed from 1,2-bis(4-pyridyl)hydrazine via solvothermal in situ reduction reaction
  • Metal-organic frameworks based on transition-metal carboxylate clusters as secondary building units
  • Heteroaromatic azo compounds under Mitsunobu conditions
  • MnII, CoII, and ZnII coordination polymers
  • Low-dimensional and porous coordination compounds capable of supramolecular aromatic interactions

Reagent in:
  • Facile Mitsunobu esterification reactions

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN7115
MKCJ9359
MKCH6194
MKCC2559
MKBV4802V

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Flexible porous coordination polymers constructed from 1, 2-bis (4-pyridyl) hydrazine via solvothermal in situ reduction of 4, 4′-azopyridine
Liu X, et al.
Dalton Transactions, 40(34), 8549-8554 (2011)
A novel 4, 4′-azopyridine-bridged binuclear zinc complex
Zhu L, et al.
Journal of Coordination Chemistry, 56(17), 1447-1453 (2003)
Heteroaromatic azo compounds as efficient and recyclable reagents for direct conversion of aliphatic alcohols into symmetrical disulfides
Iranpoor N, et al.
Tetrahedron Letters, 53(51), 6913-6915 (2012)

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