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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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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4, 4?-Azopyridine as an easily prepared and recyclable oxidant for synthesis of symmetrical disulfides from thiols or alkyl halides (tosylates)/thiourea}
Khalili, Dariush and Iranpoor
Journal of Sulfur Chemistry, 36, 544-555 (2015)
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)
A novel HgI2 adduct with an azopyridine ligand: synthesis, structure and optical refractive effect of [HgI2 (4, 4?-azopyridine)] n
Niu, Yunyin and Song
CrystEngComm, 3, 152-154 (2001)
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)
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