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705055

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
NACRES:
NA.22
PubChem Substance ID:
329762502
UNSPSC Code:
12352005
MDL number:
MFCD00129061
Form:
solid
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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

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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN7115
MKCQ8687
MKCJ9359
MKCH6194
MKCC2559

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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 4, 4′-azopyridine-bridged binuclear zinc complex
Zhu L, et al.
Journal of Coordination Chemistry, 56(17), 1447-1453 (2003)
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)
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Global Trade Item Number

SKUGTIN
705055-5G04061832842721
705055-1G04061832842714