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510459

Sigma-Aldrich

2,6-Dichloroiodobenzene

98%

Synonym(s):

1,3-Dichloro-2-iodobenzene

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About This Item

Linear Formula:
Cl2C6H3I
CAS Number:
Molecular Weight:
272.90
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

assay

98%

mp

64-67 °C (lit.)

SMILES string

Clc1cccc(Cl)c1I

InChI

1S/C6H3Cl2I/c7-4-2-1-3-5(8)6(4)9/h1-3H

InChI key

ZMPGXSFTXBOKFM-UHFFFAOYSA-N

General description

2,6-Dichloroiodobenzene, also known as 1,3-dichloro-2-iodobenzene, is a halo-substituted benzene. It couples with 1,1′-diaminoferrocene in the presence of a palladium catalyst to form substituted diamide ligands (Fc(NHAr)2).

Application

2,6-Dichloroiodobenzene may be used in the preparation of 2,6-dichlorobenzo[14C]nitrile and 2,6-terphenyl carboxylic acid ligands.
It may be used as a starting material in the multi-step synthesis of:
  • cupped oxacyclophanes
  • cuppedophanes
  • cappedophanes
  • m-terphenyls

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

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Synthesis of cuppedophanes and cappedophanes. Two new classes of cyclophanes with molecular cavities.
Vinod T and Hart H.
The Journal of Organic Chemistry, 55(3), 881-890 (1990)
Zirconium complexes incorporating diaryldiamidoferrocene ligands: generation of cationic derivatives and polymerization activity towards ethylene and 1-hexene.
Shafir A and Arnold J.
Inorgorganica Chimica Acta, 345, 216-220 (2003)
Non-interconvertible conformers of cupped oxacyclophanes.
Grewal RS and Hart H.
Tetrahedron Letters, 31(30), 4271-4274 (1990)
Encapsulation of the uranyl dication.
Beer S, et al.
Chemical Science, 1(1), 43-47 (2010)
Oxacyclophanes based on a m-terphenyl framework.
Grewal RS, et al.
The Journal of Organic Chemistry, 57(9), 2721-2726 (1992)

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