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238090

Sigma-Aldrich

1-Bromo-4-iodobenzene

98%

Synonym(s):

4-Bromo-1-iodobenzene, 4-Bromoiodobenzene, 4-Iodo-1-bromobenzene, 4-Iodophenyl bromide, p-Bromophenyl iodide, p-Iodobromobenzene

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About This Item

Linear Formula:
BrC6H4I
CAS Number:
589-87-7
Molecular Weight:
282.90
Beilstein:
1904545
EC Number:
209-662-7
MDL number:
MFCD00001051
UNSPSC Code:
12352100
PubChem Substance ID:
24854290
NACRES:
NA.22

Assay

98%

form

solid

bp

120-122 °C/14 mmHg (lit.)

mp

89-91 °C (lit.)

functional group

bromo

SMILES string

Brc1ccc(I)cc1

InChI

1S/C6H4BrI/c7-5-1-3-6(8)4-2-5/h1-4H

InChI key

UCCUXODGPMAHRL-UHFFFAOYSA-N

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General description

Vapour pressure as a function of temperature for 1-bromo-4-iodobenzene has been studied using a diaphragm manometer and torsion mass-loss effusion.

Application

1-Bromo-4-iodobenzene has been employed:
  • as reagent for in situ desilylation and coupling of silylated alkynes
  • as starting reagent in the total syntheses of ent-conduramine A and ent-7-deoxypancratistatin (alkaloids)
  • as substrate in copper-free Sonogashira coupling in aqueous acetone
  • in synthesis of β,β,dibromostyrenes

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Representation and assessment of vapour pressure data; a novel approach applied to crystalline 1-bromo-4-chlorobenzene, 1-chloro-4-iodobenzene, and 1-bromo-4-iodobenzene.
Oonk HAJ, et al.
The Journal of Chemical Thermodynamics, 30(7), 897-907 (1998)
Synlett, 1843-1843 (2007)
Synlett, 2061-2061 (2007)
Total syntheses of ent-conduramine A and ent -7-deoxypancratistatin.
Akgun H and Hudlicky T.
Tetrahedron Letters, 40(16), 3081-3084 (1999)
Rapid bi-directional synthesis of oligo (1, 4-phenylene ethynylene) s.
Huang S and Tour JM.
Tetrahedron Letters, 40(17), 3447-3450 (1999)
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