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Sigma-Aldrich

5-Bromo-2-iodotoluene

98%

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About This Item

Linear Formula:
CH3C6H3(Br)I
CAS Number:
116632-39-4
Molecular Weight:
296.93
MDL number:
MFCD00060664
UNSPSC Code:
12352100
PubChem Substance ID:
24877624
NACRES:
NA.22

assay

98%

refractive index

n20/D 1.65 (lit.)

bp

263 °C (lit.)

density

2.08 g/mL at 25 °C (lit.)

SMILES string

Cc1cc(Br)ccc1I

InChI

1S/C7H6BrI/c1-5-4-6(8)2-3-7(5)9/h2-4H,1H3

InChI key

GHTUADBHTFHMNI-UHFFFAOYSA-N

General description

5-Bromo-2-iodotoluene is a halogenated hydrocarbon. It undergoes chemoselective Suzuki reaction with phenylboronic acid to yield the corresponding carboxylic acid.

Application

5-Bromo-2-iodotoluene may be used in the synthesis of:
  • 2-bromo-5-(4-bromo-2-methylphenyl)-3-methylpyridine
  • 4-bromo-4′-(carbazol-9-yl)-2-methylbiphenyl
  • 4,4′-dibromo-2-methyl-biphenyl
  • 3-methyl-4-phenylbromobenzene
  • 4-(4-bromo-2-methylphenyl)butanoic acid

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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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M Jonathan Fray et al.
Journal of medicinal chemistry, 46(16), 3514-3525 (2003-07-25)
The pathology of chronic dermal ulcers is characterized by excessive proteolytic activity which degrades extracellular matrix (required for cell migration) and growth factors and their receptors. The overexpression of MMP-3 (stromelysin-1) and MMP-13 (collagenase-3) is associated with nonhealing wounds, whereas
Synthesis, Properties and Applications of Biphenyl Functionalized 9, 9-Bis (4-diphenylaminophenyl) fluorenes as Bifunctional Materials for Organic Electroluminescent Devices.
Thangthong A-M, et al.
European Journal of Organic Chemistry, 27, 5263-5274 (2012)
Synthesis of comb polyphenylenes by Suzuki coupling from AB macromonomers.
Zhou S, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 52(11), 1519-1524 (2014)
Synthesis of new phenylpyridyl scaffolds using the Garlanding approach.
Voisin-Chiret AS, et al.
Tetrahedron, 66(40), 8000-8005 (2010)
E Scott Priestley et al.
Journal of medicinal chemistry, 58(15), 6225-6236 (2015-07-08)
On the basis of a crystal structure of a phenylpyrrolidine lead and subsequent molecular modeling results, we designed and synthesized a novel series of macrocyclic FVIIa inhibitors. The optimal 16-membered macrocycle was 60-fold more potent than an acyclic analog. Further

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