Mesityl bromide

Mesityl bromide is an organic compound with the formula (CH3)3C6H2Br. It is a derivative of mesitylene (1,3,5-trimethylbenzene) with one ring H replaced by Br. The compound is a colorless oil. It is a standard electron-rich aryl halide substrate for cross coupling reactions.[2] With magnesium it reacts to give the Grignard reagent,[3] which is used in the preparation of tetramesityldiiron.

Mesityl bromide
Names
Other names
2-bromomesitylene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.008.552 Edit this at Wikidata
EC Number
  • 209-405-9
UNII
  • InChI=1S/C9H11Br/c1-6-4-7(2)9(10)8(3)5-6/h4-5H,1-3H3
    Key: RRTLQRYOJOSPEA-UHFFFAOYSA-N
  • CC1=CC(=C(C(=C1)C)Br)C
Properties
C9H11Br
Molar mass199.091 g·mol−1
Appearancecolorless liquid
Density1.3220 g/cm3
Melting point−1 °C (30 °F; 272 K)
Boiling point225 °C (437 °F; 498 K)
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

It is prepared by the direct reaction of bromine with mesitylene:[4]

(CH3)3C6H3 + Br2 → (CH3)3C6H2Br + HBr

References