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 InfoCard 100.008.552
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 mass 199.091 g·mol−1
Appearance colorless liquid
Density 1.3220 g/cm3
Melting point −1 °C (30 °F; 272 K)
Boiling point 225 °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).
Infobox references

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

(CH3)3C6H3 + Br2 → (CH3)3C6H2Br + HBr

References
  1. "2-Bromomesitylene". pubchem.ncbi.nlm.nih.gov.
  2. Farina, Vittorio; Krishnamurthy, Venkat; Scott, William J. (1997). "The Stille Reaction". Organic Reactions. pp. 1–652. doi:10.1002/0471264180.or050.01. ISBN 0471264180.
  3. Lee Irvin Smith (1931). "Isoodurene". Org. Synth. 11: 66. doi:10.15227/orgsyn.011.0066.
  4. Lee Irvin Smith (1931). "Bromomesitylene". Org. Synth. 11: 24. doi:10.15227/orgsyn.011.0024.
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