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Mesityl bromide

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Mesityl bromide
Names
Other names 2-bromomesitylene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.552 Edit this at Wikidata
EC Number
  • 209-405-9
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H11Br/c1-6-4-7(2)9(10)8(3)5-6/h4-5H,1-3H3Key: RRTLQRYOJOSPEA-UHFFFAOYSA-N
SMILES
  • CC1=CC(=C(C(=C1)C)Br)C
Properties
Chemical formula C9H11Br
Molar mass 199.091 g·mol
Appearance colorless liquid
Density 1.3220 g/cm
Melting point −1 °C (30 °F; 272 K)
Boiling point 225 °C (437 °F; 498 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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. With magnesium it reacts to give the Grignard reagent, which is used in the preparation of tetramesityldiiron.

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

(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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