Mesityl bromide

Mesityl bromide
Names
	Other names 2-bromomesitylene
Identifiers
CAS Number	576-83-0;
3D model (JSmol)	Interactive image;
ChemSpider	21112244;
ECHA InfoCard	100.008.552
EC Number	209-405-9;
PubChem CID	68473;
UNII	X99GJ54YDY ;
CompTox Dashboard (EPA)	DTXSID4060363 ;
	InChI InChI=1S/C9H11Br/c1-6-4-7(2)9(10)8(3)5-6/h4-5H,1-3H3 Key: RRTLQRYOJOSPEA-UHFFFAOYSA-N;
	SMILES CC1=CC(=C(C(=C1)C)Br)C;
Properties
Chemical formula	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:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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.

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

(CH₃)₃C₆H₃ + Br₂ → (CH₃)₃C₆H₂Br + HBr

References

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

[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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