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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