2-Bromoanisole

2-Bromoanisole is an organobromide with the formula BrC₆H₄OCH₃. A colorless liquid, it is one of three isomers of bromoanisole, the others being 3-bromoanisole and 4-bromoanisole. It is a standard coupling partner in metal catalyzed coupling reactions. These reactions include Heck reactions, Buchwald-Hartwig coupling,[1] Suzuki couplings, and Ullmann condensations.[2] The corresponding Grignard reagent readily forms. It is a precursor to o-anisaldehyde.[3][4]

2-Bromoanisole

Names
Other names 1-bromo-2-methoxy-benzene
Identifiers
CAS Number	578-57-4
3D model (JSmol)	Interactive image
ChemSpider	13881329
ECHA InfoCard	100.008.570
EC Number	209-425-8
PubChem CID	11358
CompTox Dashboard (EPA)	DTXSID4060367
InChI InChI=1S/C7H7BrO/c1-9-7-5-3-2-4-6(7)8/h2-5H,1H3 Key: HTDQSWDEWGSAMN-UHFFFAOYSA-N
SMILES COC1=CC=CC=C1Br
Properties
Appearance	colorless liquid
Melting point	2.5 °C (36.5 °F; 275.6 K)
Boiling point	216 °C (421 °F; 489 K)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H411
GHS precautionary statements	P273, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References

1. Klapars, Artis; Antilla, Jon C.; Huang, Xiaohua; Buchwald, Stephen L. (2001). "A General and Efficient Copper Catalyst for the Amidation of Aryl Halides and theN-Arylation of Nitrogen Heterocycles". Journal of the American Chemical Society. 123 (31): 7727–7729. doi:10.1021/ja016226z. PMID 11481007.
2. Buck, Elizabeth; Song, Zhiguo J. (2005). "Preparation of 1-Methoxy-2-(4-Methoxyphenoxy)Benzene". Organic Syntheses. 82: 69. doi:10.15227/orgsyn.082.0069.
3. Sisti, A. J. (1964). "O-Anisaldehyde". Organic Syntheses. 44: 4. doi:10.15227/orgsyn.044.0004.
4. Brinkmeyer, R. S.; Collington, E. W.; Meyers, A. I. (1974). "Aldehydes from 4,4-Dimethyl-2-oxazoline and Grignard Reagents: O-Anisaldehyde". Organic Syntheses. 54: 42. doi:10.15227/orgsyn.054.0042.