2-Bromoanisole

2-Bromoanisole
Names
	Preferred IUPAC name 1-Bromo-2-methoxybenzene
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;
UNII	X3XAZ6R3FL ;
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
Chemical formula	C7H7BrO
Molar mass	187.036 g·mol−1
Appearance	Colorless liquid
Melting point	2.5 °C (36.5 °F; 275.6 K)
Boiling point	216 °C (421 °F; 489 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H411
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

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]

References

^ 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.
^ Buck, Elizabeth; Song, Zhiguo J. (2005). "Preparation of 1-Methoxy-2-(4-Methoxyphenoxy)Benzene". Organic Syntheses. 82: 69. doi:10.15227/orgsyn.082.0069.
^ Sisti, A. J. (1964). "O-Anisaldehyde". Organic Syntheses. 44: 4. doi:10.15227/orgsyn.044.0004.
^ 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.