2-Bromoanisole
Names
Preferred IUPAC name
1-Bromo-2-methoxybenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.570
EC Number
  • 209-425-8
UNII
  • InChI=1S/C7H7BrO/c1-9-7-5-3-2-4-6(7)8/h2-5H,1H3
    Key: HTDQSWDEWGSAMN-UHFFFAOYSA-N
  • 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 labelling:
GHS09: Environmental hazard
Warning
H411
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

  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.
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