10343. Bromodimethylborane

Nomenclature

CAS number: 5158-50-9
Dimethylboron bromide; dimethylbromoborane; Me2BBr.
C2H6BBr; mol wt 120.78.
C 19.89%, H 5.01%, B 8.95%, Br 66.16%.

Description and references

Organoboron bromide reagent utilized for the cleavage of ethers, acetals, and ketals. Prepn: P. I. Paetzold, H.-J. Hansen, Z. Anorg. Allg. Chem. 345, 79 (1966) DOI; and synthetic applications: Y. Guindon et al., J. Org. Chem. 49, 3912 (1984) DOI. Additional synthetic applications: idem et al., ibid. 4538 DOI; idem et al., ibid. 52, 1680 (1987) DOI; R. L. Dorow, D. E. Gingrich, ibid. 60, 4986 (1995) DOI. Reviews: Y. Guindon et al., Pure Appl. Chem. 60, 1705-1714 (1988) DOI; Y. Guindon, P. C. Anderson in Encyclopedia of Reagents for Organic Synthesis vol. 1, L. A. Paquette, Ed. (Wiley, New York, 1995) pp 715-718; B. Y. Michel, Synlett 2008, 2893-2894 DOI.

Chemical structure

Properties

Colorless liquid. bp 30°. Flammable. Corrosive. Flash pt, closed cup: 35°F (37°C). Sol in dichloromethane, 1,2-dichloroethane, hexane. Moisture sensitive. Stable for months when stored as soln in dichloromethane or 1,2-dichloroethane at 15°C.

Use

Reagent in synthetic organic chemistry.