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Boron tribromide is used as a reactant for luminescent polystyrene derivatives with sterically protected carbazolylborane moieties, high-quality boron-doped graphene via Wurtz-type reductive coupling reaction and micrometer-sized organic molecule-DNA hybrid structures. It is also used in bromination and cyclization reactions to prepare cyclopenta[1,3]cyclopropa[1,2-b]pyrrolizin-8-one. It acts as a liquid boron source used in p-type deposition processes.
Reagent for cleavage of ethers: Synthesis, 249 (1983). Converts alcohols to alkyl bromides under mild conditions: Tetrahedron Lett., 35, 1051 (1994). Cleavage of N-methoxymethyl: Tetrahedron Lett., 42, 8633 (2001), or N-benzyl: Tetrahedron Lett., 45, 4093 (2004) protecting groups can also be achieved under mild conditions. Alkynes undergo bromoboration; the products can be transformed, e.g. to trisubstituted alkenes: Tetrahedron Lett., 29, 1811 (1988), or enyne-allenes: Tetrahedron Lett., 35, 1829 (1994).
Jourdan, J. P.; Rochais, C.; Legay, R.; Santos, J. S. O.; Dallemagne, P. An unusual boron tribromide-mediated, one-pot bromination/cyclization reaction. Application to the synthesis of a highly strained cyclopenta[1,3]cyclopropa[1,2-b]pyrrolizin-8-one. Tetrahedron Lett. 2013, 54 (9), 1133-1136.
Khusainova, L. I.; Khafizova, L. O.; Tyumkina, T. V.; Dzhemilev, U. M. Synthesis of halogen-substituted borolanes and 2,3-dihydro-1H-boroles by reactions of aluminacarbocycles with boron trichloride and boron tribromide. Russ. J. Org. Chem. 2014, 50 (3), 309-313.
Hazard Statements: H300-H330-H314-H318-H351
Fatal if swallowed. Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage. Suspected of causing cancer.
Precautionary Statements: P301+P310a-P303+P361+P353-P304+P340-P305+P351+P338-P320-P405-P501a
IF SWALLOWED: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment is urgent (see label). Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.