Subscribe to RSS
DOI: 10.1055/s-2005-868513
Boron Tribromide
Publication History
Publication Date:
29 April 2005 (online)
Introduction
Boron halides are useful reagents in organic chemistry. Among them, boron tribromide must be highlighted, due to the different reactions that it can perform, such as cleavage of ethers, amines, and thiols, and addition to allenes and alkynes. These are many examples of its use in medicinal chemistry, [1] in the synthesis of natural products, [2] and in the development of new organic materials. [3]
BBr3 is a colourless fuming liquid. It is commercially available neat, or in solution with dichloromethane or hexanes.
Precautions: BBr3 is highly moisture-sensitive and decomposes in air with evolution of HBr. It must be stored under a dry inert atmosphere. It reacts violently with protic solvents such as water and alcohols; ethers are also inappropriate solvents.
- 1
Lisowski V.Léonce S.Kraus-Berthier L.Sopková de Oliveira Santos J.Pierré A.Atassi G.Caignard D.Renard P.Rault S. J. Med. Chem. 2004, 47: 1448 - 2
Brimble MA.Brenstrum TJ. J. Chem. Soc., Perkin Trans. 1 2001, 1624 - 3
Vlachos P.Kelly SM.Mansoor B.O’Neill M. Chem. Commun. 2002, 874 - 4
Vickery EH.Pahler LF.Eisenbraun EJ. J. Org. Chem. 1979, 44: 1979 - 5
Barluenga J.Aznar F.Palomero MA. J. Org. Chem. 2003, 68: 537 - 6
Mayekar NV.Chattopadhyay S.Nayak SK. Synthesis 2003, 2041 - 7
Nordvik T.Brinker UH. J. Org. Chem. 2003, 68: 9394 - 8
Detterbeck R.Hesse M. Helv. Chim. Acta 2003, 86: 343 - 9
Qian Y.Huang J.Ding K.Zhang Y.Huang Q.Chen XP.Chan ASC.Wong WT. J. Organomet. Chem. 2002, 645: 59 - 10
Sotelo E.Coelho A.Raviña E. Tetrahedron Lett. 2001, 42: 8633 - 11
Paliakov E.Strekowski L. Tetrahedron Lett. 2004, 45: 4093 - 12
Stuhr-Hansen N. Synth. Commun. 2003, 33: 641 - 13
Stuhr-Hansen N.Christensen JB.Harrit N.Bjørnholm T. J. Org. Chem. 2003, 68: 1275 - 14
Hara S.Suzuki A. Tetrahedron Lett. 1991, 32: 6749 - 15
Kabalka GW.Wu Z.Ju Y. Org. Lett. 2002, 4: 1491 - 16
Sprott KT.Corey EJ. Org. Lett. 2003, 5: 2465