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Thermo Scientific Chemicals
Boron tribromide, 1M soln. in dichloromethane
CAS: 10294-33-4 | BBr3 | 250.52 g/mol
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化學識別
CAS10294-33-4
IUPAC Nametribromoborane
Molecular FormulaBBr3
InChI KeyILAHWRKJUDSMFH-UHFFFAOYSA-N
SMILESBrB(Br)Br
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規格
規格表
規格表Appearance (Color)Clear colorless to yellow to brown
Assay (Aqueous acid-base Titration)0.95-1.1M
CommentMay darken on storage
CommentMay develop some turbidity or precipitate. If precipitate is present, gently mix precipitate back into solution under an inert atmosphere
FormLiquid
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Miscible with ethanol and carbon tetrachloride.
Notes
Moisture sensitive. Reacts violently with water. Incompatible with alcohols, alkali metals, aluminum, sodium oxides and strong bases.
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.
Solubility
Miscible with ethanol and carbon tetrachloride.
Notes
Moisture sensitive. Reacts violently with water. Incompatible with alcohols, alkali metals, aluminum, sodium oxides and strong bases.
RUO – Research Use Only
General References:
- 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.