Disiamylborane
Appearance
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IUPAC name
Bis(1,2-dimethylpropyl)borane
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3D model (JSmol)
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CompTox Dashboard (EPA)
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Properties | |
C10H23B | |
Molar mass | 154.09 g/mol |
Melting point | 35-40 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Disiamylborane (bis(1,2-dimethylpropyl)borane, Sia2BH) is an organoborane used in organic synthesis. It is used for hydroboration–oxidation reactions of terminal alkynes, giving aldehydes via anti-Markovnikov hydration followed by tautomerization. Disiamylborane is relatively selective for terminal alkynes and alkenes vs internal alkynes and alkenes..[1] Disiamylborane is prepared by hydroboration of trimethylethylene with diborane.[1] The reaction stops at the secondary borane due to steric hindrance.
Related reagents
- 9-Borabicyclo[3.3.1]nonane (9-BBN).
- Thexylborane ((1,1,2-trimethylpropyl)borane, ThxBH2), a primary borane obtained by hydroboration of tetramethylethylene.
Naming
The name siamyl is an abbreviation for "sec-isoamyl".
References
- ^ a b Eric J. Leopold (1986). "Selective Hydroboration of a 1,3,7-Triene: Homogeraniol". Organic Syntheses. 64: 164. doi:10.15227/orgsyn.064.0164.