Disiamylborane

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Disiamylborane
Skeletal formula of disiamylborane
Ball-and-stick model of the disiamylborane molecule
Names
IUPAC name
Bis(1,2-dimethylpropyl)borane
Identifiers
3D model (Jmol)
ChemSpider
UNII
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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Infobox references

Disiamylborane (bis(1,2-dimethylpropyl)borane) is an organoborane used in organic synthesis. It is used to add water to a terminal alkyne, forming an aldehyde via anti-Markovnikov addition. Disiamylborane is relatively selective for terminal alkynes. It also is used for the selective functionalization of terminal alkenes.[1]

Naming[edit]

"Siamyl" is an abbreviation for sec-isoamyl. More modern conventions replace amyl with the pentyl group,[2] and dispense with the sec and iso naming of pentyl isomers in favor of systematic naming as a substituted alkyl chain.[3]

References[edit]

  1. ^ Eric J. Leopold (1990). "Selective Hydroboration of a 1,3,7-Triene: Homogeraniol". Org. Synth. ; Coll. Vol., 7, p. 258 
  2. ^ "Friday Dec 4 Lecture" (PDF). Amherst University. 
  3. ^ "Disiamylborane". PubChem. 

External links[edit]