Disiamylborane

Disiamylborane
Names


IUPAC name Bis(1,2-dimethylpropyl)borane
Identifiers
CAS Number	1069-54-1^Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	167251^Y
PubChem CID	192733
UNII	2O6VD8483R^N
InChI InChI=1S/C10H23B/c1-7(2)9(5)11-10(6)8(3)4/h7-11H,1-6H3^Y Key: HXJFQNUWPUICNY-UHFFFAOYSA-N^Y InChI=1/C10H23B/c1-7(2)9(5)11-10(6)8(3)4/h7-11H,1-6H3 Key: HXJFQNUWPUICNY-UHFFFAOYAY
SMILES CC(C(C)C)BC(C)C(C)C B(C(C(C)C)C)C(C)C(C)C
Properties
Chemical formula	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).
N verify (what is ^YN ?)
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

"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

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

External links

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