Disiamylborane

Disiamylborane
Names
	IUPAC name Bis(1,2-dimethylpropyl)borane
Identifiers
CAS Number	1069-54-1 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	167251 ;
PubChem CID	192733;
UNII	2O6VD8483R ;
CompTox Dashboard (EPA)	DTXSID40910174 ;
	InChI InChI=1S/C10H23B/c1-7(2)9(5)11-10(6)8(3)4/h7-11H,1-6H3 Key: HXJFQNUWPUICNY-UHFFFAOYSA-N ; 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).
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	Infobox references

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".

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References

Eric J. Leopold (1986). "Selective Hydroboration of a 1,3,7-Triene: Homogeraniol". Organic Syntheses. 64: 164. doi:10.15227/orgsyn.064.0164.

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[CV7P0258-1] Eric J. Leopold (1986). "Selective Hydroboration of a 1,3,7-Triene: Homogeraniol". Organic Syntheses. 64: 164. doi:10.15227/orgsyn.064.0164.