Diisopinocampheylborane

Diisopinocampheylborane
	Structure of (+)-Diisopinocampheylborane dimer
Names
	IUPAC name Di[(1S,2R,3S,5S)-pinan-3-yl]borane
	Systematic IUPAC name Bis[(1S,2S,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane
	Other names (+)-Di-3-pinanylborane; Diisopinocampheylborane; Ipc2BH dimer
Identifiers
CAS Number	21947-87-5;
3D model (JSmol)	Interactive image;
Abbreviations	Ipc2BH
ChemSpider	10618744;
PubChem CID	86278388;
	InChI InChI=1S/C20H35B/c1-11-15-7-13(19(15,3)4)9-17(11)21-18-10-14-8-16(12(18)2)20(14,5)6/h11-18,21H,7-10H2,1-6H3 Key: KBGJOMVTAXYPAG-UHFFFAOYSA-N; InChI=1/C20H35B/c1-11-15-7-13(19(15,3)4)9-17(11)21-18-10-14-8-16(12(18)2)20(14,5)6/h11-18,21H,7-10H2,1-6H3 Key: KBGJOMVTAXYPAG-UHFFFAOYAB;
	SMILES [H]B(C1CC2CC(C1(C))C2(C)(C))C3CC4CC(C3(C))C4(C)(C);
Properties
Chemical formula	C20H35B
Molar mass	286.31 g·mol−1
Appearance	Colorless solid
Density	1.044 g/cm3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Diisopinocampheylborane is an organoborane that is useful for asymmetric synthesis. This colourless solid is the precursor to a range of related reagents. The compound was reported in 1961 by Zweifel and Brown in a pioneering demonstration of asymmetric synthesis using boranes. The reagent is mainly used for the synthesis of chiral secondary alcohols. The reagent is often depicted as a monomer but like most hydroboranes, it is dimeric with B-H-B bridges.