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Alpine borane

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Alpine borane
Names
IUPAC name 9-(2,6,6-Trimethylbicyclohept-3-yl)-9-bora-bicyclononane
Other names Alpine-Borane; B-Isopinocampheyl-9-borabicyclononane; B-3-Pinanyl-9-borabicyclononane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.575 Edit this at Wikidata
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C18H31B/c1-12-16-10-13(18(16,2)3)11-17(12)19-14-6-4-7-15(19)9-5-8-14/h12-17H,4-11H2,1-3H3/t12-,13-,14?,15?,16+,17-/m1/s1Key: VCDGSBJCRYTLNU-AZWGFFAPSA-N
  • InChI=1/C18H31B/c1-12-16-10-13(18(16,2)3)11-17(12)19-14-6-4-7-15(19)9-5-8-14/h12-17H,4-11H2,1-3H3/t12-,13-,14?,15?,16+,17-/m1/s1Key: VCDGSBJCRYTLNU-AZWGFFAPBY
SMILES
  • CC4(C)1C4(C)(C1)B3C2CCCC3CCC2
Properties
Chemical formula C18H31B
Molar mass 258.26 g·mol
Appearance Colorless liquid
Density 0.947 g/mL
Boiling point >55 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Alpine borane is the commercial name for an organoboron compound that is used in organic synthesis. This reagent is generated by treating 9-BBN with α-pinene to give a sterically crowded trialkylborane. The resulting chiral species can stereoselectively reduce ketones, aldehydes, even deutero aldehydes in what is known as the Midland Alpine Borane Reduction, or simply the Midland Reduction:

C8H12B-pinanyl + RCDO → C8H12BOCHDR + (+)-d-pinene

Hydrolysis of the resulting borinic ester affords the alcohol:

C8H12BOCHDR + H2O → C8H12BOH + HOCHDR

It is also effective for the stereoselective reduction of certain acetylenic ketones.

Related reagents

A range of alkyl-substituted derivatives of borane and diborane are specialty reagents in organic synthesis. Two such reagents that are closely related to Alpine borane are 9-BBN and diisopinocampheylborane.

References

  1. R-Alpine-Borane and S-Alpine-Borane at Sigma-Aldrich
  2. M. Mark Midland "B-3-Pinanyl-9-borabicyclononane" in Encyclopedia of Reagents for Organic Synthesis 2001 John Wiley, New York.doi:10.1002/047084289X.rp173. Article Online Posting Date: April 15, 2001
  3. M. Mark Midland and Richard S. Graham. "Asymmetric Reduction of α,β-Acetylenic Ketones with B-3-Pinanyl-9-Borabicyclo[3.3.1]nonane: (R)-(+)-1-Octyln-3-ol". Organic Syntheses; Collected Volumes, vol. 7, p. 402.
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