Alpine borane

Alpine borane

Names
IUPAC name 9-(2,6,6-Trimethylbicyclo[3.1.1]hept-3-yl)-9-bora-bicyclo[3.3.1]nonane
Other names Alpine-Borane; B-Isopinocampheyl-9-borabicyclo[3.3.1]nonane; B-3-Pinanyl-9-borabicyclo[3.3.1]nonane
Identifiers
CAS Number	73624-47-2 (R isomer) Y 42371-63-1 (S isomer) Y
3D model (JSmol)	Interactive image
ChemSpider	17206399 Y
ECHA InfoCard	100.157.575
PubChem CID	9921373 R 10890567 S
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/s1 Y Key: VCDGSBJCRYTLNU-AZWGFFAPSA-N Y 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/s1 Key: VCDGSBJCRYTLNU-AZWGFFAPBY
SMILES CC4(C)[C@@H]1C[C@H]4[C@@H](C)[C@@H](C1)B3C2CCCC3CCC2
Properties
Chemical formula	C18H31B
Molar mass	258.26 g·mol−1
Appearance	Colorless liquid
Density	0.947 g/mL
Boiling point	> 55 °C (131 °F; 328 K)
Hazards
GHS pictograms
GHS signal word	Danger
GHS hazard statements	H250
GHS precautionary statements	P210, P222, P280, P302+334, P370+378, P422
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Alpine borane is the commercial name for an organoboron compound that is used in organic synthesis. It is a colorless liquid, although it is usually encountered as a solution.

This reagent is generated by treating 9-BBN with α-pinene.

This sterically crowded chiral trialkylborane can stereoselectively reduce ketones, aldehydes, even deutero aldehydes in what is known as the Midland Alpine Borane Reduction, or simply the Midland Reduction:

Hydrolysis of the resulting borinic ester affords the alcohol:

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

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