Skip to Content
MilliporeSigma
All Photos(2)

Documents

417203

Sigma-Aldrich

R-Alpine-Borane®

97%

Synonym(s):

B-Isopinocampheyl-9-borabicyclo[3.3.1]nonane

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C18H31B
CAS Number:
73624-47-2
Molecular Weight:
258.25
MDL number:
MFCD00074776
UNSPSC Code:
12352005
PubChem Substance ID:
24866131

assay

97%

optical activity

[α]21/D -22°, c = 12 in THF

bp

>55 °C (lit.)

density

0.947 g/mL at 25 °C (lit.)

SMILES string

C[C@H]1[C@@H](CC2CC1C2(C)C)B3C4CCCC3CCC4

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

InChI key

VCDGSBJCRYTLNU-PHPOFCCKSA-N

Related Categories

General description

R-Alpine-Borane® is a chiral reducing agent, synthesized from (+)-α-pinene via hydroboration.

Application

R-Alpine-Borane® may be used in the preparation of (22R)-hydroxy-23-acetylenic steroids with high stereoselectivity.
Reagent for the asymmetric reduction of a variety of prochiral ketones.

Legal Information

Alpine-Borane is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Flame
GHS02

signalword

Danger

hcodes

H250

Hazard Classifications

Pyr. Liq. 1

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Stereocontrolled synthesis of 22-hydroxy-23-acetylenic steroids, key intermediates in steroid side chain construction. Observation of a directive effect by an a-chiral site during asymmetric reduction with-B-3-pinanyl-9-BBN (Alpine-Borane).
Midland MM and Kwon YC.
Tetrahedron Letters, 25(52), 5981-5984 (1984)
Ramachandran, P.V. et al.
Tetrahedron Asymmetry, 4, 2399-2399 (1993)
Diisopinocampheylchloroborane, a remarkably efficient chiral reducing agent for aromatic prochiral ketones.
Chandrasekharan J, et al.
The Journal of Organic Chemistry, 50(25), 5446-5448 (1985)
Matteson DS
Stereodirected Synthesis with Organoboranes, 346-347 (2012)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service