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417203

Sigma-Aldrich

R-Alpine-Borane®

97%

Synonym(s):

B-Isopinocampheyl-9-borabicyclo[3.3.1]nonane

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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

Quality Level

100

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

Signal Word

Danger

Hazard Statements

H250

Precautionary Statements

P222 - P231 - P422

Hazard Classifications

Pyr. Liq. 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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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)
Matteson DS
Stereodirected Synthesis with Organoboranes, 346-347 (2012)
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)

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