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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

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

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

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Ramachandran, P.V. et al.
Tetrahedron Asymmetry, 4, 2399-2399 (1993)
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)
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)

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