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417041

Sigma-Aldrich

S-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:
42371-63-1
Molecular Weight:
258.25
MDL number:
MFCD00082390
UNSPSC Code:
12352000
PubChem Substance ID:
24866117

assay

97%

optical activity

[α]22/D +20°, 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-/m0/s1

InChI key

VCDGSBJCRYTLNU-NEXGVSGLSA-N

Related Categories

General description

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

Application

S-Alpine-Borane® may be used in the preparation of (-)-(4S)-5-methyl-2-hexyn-4-ol, an intermediate for the synthesis of (+)-Prelog-Djerassi lactonic aldehyde.

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)

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Application of [2,3] sigmatropic (Wittig) rearrangements in synthesis. The synthesis of (+)-Prelog-Djerassi lactone.
Tsai DJS, and Midland MM.
Journal of the American Chemical Society, 107(13), 3915-3918 (1985)
Matteson DS
Stereodirected Synthesis with Organoboranes, 346-347 (2012)

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