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417041

Sigma-Aldrich

S-Alpine-Borane®

97%

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Synonym(s):
B-Isopinocampheyl-9-borabicyclo[3.3.1]nonane
Empirical Formula (Hill Notation):
C18H31B
CAS Number:
42371-63-1
Molecular Weight:
258.25
MDL number:
MFCD00082390
UNSPSC Code:
12352000
PubChem Substance ID:
24866117

Quality Level

100

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

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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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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