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237701 Aldrich

S-Alpine-Borane® solution

0.5 M in THF

Synonym: B-isopinocampheyl-9-borabicyclo[3.3.1]nonane

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Reduction
InChI Key   VCDGSBJCRYTLNU-NEXGVSGLSA-N
optical activity   [α]22/D +1.2°, neat
concentration   0.5 M in THF
density   0.897 g/mL at 25 °C

Description

Packaging

100, 800 mL in Sure/Seal™

Application

R- and S-Alpine-Boranes are used for asymmetric reduction of aldehydes and prochiral ketones.

S-Alpine-Borane® solution may be used to prepare:
• 5(S)-methyl 5-hydroxy-8-(tetrahydropyran-2-yloxy)-6-octynoate, an intermediate for the stereocontrolled total synthesis of leukotriene B4.
• (+)-(S)-4-hydroxy-6-phenyl-5-hexynyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate
• (R)-1-(tert-Butyldiphenylsilyloxy)pent-3-yn-2-ol, an intermediate for the preparation of (S)-4,5-dihydroxypentane-2,3-dione (DPD).

General description

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

Legal Information

Alpine-Borane is a registered trademark of Sigma-Aldrich Co. LLC

Price and Availability

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Supplemental Hazard Statements 
May form explosive peroxides.
RIDADR 
UN 1993BF 3 / PGII
WGK Germany 
3
Flash Point(F) 
1.4 °F
Flash Point(C) 
-17 °C
Protocols & Articles
Peer-Reviewed Papers
15

References

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