• USA Home
  • 237701 - S-Alpine-Borane® solution

EMAIL THIS PAGE TO A FRIEND
237701 Sigma-Aldrich

S-Alpine-Borane® solution

0.5 M in THF

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

  • CAS Number 42371-63-1

  • Empirical Formula (Hill Notation) C18H31B

  • Molecular Weight 258.25

  •  MDL number MFCD00082390

  •  PubChem Substance ID 24854265

  •  NACRES NA.22

Purchase

Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Reduction
Quality Level   100
optical activity   [α]22/D +1.2°, neat
concentration   0.5 M in THF
density   0.897 g/mL at 25 °C
SMILES string   C[C@@H]1[C@H](C[C@H]2C[C@@H]1C2(C)C)B3[C@@H]4CCC[C@H]3CCC4
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

Description

General description

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

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).

Packaging

100, 800 mL in Sure/Seal™

Legal Information

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

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Target organs 
Respiratory system
Supplemental Hazard Statements 
EUH019
RIDADR 
UN 1993BF 3 / PGII
WGK Germany 
WGK 3
Flash Point(F) 
1.4 °F - closed cup
Flash Point(C) 
-17 °C - closed cup

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number
Protocols & Articles
Peer-Reviewed Papers
15

References

Related Products

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?