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232734 Sigma-Aldrich

R-Alpine-Borane® solution

0.5 M in THF

Synonym: B-Isopinocampheyl-9-borabicyclo[3.3.1]nonane solution

  • CAS Number 73624-47-2

  • Empirical Formula (Hill Notation) C18H31B

  • Molecular Weight 258.25

  •  MDL number MFCD00074776

  •  PubChem Substance ID 24853817

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Reduction
Quality Level   100
optical activity   [α]20/D −3.0°, neat
concentration   0.5 M in THF
density   0.896 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-/m1/s1
InChI key   VCDGSBJCRYTLNU-PHPOFCCKSA-N

Description

General description

R-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.

R-Alpine-Borane® solution may be used to prepare:
• (R)-5-(Benzyloxy)pent-3-y-2-ol, an intermediate for the stereoselective total synthesis of (-)-stagonolide D.
• (R)-1-(p-Tolyl)-1-pentyn-3-ol, an intermediate for the enatioselective synthesis of (R)-incrustoporin.
• N-(tert-Butyloxycarbonyl)-(4S)-[4-2H]-1-L-homoserine tert-butyl ester, an intermediate for synthesizing (4S)-[4-2H]-L-homoserine.

Packaging

100 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 
UN1993 - class 3 - PG 2 - RQ - VP <= 110kPa - Flammable liquids, n.o.s., HI: all
WGK Germany 
WGK 3
Flash Point(F) 
1.4 °F
Flash Point(C) 
-17 °C

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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