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  • 317039 - (+)-B-Methoxydiisopinocampheylborane

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317039 Sigma-Aldrich

(+)-B-Methoxydiisopinocampheylborane

Synonym: (+)-Diisopinocampheylmethoxyborane

  • CAS Number 99438-28-5

  • Empirical Formula (Hill Notation) C21H37BO

  • Molecular Weight 316.33

  •  Beilstein/REAXYS Number 6370228

  •  MDL number MFCD21332906

  •  PubChem Substance ID 24859061

  •  NACRES NA.22

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Properties

Related Categories Allylation, Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents
SMILES string   COB([C@H]1CC2CC([C@@H]1C)C2(C)C)[C@H]3CC4CC([C@@H]3C)C4(C)C
InChI   1S/C21H37BO/c1-12-16-8-14(20(16,3)4)10-18(12)22(23-7)19-11-15-9-17(13(19)2)21(15,5)6/h12-19H,8-11H2,1-7H3/t12-,13-,14+,15+,16-,17-,18-,19-/m0/s1
InChI key   IAQXEQYLQNNXJC-JPDDNCELSA-N

Description

Application

Reactant involved in:
• Oxidative cyclization and alkylation for synthesis of ionomycin
• Intramolecular conjugate addition for tetrahydropyran synthesis
• Aldol addition and Suzuki coupling reactions
• Allylation
• Synthesis of alkanols

Both (+)- and (-)-forms are precursors to B-allyldiisopinocampheylborane derivatives, which are subsequently reacted with aldehydes to give homoallylic alcohols and β-amino alcohols of high enantiomeric excess.

Packaging

5, 25, 100 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
235.4 °F - closed cup
Flash Point(C) 
113 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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