methyl bis[(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borinate

• ChemBase ID: 146719
• Molecular Formular: C21H37BO
• Molecular Mass: 316.32888
• Monoisotopic Mass: 316.2937462
• SMILES: B([C@H]1C[C@H]2C[C@@H]([C@@H]1C)C2(C)C)([C@H]1C[C@H]2C[C@@H]([C@@H]1C)C2(C)C)OC
• Canonical SMILES: COB([C@H]1C[C@H]2C[C@@H]([C@@H]1C)C2(C)C)[C@H]1C[C@H]2C[C@@H]([C@@H]1C)C2(C)C
• InChI: 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
• InChIKey: IAQXEQYLQNNXJC-JPDDNCELSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl bis[(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borinate
• IUPAC Traditional name: methyl bis(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylborinate
• Synonyms: (+)-Diisopinocampheylmethoxyborane; (+)-B-Methoxydiisopinocampheylborane; (+)-二异松蒎基甲氧基硼烷; (+)-B-甲氧基二异松蒎基硼烷

Database IDs

• CAS Number: 99438-28-5
• MDL Number: MFCD21332906
• Beilstein Number: 6370228
• PubChem SID: 162240911; 24859061
• PubChem CID: 10969110

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 6.5615
• LogD (pH = 7.4): 6.5615
• Log P: 6.5615
• Molar Refractivity: 92.4409 cm^3
• Polarizability: 39.220367 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Flash Point: 113 °C; 235.4 °F

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Empirical Formula (Hill Notation): C21H37BO

DETAILS

Sigma Aldrich - 317039

Application
Both (+)- and (-)-forms are precursors to B-allyldiisopinocampheylborane derivatives, which are subsequently reacted with aldehydes to give homoallylic alcohols6 and β-amino alcohols7 of high enantiomeric excess.8
Reactant involved in:
• Oxidative cyclization and alkylation for synthesis of ionomycin1
• Intramolecular conjugate addition for tetrahydropyran synthesis2
• Aldol addition and Suzuki coupling reactions3
• Allylation4
• Synthesis of alkanols5
Packaging
5, 25, 100 g in glass bottle