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

• ChemBase ID: 146380
• 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-BAMGFKBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl bis[(1R,2R,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borinate
• IUPAC Traditional name: methyl bis(1R,2R,3S,5R)-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: 85134-98-1
• MDL Number: MFCD00074809
• PubChem SID: 24859062; 162240578
• PubChem CID: 13549401

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 - 317047

Packaging
5, 25, 100 g in glass bottle
Application
Reactant involved in organic synthesis reactions such as:
• Double allylboration for synthesis of fragments of tetrafibricin1
• Anticancer cytotoxic monorhizopodin synthesis2
• Annulation of cyclic allylsilanes3
• Asymmetric synthesis of β-amino-α-hydroxy acid taxol side chain analogs4