317047

(−)-B-Methoxydiisopinocampheylborane

• Synonym(s): (−)-Diisopinocampheylmethoxyborane
• Empirical Formula (Hill Notation): C₂₁H₃₇BO
• CAS Number: 85134-98-1
• Molecular Weight: 316.33
• MDL number: MFCD00074809
• UNSPSC Code: 12352001
• PubChem Substance ID: 24859062
• NACRES: NA.22

Properties

• form: solid
• 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-BAMGFKBFSA-N

Description

General description

B-Methoxydiisopinocampheylborane (Ipc₂BOMe) is an organoborane compound, which is prepared from excess α-pinene, borane dimethylsulfide, and methanol via the formation of an intermediate diisocampheylborane. Ipc₂BOMe is used as a versatile reagent for the construction of C-C bonds in asymmetric synthesis.

Application

Reactant involved in organic synthesis reactions such as:

• Double allylboration for synthesis of fragments of tetrafibricin
• Anticancer cytotoxic monorhizopodin synthesis
• Annulation of cyclic allylsilanes
• Asymmetric synthesis of β-amino-α-hydroxy acid taxol side chain analogs

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): 235.4 °F - closed cup
• Flash Point(C): 113 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves