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Sigma-Aldrich

(−)-B-Methoxydiisopinocampheylborane

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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

form

solid

Quality Level

100

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

Related Categories

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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B-Methoxydiisopinocampheylborane (Ipc2BOMe): A Pinene Based Auxiliary for Asymmetric C-C Bond-Forming Reactions
Hertweck C and Boland W
J. Prakt. Chem., 341(1), 83-87 (1999)

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