| Identification | Back Directory | [Name]
Diisopinocampheylborane | [CAS]
21947-87-5 | [Synonyms]
Diisopinocampheylborane
(+)-Diisopinocampheylborane
Diisopinocampheylborane (Technical Grade)
Bis[(1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]borane
Borane,bis[(1S,2R,3S,5S)-2,6,6-triMethylbicyclo[3.1.1]hept-3-yl]-
Bis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane | [Molecular Formula]
C20H35B | [MDL Number]
MFCD23701661 | [MOL File]
21947-87-5.mol | [Molecular Weight]
286.3 |
| Chemical Properties | Back Directory | [Boiling point ]
351.5±25.0 °C(Predicted) | [storage temp. ]
Hygroscopic, Refrigerator, under inert atmosphere | [solubility ]
Dichloromethane (Slightly), THF (Slightly) | [form ]
Solid | [color ]
White Sticky to Off-White | [Stability:]
Extremely Moisture Sensitive |
| Hazard Information | Back Directory | [Chemical Properties]
White Sticky Solid | [Uses]
Diisopinocampheylborane is a hydroborane with many applications in organic synthesis of nicotine analogs, (-)-Invictolide, (+)-strictifolione and other organic compounds. | [Application]
Diisopinocampheylborane is a chiral hydroboration reagent for asymmetric hydroboration of cis-alkenes to provide access to optically active secondary alcohols. It is a precursor for the preparation of a large number of chiral reagents for asymmetric synthesis.
| [Synthesis]
(+)-diisopinocampheylborane is prepared in high enantiomeric purity and good yield (Table 1) by hydroboration of commercially available (-)-α-pinene (of low enantiomeric purity) with Borane-Dimethyl Sulfide (BMS) complex, carried out by mixing the two reagents to make a solution of known molarity in THF at 0 °C or rt (eq 1); the mixture is left without stirring at 0 °C for ~12 h for the development of crystals (the slow crystallization facilitates the incorporation of the major diastereomer in the crystalline product, leaving the undesired isomer in solution); the supernatant solution is decanted using a double-ended needle; the crystalline lumps are broken and washed with diethyl ether and dried under vacuum (~12 mmHg) at rt.
| [Precautions]
Diisopinocampheylborane is air sensitive, reacting instantaneously with protic solvents to liberate hydrogen; must be handled under an inert atmosphere (N2 or Ar); can be stored at 0 °C under inert atmosphere for several months without loss of hydride activity.
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| Company Name: |
Energy Chemical
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021-021-58432009 400-005-6266 |
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http://www.energy-chemical.com |
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