| Identification | Back Directory | [Name]
(+)-B-METHOXYDIISOPINOCAMPHEYLBORANE | [CAS]
85134-98-1 | [Synonyms]
(+)-DIISOPINOCAMPHEYLMETHOXYBORANE
()-B-Methoxydiisopinocampheylborane
(+)-B-METHOXYDIISOPINOCAMPHEYLBORANE
(-)-B-Methoxydiisopinocampheylborane
)-B-Methoxydiisopinocampheylborane
()-B-Methoxydiisopinocampheylborane hydrate
(-)-B-Methoxydiisopinocampheylborane hydrate
methoxy-bis[(1R,3S,4R,5R)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]borane
Borinic acid, B,B-bis[(1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]-, methyl ester | [Molecular Formula]
C21H37BO | [MDL Number]
MFCD00013408 | [MOL File]
85134-98-1.mol | [Molecular Weight]
316.33 |
| Chemical Properties | Back Directory | [Melting point ]
>110 °C | [Boiling point ]
365.6±9.0 °C(Predicted) | [density ]
0.95±0.1 g/cm3(Predicted) | [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [form ]
solid | [color ]
white | [Optical Rotation]
[α]20/D 72±3°, c = 1% in diethyl ether | [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?/m1/s1 | [InChIKey]
IAQXEQYLQNNXJC-CLIXPIQASA-N | [SMILES]
COB([C@@H]1CC2CC([C@H]1C)C2(C)C)[C@H]3CC4CC([C@H]3C)C4(C)C |
| Hazard Information | Back Directory | [Uses]
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
| [Application]
B-Methoxydiisopinocampheylborane is a intermediate for the synthesis of B-allyl- and B-crotyldiisopinocampheylboranes; reacts with potassium hydride
to form an asymmetric reducing agent. | [Preparation]
B-Methoxydiisopinocampheylborane is prepared in two steps from either (+)- or (-)-α-pinene (eq 1).
 | [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. |
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