| Identification | Back Directory | [Name]
Diisopropyl 2-Allyl-1,3,2-dioxaborolane-4,5-dicarboxylate | [CAS]
99417-55-7 | [Synonyms]
Diisopropyl 2-Allyl-1,3,2-dioxaborolane-4,5-dicarboxylate
diisopropyl (R,R)-2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylate
1,3,2-Dioxaborolane-4,5-dicarboxylic acid, 2-(2-propen-1-yl)-, 4,5-bis(1-methylethyl) ester, (4R,5R)- | [Molecular Formula]
C13H21BO6 | [MDL Number]
MFCD17013257 | [MOL File]
99417-55-7.mol | [Molecular Weight]
284.11 |
| Chemical Properties | Back Directory | [Boiling point ]
338.860±42.00 °C(Press: 760.00 Torr)(predicted) | [density ]
1.080±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted) | [solubility ]
sol toluene, THF, ether, CH2Cl2 |
| Hazard Information | Back Directory | [Uses]
Diisopropyl 2-Allyl-1,3,2-dioxaborolane-4,5-dicarboxylate can be used as a reagent for the asymmetric allylic borylation of aldehydes to generate homoallylic alcohols. | [Preparation]
Diisopropyl 2-Allyl-1,3,2-dioxaborolane-4,5-dicarboxylate is prepared by the reaction of Triisopropyl Borate and Allylmagnesium Bromide in Et2O followed by an acidic extractive workup and direct esterification with diisopropyl tartrate (DIPT) (eq 1).
 | [storage]
Allylboronates are typically handled as a solution in toluene (0.5-1.0 M) and transferred by syringe under an inert atmosphere. The reagent, stored neat or as a solution in toluene over 4? molecular sieves under an argon atmosphere in a refrigerator (-20 °C), is stable for several months. In the presence of water, (1) rapidly hydrolyzes to DIPT and the achiral allylboronic acid. |
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