Pinacolborane
Chemical compound
From Wikipedia, the free encyclopedia
Pinacolborane is the borane with the formula (CH3)4C2O2BH. Often pinacolborane is abbreviated HBpin.[1] It features a boron hydride functional group incorporated in a five-membered C2O2B ring. Like related boron alkoxides, pinacolborane is monomeric. It is a colorless liquid.[2] It features a reactive B-H functional group.[3]
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| Names | |
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| Preferred IUPAC name
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane | |
| Other names
HBpin | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.118.700 |
| EC Number |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C6H13BO2 | |
| Molar mass | 127.98 g·mol−1 |
| Appearance | colorless liquid |
| Density | 0.882 g/cm3 |
| Boiling point | 42–43 °C (108–109 °F; 315–316 K) 50 mmHg |
| Hazards | |
| GHS labelling: | |
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| Danger | |
| H220, H225, H260, H261, H315, H318 | |
| P210, P223, P231+P232, P233, P240, P241, P242, P243, P264, P280, P302+P352, P303+P361+P353, P305+P351+P338, P310, P321, P332+P313, P335+P334, P362, P370+P378, P377, P381, P402+P404, P403, P403+P235, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Use in organic synthesis
In the presence of catalysts, pinacolborane hydroborates alkenes and, less rapidly, alkynes.[3][4]
Pinacolborane also affects catalyst-free hydroboration of aldehydes,[5] ketones,[6] and carboxylic acids.[7]
Pinacolborane is used in borylation, a form of C-H activation.[8][9]
Dehydrogenation of pinacolborane affords dipinacolatodiborane (B2pin2):[10]
- 2 (CH3)4C2O2BH → (CH3)4C2O2B-BO2C2(CH3)4 + H2