Pinacolborane

Pinacolborane
Names
Preferred IUPAC name
4,4,5,5-Tetramethyl-1,3,2-dioxaborolane
Other names
HBpin
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.118.700 Edit this at Wikidata
EC Number
  • 607-485-3
  • InChI=1S/C6H12BO2/c1-5(2)6(3,4)9-7-8-5/h1-4H3
    Key: LZPWAYBEOJRFAX-UHFFFAOYSA-N
  • [B]1OC(C(O1)(C)C)(C)C
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:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
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).

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]

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

References

  1. ^ "4,4,5,5-Tetramethyl-1,3,2-dioxaborolane".
  2. ^ Ramachandran, P. Veeraraghavan; Chandra, J. Subash; Ros, Abel; Fernández, Rosario; Lassaletta, José M.; Aggarwal, Varinder K.; Blair, Daniel J. (2017). "Pinacolborane". Encyclopedia of Reagents for Organic Synthesis. pp. 1–12. doi:10.1002/047084289X.rn00574.pub3. ISBN 9780470842898.
  3. ^ a b Brown, H.C.; Zaidlewicz, M. (2001). Organic Syntheses Via Boranes, Vol. 2. Milwaukee, WI: Aldrich Chemical Co. ISBN 978-0-9708441-0-1.
  4. ^ Ely, Robert J.; Morken, James P. (2011). "Stereoselective Nickel-Catalyzed 1,4-Hydroboration of 1,3-Dienes". Organic Syntheses. 88: 342. doi:10.15227/orgsyn.088.0342.
  5. ^ Stachowiak, Hanna; Kaźmierczak, Joanna; Kuciński, Krzysztof; Hreczycho, Grzegorz (2018). "Catalyst-free and solvent-free hydroboration of aldehydes". Green Chemistry. 20 (8): 1738–1742. doi:10.1039/C8GC00042E. ISSN 1463-9262.
  6. ^ Wang, Weifan; Luo, Man; Yao, Weiwei; Ma, Mengtao; Pullarkat, Sumod A.; Xu, Li; Leung, Pak-Hing (2019). "Catalyst-free and solvent-free hydroboration of ketones". New Journal of Chemistry. 43 (27): 10744–10749. doi:10.1039/C9NJ02722J. ISSN 1144-0546. S2CID 197130591.
  7. ^ Harinath, Adimulam; Bhattacharjee, Jayeeta; Panda, Tarun K. (2019). "Facile Reduction of carboxylic acids to primary alcohols under catalyst-free and solvent-free conditions". Chemical Communications. 55 (10): 1386–1389. doi:10.1039/C8CC08841A. ISSN 1359-7345. PMID 30607398. S2CID 58570916.
  8. ^ Amaike, K.; Loach, R. P.; Movassaghi, M. (2015). "Direct C7 Functionalization of Tryptophan. Synthesis of Methyl (S)-2-((tert-Butoxycarbonyl)amino)-3-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate" (PDF). Organic Syntheses. 92: 373–385. doi:10.15227/orgsyn.092.0373. PMC 4733874. PMID 26839440.
  9. ^ Ishiyama, Tatsuo; Takagi, Jun; Nobuta, Yusuke; Miyaura, Norio (2005). "Iridium-Catalyzed C-H Borylation of Arenes and Heteroarenes: 1-Chloro-3-Iodo-5-(4,4,5,5-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Benzene and 2-(4,4,5,5,-Tetramethyl-1,3,2-Dioxaborolan-2-Yl)Indole". Organic Syntheses. 82: 126. doi:10.15227/orgsyn.082.0126. hdl:2115/56319.
  10. ^ Neeve, Emily C.; Geier, Stephen J.; Mkhalid, Ibraheem A. I.; Westcott, Stephen A.; Marder, Todd B. (2016). "Diboron(4) Compounds: From Structural Curiosity to Synthetic Workhorse". Chemical Reviews. 116 (16): 9091–9161. doi:10.1021/acs.chemrev.6b00193. hdl:1807/78811. PMID 27434758.

Content Disclaimer

Informasi ini disarikan dari Wikipedia dan disajikan kembali untuk tujuan edukasi. Konten tersedia di bawah lisensi CC BY-SA 3.0. Kami tidak bertanggung jawab atas ketidakakuratan data yang bersumber dari kontribusi publik tersebut.

  1. The information displayed on this website is sourced in part or in whole from Wikipedia and has been adapted for the purpose of restating it. We strive to provide accurate and relevant information, however:
  2. There is no guarantee of absolute accuracy. Wikipedia is an open, collaborative project that can be edited by anyone, so information is subject to change.
  3. It is not intended to constitute professional advice. The content displayed is for informational and educational purposes only. For important decisions (e.g., medical, legal, or financial), please consult a professional.
  4. Content copyright. Wikipedia is licensed under the Creative Commons Attribution-ShareAlike License (CC BY-SA). This means that content may be reused with appropriate attribution and shared under a similar license.
  5. Responsible use. Any risk arising from the use of information from this website is entirely the responsibility of the user.