Pinacolborane

Pinacolborane
Names
	IUPAC name 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane
	Other names HBpin
Identifiers
CAS Number	25015-63-8;
3D model (JSmol)	Interactive image;
ChemSpider	2016512;
EC Number	607-485-3;
PubChem CID	6364989;
CompTox Dashboard (EPA)	DTXSID30422852;
	InChI InChI=1S/C6H12BO2/c1-5(2)6(3,4)9-7-8-5/h1-4H3 Key: LZPWAYBEOJRFAX-UHFFFAOYSA-N;
	SMILES [B]1OC(C(O1)(C)C)(C)C;
Properties
Chemical formula	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 pictograms
GHS Signal word	Danger
GHS hazard statements	H220, H225, H260, H261, H315, H318
GHS precautionary statements	P210, P223, P231+232, P233, P240, P241, P242, P243, P264, P280, P302+352, P303+361+353, P305+351+338, P310, P321, P332+313, P335+334, P362, P370+378, P377, P381, P402+404, P403, P403+235, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Pinacolborane is the borane with the formula (CH₃)₄C₂O₂BH. It features a five-membered C₂O₂B ring. Owing to the presence of the alkoxide substituents, it is a monomer. It is a colorless liquid prepared by treating borane adducts with pinacol.[1] It features a reactive B-H functional group.[2]

Use in organic synthesis

In the presence of catalysts, pinacolborane hydroborates alkenes and, less rapidly, alkynes.[2][3]

Pinacolborane also effects catalyst-free hydroboration of aldehydes,[4] ketones,[5] and carboxylic acids.[6]

Pinacolborane is used in borylation, a form of C-H activation.[7][8]

Related compounds

Catecholborane

References

Ramachandran, P. Veeraraghavan; Chandra, J. Subash; Ros, Abel; Fernández, Rosario; Lassaleta, José M. (2014). "Pinacolborane". Encyclopedia of Reagents for Organic Synthesis. pp. 1–7. doi:10.1002/047084289X.rn00574.pub2. ISBN 9780470842898.
Brown, H.C.; Zaidlewicz, M. (2001). Organic Syntheses Via Boranes, Vol. 2. Milwaukee, WI: Aldrich Chemical Co. ISBN 978-0-9708441-0-1.
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.
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.
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.
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.
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". Organic Syntheses. 92: 373–385. doi:10.15227/orgsyn.092.0373 (inactive 2021-01-11). PMC 4733874. PMID 26839440.CS1 maint: DOI inactive as of January 2021 (link)
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.

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[1] Ramachandran, P. Veeraraghavan; Chandra, J. Subash; Ros, Abel; Fernández, Rosario; Lassaleta, José M. (2014). "Pinacolborane". Encyclopedia of Reagents for Organic Synthesis. pp. 1–7. doi:10.1002/047084289X.rn00574.pub2. ISBN 9780470842898.

[HCC-2] Brown, H.C.; Zaidlewicz, M. (2001). Organic Syntheses Via Boranes, Vol. 2. Milwaukee, WI: Aldrich Chemical Co. ISBN 978-0-9708441-0-1.

[3] 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.

[4] 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.

[5] 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.

[6] 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.

[7] 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". Organic Syntheses. 92: 373–385. doi:10.15227/orgsyn.092.0373 (inactive 2021-01-11). PMC 4733874. PMID 26839440.CS1 maint: DOI inactive as of January 2021 (link)

[8] 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.