Sodium triethylborohydride

Sodium triethylborohydride
Identifiers
CAS Number	17979-81-6;
3D model (JSmol)	Interactive image;
ChemSpider	2006279;
ECHA InfoCard	100.038.079
EC Number	241-903-1;
PubChem CID	23667700;
	InChI InChI=1S/C6H15B.Na/c1-4-7(5-2)6-3;/h4-6H2,1-3H3;/q-1;+1 Key: UKYGKELSBAWRAN-UHFFFAOYSA-N;
	SMILES [B-](CC)(CC)CC.[Na+];
Properties
Chemical formula	C6H16BNa
Molar mass	121.99
Appearance	white solid
Melting point	30 °C
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	pyrophoric
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H261, H314
Precautionary statements	P231+P232, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P402+P404, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Sodium triethylborohydride is an organoboron compound with the formula NaBH(C₂H₅)₃. It is a colorless, pyrophoric solid that is commercially available in toluene solution, unlike the related LiBH(C₂H₅)₃ which is typically sold as a THF solution.^[1] It is commonly used for the reductive activation of homogeneous catalysts, converting metal halides to hydrides. Sodium triethylborohydride has been prepared by treating a hot toluene slurry of sodium hydride with triethylborane.^[2] The trimethylborohydride analogue, which is assumed to be structurally similar to the triethylborohydride, adopts a tetrameric structure in toluene solution.^[3] NaBHEt₃ forms a dimeric adduct with tmeda.^[4]

References

^ "Callery Borane Products | Callery.com | Callery". Callery. 2017-03-05. Retrieved 2017-03-05.
^ Binger, P.; Köster, R., "Sodium triethylhydroborate, sodium tetraethylborate, and sodium triethyl-1-propynylborate", Inorg. Synth. 1974, 15, 136-141. doi:10.1002/9780470132463.ch31
^ Bell, N. A.; Coates, G. E.; Heslop, J. A., "Sodium hydridotrimethylboronate and its ether solvate. Study of hydridotrialkylboronates as reagents for the preparation of beryllium hydrides", J. Organomet. Chem. 1987, volume 329, 287-291. doi:10.1016/0022-328X(87)80062-1
^ Haywood, Joanna; Wheatley, Andrew E. H. (2009). "Metal-Hydride Bonding in Higher Alkali Metal Boron Monohydrides". European Journal of Inorganic Chemistry. 2009 (33): 5010–5016. doi:10.1002/ejic.200900756.

[1] "Callery Borane Products | Callery.com | Callery". Callery. 2017-03-05. Retrieved 2017-03-05.

[2] Binger, P.; Köster, R., "Sodium triethylhydroborate, sodium tetraethylborate, and sodium triethyl-1-propynylborate", Inorg. Synth. 1974, 15, 136-141. doi:10.1002/9780470132463.ch31

[3] Bell, N. A.; Coates, G. E.; Heslop, J. A., "Sodium hydridotrimethylboronate and its ether solvate. Study of hydridotrialkylboronates as reagents for the preparation of beryllium hydrides", J. Organomet. Chem. 1987, volume 329, 287-291. doi:10.1016/0022-328X(87)80062-1

[4] Haywood, Joanna; Wheatley, Andrew E. H. (2009). "Metal-Hydride Bonding in Higher Alkali Metal Boron Monohydrides". European Journal of Inorganic Chemistry. 2009 (33): 5010–5016. doi:10.1002/ejic.200900756.

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