sodium triethylborohydride
{{Chembox
|ImageFile=NaBHEt3.svg
|Section1={{Chembox Identifiers
|CASNo = 17979-81-6
|ChemSpiderID = 2006279
|EINECS = 241-903-1
|PubChem = 23667700
|StdInChI=1S/C6H15B.Na/c1-4-7(5-2)6-3;/h4-6H2,1-3H3;/q-1;+1
|StdInChIKey = UKYGKELSBAWRAN-UHFFFAOYSA-N
|SMILES = [B-](CC)(CC)CC.[Na+]
}}
|Section2={{Chembox Properties
|Formula = C6H16BNa
|MolarMass =121.99
|Appearance = white solid
|MeltingPt = 30 °C
}}
|Section3={{Chembox Hazards
|GHSPictograms = {{GHS02}}{{GHS05}}
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|261|314}}
|PPhrases = {{P-phrases|231+232|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|370+378|402+404|405|501}}
|MainHazards = pyrophoric
}}
}}
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.{{cite web|url=http://www.callery.com/products/boranes|title=Callery Borane Products {{!}} Callery.com {{!}} Callery|date=2017-03-05|website=Callery|language=en-us|access-date=2017-03-05}} 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.Binger, P.; Köster, R., "Sodium triethylhydroborate, sodium tetraethylborate, and sodium triethyl-1-propynylborate", Inorg. Synth. 1974, 15, 136-141. {{doi|10.1002/9780470132463.ch31}} The trimethylborohydride analogue, which is assumed to be structurally similar to the triethylborohydride, adopts a tetrameric structure in toluene solution.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}} NaBHEt3 forms a dimeric adduct with TMEDA.{{cite journal |doi=10.1002/ejic.200900756 |title=Metal-Hydride Bonding in Higher Alkali Metal Boron Monohydrides |date=2009 |last1=Haywood |first1=Joanna |last2=Wheatley |first2=Andrew E. H. |journal=European Journal of Inorganic Chemistry |volume=2009 |issue=33 |pages=5010–5016 }}