Sodium triacetoxyborohydride

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Sodium triacetoxyborohydride
Sodium_triacetoxyborohydride
Names
Other names
NaBH(OAc)3; STAB; STABH; Sodium triacetoxyhydroborate
Identifiers
3D model (JSmol)
ECHA InfoCard 100.115.747 Edit this at Wikidata
UNII
  • InChI=1S/C6H9BO6.Na/c1-4(8)11-7(12-5(2)9)13-6(3)10;/h1-3H3;/q-1;+1
    Key: AGGHKNBCHLWKHY-UHFFFAOYSA-N
  • [B-H](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]
Properties
C6H10BNaO6
Molar mass 211.94 g·mol−1
Appearance White powder
Density 1.20 g/cm3
Melting point 116 to 120 °C (241 to 248 °F; 389 to 393 K) decomposes
decomposition
Hazards
Safety data sheet (SDS) External MSDS
NFPA 704 (fire diamond)
3
4
2
Related compounds
Other anions
 Sodium cyanoborohydride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a chemical compound with the formula Na(CH3COO)3BH. Like other borohydrides, it is used as a reducing agent in organic synthesis. This colourless salt is prepared by protonolysis of sodium borohydride with acetic acid:[1]

NaBH4 + 3 HO2CCH3 → NaBH(O2CCH3)3 + 3 H2

Comparison with related reagents[]

Sodium triacetoxyborohydride is a milder reducing agent than sodium borohydride or even sodium cyanoborohydride. It reduces aldehydes but not most ketones. It is especially suitable for reductive aminations of aldehydes and ketones.[2][3][4]

However, unlike sodium cyanoborohydride, the triacetoxyborohydride hydrolyzes readily, nor is it compatible with methanol. It reacts only slowly with ethanol and isopropanol and can be used with these.[3]


Reductive amination with STAB

NaBH(OAc)3 may also be used for reductive alkylation of secondary amines with aldehyde-bisulfite adducts. [5]

Monoacetoxyborohydride[]

The combination of NaBH4 with carboxylic acids results in the formation of acyloxyborohydride species other than sodium triacetoxyborohydride. These modified species can perform a variety of reductions not normally associated with borohydride chemistry, such as alcohols to hydrocarbons and nitriles to primary amines.[6]

See also[]


References[]

  1. ^ Gordon W. Gribble, Ahmed F. Abdel-Magid, "Sodium Triacetoxyborohydride" Encyclopedia of Reagents for Organic Synthesis, 2007, John Wiley & Sons.doi:10.1002/047084289X.rs112.pub2
  2. ^ Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. (1996). "Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures1". The Journal of Organic Chemistry. 61 (11): 3849–3862. doi:10.1021/jo960057x. PMID 11667239.
  3. ^ a b Abdel-Magid, A. F.; Mehrman, S. J. (2006). "A Review on the Use of Sodium Triacetoxyborohydride in the Reductive Amination of Ketones and Aldehydes". Organic Process Research & Development. 10 (5): 971. doi:10.1021/op0601013.
  4. ^ Magano, Javier; Kiser, E. Jason; Shine, Russell J.; Chen, Michael H. (2013). "Oxindole Synthesis via Palladium-catalyzed C-H Functionalization". Organic Syntheses. 90: 74. doi:10.15227/orgsyn.090.0074.
  5. ^ Pandit, C. R.; Mani, N. S. (2009). "Expedient reductive amination of aldehyde bisulfite adducts". Synthesis (23): 4032–4036.
  6. ^ Gribble, Gordon, W. (1998). "Sodium borohydride in carboxylic acid media: a phenomenal reduction system". Chemical Society Reviews. 27 (6): 395. doi:10.1039/A827395Z. S2CID 96906861.
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