Sodium triacetoxyborohydride

Sodium triacetoxyborohydride
Names
	Other names NaBH(OAc)3; STAB; STABH; Sodium triacetoxyhydroborate
Identifiers
CAS Number	56553-60-7 ;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.115.747
PubChem CID	23676153;
UNII	4VU0JE4YSK ;
CompTox Dashboard (EPA)	DTXSID8074368 ;
	InChI 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;
	SMILES [B-H](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+];
Properties
Chemical formula	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
Solubility in water	decomposition
Hazards
Safety data sheet	External MSDS
NFPA 704 (fire diamond)	4 3 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).
	verify (what is ?)
	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

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]

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. [4]

References

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
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.
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.
Pandit, C. R.; Mani, N. S. (2009). "Expedient reductive amination of aldehyde bisulfite adducts". Synthesis (23): 4032–4036.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[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.

[oprd-3] 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] Pandit, C. R.; Mani, N. S. (2009). "Expedient reductive amination of aldehyde bisulfite adducts". Synthesis (23): 4032–4036.

Sodium triacetoxyborohydride

See also

References