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Sodium triacetoxyborohydride information


Sodium triacetoxyborohydride
Sodium_triacetoxyborohydride
Names
Other names
NaBH(OAc)3; STAB; STABH; Sodium triacetoxyhydroborate
Identifiers
CAS Number
  • 56553-60-7 checkY
3D model (JSmol)
  • Interactive image
ECHA InfoCard 100.115.747 Edit this at Wikidata
PubChem CID
  • 23676153
UNII
  • 4VU0JE4YSK checkY
CompTox Dashboard (EPA)
  • DTXSID8074368 Edit this at Wikidata
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
  • [BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]
Properties
Chemical formula
Na[(CH3COO)3BH]
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
Structure
Coordination geometry
4 at boron atom
Molecular shape
Tetrahedral at boron atom
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
3
4
2
Safety data sheet (SDS) External MSDS
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]

Na[BH4] + 3 CH3COOH → Na[(CH3COO)3BH] + 3 H2
  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

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Sodium triacetoxyborohydride

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Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a chemical compound with the formula Na[(CH3COO)3BH]...

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Sodium borohydride

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synthesis. Sodium triacetoxyborohydride, a milder reductant owing to the presence of more electron-withdrawing acetate in place of hydride. Sodium triethylborohydride...

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Reductive amination

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January 1996). "Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures...

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Sodium cyanoborohydride

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to use sodium cyanide and borane in THF making the process safer. Sodium triacetoxyborohydride – a milder reductant, but unstable in water Sodium borohydride...

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Stab

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song by Built to Spill from There's Nothing Wrong with Love Sodium triacetoxyborohydride, a reducing agent used in organic synthesis St. Anne's-Belfield...

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Protonolysis

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of one or more B-H bonds. Protonolysis of sodium borohydride with acetic acid gives triacetoxyborohydride: NaBH4 + 3 HO2CCH3 → NaBH(O2CCH3)3 + 3 H2 Related...

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Oxocarbenium

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sodium cyanoborohydride (Na+[H3B(CN)]−) or sodium triacetoxyborohydride (Na+[HB(OAc)3]−) as a reagent. Bearing an electron-withdrawing group, sodium cyanoborohydride...

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DEA list of chemicals

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anhydrous hydrogen chloride) Sulfuric acid Methyl isobutyl ketone (MIBK) Sodium permanganate All listed chemicals as specified in 21 CFR 1310.02 (a) or...

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Methyl pyruvate

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(1996). "Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures"...

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Torcetrapib

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with the bis-trifuoromethyl benzaldehyde in the presence of sodium triacetoxyborohydride followed by acylation with methyl chloroformate completes the...

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Connorstictic acid

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by the direct reduction of norstictic acid by the addition of sodium triacetoxyborohydride, or by catalytic reduction. In 1981, Chicita Culberson and colleagues...

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