Home Categories Organic Chemistry Sodium triacetoxyborohydride
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Sodium triacetoxyborohydride , 90% , 56553-60-7

Synonym(s):
STAB

CAS NO.:56553-60-7

Empirical Formula: C6H10BNaO6

Molecular Weight: 211.94

MDL number: MFCD00012211

EINECS: 411-950-4

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Update time: 2022-07-08

PRODUCT Properties

Melting point: 116-120 °C (dec.) (lit.)
Boiling point: 111.1℃[at 101 325 Pa]
Density  1.36[at 20℃]
vapor pressure  0Pa at 25℃
storage temp.  Inert atmosphere,Room Temperature
solubility  Soluble in dimethyl sulfoxide, methanol, benzene, toluene, terahydrofuran, dioxane and methylene chloride.
form  Powder
color  White
Water Solubility  reacts
Sensitive  Moisture Sensitive
Merck  14,8695
BRN  4047608
InChIKey HHYFEYBWNZJVFQ-UHFFFAOYSA-N
LogP -2.88--1.09 at 20℃
CAS DataBase Reference 56553-60-7(CAS DataBase Reference)
EPA Substance Registry System Borate(1-), tris(acetato-.kappa.O)hydro-, sodium, (T-4)- (56553-60-7)

Description and Uses

Sodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a white hygroscopic solid that emits hydrogen gas when hydrolysed in water, which is flammable. STAB is a milder reducing agent than sodium borohydride or even sodium cyanoborohydride. Even sodium cyanoborohydride is a milder reducing agent than sodium borohydride, and is particularly suitable for the reductive amination of aldehydes and ketones. It can reduce aldehydes but not most ketones. It can also be used in the reductive alkylation of secondary amines in aldehyde-bisulfite adducts.

Sodium Triacetoxyborohydride(STAB) is a hydride reagent used in stereoselective reductive amination. It is able to replace toxic sodium cyanoborohydride under most conditions. It is selective in reducing aldehydes to alcohols in the presence of ketones. STAB is also stable in anhydrous acids, which enables reductive amination of aldehydes and ketones. It used in reductive amination of ketones and aldehydes and reductive amination/lactamization of carbonyl compounds with amines. The advantage of STAB compared to sodium cyanoborohydride is evident. STAB, being non-toxic, is easier to handle and forms no toxic by-products, making the treatment of process waste after the reaction simple and less costly.

Safety

Symbol(GHS) 
GHS02,GHS05,GHS07,GHS08
Signal word  Danger
Hazard statements  H228-H260-H302-H318-H360FD
Precautionary statements  P210-P231+P232-P280-P301+P312-P305+P351+P338-P308+P313
Hazard Codes  F,Xi,C
Risk Statements  15-34-14/15-37/38-11
Safety Statements  43-7/8-45-36/37/39-26
RIDADR  UN 1409 4.3/PG 2
WGK Germany  3
10-21
Hazard Note  Irritant/Flammable
TSCA  Yes
HazardClass  4.3
PackingGroup  III
HS Code  29319090

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