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Sodium triacetoxyborohydride

Product Name
Sodium triacetoxyborohydride
CAS No.
56553-60-7
Chemical Name
Sodium triacetoxyborohydride
Synonyms
stab;sodium tris(acetoxy)borohydride;SODIUM TRIACETOXYHYDROBORATE;Sodium Triacetoxyborohyride;Sodium triacetoborohydride;sodium bis(acetyloxy)boranuidyl acetate;Sodium triacetoxy;Sodium triacetoboro;Sodium triacetoboroh;triacetyloxyboron(1-)
CBNumber
CB3321854
Molecular Formula
C6H10BNaO6
Formula Weight
211.94
MOL File
56553-60-7.mol
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Sodium triacetoxyborohydride Property

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)
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Safety

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
F 
10-21
Hazard Note 
Irritant/Flammable
TSCA 
Yes
HazardClass 
4.3
PackingGroup 
III
HS Code 
29319090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H228Flammable solid

H260In contact with water releases flammable gases which may ignite spontaneously

H302Harmful if swallowed

H318Causes serious eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P231+P232Handle under inert gas. Protect from moisture.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
316393
Product name
Sodium triacetoxyborohydride
Purity
97%
Packaging
25g
Price
$53.5
Updated
2024/03/01
Sigma-Aldrich
Product number
316393
Product name
Sodium triacetoxyborohydride
Purity
97%
Packaging
100g
Price
$157
Updated
2024/03/01
Sigma-Aldrich
Product number
8.43705
Product name
Sodium triacetoxyborohydride
Purity
for synthesis
Packaging
25G
Price
$135
Updated
2023/06/20
Sigma-Aldrich
Product number
8.43705
Product name
Sodium triacetoxyborohydride
Purity
for synthesis
Packaging
100G
Price
$416
Updated
2023/06/20
TCI Chemical
Product number
S0394
Product name
Sodium Triacetoxyborohydride
Purity
>80.0%(T)
Packaging
25g
Price
$55
Updated
2024/03/01
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Sodium triacetoxyborohydride Chemical Properties,Usage,Production

Description

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.

Chemical Properties

Sodium triacetoxyborohydride (STAB-H) is commercially available as a hygroscopic white powder with a melting point of 116-120 °C. freely soluble in benzene. It is prepared by the reaction of NaBH4 with excess acetic acid in benzene or toluene.

Uses

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.

Application

Sodium triacetoxyborohydride is a mild reagent that exhibits remarkable selectivity as a reducing agent. It reduces aldehydes but not ketones; however, beta-hydroxyketones can be reduced selectively to give 1,3-trans diols.The steric and the electron-withdrawing effects of the three acetoxy groups stabilize the boron-hydrogen bond and are responsible for its mild reducing properties.
Sodium triacetoxyborohydride or [NaBH(OAc)3] can be used as a reagent:
In the reductive amination of ketones and aldehydes.
To prepare N-benzyl-γ-valerolactam by reacting with methyl 4-oxopentanoate and benzylamine via reductive amination/lactamization.
To reduce imines and enamines to corresponding amines.
To reduce quinolines and isoquinolines to corresponding tetrahydro derivatives.
In the hydroboration of alkenes.
To synthesize nitroxide biradicals for creating high relaxivity terminal groups linkage to dendrimers.

Reactions

Sodium Triacetoxyborohydride is selective reducing agent in organic synthesis. It is especially suitable for reductive aminations. Since the reaction rate for the reduction of iminium ions is much faster than for ketones or even aldehydes, the reductive amination can be carried out as a one-pot procedure by introducing the reducing agent into a mixture of the amine and carbonyl compound. The presence of a stoichiometric amount of acetic acid, which catalyzes the imine formation and provides the iminium ion, doesn't present any problem under these conditions.

Reductive amination (simplified)

Sodium triacetoxyborohydride Preparation Products And Raw materials

Raw materials

Ethyl 2-(Chlorosulfonyl)acetate tert-Butyl methyl ether Toluene Sodium Sodium borohydride Tetrahydrofuran Diethyl ether Acetic acid PETROLEUM ETHER

Preparation Products

4-(2-KETO-1-BENZIMIDAZOLINYL)PIPERIDINE 1-(4-PYRIDYLMETHYL)PIPERAZINE
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View Lastest Price from Sodium triacetoxyborohydride manufacturers

Dorne Chemical Technology co. LTD
Product
Sodium triacetoxyborohydride 56553-60-7
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
1000kg
Release date
2024-03-26
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Sodium triacetoxyborohydride 56553-60-7
Price
US $30.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-04-30
Hebei Miaoyin Technology Co.,Ltd
Product
Sodium Triacetoxyborohydride 56553-60-7
Price
US $20.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10000
Release date
2023-04-06

56553-60-7, Sodium triacetoxyborohydrideRelated Search:

Acetoxyacetic acid Sodium hydroxide Sodium bicarbonate Sodium citrate Sodium cyanoborohydride (Triacetoxy)ethylsilane Methyltriacetoxysilane Sodium chloride Trisodium phosphate Diclofenac sodium Sodium alginate SILICON TETRAACETATE n-Propyltriacetoxysilane Sodium acetate Sodium benzoate SODIUM TRIETHYLBOROHYDRIDE Vinyltrimethoxyacyloxygroupsilanes Vinyltriacetoxysilane

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