Sodium triacetoxyborohydride

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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)

reaction suitability

reagent type: reductant

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

Hebei Mujin Biotechnology Co.,Ltd

Product: Sodium triacetoxyborohydride 56553-60-7
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 50000KG/month
Release date: 2023-10-10

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

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

56553-60-7, Sodium triacetoxyborohydrideRelated Search:

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Sodium triacetoxyborohydride CAS 56553-60-7 with best price

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SODIUM TRIACETOXY BOROHYDRIDE For Synthesis

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Manganese carbonate 598-62-9

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SODIUMTRIACETOXY BOROHYDRIDE >95% (An excellent reducing agent) puriss for synthesis.

Sodium triacetoboroh

56553-60-7

56553-60-3

NaBHOAc3

CH3COO3BHNa

C6H10BNaO6

C6H10BO6Na