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
- Molecular Weight:
- 211.94
- MDL Number:
- MFCD00012211
- MOL File:
- 56553-60-7.mol
- MSDS File:
- SDS
| 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) |
| FDA UNII | 4VU0JE4YSK |
| EPA Substance Registry System | Borate(1-), tris(acetato-.kappa.O)hydro-, sodium, (T-4)- (56553-60-7) |
SAFETY
Risk and Safety Statements
| 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 | |||||||||
| F | 10-21 | |||||||||
| Hazard Note | Irritant/Flammable | |||||||||
| TSCA | Yes | |||||||||
| HazardClass | 4.3 | |||||||||
| PackingGroup | III | |||||||||
| HS Code | 29319090 | |||||||||
| NFPA 704 |
|
Sodium triacetoxyborohydride price More Price(36)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 316393 | Sodium triacetoxyborohydride 97% | 56553-60-7 | 25g | $53.5 | 2024-03-01 | Buy |
| Sigma-Aldrich | 316393 | Sodium triacetoxyborohydride 97% | 56553-60-7 | 100g | $157 | 2024-03-01 | Buy |
| Sigma-Aldrich | 8.43705 | Sodium triacetoxyborohydride for synthesis | 56553-60-7 | 25G | $135 | 2023-06-20 | Buy |
| Sigma-Aldrich | 8.43705 | Sodium triacetoxyborohydride for synthesis | 56553-60-7 | 100G | $416 | 2023-06-20 | Buy |
| TCI Chemical | S0394 | Sodium Triacetoxyborohydride >80.0%(T) | 56553-60-7 | 25g | $55 | 2024-03-01 | Buy |
Sodium triacetoxyborohydride Chemical Properties,Uses,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
1of2
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Shandong Believe Chemical PTE.LTD | +86-18553607090 +8618553607090 | 1093908296@qq.com | China | 1667 | 58 |
| Wuhan wingroup Pharmaceutical Co., Ltd | +86-13296627870; +8613296627870 | info@whwingroup.com | China | 695 | 58 |
| Wuhan Mayue Longteng Technology Development Co., Ltd. | +undefined15171477138 | helen.yan@lantu-tech.com | China | 300 | 58 |
| Hebei Weibang Biotechnology Co., Ltd | +8615531157085 | abby@weibangbio.com | China | 8810 | 58 |
| Hebei Mojin Biotechnology Co., Ltd | +86 13288715578 +8613288715578 | sales@hbmojin.com | China | 12837 | 58 |
| Shanghai UCHEM Inc. | +862156762820 +86-13564624040 | sales@myuchem.com | China | 7629 | 58 |
| Dorne Chemical Technology co. LTD | +86-86-13583358881 +8618560316533 | Ethan@dornechem.com | China | 3097 | 58 |
| Hebei Weibang Biotechnology Co., Ltd | +8617732866630 | bess@weibangbio.com | China | 18152 | 58 |
| Hebei Kingfiner Technology Development Co.Ltd | +86-15532196582 +86-15373005021 | lisa@kingfinertech.com | China | 3010 | 58 |
| Shaanxi Haibo Biotechnology Co., Ltd | +undefined18602966907 | qinhe02@xaltbio.com | China | 997 | 58 |
Related articles
- Sodium triacetoxyborohydride: Applications in Selective Reductive Amination and its Detection Method
- Sodium triacetoxyborohydride enables precise amine synthesis via selective reduction of imines and can be detected by GC metho....
- Dec 16，2024
View Lastest Price from Sodium triacetoxyborohydride manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-12-18 | Sodium triacetoxyborohydride
56553-60-7
|
US $1.00 / g | 1g | 99% | 1000kg | Dorne Chemical Technology co. LTD | |
 |
2024-12-18 | Sodium triacetoxyborohydride
56553-60-7
|
US $30.00 / kg | 1kg | 99% | 20ton | Hebei Zhuanglai Chemical Trading Co.,Ltd | |
 |
2024-12-17 | Sodium Triacetoxyborohydride
56553-60-7
|
US $20.00 / kg | 1kg | 99% | 10000 | Hebei Miaoyin Technology Co.,Ltd |
-
- Sodium triacetoxyborohydride
56553-60-7
- US $1.00 / g
- 99%
- Dorne Chemical Technology co. LTD
-
- Sodium triacetoxyborohydride
56553-60-7
- US $30.00 / kg
- 99%
- Hebei Zhuanglai Chemical Trading Co.,Ltd
-
- Sodium Triacetoxyborohydride
56553-60-7
- US $20.00 / kg
- 99%
- Hebei Miaoyin Technology Co.,Ltd