Sodium triacetoxyborohydride
stab · NaBH（OAc）3 · sodium tris(acetoxy)borohydride · SODIUM TRIACETOXYHYDROBORATE · Sodium Triacetoxyborohyride · Sodium triacetoborohydride · sodium bis(acetyloxy)boranuidyl acetate · Sodium triacetoxy
Identifiers & Physical Properties
| CAS No. | 56553-60-7 |
|---|---|
| Molecular formula | C6H10BNaO6 |
| Average molar mass | 211.94 g/mol |
| Monoisotopic mass | 212.0468125 g/mol |
| SMILES | CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+] |
| InChIKey | HHYFEYBWNZJVFQ-UHFFFAOYSA-N |
| PubChem CID | 5049666 |
| EC No. | 435-580-8 |
| DTXSID | DTXSID8074368 |
Chemical & Physical Properties
| Topological polar surface area | 78.9 |
|---|---|
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 7 |
| Rotatable bonds | 6 |
| Heavy atoms | 14 |
| Formal charge | 0 |
| Complexity | 192 |
| Physical Description | White crystalline powder[Alfa Aesar MSDS] |
| 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 conditions | Inert atmosphere,Room Temperature |
| Solubility | Soluble in dimethyl sulfoxide, methanol, benzene, toluene, terahydrofuran, dioxane and methylene chloride.reacts |
| Physical state | Powder |
| Color | White |
| Sensitivity | Moisture Sensitive |
| Merck | 14,8695 |
| BRN | 4047608 |
| InChI | 1S/C6H10BO6.Na/c1-4(8)11-7(12-5(2)9)13-6(3)10/h7H,1-3H3/q-1+1 |
| InChIKey | HHYFEYBWNZJVFQ-UHFFFAOYSA-N |
| SMILES | [Na+].CC(=O)O[BH-](OC(C)=O)OC(C)=O |
| LogP (partition coefficient) | -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) |
| UNSPSC Code | 12352302 |
| NACRES | NA.22 |
| GHS pictogram | GHS02,GHS05,GHS07,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H228-H260-H302-H318-H360FD |
| GHS precautionary statements | P210-P231+P232-P280-P301+P312-P305+P351+P338-P308+P313 |
| Hazard symbols | F,Xi,C |
| Risk statements (R) | 15-34-14/15-37/38-11 |
| Safety statements (S) | 43-7/8-45-36/37/39-26 |
| UN transport number | UN 1409 4.3/PG 2 |
| Water hazard class (WGK) | 3 |
| F | 10-21 |
| Hazard Note | Irritant/Flammable |
| TSCA inventory status | TSCA listed |
| Hazard class | 4.3Acute Tox. 4 OralEye Dam. 1Flam. Sol. 1Repr. 1BWater-react 1 |
| Packing group | III |
| Customs code | 29319090 |
| Storage class | 4.3 - Hazardous materials which set free flammable gases upon contact with water |
| REACH registrations | Active |
| Limited quantities | 0.5 Kg (1.1 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | DangerH228 (38.3%): Flammable solid [Danger Flammable solids]H260 (68.9%): In contact with water releases flammable gases which may ignite spontaneously [Danger Substances and mixtures which in contact with water, emit flammable gases]H261 (31.1%): In contact with water releases flammable gas [Danger Substances and mixtures which in contact with water, emit flammable gases]H314 (11.1%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H315 (83%): Causes skin irritation [Warning Skin corrosion/irritation]H318 (65.1%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H335 (26%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H360 (50.2%): May damage fertility or the unborn child [Danger Reproductive toxicity]P203, P210, P223, P231+P232, P240, P241, P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P335+P334, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P332+P317, P362+P364, P363, P370+P378, P402+P404, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 235 reports by companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Status: Active Update: 22-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/20512Status: Active Update: 11-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/17743Borate(1-), tris(acetato-.kappa.O)hydro-, sodium, (T-4)-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | Reacts with water evolving flammable gasesAn irritant that may cause serious eye injury[Alfa Aesar MSDS] See Lithium borohydride and Sodium borohydride. See Boric acid. |
| Hazard Classes and Categories | Flam. Sol. 2 (38.3%)Water-react. 1 (68.9%)Water-react. 3 (31.1%)Skin Corr. 1B (11.1%)Skin Irrit. 2 (83%)Eye Dam. 1 (65.1%)STOT SE 3 (26%)Repr. 1B (50.2%) |
| F | 10-21 |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| UN transport number | UN 1409 4.3/PG 2 |
| Customs code | 29319090 |
| Risk statements (R) | 15-34-14/15-37/38-11 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS05,GHS07,GHS08 |
| Hazard symbols | F,Xi,C |
| hazard_note | Irritant/Flammable |
| Safety statements (S) | 43-7/8-45-36/37/39-26 |
| Hazard class | 4.3Acute Tox. 4 OralEye Dam. 1Flam. Sol. 1Repr. 1BWater-react 1 |
| Storage class | 4.3 - Hazardous materials which set free flammable gases upon contact with water |
| Packing group | III |
| GHS hazard statements | H228-H260-H302-H318-H360FD |
| Limited quantities | 0.5 Kg (1.1 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
| REACH registrations | Active |
| GHS precautionary statements | P210-P231+P232-P280-P301+P312-P305+P351+P338-P308+P313 |
Applications & Uses
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.
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.