ナトリウムトリアセトキシボロヒドリド
ナトリウムトリアセトキシボロヒドリド · トリアセトキシ硼酸水素ナトリウム · トリアセトキシ水素化ほう素ナトリウム · トリアセトキシ水素化ほう素ナトリウム, 95% · トリアセトキシ水素化ほう素ナトリウム, min. 95% · stab · NaBH（OAc）3 · sodium tris(acetoxy)borohydride
識別子と物理属性
| CAS No. | 56553-60-7 |
|---|---|
| 分子式 | C6H10BNaO6 |
| 平均分子量 | 211.94 g/mol |
| 単同位体質量 | 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 |
| 現地名 | ナトリウムトリアセトキシボロヒドリド |
化学・物理的性質
| 極性表面積 | 78.9 |
|---|---|
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 7 |
| 回転可能結合数 | 6 |
| 重原子数 | 14 |
| 形式電荷 | 0 |
| 複雑度 | 192 |
| Physical Description | White crystalline powder[Alfa Aesar MSDS] |
| 融点 | 116-120 °C (dec.) (lit.) |
| 沸点 | 111.1℃[at 101 325 Pa] |
| 密度 | 1.36[at 20℃] |
| 蒸気圧 | 0Pa at 25℃ |
| 貯蔵条件 | Inert atmosphere,Room Temperature |
| 溶解度 | ジメチルスルホキシド、メタノール、ベンゼン、トルエン、テトラヒドロフラン、ジオキサン、ジクロロメタンに可溶。反応する |
| 外観・状態 | 粉 |
| 色 | 白い |
| 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（分配係数） | -2.88--1.09 at 20℃ |
| CAS データベース | 56553-60-7(CAS DataBase Reference) |
| EPAの化学物質情報 | Borate(1-), tris(acetato-.kappa.O)hydro-, sodium, (T-4)- (56553-60-7) |
化学的特性
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.
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | 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 |
| 有害性の概要 | 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 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| 輸送番号（UN） | UN 1409 4.3/PG 2 |
| PRTR法 | 第一種指定化学物質 |
| 税関コード | 29319090 |
| 危険文句（R） | 15-34-14/15-37/38-11 |
| 化審法 | (2)-4147 |
| 消防法 | 危-3-II |
| 危険表示 | F,Xi,C |
| hazard_note | Irritant/Flammable |
| 安全措置（S） | 43-7/8-45-36/37/39-26 |
| 危険等級 | 4.3Acute Tox. 4 OralEye Dam. 1Flam. Sol. 1Repr. 1BWater-react 1 |
| 包装等級 | III |
| 貯蔵分類 | 4.3 - Hazardous materials which set free flammable gases upon contact with water |
用途
使用
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.