Tetrahydrofuran-Boran
BH3-THF · BORANE · (T-4)-Trihydro(tetrahydrofuran)boron · BORANE TETRAHYDROFURAN COMPLEX · BORANE-TETRAHYDROFURAN · Trihydro(tetrahydrofuran)boron · BTHF · BORAN-TETRAHYDROFURANCOMPLEX
Identifikatoren & physikalische Daten
| CAS No. | 14044-65-6 |
|---|---|
| Summenformel | C4H8BO |
| Durchschnittliche Molmasse | 82,92 g/mol |
| SMILES | C1CCOC1.[B] |
| InChIKey | UWTDFICHZKXYAC-UHFFFAOYSA-N |
| PubChem CID | 11062302 |
| EC No. | 237-881-8 |
| Lokaler Name | Tetrahydrofuran-Boran |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 9,2 |
|---|---|
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 22,8 |
| Stoffklassen | Metals -> Metalloid Compounds (Boron) |
| Dichte | 0.898 @25 °C0.898 g/mL at 25 °C |
| Physical Description | Liquid[Merck Index] 10% Solution in tetrahydrofuran: Colorless liquid with an acrid odor[Alfa Aesar MSDS] |
| Schmelzpunkt | -17 °C |
| Siedepunkt | 35 °C |
| Flammpunkt | 1 °F |
| Lagerbedingungen | Store at <= 20°C. |
| Aggregatzustand | Liquid |
| Farbe | Colorless |
| Explosionsgrenze | 1.58-12.42% (v/v) |
| Löslichkeit | REACTS |
| BRN | 3668402 |
| Stabilität | Stable, but may form explosive peroxides in contact with air. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents, alcohols. Reacts violently with water. Highly flammable. Store under inert gas. |
| InChI | 1S/C4H8O.BH3/c1-2-4-5-3-1/h1-4H21H3 |
| InChIKey | RMCYTHFAWCWRFA-UHFFFAOYSA-N |
| SMILES | B.C1CCOC1 |
| CAS Datenbank | 14044-65-6(CAS DataBase Reference) |
| EPA chemische Informationen | Boron, trihydro(tetrahydrofuran)-, (T-4)- (14044-65-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 5.9% (11 of 188) of reports.DangerH225 (94.1%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P223, P231+P232, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P335+P334, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P402+P404, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 188 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 27-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/12062Boron, trihydro(tetrahydrofuran)-, (T-4)-: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Reacts violently with water[Merck Index] 10% Solution in tetrahydrofuran (CAS# 109-99-9): Reacts violently with water evolving extremely flammable gasesMay form explosive peroxidesAn irritant that may cause serious eye injuryHarmful by ingestion[Alfa Aesar MSDS] See Borane. |
| Hazard Classes and Categories | Flam. Liq. 2 (94.1%) |
| CSL Reaction Information | CSL00083BORANE-TETRAHYDROFURAN COMPLEXtemperatures over 40C may lead to a self-sustaining exothermic reaction—if temperature reaches 60C, a violent decomposition reaction may occurExplosiveUser-Reported7/8/18 |
| Protective Action Criteria (PAC) | 12 [mg/m3]130 [mg/m3]790 [mg/m3] |
| F | 1-10-13-34 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3399 4.3/PG 1 |
| Zollcode | 29321900 |
| R-Sätze (R) | 14/15-19-22-36/37/38-41-37/38-11-67-66-40-36/37 |
| Gefahrensymbole | F,Xn,Xi |
| Sicherheitshinweise (S) | 16-33-36/37/39-7/9-7/8-43-37/39-26-36-29-36/37 |
| Gefahrenklasse | 4.3Acute Tox. 4 OralCarc. 2Eye Dam. 1Flam. Liq. 2STOT SE 3Water-react 1 |
| Verpackungsgruppe | I |
| Lagerklasse | 4.3 - Hazardous materials which set free flammable gases upon contact with water |
| Selbstentzündungstemperatur | 103°C |
Anwendungen & Verwendung
Beschreibung
Borane tetrahydrofuran complex (BH3-THF) is widely used as a reducing agent in organic synthesis. It is also used as a reagent in hydroboration reactions.It is a charge-transfer complex that is a useful surrogate for diborane1 in organic synthesis. It can be used to reduce carboxylic acids to alcohols or nitriles to primary amines. It reacts with olefins to add the BH2 functional group. Alkyl- or arylboranes formed in this way can further react with unsaturated compounds such as olefins, imines, ketones, and alkynes (the hydroboration reaction) to make useful boron-containing intermediates.
Verwenden
Borane-tetrahydrofuran complex is used to reduce Nylon surface amide groups to secondary amines.It is an important reagent used in the reduction of certain functional groups viz. aldehyde, ketone, carboxylic acid, amide, oxime, imine and nitrile. It is also used as hydro borating agent. It acts as a borane source for oxazaborolidine catalyzed asymmetric reductions.