Diisobutylaluminiumhydrid
DIBAL-H · Dibal · DIISOBUTYLALUMINUM HYDRIDE · DIBAH · DABAL-H · Diisobutylaluminum · Bis(2-methylpropyl)alumane · diisobutylaluminum hydride solution
Identifikatoren & physikalische Daten
| CAS No. | 1191-15-7 |
|---|---|
| Summenformel | C8H19Al |
| Durchschnittliche Molmasse | 142,22 g/mol |
| Monoisotopische Masse | 142,13021424 g/mol |
| SMILES | CC(C)[CH2][AlH][CH2]C(C)C |
| InChIKey | AZWXAPCAJCYGIA-UHFFFAOYSA-N |
| PubChem CID | 14487 |
| EC No. | 214-729-9 |
| DTXSID | DTXSID4041866 |
| Lokaler Name | Diisobutylaluminiumhydrid |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 0 |
|---|---|
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 49,6 |
| Stoffklassen | Metals -> Metals, Organic CompoundsFlammable agents - 4th degree |
| Dichte | 0.798 g/mL0.798 @25 °C1.23 g/mL at 25 °C |
| Viscosity | 18.0 mPa-s (millipascal second) at 25 °C |
| Color/Form | Colorless liquid |
| Löslichkeit | Miscible with hydrocarbon solventsMiscible with organic solvents.vigorous reaction |
| Siedepunkt | 105 °C @ 0.2 mm Hg65 °C |
| Schmelzpunkt | -80 °C (Freezing point)-70 °C |
| Heat of Combustion | -6412 kJ/mol (kilojoules/mole) |
| Physical Description | CBIColorless liquid[Hawley] |
| Stability/Shelf Life | Low melting solids or colorless, volatile liquids. /Alkylaluminum halides/Less sensitive than trialkylaminums to oxidation upon exposure to air. /Alkylaluminum halides/ |
| Other Experimental Properties | Pyrophoricdilute solutions nonpyrophoricSpecific heat: 2.15 J/g at 57 °CThe fumes are white, possess a characteristic musty odor at low concentrations, and thus have suitable warning properties. /Aluminum alkyls/Dialkylaluminum hydrides are trimeric, with bridging hydrides. |
| Dampfdruck | 13.3Pa at 90℃ |
| Flammpunkt | 40 °F |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Solution |
| Wichte | 0.860 |
| Farbe | Clear |
| BRN | 4123663 |
| InChI | 1S/2C4H9.Al.H/c2*1-4(2)3/h2*4H,1H2,2-3H3 |
| InChIKey | AZWXAPCAJCYGIA-UHFFFAOYSA-N |
| SMILES | CC(C)C[AlH]CC(C)C |
| LogP (Verteilungskoeffizient) | 4.22 |
| CAS Datenbank | 1191-15-7(CAS DataBase Reference) |
| NIST chemische Informationen | Diisobutylaluminum hydride(1191-15-7) |
| EPA chemische Informationen | Diisobutylaluminum hydride (1191-15-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH250 (97.7%): Catches fire spontaneously if exposed to air [Danger Pyrophoric liquids]P210, P222, P223, P231, P231+P232, P233, P260, P264, P264+P265, P280, P301+P330+P331, P302+P335+P334, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P370+P378, P402+P404, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 173 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Aluminium, hydrobis(2-methylpropyl)-Aluminum, hydrobis(2-methylpropyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Aluminum, hydrobis(2-methylpropyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 20-12-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13341Aluminium, hydrobis(2-methylpropyl)-: HSNO Approval: HSR001272 Approved with controlsThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Aluminium, hydrobis(2-methylpropyl)-: Human health tier I assessment |
| Brandpotenzial | The undiluted material ignites in air unless diluted to below 25% concentration.Ignites spontaneously in air.Certain polymerization catalysts, such as aluminum alkyls, react & burn violently on contact with water. /Aluminum alkyls/Aluminum alkyls are organic aluminum compounds that are highly reactive and dangerous because of spontaneous burning in air. /Aluminum alkyls/Prophoric material in flammable solvent. Vapors are heavier than air & may travel to a source of ignition & flash back. /Aluminum alkyls/ |
| Gefahrenübersicht | Spontaneously ignites in air[Hawley] Stored 25% w/w in hexanePyrophoricReacts violently with water, evolving extremely flammable gases |
Anwendungen & Verwendung
Beschreibung
Diisobutylaluminium hydride (DIBALH, DIBAL, DIBAL-H or DIBAH) is a reducing agent with the formula (i-Bu2AlH)2, where i-Bu represents isobutyl (-CH2CH(CH3)2). It can be used for various homogeneous reductions such as alkynes to alkenes, esters or nitriles to aldehydes. It is available commercially as the neat reagent and as a solution in several different solvents (hexane, dichloromethane, tetrahydrofuran, etc.). The neat reagent is a liquid and is supplied in metal cylinders. It is pyrophoric and highly reactive and therefore must be handled with great care. The molar solutions in organic solvents are more stable and easier to handle provided that the normal precautions are taken for working with air-sensitive compounds. They must all be handled in an atmosphere free from oxygen and water. Commonly used solvents for diisobutylaluminium hydride are dichloromethane, diglyme, dioxane and tetrahydrofuran. Even when the substrate is not completely soluble in these solvents successful reductions can be accomplished.
Verwenden
Diisobutylaluminum hydride is commonly used as a reducing agent in organic synthesis.Diisobutylaluminum hydride can be used in the following protocols:As a promotor of Tishchenko reaction of aldehydes.Conversion of benzylidene acetals of 1,2-and 1,3-glycols to the corresponding monobenzyl ethers of the glycols.To generate a novel chiral reducing agent based on (S)-proline for the asymmetric reduction of prochiral ketones.