Butyllithium
N-BULI · BUTYLLITHIUM · BuLi · Lithiumn-butyl · Butyllithium solution · n-ButyllithiuM(BULI) · ButyllithiuminhexaneM · n-BuLi, Lithium-1-butanide
Identifikatoren & physikalische Daten
| CAS No. | 109-72-8 |
|---|---|
| Summenformel | C4H9Li |
| Durchschnittliche Molmasse | 64,1 g/mol |
| SMILES | [CH2-]CCC.[Li+] |
| InChIKey | DLEDOFVPSDKWEF-UHFFFAOYSA-N |
| PubChem CID | 61028 |
| ChEBI | CHEBI:51469 |
| Lokaler Name | Butyllithium |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 0 |
|---|---|
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 7,6 |
| Schmelzpunkt | -95 °C |
| Siedepunkt | 80 °C |
| Dichte | 0.68 g/mL at 20 °C |
| Dampfdruck | 163 hPa ( 20 °C) |
| Flammpunkt | 10 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Miscible with diethyl ether and cyclohexane.vigorous reaction |
| Aggregatzustand | liquid |
| Farbe | yellow |
| Wichte | 0.695 |
| Geruch | Odor of the solvent |
| Explosionsgrenze | 1.2-7.8% (v/v) |
| BRN | 1209227 |
| InChI | 1S/C4H9.Li/c1-3-4-2/h1,3-4H2,2H3 |
| InChIKey | MZRVEZGGRBJDDB-UHFFFAOYSA-N |
| SMILES | [Li]CCCC |
| LogP (Verteilungskoeffizient) | 1.25-2.31 |
| CAS Datenbank | 109-72-8(CAS DataBase Reference) |
| NIST chemische Informationen | Butyl lithium(109-72-8) |
| EPA chemische Informationen | Lithium, butyl- (109-72-8) |
Sicherheit & Vorschriften
| CSL Reaction Information | CSL00127Perfluorethyllithium + Phosphorus Trichloride,Phosphorus + N-BUTYLLITHIUM + CHLOROPENTAFLUOROETHANEAvoid temperatures below -90 CSubstitutionSeveral times in our laboratory, we have experienced a violent decomposition of the ethereal C2F5Cl/n-BuLi solution after the addition of just a few drops of (R)nPCl3=n. In each of these cases, the metal-halogen exchange temperature was maintained below -90 C. We believe that this problem is due to a buildup of starting reagents at low temperatures.C&EN |
|---|---|
| F | 3-10 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3399 4.3/PG 1 |
| Zollcode | 29319090 |
| R-Sätze (R) | 14/15-17-34-48/20-51/53-62-65-67-63-35-11-15-50/53-66 |
| Toxizität | There is little toxicity data available for the butyllithiumsfor data on ether and hydrocarbon solvents, see the appropriate LCSSs. |
| Gefahrensymbole | F,C,N |
| Sicherheitshinweise (S) | 6-9-16-26-36/37/39-45-61-62-6A-46-43B-43-60-33-29-5 |
| Gefahrenklasse | 4.3Aquatic Chronic 2Asp. Tox. 1Eye Dam. 1Flam. Liq. 2Pyr. Liq. 1Skin Corr. 1BSTOT SE 3Water-react 1 |
| Verpackungsgruppe | I |
| Lagerklasse | 4.2 - Pyrophoric and self-heating hazardous materials |
| Selbstentzündungstemperatur | 240°C |
Anwendungen & Verwendung
Verwenden
n-Butyllithium is used as a polymerization initiator in the production of elastomers like polybutadiene and styrene- butadiene- styrene. As a strong base, it is utilized in the synthesis of organic compounds. It undergoes thermal decomposition to prepare 1-butene.
Herstellung & Synthese
synthetische
Industrially, n-butyllithium is produced by the reaction of n-butyl chloride with lithium metal dispersion in various hydrocarbon solvents. Hexane is the most commonly used solvent. Up to one-half of the lithium is replaced with sodium in order to lower the cost of the butyllithium and increase the reactivity of the dispersion. The reaction is carried out below the boiling point of the solvent.The laboratory procedure is essentially the same except that pentane and diethyl ether are two of the more popular solvents. The preparation runs smoothly in ether at lower temperatures but the product must either be used immediately or kept refrigerated due to the rapid cleavage of ether by n-butyllithium.