sec-Butyllithium
S-BULI · sec-BuLi · sec-Butyllithium solution · S-BUTYLLITHIUM · butan-2-yllithiuM · sec-Butyllithium, 1.3M sol. in cyclohexane/hexane (92/8), AcroSeal · sec-Butyllithium, 12% (ca 1.4M) in cyclohexane/hexane, packaed in resealable septum seal bottle · sec-Butyllithium
Identifikatoren & physikalische Daten
| CAS No. | 598-30-1 |
|---|---|
| Summenformel | C4H9Li |
| Durchschnittliche Molmasse | 64,1 g/mol |
| Monoisotopische Masse | 64,08642872 g/mol |
| SMILES | C[CH-]CC.[Li+] |
| InChIKey | WGOPGODQLGJZGL-UHFFFAOYSA-N |
| PubChem CID | 102446 |
| EC No. | 209-927-7 |
| DTXSID | DTXSID80883459 |
| Lokaler Name | sec-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 |
| Stoffklassen | Metals -> Metals, Organic Compounds |
| Dichte | 0.769 @25 °C0.769 g/mL at 25 °C |
| Schmelzpunkt | 17.22 °C |
| Physical Description | Large CrystalsWet SolidLiquid10-20% solution in cyclohexane: Liquid[Sigma-Aldrich MSDS] |
| Flammpunkt | 1 °F |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless |
| BRN | 3587206 |
| InChI | InChI=1S/C4H9.Li/c1-3-4-2/h3H,4H2,1-2H3 |
| InChIKey | VATDYQWILMGLEW-UHFFFAOYSA-N |
| SMILES | C(C)([Li])CC |
| CAS Datenbank | 598-30-1(CAS DataBase Reference) |
| EPA chemische Informationen | Lithium, (1-methylpropyl)- (598-30-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH250 (100%): 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 98 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Lithium, (1-methylpropyl)-Lithium, (1-methylpropyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Lithium, (1-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)REACH registered substance: sec-butyllithium (EC: 209-927-7)Lithium, (1-methylpropyl)-: HSNO Approval: HSR007603 Approved with controls |
| Weitere Sicherheitsinformationen | IMAP assessments - Lithium, (1-methylpropyl)-: Environment tier I assessment |
| Gefahrenübersicht | 10-20% solution in cyclohexane (CAS# 110-82-7): PyrophoricReacts violently with water--may spontaneously igniteCauses burnsInhalation may cause corrosive injuries to upper respiratory tract and lungs[Sigma-Aldrich MSDS] See Butyllithium. |
| Hazard Classes and Categories | Pyr. Liq. 1 (100%) |
| Protective Action Criteria (PAC) | 1.8 [mg/m3]4.5 [mg/m3]27 [mg/m3] |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns. |
| F | 1-10 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer |
Anwendungen & Verwendung
Beschreibung
sec-Butyllithium. [598-30-1], sec-C4H9Li, Mr 64.06, is a spontaneously flammable, colorless, viscous liquid that forms tetramers in hydrocarbon solvents. It is commercially available only as 12 % solution in cyclohexane and methylcyclohexane. sec-Butyllithium is more nucleophilic and decomposes more readily than n-butyllithium. A 12 % solutionin cyclohexane at 20 ℃ undergoesthermal decomposition to the extent of 1.4 % of the active material per month. The thermal decomposition yields butene gas and LiH; the latter is insoluble and responsible for the increasing turbidity of secbutyllithium solutions on prolonged storage. Therefore solutions of sec-butyllithium must be kept cool during storage and transportation.
Verwenden
sec-Butyllithium is used almost exclusively as a polymerization catalyst. It is more expensive than n-butyllithium and is used mainly because of its greater reactivity and faster polymerization initiation.
Herstellung & Synthese
synthetische
sec-Butyllithium is produced by the reaction of sec-butyl chloride with lithium metal dispersion in hydrocarbon solvents. The lithium metal should contain catalytic amounts of up to 2 % sodium metal to attain a rapid reaction with the chloride and to minimize coupling. Massive substitution of sodium metal for lithium metal as is done in the preparation of n-butyllithium results in lower yields. Isopentane, hexane and cyclohexahe are typical solvents. Industrial and laboratory preparations are similar.