1,1,3,3-Tetramethylbutylisocyanat
2-isocyano-2,4,4-triMethylpentane · Pentane, 2-isocyano-2,4,4-trimethyl- · WALBORSKY REAGENT · WALBORSKY'S REAGENT · TERT-OCTYLISONITRILE · TERT-OCTYL ISOCYANIDE · 2-isocyano-2,4,4-trimethyl-pentan · 1,1,3,3-TETRAMETHYLBUTYLISONITRILE
Identifikatoren & physikalische Daten
| CAS No. | 14542-93-9 |
|---|---|
| Summenformel | C9H17N |
| Durchschnittliche Molmasse | 139,24 g/mol |
| Monoisotopische Masse | 139,13609954 g/mol |
| SMILES | [C-]#[N+]C(C)(C)CC(C)(C)C |
| InChIKey | YVPXQMYCTGCWBE-UHFFFAOYSA-N |
| PubChem CID | 26725 |
| ChEMBL | CHEMBL5567109 |
| DTXSID | DTXSID9065784 |
| Lokaler Name | 1,1,3,3-Tetramethylbutylisocyanat |
Chemische & physikalische Eigenschaften
| XLogP | 2,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 4,4 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 151 |
| Stoffklassen | Nitrogen Compounds -> Other Nitrogen Compounds |
| Physical Description | Clear colorless liquid[Acros Organics MSDS] |
| Siedepunkt | 55-57 °C11 mm Hg(lit.) |
| Dichte | 0.794 g/mL at 25 °C(lit.) |
| Brechungsindex | n20/D 1.422(lit.) |
| Flammpunkt | 125 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | insol watersol common organic solvents |
| Aggregatzustand | clear liquid |
| Farbe | Colorless to Almost colorless |
| BRN | 2076559 |
| InChI | InChI=1S/C9H17N/c1-8(2,3)7-9(4,5)10-6/h7H2,1-5H3 |
| InChIKey | YVPXQMYCTGCWBE-UHFFFAOYSA-N |
| SMILES | C(C(C)(C)C)C(C)(C)[N+]#[C-] |
| CAS Datenbank | 14542-93-9(CAS DataBase Reference) |
| EPA chemische Informationen | Pentane, 2-isocyano-2,4,4-trimethyl- (14542-93-9) |
Sicherheit & Vorschriften
| Regulatorische Informationen | 1,1,3,3-Tetramethylbutyl isocyanide: Does not have an individual approval but may be used under an appropriate group standard |
|---|---|
| Gefahrenübersicht | An irritantHarmful by ingestion, inhalation, and skin absorption (may be metabolized to cyanide)[Acros Organics MSDS] See Ethyl isocyanide. |
| F | 10-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1993 3/PG 3 |
| Zollcode | 2929 90 00 |
| R-Sätze (R) | 10-20/21/22 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 23-36/37 |
| Gefahrenklasse | 3.2Flam. Liq. 3 |
| Verpackungsgruppe | III |
| Lagerklasse | 3 - Flammable liquids |
Anwendungen & Verwendung
Verwenden
1,1,3,3-Tetramethylbutyl isocyanide was used in the synthesis of substituted furans and imides.
Herstellung & Synthese
synthetische
To a stirred solution of 83.0 g (0.528 mole) of N-(l,l,3,3-tetramethylbutyl) formamide in 11 of DMF was added dropwise, under a nitrogen atmosphere, a solution made up of thionyl chloride (40.3 ml, 0.55 mole) dissolved in 150 ml of DMF. The addition was at such a rate that the temperature did not exceed -50°C. After the addition, the cooling bath was removed momentarily to allow the temperature to increase to -35°C and then it was replaced while 118.0 g (1.11 mole) of sodium carbonate (anhydrous grade) was added. Then the cooling bath was removed and the reaction mixture was diluted with ice-cold water in a separatory funnel and then extracted with pentane. The pentane extract was dried over sodium sulfate and concentrated, and the product distilled to yield 68.4 g (93% yield), b.p. 55.5-56.6°C (11 mm). Infrared spectrum (neat) 2110 c m " 1 (s); nmr (neat) 51.08 [s, 9, C(CH3) 2] , 1.43 [t, 6, J = 2Hz, C(CH3) 2] , 1.58 (t, 2, J = 2.3 Hz, CH2).