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1,4,10,13-Pentaoxacyclopentadecan
crown ether · 1,4,7,10,13-PENTAOXACYCLOPENTADECANE · 15-Crown-6 · 15-Crown-5 98% · 15-CROWN 5-ETHER · 15-CROWN-5 · 15-ether-5 · Crownethers
Identifikatoren & physikalische Daten
| CAS No. | 33100-27-5 |
|---|---|
| Summenformel | C10H20O5 |
| Durchschnittliche Molmasse | 220,26 g/mol |
| Monoisotopische Masse | 220,13107374 g/mol |
| SMILES | C1COCCOCCOCCOCCO1 |
| InChIKey | VFTFKUDGYRBSAL-UHFFFAOYSA-N |
| PubChem CID | 36336 |
| ChEMBL | CHEMBL156289 |
| ChEBI | CHEBI:32401 |
| EC No. | 251-379-6 |
| DTXSID | DTXSID7067746 |
| Lokaler Name | 1,4,10,13-Pentaoxacyclopentadecan |
Chemische & physikalische Eigenschaften
| XLogP | -0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 46,2 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 86,2 |
| Stoffklassen | Other Classes -> Other Organic Compounds |
| SpringerMaterials Properties | Chemical shift |
| LogP (Verteilungskoeffizient) | -0.48 |
| Dampfdruck | 0.00144 [mmHg]0.5-0.82Pa at 20-25℃ |
| Physical Description | Clear colorless liquid[Aldrich MSDS] |
| Schmelzpunkt | -20°C(lit.) |
| Siedepunkt | 93-96 °C/0.05 mmHg (lit.) |
| Dichte | 1.113 g/mL at 20 °C (lit.) |
| Brechungsindex | n20/D 1.465(lit.) |
| Flammpunkt | >230 °F |
| Lagerbedingungen | room temp |
| Löslichkeit | Miscible with organic solvents. |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless to light yellow |
| Wichte | 1.109 |
| BRN | 1618144 |
| Stabilität | Stable. Incompatible with oxidizing agents, strong acids. Avoid exposure to water or moist air. |
| InChI | 1S/C10H20O5/c1-2-12-5-6-14-9-10-15-8-7-13-4-3-11-1/h1-10H2 |
| InChIKey | VFTFKUDGYRBSAL-UHFFFAOYSA-N |
| SMILES | O1CCOCCOCCOCCOCC1 |
| LogP (Verteilungskoeffizient) | -0.9 at 20℃ and pH7.7 |
| Oberflächenspannung | 68.5mN/m at 1g/L and 20℃ |
| CAS Datenbank | 33100-27-5(CAS DataBase Reference) |
| NIST chemische Informationen | 15-Crown-5(33100-27-5) |
| EPA chemische Informationen | 1,4,7,10,13-Pentaoxacyclopentadecane (33100-27-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (98.9%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 176 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: 14-03-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33251Crown ether 15-crown-5: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | A mild skin and moderate eye irritantCauses tremor, convulsions, and weight loss in dermal lethal-dose studies of rabbitsCauses tremor, convulsions, weight loss, tetany, other changes in lungs, and other liver changes in intraperitoneal lethal-dose studies of rats[RTECS] An irritantHarmful by ingestion[Aldrich MSDS] See 18-Crown-6. |
| Peroxide Forming Chemical | 15-Crown-5 etherD*: Other compounds that may form peroxides1 samples, >8 yrs, 1 ppmManagement of time-sensitive chemicals (JCHAS) |
| Hazard Classes and Categories | Acute Tox. 4 (98.9%) |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxin |
| F | 10-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 2810 |
| Zollcode | 29329995 |
| RTECS-Nr. | SB0200000 |
| R-Sätze (R) | 22-36/38-36-20/22-36/37/38-20/21/22 |
| Toxizität | LD50 orl-rat: 1410 mg/kg DCTODJ 1,339,78 |
| Gefahrensymbole | Xn,Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-39-36 |
| Gefahrenklasse | 6.1(b)Acute Tox. 4 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 10 - Combustible liquids |
Anwendungen & Verwendung
Verwenden
15-Crown-5 is used as an efficient phase transfer catalyst and as a complexing agent. It is used to isolate oxonium ion (H7O3)+ salts especially from a solution of tetrchloroauric acid. It catalyzes the O-alkylation of the sodium salts of carboxylic acids in the penicillin and cephalosporin series, thereby facilitating esterification reaction without usage of acid. It is also used to facilitate the Williamson synthesis of ethers with hindered alcohols and sodium hydride. It is used with lithium aluminum hydride, for performing reduction reactions in hydrocarbon solvents. Further, it is involved in the Horner-Wadsworth-Emmons reaction to prepare stilbenes from aldehydes.