Dibenzyldisulfid
1,2-dibenzyldisulfane · BDS · FEMA 3617 · BENZYL DISULFIDE · DIBENZYL DISULPHIDE · S 700 · NSC 6841 · NSC 677465
Identifikatoren & physikalische Daten
| CAS No. | 150-60-7 |
|---|---|
| Summenformel | C14H14S2 |
| Durchschnittliche Molmasse | 246,4 g/mol |
| Monoisotopische Masse | 246,05369279 g/mol |
| SMILES | c1ccc(CSSCc2ccccc2)cc1 |
| InChIKey | GVPWHKZIJBODOX-UHFFFAOYSA-N |
| PubChem CID | 9012 |
| ChEMBL | CHEMBL121047 |
| ChEBI | CHEBI:72752 |
| EC No. | 205-764-0 |
| DTXSID | DTXSID6059738 |
| Lokaler Name | Dibenzyldisulfid |
Chemische & physikalische Eigenschaften
| XLogP | 3,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 50,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 16 |
| Formalladung | 0 |
| Komplexität | 150 |
| Stoffklassen | Other Classes -> Sulfur Compounds |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Aromastoffe | EU Flavoring substances |
| Löslichkeit | insoluble or slightly soluble in watersoluble in hot alcohol, ether(in ethanol)Chloroform (Slightly), Ethyl Acetate (Slightly) |
| Siedepunkt | 270.00 °C. @ 760.00 mm Hg>270 °C (with decomposition)210-216°C 18mm |
| Schmelzpunkt | 71 - 72 °C69-72 °C (lit.) |
| Physical Description | Solid[Merck Index] Faintly beige crystalsStrong, offensive odorInsoluble at room temperature[MSDSonline]pale yellowish leafy crystals or leaflets with "burnt caramellic" odour |
| Dichte | 1.3 |
| Brechungsindex | 1.6210 (estimate) |
| FEMA | 3617 | BENZYL DISULFIDE |
| Flammpunkt | 150°C |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Solid |
| Farbe | White |
| Geruch | at 0.10 % in propylene glycol. smoky burnt earthy green caramel |
| Geruchsart | smoky |
| Biologische Quelle | synthetic |
| JECFA Number | 579 |
| Merck | 14,3013 |
| BRN | 1110443 |
| Hauptanwendungen | cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care |
| InChI | 1S/C14H14S2/c1-3-7-13(8-4-1)11-15-16-12-14-9-5-2-6-10-14/h1-10H,11-12H2 |
| InChIKey | GVPWHKZIJBODOX-UHFFFAOYSA-N |
| SMILES | C(SSCc1ccccc1)c2ccccc2 |
| LogP (Verteilungskoeffizient) | 5.29 |
| CAS Datenbank | 150-60-7(CAS DataBase Reference) |
| NIST chemische Informationen | Benzyl disulfide(150-60-7) |
| EPA chemische Informationen | Disulfide, bis(phenylmethyl) (150-60-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 71.1% (113 of 159) of all reports.WarningH317 (28.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 159 reports by companies from 5 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: Disulfide, bis(phenylmethyl)Disulfide, bis(phenylmethyl): Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | An irritantMay cause skin sensitization[MSDSonline] |
| Hazard Classes and Categories | Skin Sens. 1 (28.9%) |
| Unerwünschte Wirkungen | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29309090 |
| RTECS-Nr. | JO1750000 |
| R-Sätze (R) | 43 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 22-36/37-37-24 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Skin Sens. 1 |
Anwendungen & Verwendung
Verwenden
Dibenzyl disulfide has been used in lubricating oil formulations to improve thermal and aging resistance of the oil. It is used an antioxidant in rubber compounding, stabilizer for petroleum fractions, additive to silicone oils. The soly in oils is increased by the presence of benzyl alcohol.
Herstellung & Synthese
synthetische
Dibenzyl disulfide is synthesized from benzyl chloride and Na2S2; also from benzyl mercaptan via oxidation.Md. Tajbakhsh et al. (2004) synthesized disulfide from thiols by oxidation with 2,6- DCPCC in acetonitirle at room temperature. For synthesis of DBDS, they used benzyl mercaptan. In 8 min, 96% yield was obtained.Vivek Polshettiwar et al. (2003) obtained disulfide from reaction of alkyl halide with reagent (C6H5CH2N(Et)3)6Mo7S24 in presence of CHCl3 at room temperature. Pure disulfide was obtained by purification by column chromatography method on silica gel. 89% yield was obtained.