1,3,5-Hexatrien
Hexatriene · Divinylethylene · 1,3,5-HEXATRIENE · Hexa-1,3,5-triene · (3E)-1,3,5-Hexatriene · hexa-1,3,5-triene, mixed isomers · 1,3,5-hexatriene,mixtureofisomers · 1,3,5-HEXATRIENE, MIXTURE OF ISOMERS, STAB.
Identifikatoren & physikalische Daten
| CAS No. | 2235-12-3 |
|---|---|
| Summenformel | C6H8 |
| Durchschnittliche Molmasse | 80,13 g/mol |
| Monoisotopische Masse | 80,06260026 g/mol |
| SMILES | C=CC=CC=C |
| InChIKey | AFVDZBIIBXWASR-UHFFFAOYSA-N |
| PubChem CID | 16695 |
| EC No. | 218-789-7 |
| DTXSID | DTXSID3062283 |
| Lokaler Name | 1,3,5-Hexatrien |
Chemische & physikalische Eigenschaften
| XLogP | 2,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 58 |
| Schmelzpunkt | -11.7°C |
| Siedepunkt | 76-79°C |
| Dichte | 0,737 g/cm3 |
| Brechungsindex | n20/D 1.511(lit.) |
| Flammpunkt | 38 °C |
| Lagerbedingungen | −20°C |
| EPA chemische Informationen | 1,3,5-Hexatriene (2235-12-3) |
Sicherheit & Vorschriften
| TSCA-Inventar-Status | TSCA listed |
|---|---|
| UN-Transportnummer | 1992 |
| RTECS-Nr. | MP5425000 |
| R-Sätze (R) | 10-22-36-65 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-36-62 |
| Gefahrenklasse | 3.2 |
| Verpackungsgruppe | III |
Anwendungen & Verwendung
Beschreibung
1,3,5-hexatriene is the simplest conjugated triene, and its structure predicts two geometrical isomers, the cis form being the open chain analog of benzene. With a single sigma bond separating the pi bonds of 1,3,5-hexatriene it is a conjugated system and some of the pi electron density will be delocalized between each of the C-C bonds, not just those written as double bonds in the Lewis structure. There are six adjacent carbon atoms involved in the pi system and the combination of a p orbital from each of these six atoms will result in six pi molecular orbitals: ψ1, ψ2, ψ3, ψ4*, ψ5*, and ψ6* (also referred to as π1, π2, π3, π4*, π5*and π6*).
Herstellung & Synthese
synthetische
1,3,5-Hexatriene has been prepared by pyrolysis of s-divinylglycol diformate, condensation of allyl chloride with sodamide, phthalic anhydride dehydration of 1,5-hexadiene-3-ol and debromination of 3,4-dibromohexa-diene-1,5 with zinc. The product in method contained cyclohexadiene, and the purification of the substance seems to have been incomplete in all cases.