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Xylene
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==Properties== The physical properties of the isomers of xylene differ slightly. The melting point ranges from {{convert|−47.87|°C|°F|2}} (''m''-xylene) to {{convert|13.26|°C|°F|2}} (''p''-xylene)—as usual, the para isomer's melting point is much higher because it packs more readily in the crystal structure. The boiling point for each isomer is around {{convert|140|°C|°F|0}}. The density of each isomer is around {{convert|0.87|g/mL|lb/gal lb/impgal|abbr=on}} and thus is less dense than [[properties of water|water]]. The odor of xylene is detectable at concentrations as low as 0.08 to 3.7 ppm (parts of xylene per million parts of air) and can be tasted in water at 0.53 to 1.8 ppm.<ref name="Kandyala" /> <!-- Here is a table of data; skip past it to edit the text. --> {| align="center" class="wikitable" style="background:white; border-color:#C0C090; text-align:center;" ! {{Chemical datatable header}} colspan="5" | Xylene isomers |- <!--| align="center" colspan="5" | [[Image:Xylene Isomers.PNG|400px|{{PAGENAME}}]] replace if not identical with the pagename --> |- ! {{Chemical datatable header}} colspan="5" | General |- style="font-weight:bold;" | Common name | Xylenes<br>(mixture) | [[o-Xylene|''o''-Xylene]] | [[m-Xylene|''m''-Xylene]] | [[p-Xylene|''p''-Xylene]] |- | [[IUPAC nomenclature|Systematic name]] | Dimethylbenzene | 1,2-Dimethylbenzene | 1,3-Dimethylbenzene | 1,4-Dimethylbenzene |- | Other names | Xylol | ''o''-Xylol;<br>Orthoxylene | ''m''-Xylol;<br>Metaxylene | ''p''-Xylol;<br>Paraxylene |- | [[Chemical formula|Molecular formula]] | colspan="4" | C<sub>8</sub>H<sub>10</sub> |- | [[Simplified molecular input line entry specification|SMILES]] | | Cc1c(C)cccc1 | Cc1cc(C)ccc1 | Cc1ccc(C)cc1 |- | [[Molar mass]] | colspan="4" | 106.16 g/mol |- | Appearance | colspan="4" | Clear, colorless liquid |- | [[CAS registry number|CAS number]] | [1330-20-7] | [95-47-6] | [108-38-3] | [106-42-3] |- ! {{Chemical datatable header}} colspan="5" | Properties |- | [[Density]] and [[phase (matter)|phase]] | 0.864 g/mL, liquid | 0.88 g/mL, liquid | 0.86 g/mL, liquid | 0.86 g/mL, liquid |- | [[Soluble|Solubility]] in water | colspan="4" | Practically insoluble |- | colspan="5" | Soluble in non-polar solvents such as [[aromatic hydrocarbon]]s |- | [[Melting point]] | −47.4 °C (−53.3 °F; 226 K) | −25 °C (−13 °F; 248 K) | −48 °C (−54 °F; 225 K) | 13 °C (55 °F; 286 K) |- | [[Boiling point]] | 138.5 °C (281.3 °F; 412 K) | 144 °C (291 °F; 417 K) | 139 °C (282 °F; 412 K) | 138 °C (280 °F; 411 K) |- | [[Viscosity]] | | 0.812 c[[Poise (unit)|P]] at {{convert|20|°C|°F|0}} | 0.62 c[[Poise (unit)|P]] at {{convert|20|°C|°F|0}} | 0.34 c[[Poise (unit)|P]] at {{convert|30|°C|°F|0}} |- ! {{Chemical datatable header}} colspan="5" | Hazards <!-- Summary only- MSDS entry provides more complete information --> |- | [[Safety data sheet|SDS]] | [https://www.fishersci.com/store/msds?partNumber=X5FB50&productDescription=XYLENES+ACS+FB+50L&vendorId=VN00033897&countryCode=US&language=en Xylenes] | [https://fscimage.fishersci.com/msds/17180.htm ''o''-Xylene] | [https://fscimage.fishersci.com/msds/95260.htm ''m''-Xylene] | [https://fscimage.fishersci.com/msds/95257.htm ''p''-Xylene] |- | [[GHS hazard pictograms|EU pictograms]] | colspan="4" | {{GHS02}}{{GHS07}}{{GHS08}} |- | [[NFPA 704]] | colspan="4" | {{NFPA 704 diamond| H=2 | F=3 | R=0 }} |- | [[Flash point]] | {{convert|30|°C|°F|0}} | {{convert|17|°C|°F|0}} | {{convert|25|°C|°F|0}} | {{convert|25|°C|°F|0}} |- | [[GHS hazard statements|H]] & [[GHS precautionary statements|P phrases]] | colspan="4" | {{H-phrases|225|226|304|312|315|319|332|335|412}}<br/> {{P-phrases|210|233|240|241|242|243|261|264|271|273|280 |301+310|302+352|303+361+353|304+312|304+340|305+351+338|312|321|322|331|332+313|337+313|362|363|370+378 |403+233|403+235|405|501}} |- | [[RTECS]] number | | ZE2450000 | ZE2275000 | ZE2625000 |- ! {{Chemical datatable header}} colspan="5" | Related compounds |- | Related aromatic<br>hydrocarbons | colspan="4" | [[Toluene]], [[mesitylene]], [[benzene]], [[ethylbenzene]] |- | Related compounds | colspan="4" | Xylenols – types of [[phenols]] |- | {{Chemical datatable header}} colspan="5" | <small>Except where noted otherwise, data are given for materials in their [[standard state|standard state (at 25{{nbsp}}°C, 100{{nbsp}}kPa)]]<br/>[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small> |} Xylenes form [[azeotrope]]s with water and a variety of alcohols. The azeotrope with water consists of 60% xylenes and boils at 94.5 °C.<ref name="Ullmann" /> As with many [[alkylbenzene]] compounds, xylenes form complexes with various [[halocarbon]]s.<ref>{{cite journal |title= Separation of Xylenes |journal= Ind. Eng. Chem. |year= 1955 |volume= 47 |issue= 2 |pages= 250–253 |doi= 10.1021/ie50542a028 |author1=Clark J. E. |author2=Luthy, R. V. }}</ref> The complexes of different isomers often have dramatically different properties from each other.<ref>{{cite journal |doi = 10.1021/ac980221b |title = Separation of Closely Boiling Isomers and Identically Boiling Isotopomers via Electron-Transfer-Assisted Extraction |journal = Analytical Chemistry |volume = 70 |issue = 18 |pages = 3880 |year = 1998 |last1 = Stevenson |first1 = Cheryl D. |last2 = McElheny |first2 = Daniel J. |last3 = Kage |first3 = David E. |last4 = Ciszewski |first4 = James T. |last5 = Reiter |first5 = Richard C.}}</ref>
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