| Revision as of 14:25, 24 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Saving copy of the {{chembox}} taken from revid 444031646 of page O-Xylene for the Chem/Drugbox validation project (updated: 'ChEMBL'). |
Latest revision as of 20:51, 19 October 2024 edit Christian75 (talk | contribs)Extended confirmed users, New page reviewers, Pending changes reviewers, Rollbackers114,911 edits revert renumbering of chembox sections - see Template_talk:Chembox/Archive_13#Renaming_sections |
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{{DISPLAYTITLE:''o''-Xylene}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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|Watchedfields = changed |
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| verifiedrevid = 444030153 |
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|verifiedrevid = 462263866 |
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| Name = o-Xylene |
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|Name = ''o''-Xylene |
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| ImageFileL1 = Ortho-Xylol - ortho-xylene 2.svg |
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|ImageFileL1 = Ortho-Xylene-2D-structure.svg |
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| ImageSizeL1 = 100px |
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| ImageNameL1 = Skeletal formula |
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|ImageNameL1 = Skeletal formula |
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| ImageFileR1 = o-xylene-spaceFill.png |
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|ImageFileR1 = o-xylene-spaceFill.png |
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| ImageSizeR1 = 150px |
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|ImageSizeR1 = 150px |
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| ImageNameR1 = Space-filling model |
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|ImageNameR1 = Space-filling model |
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|PIN = 1,2-Xylene<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | pages = 121, 139, 653 | doi = 10.1039/9781849733069 | isbn = 978-0-85404-182-4}}</ref> |
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| Section1 = {{Chembox Identifiers |
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|SystematicName = 1,2-Dimethylbenzene<ref name=iupac2013 /> |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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|OtherNames = ''o''-Xylene,<ref name=iupac2013 /> o-Xylol <!-- not o-methyltoluene, substitution of toluene by additional methyl groups is not allowed --> |
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| DrugBank = DB03029 |
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|Section1={{Chembox Identifiers |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = Z2474E14QP |
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|CASNo = 95-47-6 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|Beilstein = 1815558 |
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| ChEBI = 28063 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| SMILES = CC1=C(C)C=CC=C1 |
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| CASNo = 95-47-6 |
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|ChEBI = 28063 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| KEGG = C07212 |
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|ChEMBL = 45005 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|ChemSpiderID = 6967 |
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| RTECS = ZE2450000 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| ChEMBL = 45005 |
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|DrugBank = DB03029 |
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|EC_number = 202-422-2 |
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| ChemSpiderID = 6967 |
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|Gmelin = 67796 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| StdInChI = 1S/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3 |
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|KEGG = C07212 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|PubChem = 7237 |
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| StdInChIKey = CTQNGGLPUBDAKN-UHFFFAOYSA-N |
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|RTECS = ZE2450000 |
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| InChI = 1/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| InChIKey = CTQNGGLPUBDAKN-UHFFFAOYAE |
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|UNII = Z2474E14QP |
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}} |
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|UNNumber = 1307 |
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| Section2 = {{Chembox Properties |
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|SMILES = CC1=C(C)C=CC=C1 |
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| Formula = C<sub>8</sub>H<sub>10</sub> |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| MolarMass = 106.16 g/mol |
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|StdInChI = 1S/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3 |
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| Appearance = Colorless liquid |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| MeltingPtC = -24 |
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|StdInChIKey = CTQNGGLPUBDAKN-UHFFFAOYSA-N |
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| BoilingPtC = 144.4 |
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|InChI = 1/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3 |
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| Solubility = insoluble |
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|InChIKey = CTQNGGLPUBDAKN-UHFFFAOYAE |
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| Solubility1 = very soluble |
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| Solvent1 = ethanol |
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| Solubility2 = very soluble |
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| Solvent2 = diethyl ether |
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| RefractIndex = 1.50545 |
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| Viscosity = 11.049 c] at 0 °C<br>8.102 c] at 20 °C |
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}} |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = |
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| EUClass = Harmful ('''Xn''') Flammable ('''F''') |
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| FlashPt = 32 °C |
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| NFPA-H = 2 |
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| NFPA-F = 3 |
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| NFPA-R = 0 |
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| NFPA-O = |
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| RPhrases = {{R11}} {{R20}} {{R21}} {{R38}} |
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| SPhrases = {{S25}} |
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}} |
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| Section8 = {{Chembox Related |
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| Function = ]s |
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| OtherFunctn = ]<br>]<br>] |
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}} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|C=8 | H=10 |
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|Appearance = Colorless liquid |
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|Density = 0.88 g/ml |
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|MeltingPtC = -24 |
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|BoilingPtC = 144.4 |
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|Solubility = 0.02% (20°C)<ref name=PGCH/> |
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|Solubility1 = very soluble |
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|Solvent1 = ethanol |
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|Solubility2 = very soluble |
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|Solvent2 = diethyl ether |
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|RefractIndex = 1.50545 |
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|Viscosity = 1.1049 c] at 0 °C<br>0.8102 c] at 20 °C |
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|VaporPressure = 7 mmHg (20°C)<ref name=PGCH/> |
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|MagSus = -77.78·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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|Section3={{Chembox Structure |
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|Dipole = 0.64 ]<ref>{{Cite journal | doi = 10.1016/0022-2852(73)90016-7 | title = Microwave spectrum, barrier for methyl rotation, methyl conformation, and dipole moment of ortho-xylene | year = 1973 | last1 = Rudolph | first1 = H.D. | last2 = Walzer | first2 = K. | last3 = Krutzik | first3 = Irmhild | journal = Journal of Molecular Spectroscopy | volume = 47 | issue = 2 | pages = 314| bibcode = 1973JMoSp..47..314R }}</ref>}} |
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|Section7={{Chembox Hazards |
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|MainHazards = Mildly toxic |
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|ExternalSDS = |
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|FlashPtC = 32 |
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|NFPA-H = 2 |
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|NFPA-F = 3 |
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|NFPA-R = 0 |
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|GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|225|226|304|305|312|315|319|332|335|412}} |
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|PPhrases = {{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}} |
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|PEL = TWA 100 ppm (435 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0668}}</ref> |
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|ExploLimits = 0.9%-6.7%<ref name=PGCH/> |
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|IDLH = 900 ppm<ref name=PGCH/> |
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|REL = TWA 100 ppm (435 mg/m<sup>3</sup>) ST 150 ppm (655 mg/m<sup>3</sup>)<ref name=PGCH/> |
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|TLV-TWA = 100 ppm<ref name=ICSC>{{cite web |url = https://www.cdc.gov/niosh/ipcsneng/neng0084.html |work = International Chemical Safety Cards |publisher = ICSC/NIOSH | title = o-Xylene |date = July 1, 2014}}</ref> |
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|TLV-STEL = 150 ppm<ref name=ICSC/> |
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|AutoignitionPtC = 463 |
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|AutoignitionPt_ref = <ref name=ICSC/> |
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|LD50 = 4300 mg/kg (rats, ]ly)<ref>O-xylene toxicity</ref> |
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|LCLo = 6125 ppm (rat, 12 hr)<br/>6125 ppm (human, 12 hr)<ref>{{IDLH|95476|Xylene (o-, m-, p-isomers)}}</ref> |
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}} |
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|Section9={{Chembox Related |
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|OtherFunction_label = ]s |
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|OtherFunction = ]<br>]<br>] |
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}} |
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}} |
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'''''o''-Xylene''' ('''''ortho''-xylene''') is an ] with the ] C<sub>6</sub>H<sub>4</sub>(CH<sub>3</sub>)<sub>2</sub>, with two ] ]s bonded to adjacent carbon ]s of a ] ] (the ] configuration). It is a ] of ] and ], the mixture being called ] or xylenes. ''o''-Xylene is a ]less slightly ]y flammable ].<ref name="Ullmann">{{Ullmann|author1=Fabri, Jörg |author2=Graeser, Ulrich|author3= Simo, Thomas A.|title=Xylenes|year=2000|doi=10.1002/14356007.a28_433}}</ref> |
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==Production and use== |
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] contains about one weight percent xylenes. Most ''o''-xylene is produced by cracking ], which affords a distribution of aromatic compounds, including xylene isomers. ''m''-Xylene is isomerized to ''o''-xylene. Net production was approximately 500,000 tons in the year 2000. |
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''o''-Xylene is largely used in the production of ], which is a precursor to many materials, drugs, and other chemicals.<ref name="Ullmann"/> Related to their easy oxidation, the methyl groups are susceptible to halogenation. When treated with elemental ], these groups are brominated, yielding ]:<ref>{{cite journal|author=Emily F. M. Stephenson|year=1954|title=o-Xylylene Dibromide|journal=Organic Syntheses|volume=34|page=100|doi=10.15227/orgsyn.034.0100}}</ref> |
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:C<sub>6</sub>H<sub>4</sub>(CH<sub>3</sub>)<sub>2</sub> + 2 Br<sub>2</sub> → C<sub>6</sub>H<sub>4</sub>(CH<sub>2</sub>Br)<sub>2</sub> + 2 HBr |
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==Toxicity and exposure== |
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Xylenes are not acutely toxic, for example the {{LD50}} (rat, oral) is 4300 mg/kg. Effects vary with animal and xylene isomer. Concerns with xylenes focus on narcotic effects.<ref name="Ullmann"/> |
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==References== |
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{{reflist}} |
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{{Hydrocarbons}} |
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{{DEFAULTSORT:Xylene, o-}} |
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] |
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] |