Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and O-Xylene: Difference between pages

{{DISPLAYTITLE:''o''-Xylene}}

|Watchedfields = changed

|verifiedrevid = 462263866

|Name = ''o''-Xylene

|ImageFileL1 = Ortho-Xylene-2D-structure.svg

|ImageNameL1 = Skeletal formula

|ImageFileR1 = o-xylene-spaceFill.png

|ImageSizeR1 = 150px

|ImageNameR1 = Space-filling model

|PIN = 1,2-Xylene<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | pages = 121, 139, 653 | doi = 10.1039/9781849733069 | isbn = 978-0-85404-182-4}}</ref>

|SystematicName = 1,2-Dimethylbenzene<ref name=iupac2013 />

|OtherNames = ''o''-Xylene,<ref name=iupac2013 /> o-Xylol <!-- not o-methyltoluene, substitution of toluene by additional methyl groups is not allowed -->

|Section1={{Chembox Identifiers

|CASNo = 95-47-6

|CASNo_Ref = {{cascite|correct|CAS}}

|Beilstein = 1815558

|ChEBI_Ref = {{ebicite|correct|EBI}}

|ChEBI = 28063

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 45005

|ChemSpiderID = 6967

|DrugBank_Ref = {{drugbankcite|correct|drugbank}}

|DrugBank = DB03029

|EC_number = 202-422-2

|Gmelin = 67796

|KEGG_Ref = {{keggcite|correct|kegg}}

|KEGG = C07212

|PubChem = 7237

|RTECS = ZE2450000

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = Z2474E14QP

|UNNumber = 1307

|SMILES = CC1=C(C)C=CC=C1

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = CTQNGGLPUBDAKN-UHFFFAOYSA-N

|InChI = 1/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3

|InChIKey = CTQNGGLPUBDAKN-UHFFFAOYAE

|Section2={{Chembox Properties

|C=8 | H=10

|Appearance = Colorless liquid

|Density = 0.88 g/ml

|MeltingPtC = -24

|BoilingPtC = 144.4

|Solubility = 0.02% (20°C)<ref name=PGCH/>

|Solubility1 = very soluble

|Solvent1 = ethanol

|Solubility2 = very soluble

|Solvent2 = diethyl ether

|RefractIndex = 1.50545

|Viscosity = 1.1049 c[[Poise (unit)|P]] at 0 °C<br>0.8102 c[[Poise (unit)|P]] at 20 °C

|VaporPressure = 7 mmHg (20°C)<ref name=PGCH/>

|MagSus = -77.78·10⁻⁶ cm³/mol

}}

|Section3={{Chembox Structure

|Dipole = 0.64 [[Debye|D]]<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>}}

|Section4={{Chembox Hazards

|MainHazards = Mildly toxic

|ExternalSDS = [http://www.jtbaker.com/msds/englishhtml/x2200.htm External MSDS]

|FlashPtC = 32

|NFPA-H = 2

|NFPA-F = 3

|NFPA-R = 0

|GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}

|GHSSignalWord = Danger

|HPhrases = {{H-phrases|225|226|304|305|312|315|319|332|335|412}}

|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}}

|PEL = TWA 100 ppm (435 mg/m³)<ref name=PGCH>{{PGCH|0668}}</ref>

|ExploLimits = 0.9%-6.7%<ref name=PGCH/>

|IDLH = 900 ppm<ref name=PGCH/>

|REL = TWA 100 ppm (435 mg/m³) ST 150 ppm (655 mg/m³)<ref name=PGCH/>

|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>

|TLV-STEL = 150 ppm<ref name=ICSC/>

|AutoignitionPtC = 463

|AutoignitionPt_ref = <ref name=ICSC/>

|LD50 = 4300 mg/kg (rats, [[Oral administration|oral]]ly)<ref>O-xylene toxicity</ref>

|LCLo = 6125 ppm (rat, 12 hr)<br/>6125 ppm (human, 12 hr)<ref>{{IDLH|95476|Xylene (o-, m-, p-isomers)}}</ref>

}}

|Section5={{Chembox Related

|OtherFunction_label = [[aromatic hydrocarbon]]s

|OtherFunction = [[M-Xylene|''m''-xylene]]<br>[[P-Xylene|''p''-xylene]]<br>[[toluene]]

}}

}}

'''''o''-Xylene''' ('''''ortho''-xylene''') is an [[aromatic hydrocarbon]] with the [[formula]] C₆H₄(CH₃)₂, with two [[methyl]] [[substituent]]s bonded to adjacent carbon [[atom]]s of a [[benzene]] [[Ring (chemistry)|ring]] (the [[Arene substitution pattern|ortho]] configuration). It is a [[constitutional isomer]] of [[M-Xylene|''m''-xylene]] and [[P-Xylene|''p''-xylene]], the mixture being called [[xylene]] or xylenes. ''o''-Xylene is a [[colour]]less slightly [[oil]]y flammable [[liquid]].<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>

==Production and use==

[[Petroleum]] contains about one weight percent xylenes. Most ''o''-xylene is produced by cracking [[petroleum]], 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.

''o''-Xylene is largely used in the production of [[phthalic anhydride]], 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 [[bromine]], these groups are brominated, yielding [[xylylene dibromide]]:<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>

:C₆H₄(CH₃)₂ + 2 Br₂ → C₆H₄(CH₂Br)₂ + 2 HBr

==Toxicity and exposure==

Xylenes are not acutely toxic, for example the {{LD50}} (rat, oral) is 4300&nbsp;mg/kg. Effects vary with animal and xylene isomer. Concerns with xylenes focus on narcotic effects.<ref name="Ullmann"/>

==References==

{{reflist}}

{{Hydrocarbons}}

{{DEFAULTSORT:Xylene, o-}}

[[Category:Alkylbenzenes]]

[[Category:C2-Benzenes]]