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{{DISPLAYTITLE:''o''-Xylene}}
{{DISPLAYTITLE:''o''-Xylene}}
{{chembox
{{chembox
| Watchedfields = changed
|Watchedfields = changed
| verifiedrevid = 462263866
|verifiedrevid = 462263866
| Name = ''o''-Xylene
|Name = ''o''-Xylene
| ImageFileL1 = Ortho-Xylol - ortho-xylene 2.svg
|ImageFileL1 = Ortho-Xylene-2D-structure.svg
| ImageNameL1 = Skeletal formula
|ImageNameL1 = Skeletal formula
| ImageFileR1 = o-xylene-spaceFill.png
|ImageFileR1 = o-xylene-spaceFill.png
| ImageSizeR1 = 150px
|ImageSizeR1 = 150px
| ImageNameR1 = Space-filling model
|ImageNameR1 = Space-filling model
| PIN = 1,2-Xylene <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->
|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 =
|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 -->
| OtherNames = ''ortho''-Xylene
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
|CASNo = 95-47-6
⚫
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫
|CASNo_Ref = {{cascite|correct|CAS}}
⚫
| DrugBank = DB03029
|Beilstein = 1815558
⚫
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
|ChEBI_Ref = {{ebicite|correct|EBI}}
⚫
| UNII = Z2474E14QP
⚫
|ChEBI = 28063
⚫
| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫
| ChEBI = 28063
|ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫
| SMILES = CC1=C(C)C=CC=C1
| CASNo = 95-47-6
|ChEMBL = 45005
⚫
|ChemSpiderID = 6967
| KEGG_Ref = {{keggcite|correct|kegg}}
⚫
|DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| KEGG = C07212
⚫
|DrugBank = DB03029
⚫
| CASNo_Ref = {{cascite|correct|CAS}}
|EC_number = 202-422-2
⚫
| RTECS = ZE2450000
|Gmelin = 67796
⚫
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
|KEGG_Ref = {{keggcite|correct|kegg}}
| ChEMBL = 45005
|KEGG = C07212
|PubChem = 7237
⚫
| ChemSpiderID = 6967
⚫
|RTECS = ZE2450000
⚫
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫
|UNII_Ref = {{fdacite|correct|FDA}}
⚫
| StdInChI = 1S/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3
⚫
|UNII = Z2474E14QP
⚫
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|UNNumber = 1307
⚫
| StdInChIKey = CTQNGGLPUBDAKN-UHFFFAOYSA-N
⚫
|SMILES = CC1=C(C)C=CC=C1
⚫
| InChI = 1/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3
⚫
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫
| InChIKey = CTQNGGLPUBDAKN-UHFFFAOYAE
⚫
|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
|Section2={{Chembox Properties
| C=8 | H=10
|C=8 | H=10
| Appearance = Colorless liquid
|Appearance = Colorless liquid
| Density = 0.88 g/ml
|Density = 0.88 g/ml
| MeltingPtC = -24
|MeltingPtC = -24
| BoilingPtC = 144.4
|BoilingPtC = 144.4
| Solubility = 0.02% (20°C)<ref name=PGCH/>
|Solubility = 0.02% (20°C)<ref name=PGCH/>
| Solubility1 = very soluble
|Solubility1 = very soluble
| Solvent1 = ethanol
|Solvent1 = ethanol
| Solubility2 = very soluble
|Solubility2 = very soluble
| Solvent2 = diethyl ether
|Solvent2 = diethyl ether
| RefractIndex = 1.50545
|RefractIndex = 1.50545
| Viscosity = 1.1049 c[[Poise (unit)|P]] at 0 °C<br>0.8102 c[[Poise (unit)|P]] at 20 °C
|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/>
|VaporPressure = 7 mmHg (20°C)<ref name=PGCH/>
| MagSus = -77.78·10<sup>−6</sup> cm<sup>3</sup>/mol
|MagSus = -77.78·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
}}
|Section3={{Chembox Structure
|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>
|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]
⚫
|Section7={{Chembox Hazards
|FlashPtC = 32
⚫
| ExternalSDS = [http://www.jtbaker.com/msds/englishhtml/x2200.htm External MSDS]
⚫
|NFPA-H = 2
| EUClass = Harmful ('''Xn''') Flammable ('''F''')
| FlashPtC = 32
|NFPA-F = 3
| NFPA-H = 2
|NFPA-R = 0
|GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}
⚫
| NFPA-F = 3
|GHSSignalWord = Danger
| NFPA-R = 0
|HPhrases = {{H-phrases|225|226|304|305|312|315|319|332|335|412}}
| NFPA-S =
|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}}
| RPhrases = {{R11}} {{R20}} {{R21}} {{R38}}
⚫
|PEL = TWA 100 ppm (435 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0668}}</ref>
| SPhrases = {{S25}}
| PEL = TWA 100 ppm (435 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0668}}</ref>
|ExploLimits = 0.9%-6.7%<ref name=PGCH/>
| ExploLimits = 0.9%-6.7%<ref name=PGCH/>
|IDLH = 900 ppm<ref name=PGCH/>
| IDLH = 900 ppm<ref name=PGCH/>
|REL = TWA 100 ppm (435 mg/m<sup>3</sup>) ST 150 ppm (655 mg/m<sup>3</sup>)<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>
⚫
| REL = TWA 100 ppm (435 mg/m<sup>3</sup>) ST 150 ppm (655 mg/m<sup>3</sup>)<ref name=PGCH/>
⚫
|TLV-STEL = 150 ppm<ref name=ICSC/>
⚫
| 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>
⚫
|AutoignitionPtC = 463
⚫
| TLV-STEL = 150 ppm<ref name=ICSC/>
⚫
|AutoignitionPt_ref = <ref name=ICSC/>
⚫
| AutoignitionPtC = 463
|LD50 = 4300 mg/kg (rats, [[Oral administration|oral]]ly)<ref>O-xylene toxicity</ref>
⚫
| AutoignitionPt_ref = <ref name=ICSC/>
| LCLo = 6125 ppm (rat, 12 hr)<br/>6125 ppm (human, 12 hr)<ref>{{IDLH|95476|Xylene (o-, m-, p-isomers)}}</ref>
|LCLo = 6125 ppm (rat, 12 hr)<br/>6125 ppm (human, 12 hr)<ref>{{IDLH|95476|Xylene (o-, m-, p-isomers)}}</ref>
}}
}}
|Section8={{Chembox Related
|Section5={{Chembox Related
| OtherFunction_label = [[aromatic hydrocarbon]]s
|OtherFunction_label = [[aromatic hydrocarbon]]s
| OtherFunction = [[M-Xylene|''m''-xylene]]<br>[[P-Xylene|''p''-xylene]]<br>[[toluene]]
|OtherFunction = [[M-Xylene|''m''-xylene]]<br>[[P-Xylene|''p''-xylene]]<br>[[toluene]]
}}
}}
}}
}}


'''''o''-Xylene''' ('''''ortho''-xylene''') is an [[aromatic]] [[hydrocarbon]] with the formula C<sub>6</sub>H<sub>4</sub>(CH<sub>3</sub>)<sub>2</sub>. with two [[methyl]] [[substituent]]s bonded to adjacent carbon atoms of a benzene 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 colorless slightly oily 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>
'''''o''-Xylene''' ('''''ortho''-xylene''') is an [[aromatic hydrocarbon]] with the [[formula]] C<sub>6</sub>H<sub>4</sub>(CH<sub>3</sub>)<sub>2</sub>, 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==
==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.
[[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 bromine, these groups are brominated, leading ultimately to [[Tetrabromo-o-xylene|the tetrabromide]]:<ref name=OS>{{cite journal |doi=10.15227/orgsyn.034.0082|title=o-Phthalaldehyde|journal=Organic Syntheses|year=1954|first1=J. C.|last1=Bill|first2=D. S.|last2=Tarbell |volume=34|page=82}}</ref>
''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>
:C<sub>6</sub>H<sub>4</sub>(CH<sub>3</sub>)<sub>2</sub> + 4 Br<sub>2</sub> → C<sub>6</sub>H<sub>4</sub>(CHBr<sub>2</sub>)<sub>2</sub> + 4 HBr
: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


==Toxicity and exposure==
==Toxicity and exposure==
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"/>
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==
==References==
{{reflist}}
{{reflist}}


{{Hydrocarbons}}
{{DEFAULTSORT:Xylene, o-}}
{{DEFAULTSORT:Xylene, o-}}


[[Category:Alkylbenzenes]]
[[Category:Alkylbenzenes]]
[[Category:C2-Benzenes]]

Latest revision as of 09:02, 17 March 2024

o-Xylene
Skeletal formula
Skeletal formula
Space-filling model
Space-filling model
Names
Preferred IUPAC name
1,2-Xylene[1]
Systematic IUPAC name
1,2-Dimethylbenzene[1]
Other names
o-Xylene,[1] o-Xylol
Identifiers
3D model (JSmol)
1815558
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.002.203 Edit this at Wikidata
EC Number
  • 202-422-2
67796
KEGG
RTECS number
  • ZE2450000
UNII
UN number 1307
  • InChI=1S/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3 checkY
    Key: CTQNGGLPUBDAKN-UHFFFAOYSA-N checkY
  • InChI=1/C8H10/c1-7-5-3-4-6-8(7)2/h3-6H,1-2H3
    Key: CTQNGGLPUBDAKN-UHFFFAOYAE
  • CC1=C(C)C=CC=C1
Properties
C8H10
Molar mass 106.168 g·mol−1
Appearance Colorless liquid
Density 0.88 g/ml
Melting point −24 °C (−11 °F; 249 K)
Boiling point 144.4 °C (291.9 °F; 417.5 K)
0.02% (20°C)[2]
Solubility in ethanol very soluble
Solubility in diethyl ether very soluble
Vapor pressure 7 mmHg (20°C)[2]
-77.78·10−6 cm3/mol
1.50545
Viscosity 1.1049 cP at 0 °C
0.8102 cP at 20 °C
Structure
0.64 D[3]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Mildly toxic
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
Danger
H225, H226, H304, H305, H312, H315, H319, H332, H335, H412
P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P301+P310, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P331, P332+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
Flash point 32 °C (90 °F; 305 K)
463 °C (865 °F; 736 K)[4]
Explosive limits 0.9%-6.7%[2]
100 ppm[4] (TWA), 150 ppm[4] (STEL)
Lethal dose or concentration (LD, LC):
4300 mg/kg (rats, orally)[5]
6125 ppm (rat, 12 hr)
6125 ppm (human, 12 hr)[6]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 100 ppm (435 mg/m3)[2]
REL (Recommended)
 TWA 100 ppm (435 mg/m3) ST 150 ppm (655 mg/m3)[2]
IDLH (Immediate danger)
 900 ppm[2]
Safety data sheet (SDS) External MSDS
Related compounds
m-xylene
p-xylene
toluene
Supplementary data page
O-Xylene (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

o-Xylene (ortho-xylene) is an aromatic hydrocarbon with the formula C6H4(CH3)2, with two methyl substituents bonded to adjacent carbon atoms of a benzene ring (the ortho configuration). It is a constitutional isomer of m-xylene and p-xylene, the mixture being called xylene or xylenes. o-Xylene is a colourless slightly oily flammable liquid.[7]

Production and use

[edit]

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.[7] Related to their easy oxidation, the methyl groups are susceptible to halogenation. When treated with elemental bromine, these groups are brominated, yielding xylylene dibromide:[8]

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

Toxicity and exposure

[edit]

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.[7]

References

[edit]
  1. ^ a b c Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 121, 139, 653. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0668". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Rudolph, H.D.; Walzer, K.; Krutzik, Irmhild (1973). "Microwave spectrum, barrier for methyl rotation, methyl conformation, and dipole moment of ortho-xylene". Journal of Molecular Spectroscopy. 47 (2): 314. Bibcode:1973JMoSp..47..314R. doi:10.1016/0022-2852(73)90016-7.
  4. ^ a b c "o-Xylene". International Chemical Safety Cards. ICSC/NIOSH. July 1, 2014.
  5. ^ O-xylene toxicity
  6. ^ "Xylene (o-, m-, p-isomers)". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  7. ^ a b c Fabri, Jörg; Graeser, Ulrich; Simo, Thomas A. (2000). "Xylenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a28_433. ISBN 978-3527306732.
  8. ^ Emily F. M. Stephenson (1954). "o-Xylylene Dibromide". Organic Syntheses. 34: 100. doi:10.15227/orgsyn.034.0100.
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