| Revision as of 05:33, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 462326185 of page Alpha-Methylstyrene for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 06:00, 24 December 2024 edit Flidbouillon (talk | contribs)19 editsm →Synthesis and reactions: Added linksTags: canned edit summary Mobile edit Mobile app edit Android app edit App section source |
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{{lowercase title}} |
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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 = 443945694 |
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|verifiedrevid = 477319488 |
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| Name = α-Methylstyrene |
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|Name = α-Methylstyrene |
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| Reference = <ref> at chemicalland21.com</ref> |
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| ImageFileL1 = alpha-methylstyrene.png |
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|ImageFileL1 = Alpha-methylstyrol.svg |
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|ImageNameL1 = Skeletal formula |
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| ImageSizeL1 = 120px |
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|ImageFileR1 = Alpha-methylstyrene-from-xtal-3D-bs-17.png |
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| ImageNameL1 = Skeletal formula |
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|ImageNameR1 = Ball-and-stick model |
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| ImageFileR1 = Alpha-Methylstyrene-3D-balls.png |
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|PIN =(Prop-1-en-2-yl)benzene |
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| ImageSizeR1 = 120px |
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|OtherNames =<small>2-Phenylpropene; 2-Phenylpropylene; 1-Methyl-1-phenylethylene; 1-Methyl-1-phenylethene; 1-Phenyl-1-methylethylene; 1-Phenyl-1-methylethene; (1-Methylethenyl)benzene; β-Phenylpropene; β-Phenylpropylene; α-Methylstyrol; α-Methylvinylbenzene; Isopropenylbenzene</small> |
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| ImageNameR1 = Ball-and-stick model |
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|IUPACName=Isopropenylbenzene |
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|OtherNames=<small>α-Methylstyrene; 2-Phenyl-1-propene; 1-Methyl-1-phenylethylene; 2-Phenylpropene; (1-Methylethenyl)benzene; beta-Phenylpropene; 2-Phenylpropylene; beta-Phenylpropylene; alpha-Methylstyrol; 1-Phenyl-1-methylethylene; 2-Phenyl-2-propene</small> |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| Abbreviations = AMS |
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|Abbreviations = AMS |
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| ChEBI = 35060 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7129 |
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| ChEMBL = 1344773 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID = 7129 |
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| KEGG = C14395 |
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| EC_number = 202-705-0 |
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| InChI = 1/C9H10/c1-8(2)9-6-4-3-5-7-9/h3-7H,1H2,2H3 |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| InChIKey = XYLMUPLGERFSHI-UHFFFAOYAS |
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|KEGG = C14395 |
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| SMILES1 = CC(=C)c1ccccc1 |
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|InChI = 1/C9H10/c1-8(2)9-6-4-3-5-7-9/h3-7H,1H2,2H3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|InChIKey = XYLMUPLGERFSHI-UHFFFAOYAS |
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| StdInChI = 1S/C9H10/c1-8(2)9-6-4-3-5-7-9/h3-7H,1H2,2H3 |
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|SMILES1 = CC(=C)c1ccccc1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = XYLMUPLGERFSHI-UHFFFAOYSA-N |
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|StdInChI = 1S/C9H10/c1-8(2)9-6-4-3-5-7-9/h3-7H,1H2,2H3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo=98-83-9 |
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|StdInChIKey = XYLMUPLGERFSHI-UHFFFAOYSA-N |
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| PubChem=7407 |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| SMILES = C=C(c1ccccc1)C |
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|CASNo=98-83-9 |
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| RTECS = WL5075300 |
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| UNNumber = 2303 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII = D46R9753IK |
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|PubChem=7407 |
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|SMILES = C=C(c1ccccc1)C |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 9 |
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|C = 9 |
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| H = 10 |
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|H = 10 |
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| Appearance=Colorless liquid |
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|Appearance=Colorless liquid |
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| Density= 0.91 g/cm<sup>3</sup> |
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|Density= 0.91 g/cm<sup>3</sup> |
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| MeltingPtC= -24 |
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|MeltingPtC= -24 |
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| BoilingPtCL = 165 |
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|BoilingPtC = 165 to 169 |
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|Solubility=Insoluble |
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| BoilingPtCH = 169 |
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|VaporPressure = 2 mmHg (20 °C)<ref name=PGCH/> |
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| Solubility=Insoluble |
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|MagSus = -80.1·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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}} |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| GHS_ref=<ref>{{cite web |title=alpha-Methylstyrene |url=https://pubchem.ncbi.nlm.nih.gov/compound/7407#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> |
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| MainHazards= |
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| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS09}} |
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| FlashPt= |
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| GHSSignalWord = Warning |
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| Autoignition= |
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| HPhrases = {{H-phrases|226|319|335|411}} |
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| NFPA-H = 3 |
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| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264+265|271|273|280|303+361+353|304+340|305+351+338|319|337+317|370+378|391|403+233|403+235|405|501}} |
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| NFPA-F = 0 |
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|MainHazards= |
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| NFPA-R = 0 |
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| NFPA-O = |
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|NFPA-H = 3 |
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| RPhrases = |
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|NFPA-F = 0 |
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| SPhrases = |
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|NFPA-R = 0 |
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| RSPhrases = |
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|FlashPtC = 45 |
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|ExploLimits = 1.9–6.1%<ref name=PGCH/> |
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| FlashPt = 45 °C |
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|PEL = C 100 ppm (480 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0429}}</ref> |
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| Autoignition = |
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|IDLH = 700 ppm<ref name=PGCH/> |
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| ExploLimits = |
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|REL = TWA 50 ppm (240 mg/m<sup>3</sup>) ST 100 ppm (485 mg/m<sup>3</sup>)<ref name=PGCH/> |
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| LD50 = Oral rat: 4900 mg/kg |
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|LD50 = 4900 mg/kg (oral, rat)<ref>{{IDLH|98839|alpha-Methyl styrene}}</ref> |
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}} |
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}} |
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}} |
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'''α-Methylstyrene''' ('''AMS''') is an ] with the formula C<sub>6</sub>H<sub>5</sub>C(CH<sub>3</sub>)=CH<sub>2</sub>. It is a colorless oil.<ref name="ullstyrene">{{Ullmann |first1=Denis H. |last1=James |first2=William M. |last2=Castor |title=Styrene |year=2007 |doi=10.1002/14356007.a25_329.pub2}}</ref> |
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==Synthesis and reactions == |
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AMS is formed as a by-product of the ]. In this procedure, ] is converted to its ], through a reaction with oxygen. |
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:] |
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Normally these cumene radicals are converted to ], however they can also undergo ] to form AMS. |
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:] |
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Although this is only a minor ], the cumene process is run at such a large scale that the recovery of AMS is commercially viable and satisfies much of the global demand. AMS can also be produced by dehydrogenation of cumene. |
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The homopolymer obtained from this ], poly(α-methylstyrene), is unstable, being characterized by a low ] of 65°C.<ref>{{cite book|last=Stevens|first=Malcolm P.|title=Polymer Chemistry an Introduction|year=1999|publisher=Oxford University Press|location=New York|isbn=978-0-19-512444-6|pages=193–194|edition=3rd|chapter=6}}</ref><ref>{{cite journal | pmc=10176471 | date=2023 | last1=Jones | first1=G. R. | last2=Wang | first2=H. S. | last3=Parkatzidis | first3=K. | last4=Whitfield | first4=R. | last5=Truong | first5=N. P. | last6=Anastasaki | first6=A. | title=Reversed Controlled Polymerization (RCP): Depolymerization from Well-Defined Polymers to Monomers | journal=Journal of the American Chemical Society | volume=145 | issue=18 | pages=9898–9915 | doi=10.1021/jacs.3c00589 | pmid=37127289 }}</ref> |
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== Side effects in humans == |
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The ] (2009) defined occupational exposure limits of 10 ppm for airborne concentrations of a-methylstyrene.<ref name="Morgan 187–194">{{Cite journal |last1=Morgan |first1=D. L. |last2=Mahler |first2=J. F. |last3=Kirkpatrick |first3=D. T. |last4=Price |first4=H. C. |last5=O'Connor |first5=R. W. |last6=Wilson |first6=R. E. |last7=Moorman |first7=M. P. |date=February 1999 |title=Characterization of inhaled alpha-methylstyrene vapor toxicity for B6C3F1 mice and F344 rats |journal=Toxicological Sciences|volume=47 |issue=2 |pages=187–194 |doi=10.1093/toxsci/47.2.187 |issn=1096-6080 |pmid=10220856|doi-access=free}}</ref> based on allergic reactions, and effects on the central nervous system.<ref name="Morgan 187–194"/><ref>{{Cite web |work=OSHA |title=α-METHYL STYRENE† |url=https://www.osha.gov/chemicaldata/776}}</ref> |
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==References== |
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{{reflist}} |
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{{DEFAULTSORT:Methylstyrene, alpha-}} |
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] |
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