Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Α-Methylstyrene: Difference between pages

{{lowercase title}}

|Watchedfields = changed

|verifiedrevid = 477319488

|Name = α-Methylstyrene

|ImageFileL1 = Alpha-methylstyrol.svg

|ImageNameL1 = Skeletal formula

|ImageFileR1 = Alpha-methylstyrene-from-xtal-3D-bs-17.png

|ImageNameR1 = Ball-and-stick model

|PIN =(Prop-1-en-2-yl)benzene

|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>

|Abbreviations = AMS

| ChEBI = 35060

| ChEMBL = 1344773

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

|ChemSpiderID = 7129

| EC_number = 202-705-0

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

|KEGG = C14395

|InChI = 1/C9H10/c1-8(2)9-6-4-3-5-7-9/h3-7H,1H2,2H3

|InChIKey = XYLMUPLGERFSHI-UHFFFAOYAS

|SMILES1 = CC(=C)c1ccccc1

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

|StdInChI = 1S/C9H10/c1-8(2)9-6-4-3-5-7-9/h3-7H,1H2,2H3

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

|StdInChIKey = XYLMUPLGERFSHI-UHFFFAOYSA-N

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

|CASNo=98-83-9

| RTECS = WL5075300

| UNNumber = 2303

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

|UNII = D46R9753IK

|PubChem=7407

|SMILES = C=C(c1ccccc1)C

|C = 9

|H = 10

|Appearance=Colorless liquid

|Density= 0.91 g/cm³

|MeltingPtC= -24

|BoilingPtC = 165 to 169

|Solubility=Insoluble

|VaporPressure = 2 mmHg (20&nbsp;°C)<ref name=PGCH/>

|MagSus = -80.1·10⁻⁶ cm³/mol

}}

| 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>

| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS09}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|226|319|335|411}}

| 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}}

|MainHazards=

|NFPA-H = 3

|NFPA-F = 0

|NFPA-R = 0

|FlashPtC = 45

|ExploLimits = 1.9–6.1%<ref name=PGCH/>

|PEL = C 100 ppm (480 mg/m³)<ref name=PGCH>{{PGCH|0429}}</ref>

|IDLH = 700 ppm<ref name=PGCH/>

|REL = TWA 50 ppm (240 mg/m³) ST 100 ppm (485 mg/m³)<ref name=PGCH/>

|LD50 = 4900 mg/kg (oral, rat)<ref>{{IDLH|98839|alpha-Methyl styrene}}</ref>

}}

'''α-Methylstyrene''' ('''AMS''') is an [[organic compound]] with the formula C₆H₅C(CH₃)=CH₂. 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>

==Synthesis and reactions ==

AMS is formed as a by-product of the [[Cumene process]]. In this procedure, cumene is converted to its [[radical (chemistry)|radical]], through a reaction with oxygen.

:[[Image:Cumene-radical-formation-2D-skeletal.png|200px]]

Normally these cumene radicals are converted to [[cumene hydroperoxide]], however they can also undergo [[radical disproportionation]] to form AMS.

:[[Image:Cumolhydroperoxid-Verfahren Kettenabbruch V1.2.svg|300px]]

Although this is only a minor [[side reaction]], 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.

The homopolymer obtained from this [[monomer]], poly(α-methylstyrene), is unstable, being characterized by a low [[ceiling temperature]] 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>

== Side Effects in Humans ==

The [[American Conference of Governmental Industrial Hygienists]] (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 |date= |work=OSHA |title=α-METHYL STYRENE† |url=https://www.osha.gov/chemicaldata/776}}</ref>

==References==

{{reflist}}

{{DEFAULTSORT:Methylstyrene, alpha-}}

[[Category:Isopropenyl compounds]]

[[Category:Benzene derivatives]]

[[Category:Monomers]]

[[Category:IARC Group 2B carcinogens]]