α-Methylstyrene
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
(Prop-1-en-2-yl)benzene
Other names
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
Identifiers
3D model (JSmol)
Abbreviations AMS
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.459
EC Number
  • 202-705-0
KEGG
RTECS number
  • WL5075300
UNII
UN number 2303
  • InChI=1S/C9H10/c1-8(2)9-6-4-3-5-7-9/h3-7H,1H2,2H3 checkY
    Key: XYLMUPLGERFSHI-UHFFFAOYSA-N checkY
  • InChI=1/C9H10/c1-8(2)9-6-4-3-5-7-9/h3-7H,1H2,2H3
    Key: XYLMUPLGERFSHI-UHFFFAOYAS
  • C=C(c1ccccc1)C
  • CC(=C)c1ccccc1
Properties
C9H10
Molar mass 118.179 g·mol−1
Appearance Colorless liquid
Density 0.91 g/cm3
Melting point −24 °C (−11 °F; 249 K)
Boiling point 165 to 169 °C (329 to 336 °F; 438 to 442 K)
Insoluble
Vapor pressure 2 mmHg (20 °C)[1]
-80.1·10−6 cm3/mol
Hazards
GHS labelling:[2]
GHS02: FlammableGHS07: Exclamation markGHS09: Environmental hazard
Warning
H226, H319, H335, H411
P210, P233, P240, P241, P242, P243, P261, P264+P265, P271, P273, P280, P303+P361+P353, P304+P340, P305+P351+P338, P319, P337+P317, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
3
0
0
Flash point 45 °C (113 °F; 318 K)
Explosive limits 1.9–6.1%[1]
Lethal dose or concentration (LD, LC):
4900 mg/kg (oral, rat)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
 C 100 ppm (480 mg/m3)[1]
REL (Recommended)
 TWA 50 ppm (240 mg/m3) ST 100 ppm (485 mg/m3)[1]
IDLH (Immediate danger)
 700 ppm[1]
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 ?)
Infobox references

α-Methylstyrene (AMS) is an organic compound with the formula C6H5C(CH3)=CH2. It is a colorless oil.[4]

Synthesis and reactions

AMS is a precursor to plasticizers, resins, and polymers.[5]

AMS and acetophenone are byproducts formed in a variation of the cumene process. It 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.[6][7]

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.[8] based on allergic reactions, and effects on the central nervous system.[8][9]

References

  1. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0429". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ "alpha-Methylstyrene". pubchem.ncbi.nlm.nih.gov.
  3. ↑ "alpha-Methyl styrene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ James, Denis H.; Castor, William M. (2007). "Styrene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a25_329.pub2. ISBN 978-3527306732.
  5. ↑ "What is alpha-methylstyrene (AMS)?". Archived from the original on 2007-02-28. Retrieved 2009-01-07.
  6. ↑ Stevens, Malcolm P. (1999). "6". Polymer Chemistry an Introduction (3rd ed.). New York: Oxford University Press. pp. 193–194. ISBN 978-0-19-512444-6.
  7. ↑ Jones, G. R.; Wang, H. S.; Parkatzidis, K.; Whitfield, R.; Truong, N. P.; Anastasaki, A. (2023). "Reversed Controlled Polymerization (RCP): Depolymerization from Well-Defined Polymers to Monomers". Journal of the American Chemical Society. 145 (18): 9898–9915. doi:10.1021/jacs.3c00589. PMC 10176471. PMID 37127289.
  8. 1 2 Morgan, D. L.; Mahler, J. F.; Kirkpatrick, D. T.; Price, H. C.; O'Connor, R. W.; Wilson, R. E.; Moorman, M. P. (February 1999). "Characterization of inhaled alpha-methylstyrene vapor toxicity for B6C3F1 mice and F344 rats". Toxicological Sciences. 47 (2): 187–194. doi:10.1093/toxsci/47.2.187. ISSN 1096-6080. PMID 10220856.
  9. ↑ "α-METHYL STYRENE†". OSHA.
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