α-Methylstyrene

α-Methylstyrene
Skeletal formula	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
CAS Number	98-83-9 ;
3D model (JSmol)	Interactive image; Interactive image;
Abbreviations	AMS
ChEBI	CHEBI:35060;
ChEMBL	ChEMBL1344773;
ChemSpider	7129 ;
ECHA InfoCard	100.002.459
EC Number	202-705-0;
KEGG	C14395 ;
PubChem CID	7407;
RTECS number	WL5075300;
UNII	D46R9753IK ;
UN number	2303
CompTox Dashboard (EPA)	DTXSID9025661 ;
	InChI InChI=1S/C9H10/c1-8(2)9-6-4-3-5-7-9/h3-7H,1H2,2H3 Key: XYLMUPLGERFSHI-UHFFFAOYSA-N ; InChI=1/C9H10/c1-8(2)9-6-4-3-5-7-9/h3-7H,1H2,2H3 Key: XYLMUPLGERFSHI-UHFFFAOYAS;
	SMILES C=C(c1ccccc1)C; CC(=C)c1ccccc1;
Properties
Chemical formula	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)
Solubility in water	Insoluble
Vapor pressure	2 mmHg (20 °C)
Magnetic susceptibility (χ)	-80.1·10−6 cm3/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H319, H335, H411
Precautionary statements	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)	3 0 0
Flash point	45 °C (113 °F; 318 K)
Explosive limits	1.9–6.1%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	4900 mg/kg (oral, rat)
	NIOSH (US health exposure limits):
PEL (Permissible)	C 100 ppm (480 mg/m3)
REL (Recommended)	TWA 50 ppm (240 mg/m3) ST 100 ppm (485 mg/m3)
IDLH (Immediate danger)	700 ppm
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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

Synthesis and reactions edit

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 edit

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 edit

^ ^a ^b ^c ^d ^e NIOSH Pocket Guide to Chemical Hazards. "#0429". National Institute for Occupational Safety and Health (NIOSH).
^ "alpha-Methyl styrene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ "alpha-Methylstyrene". pubchem.ncbi.nlm.nih.gov.
^ 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.
^ "What is alpha-methylstyrene (AMS)?". Archived from the original on 2007-02-28. Retrieved 2009-01-07.
^ 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.
^ 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.
^ ^a ^b 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.
^ "α-METHYL STYRENE†". OSHA.

[PGCH-1] NIOSH Pocket Guide to Chemical Hazards. "#0429". National Institute for Occupational Safety and Health (NIOSH).

[2] "alpha-Methyl styrene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[3] "alpha-Methylstyrene". pubchem.ncbi.nlm.nih.gov.

[ullstyrene-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.

[Morgan_187–194-8] 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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