2-Phenyl-2-propanol

2-Phenyl-2-propanol
Names
	IUPAC name 2-Phenyl-2-propanol
Identifiers
CAS Number	617-94-7;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:131607;
ChEMBL	ChEMBL3185495;
ChemSpider	11556;
ECHA InfoCard	100.009.582
EC Number	210-539-5;
PubChem CID	12053;
UNII	JE030BGE05;
CompTox Dashboard (EPA)	DTXSID3027247 ;
	InChI InChI=1S/C9H12O/c1-9(2,10)8-6-4-3-5-7-8/h3-7,10H,1-2H3 Key: BDCFWIDZNLCTMF-UHFFFAOYSA-N;
	SMILES CC(C)(C1=CC=CC=C1)O;
Properties
Chemical formula	C9H12O
Molar mass	136.19 g/mol
Appearance	White to pale yellow odorless solid
Density	0.973 g/cm3
Melting point	28–32 °C (301–305 K)
Boiling point	202 °C (396 °F; 475 K)
Solubility in water	Practically insoluble
Solubility	Soluble in ethanol and benzene
Refractive index (nD)	1.49146 (20 °C)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H315, H319
Precautionary statements	P280, P301+P330+P331, P302+P352, P305+P351+P338, P362
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	4300mg/kg (rabbit,transdermal); 1300mg/kg (rat, oral)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2-Phenyl-2-propanol is a chemical compound that belongs to the alcohol group. It is a derivative of cumene.

Synthesis

2-Phenyl-2-propanol can be synthesized through Grignard reaction between phenylmagnesium bromide and acetone.^[5]^[6]

Properties

2-Phenyl-2-propanol is a white to pale-yellow, odorless solid which is combustible yet difficult to ignite and barely dissolves in water.^[1]^[2]

Applications

2-Phenyl-2-propanol can either be applied in organic syntheses, or be reactants or intermediates in agrochemical, medical, and dyestuff fields.^[2]

2-Phenyl-2-propanol is the main metabolite of cumene, and therefore 2-phenyl-2-propanol can serve as a biomarker of cumene.^[7]

Hazards

According to a report of Federal Institute for Risk Assessment in 2008, there is strong evidence that 2-phenyl-2-propanol may lead to allergic reactions for humans.^[8]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Record of 2-Phenyl-2-propanol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2017-04-16.
^ ^a ^b ^c 2-Phenyl-2-propanol, 98+% at AlfaAesar, accessed on 2017-04-16 (PDF) (JavaScript required).^{[dead link‍]}
^ Gail Vance Civille, B. Thomas Carr (2015), Sensory Evaluation Techniques, Fifth Edition, CRC Press, p. 204, ISBN 978-1-4822-0867-2
^ Sigma-Aldrich Co., 2-Phenyl-2-propanol, 97%.
^ William Brown; Christopher Foote; Brent Iverson; Eric Anslyn (2008), Organic Chemistry, Cengage Learning, p. 568, ISBN 978-0-495-38857-9
^ Albany College of Pharmacy and Health Sciences: Preparation of 2-Phenyl-2-propanol (Grignard Reaction), retrieved 16 April 2017.
^ Knecht, U. (2002), "2-Phenyl-2-propanol in Urin [Biomonitoring Methods in German language, 2012]", The MAK-Collection for Occupational Health and Safety, Wiley-VCH Verlag & Co. KGaA, pp. 1–10, doi:10.1002/3527600418.bi9882d0020, ISBN 978-3-527-60041-0
^ BfR: Verbraucher sollten Plastik-Clogs mit starkem Geruch meiden, Stellungnahme Nr. 047/2008 des BfR of 5 November 2008.

[GESTIS-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Record of 2-Phenyl-2-propanol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2017-04-16.

[Alfa-2] 2-Phenyl-2-propanol, 98+% at AlfaAesar, accessed on 2017-04-16 (PDF) (JavaScript required).^{[dead link‍]}

[Gail_Vance_Civille,_B._Thomas_Carr-3] Gail Vance Civille, B. Thomas Carr (2015), Sensory Evaluation Techniques, Fifth Edition, CRC Press, p. 204, ISBN 978-1-4822-0867-2

[Sigma-4] Sigma-Aldrich Co., 2-Phenyl-2-propanol, 97%.

[William_Brown,_Christopher_Foote,_Brent_Iverson,_Eric_Anslyn-5] William Brown; Christopher Foote; Brent Iverson; Eric Anslyn (2008), Organic Chemistry, Cengage Learning, p. 568, ISBN 978-0-495-38857-9

[Albany-6] Albany College of Pharmacy and Health Sciences: Preparation of 2-Phenyl-2-propanol (Grignard Reaction), retrieved 16 April 2017.

[7] Knecht, U. (2002), "2-Phenyl-2-propanol in Urin [Biomonitoring Methods in German language, 2012]", The MAK-Collection for Occupational Health and Safety, Wiley-VCH Verlag & Co. KGaA, pp. 1–10, doi:10.1002/3527600418.bi9882d0020, ISBN 978-3-527-60041-0

[BfR-8] BfR: Verbraucher sollten Plastik-Clogs mit starkem Geruch meiden, Stellungnahme Nr. 047/2008 des BfR of 5 November 2008.

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