2-Phenyl-2-propanol

2-Phenyl-2-propanol is a chemical compound that belongs to the alcohol group.

2-Phenyl-2-propanol
Names
IUPAC name
2-Phenyl-2-propanol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.582
EC Number
  • 210-539-5
UNII
  • InChI=1S/C9H12O/c1-9(2,10)8-6-4-3-5-7-8/h3-7,10H,1-2H3
    Key: BDCFWIDZNLCTMF-UHFFFAOYSA-N
  • CC(C)(C1=CC=CC=C1)O
Properties
C9H12O
Molar mass 136.19 g/mol
Appearance White to pale yellow odorless solid[1]
Density 0.973 g/cm3[1]
Melting point 28–32 °C (301–305 K)[1]
Boiling point 202[1] °C (396 °F; 475 K)
Practically insoluble[2]
Solubility Soluble in ethanol and benzene[3]
1.49146 (20 °C)[4]
Hazards
GHS labelling:
GHS07: Exclamation mark[1]
Danger
H302, H315, H319
P280, P301+P330+P331, P302+P352, P305+P351+P338, P362[1]
Lethal dose or concentration (LD, LC):
4300mg/kg (rabbit,transdermal);[1] 1300mg/kg (rat, oral) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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
  1. Record of 2-Phenyl-2-propanol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2017-04-16.
  2. 2-Phenyl-2-propanol, 98+% at AlfaAesar, accessed on 2017-04-16 (PDF) (JavaScript required).
  3. Gail Vance Civille, B. Thomas Carr (2015), Sensory Evaluation Techniques, Fifth Edition, CRC Press, p. 204, ISBN 978-1-4822-0867-2
  4. Sigma-Aldrich Co., 2-Phenyl-2-propanol, 97%.
  5. William Brown; Christopher Foote; Brent Iverson; Eric Anslyn (2008), Organic Chemistry, Cengage Learning, p. 568, ISBN 978-0-495-38857-9
  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
  8. BfR: Verbraucher sollten Plastik-Clogs mit starkem Geruch meiden, Stellungnahme Nr. 047/2008 des BfR of 5 November 2008.
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