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135380 Aldrich

Phenylacetone

99%

Synonym: Benzyl methyl ketone, Phenyl-2-propanone

  • CAS Number 103-79-7

  • Linear Formula C6H5CH2COCH3

  • Molecular Weight 134.18

  •  Beilstein Registry Number 742120

  •  EC Number 203-144-4

  •  MDL number MFCD00017249

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Properties

Related Categories Building Blocks, C9, Carbonyl Compounds, Chemical Synthesis, Ketones,
assay   99%
drug control   USDEA Schedule II
availability   available only in EU
density   1.003 g/mL at 20 °C(lit.)

Description

General description

Phenylacetone is the immediate precursor for clandestine production of amphetamine and methamphetamine1. Phenylacetone on anaerobic incubations with rat liver mitochondria gets reduced to phenylisopropanol2.

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Safety & Documentation

Safety Information

WGK Germany 
3
RTECS 
UC3500100
Flash Point(F) 
194 °F
Flash Point(C) 
90 °C

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

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1. Comparative analysis of 1-phenyl-2-propanone (P2P), an amphetamine-type stimulant precursor, using stable isotope ratio mass spectrometry: presented in part as a poster at the 2nd meeting of the Joint European Stable Isotope User Meeting (JESIUM), Giens, France, September 2008. Schneiders S, Holdermann T, and Dahlenburg R Sci. Justice 49(2), 94-101, (2009)

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2. [Biotransformation of amphetamine derivatives by rat liver mitochondria/2nd communication; Oxidative deamination of amphetamine and reduction of phenylacetone]. Blume H Arzneimittelforschung 31(6), 994-7, (1981)

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Crystal structure of a Baeyer-Villiger monooxygenase. Malito E, Alfieri A, Fraaije MW, et al. Proc. Natl. Acad. Sci. U. S. A. 101(36), 13157-62, (2004)

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Snapshots of enzymatic Baeyer-Villiger catalysis: oxygen activation and intermediate stabilization. Orru R, Dudek HM, Martinoli C, et al. J. Biol. Chem. 286(33), 29284-91, (2011)

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The prodrug activator EtaA from Mycobacterium tuberculosis is a Baeyer-Villiger monooxygenase. Fraaije MW, Kamerbeek NM, Heidekamp AJ, et al. J. Biol. Chem. 279(5), 3354-60, (2004)

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Mapping the substrate binding site of phenylacetone monooxygenase from Thermobifida fusca by mutational analysis. Dudek HM, de Gonzalo G, Pazmiño DE, et al. Appl. Environ. Microbiol. 77(16), 5730-8, (2011)

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Blending Baeyer-Villiger monooxygenases: using a robust BVMO as a scaffold for creating chimeric enzymes with novel catalytic properties. van Beek HL, de Gonzalo G, and Fraaije MW Chem. Commun. (Camb.) 48(27), 3288-90, (2012)

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The analysis of substituted cathinones. Part 2: an investigation into the phenylacetone based isomers of 4-methylmethcathinone and N-ethylcathinone. McDermott SD, Power JD, Kavanagh P, et al. Forensic Sci. Int. 212(1-3), 13-21, (2011)

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Investigating the coenzyme specificity of phenylacetone monooxygenase from Thermobifida fusca. Dudek HM, Torres Pazmiño DE, Rodríguez C, et al. Appl. Microbiol. Biotechnol. 88(5), 1135-43, (2010)

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Exploring the structural basis of substrate preferences in Baeyer-Villiger monooxygenases: insight from steroid monooxygenase. Franceschini S, van Beek HL, Pennetta A, et al. J. Biol. Chem. 287(27), 22626-34, (2012)

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Impurity profiling/comparative analyses of samples of 1-phenyl-2-propanone. Krawczyk W, Kunda T, Perkowska I, et al. Bull. Narc. 57(1-2), 33-62, (2005)

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Induced allostery in the directed evolution of an enantioselective Baeyer-Villiger monooxygenase. Wu S, Acevedo JP, and Reetz MT Proc. Natl. Acad. Sci. U. S. A. 107(7), 2775-80, (2010)

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Impurities in illicit amphetamine: review. Sinnema A and Verweij AM Bull. Narc. 33(3), 37-54, (1981)

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Comparison of amphetamine metabolism using isolated hepatocytes from five species including human. Green CE, LeValley SE, and Tyson CA J. Pharmacol. Exp. Ther. 237(3), 931-6, (1986)

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A stepwise approach for the reproducible optimization of PAMO expression in Escherichia coli for whole-cell biocatalysis. van Bloois E, Dudek HM, Duetz WA, et al. BMC Biotechnol. 12, 31, (2012)

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Improvement of the biocatalytic properties of one phenylacetone monooxygenase mutant in hydrophilic organic solvents. de Gonzalo G, Rodríguez C, Rioz-Martínez A, et al. Enzyme Microb. Technol. 50(1), 43-9, (2012)

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A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone. Dal Cason TA Forensic Sci. Int. 119(2), 168-94, (2001)

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The effects of cofactor and species differences on the in vitro metabolism of propiophenone and phenylacetone. Coutts RT, Prelusky DB, and Jones GR Can. J. Physiol. Pharmacol. 59(2), 195-201, (1981)

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CE assay for simultaneous determination of charged and neutral impurities in dexamphetamine sulfate using a dual CD system. Wongwan S, Sungthong B, and Scriba GK Electrophoresis 31(9), 1475-81, (2010)

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A Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase mutant derivative highly active and stereoselective on phenylacetone and benzylacetone. Ziegelmann-Fjeld KI, Musa MM, Phillips RS, et al. Protein Eng. Des. Sel. 20(2), 47-55, (2007)

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Microbial degradation of illicit drugs, their precursors, and manufacturing by-products: implications for clandestine drug laboratory investigation and environmental assessment. Janusz A, Kirkbride KP, Scott TL, et al. Forensic Sci. Int. 134(1), 62-71, (2003)

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Rotational spectra and conformational structures of 1-phenyl-2-propanol, methamphetamine, and 1-phenyl-2-propanone. Tubergen MJ, Lavrich RJ, Plusquellic DF, et al. J. Phys. Chem. A 110(49), 13188-94, (2006)

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Analysis of the infrared and Raman spectra of the symmetrically substituted 1,3-diphenylurea and 1,3-diphenylacetone (dibenzyl ketone). Badawi HM and Förner W Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 95, 435-41, (2012)

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New chiral phosphoramidite complexes of iron as catalytic precursors in the oxidation of activated methylene groups. Shejwalkar P, Rath NP, and Bauer EB Molecules 15(4), 2631-50, (2010)

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The clandestine drug laboratory situation in the United States. Frank RS J. Forensic Sci. 28(1), 18-31, (1983)

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Merck 14,7269

Beil. 7,IV,687

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