Phenylacetone

Base Information

• Chemical Name: Phenylacetone
• CAS No.: 103-79-7
• Deprecated CAS: 136675-26-8,823270-75-3,823270-75-3
• Molecular Formula: C9H10O
• Molecular Weight: 134.178
• Hs Code.: 2914.30
• European Community (EC) Number: 203-144-4
• NSC Number: 9827
• UNII: O7IZH10V9Y
• DSSTox Substance ID: DTXSID1059280
• Nikkaji Number: J31.101D
• Wikipedia: Phenylacetone
• Wikidata: Q418831
• Metabolomics Workbench ID: 58057
• ChEMBL ID: CHEMBL3800510
• Mol file: 103-79-7.mol

Synonyms:1-phenyl-2-propanone;benzyl methyl ketone;phenylacetone

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Chemical Property of Phenylacetone

Chemical Property:

• Appearance/Colour: colorless to pale yellow liquid
• Vapor Pressure: 0.159mmHg at 25°C
• Melting Point: -15 °C
• Refractive Index: 1.516
• Boiling Point: 214 °C at 760 mmHg
• Flash Point: 87.5 °C
• PSA: 17.07000
• Density: 1.015 g/cm³
• LogP: 1.81810
• Storage Temp.: Controlled Substance, -20°C Freezer
• Water Solubility.: Insoluble
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 134.073164938
• Heavy Atom Count: 10
• Complexity: 112

Purity/Quality:

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones
• Canonical SMILES: CC(=O)CC1=CC=CC=C1
• Description: Phenylacetone (exempt preparation) (Item No. 16444) is an analytical reference standard categorized as a precursor in the synthesis of amphetamine and methamphetamine. Phenylacetone is regulated as a Schedule II compound in the United States. Phenylacetone (exempt preparation) (Item No. 16444) is provided as a DEA exempt preparation. This product is intended for research and forensic applications.
• Uses: A metabolite of Lisdexamfetamine dimesylate. In organic synthesis; production of benzyl radicals by photolysis.

Technology Process of Phenylacetone

There total 521 articles about Phenylacetone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

1-propenylbenzene (873-66-5) → benzaldehyde (100-52-7) + 1-phenyl-acetone (103-79-7,136675-26-8) + 1-phenylpropylene oxide (23355-97-7)

Guidance literature:

With iodosylbenzene; Ni(cyclam)(NO₃)2; In acetonitrile; for 5h; Ambient temperature;

DOI:10.1021/ja00226a029

Reference yield: 58.0%

trans-2-methyl-3-phenyloxirane → benzaldehyde (100-52-7) + 1-phenyl-acetone (103-79-7,136675-26-8)

Guidance literature:

With tert.-butylhydroperoxide; μ-oxo-bis[dioxo-[(3'S,4'S)-2-(3',4'-dihydro-3'-phenyl-4'-methyloxy-methyl-2'-oxazolyl)pyridine-κ2-N,N](isothiocyanato)molybdenum(VI)]; In decane; dichloromethane; at 30 ℃; for 22h; Inert atmosphere; Ionic liquid;

DOI:10.1016/j.apcata.2011.03.024

Reference yield: 46.0%

1-phenylpropylene oxide (4436-22-0) → ethylbenzene (100-41-4,27536-89-6) + 2-Phenylpropanal (34713-70-7) + 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7) + 1-phenyl-acetone (103-79-7,136675-26-8)

Guidance literature:

at 600 ℃;

DOI:10.1007/BF00696928

upstream raw materials:

diazomethane

acetophenone

allylbenzene

phenylacetic acid

Downstream raw materials:

1-(1-methyl-2-phenyl-ethyl)-pyrrolidine

1-(1-methyl-2-phenyl-vinyl)-piperidine

(+/-)-1-(1-methyl-2-phenylethyl)piperidine

12-phenylnaphtho<2,3-b>indolizine-6,11-dione

Refernces

• 1、 McKillop et al.. "-". . p. 5275. Retrieved 1970.
• 2、 MacLean, Mark A.,Wheaton, Craig A.,Stradiotto, Mark. "Developing backbone-modified Mor-DalPhos ligand variants for use in palladium-catalyzed C-N and C-C cross-coupling". . p. 712 - 721. Retrieved 2018.
• 3、 Jones et al.. "-". . p. 3369. Retrieved 1972.
• 4、 Gatto, Mattia,Baratta, Walter,Belanzoni, Paola,Belpassi, Leonardo,Del Zotto, Alessandro,Tarantelli, Francesco,Zuccaccia, Daniele. "Hydration and alkoxylation of alkynes catalyzed by NHC-Au-OTf". . p. 2125 - 2134. Retrieved 2018.
• 5、 Dormond, Alain,Elbouadili, Abdelaziz,Moise, Claude. "Uranium Metallacycle 2(cycloUCH2Si(Me2)N)SiMe3: A Mild Reagent for the Synthesis of Methyl Ketones from Nitriles". . p. 3747 - 3748. Retrieved 1989.
• 6、 Dornan, Laura M.,Clendenning, Grainne M. A.,Pitak, Mateusz B.,Coles, Simon J.,Muldoon, Mark J.. "N,O-ligated Pd(ii) complexes for catalytic alcohol oxidation". . p. 2526 - 2534. Retrieved 2014.
• 7、 Vinogradova, M. G.,Min, R. S.,Aksenov, V. S.,Nikishin, G. I.. "KINETICS OF THE OXIDATIVE ADDITION OF ACETONE TO AROMATIC COMPOUNDS UNDER THE ACTION OF Mn(III) ACETATE". . p. 1760 - 1765. Retrieved 1982.
• 8、 Hamamoto, Hiromi,Suzuki, Yachiyo,Yamada, Yoichi M. A.,Tabata, Hidetsugu,Takahashi, Hideyo,Ikegami, Shiro. "A recyclable catalytic system based on a temperature-responsive catalyst". . p. 4536 - 4538. Retrieved 2005.
• 9、 Arisawa,Torisawa,Nakagawa. "Practical synthesis of (E)-pent-3-en-2-one and its conversion to (E)-2-triethylsilyloxypenta-1,3-diene". . p. 1371 - 1372. Retrieved 1995.
• 10、 Shirini, Farhad,Zolfigol, Mohammad Ali,Mollarazi, Esmail. "KBrO3/ZrClO2 · 8H2O: An efficient reagent system for the oxidation of alcohols". . p. 1541 - 1545. Retrieved 2005.