4-(4-Methoxyphenyl)-2-butanone

Base Information

• Chemical Name: 4-(4-Methoxyphenyl)-2-butanone
• CAS No.: 104-20-1
• Molecular Formula: C11H14O2
• Molecular Weight: 178.231
• Hs Code.: 29145090
• European Community (EC) Number: 203-184-2
• NSC Number: 405366
• UNII: GVG47S4S5V
• DSSTox Substance ID: DTXSID5047166
• Nikkaji Number: J5.026A
• Wikidata: Q15632756
• Metabolomics Workbench ID: 46124
• ChEMBL ID: CHEMBL3184371
• Mol file: 104-20-1.mol

Synonyms:4-(4-Methoxyphenyl)-2-butanone;104-20-1;Anisylacetone;4-(4-Methoxyphenyl)butan-2-one;2-BUTANONE, 4-(4-METHOXYPHENYL)-;Raspberry ketone methyl ether;4-Methoxybenzylacetone;4-(p-Methoxyphenyl)-2-butanone;Anisylacetone, p-;2-Butanone, 4-(p-methoxyphenyl)-;Methyl oxanone;1-(4-Methoxyphenyl)-3-butanone;p-Methoxyphenylbutanone;Rasberry ketone methyl ether;ANISYL ACETONE;FEMA No. 2672;ENT 20,279;Methoxybenzylacetone, p-;1-(p-Methoxyphenyl)-3-butanone-;NSC 405366;p-Methoxybenzylacetone;1-(p-Methoxyphenyl)-3-butanone;4-(4-methoxyphenyl)-butan-2-one;EINECS 203-184-2;UNII-GVG47S4S5V;BRN 1869592;GVG47S4S5V;4-(p-Methoxyphenyl)-2-butanone (natural);AI3-20279;DTXSID5047166;4-(4-methoxy-phenyl)-butan-2-one;NSC-405366;2-Butanone, 4-(p-methoxyphenyl)- (6CI,7CI,8CI);DTXCID3027166;CAS-104-20-1;MFCD00008791;SCHEMBL1334;4-p-methoxyphenyl-2-butanone;CHEMBL3184371;4-(4-methoxyphenyl)butan-2-on;FEMA 2672;CHEBI:169538;2-butanona, 4-(4-metoxifenil)-;4-(para-methoxyphenyl)-2-butanone;Tox21_113654;Tox21_301165;BBL027730;ENT-20279;NSC405366;STL146341;AKOS000120662;LS-2896;4-(4-Methoxyphenyl)-2-butanone, 98%;NCGC00248312-01;NCGC00248312-02;NCGC00255063-01;4-(P- METHOXYPHENYL)-2-BUTANONE;AS-60156;4 - (4 - methoxyphenyl)butan - 2 - one;4-P-METHOXYPHENYL-2-BUTANONE [FCC];CS-0063594;FT-0616645;M0756;EN300-16160;4-(P-METHOXYPHENYL)-2-BUTANONE [FHFI];D70489;SR-01000944748;SR-01000944748-1;W-108822;4-(4-Methoxyphenyl)-2-butanone, >=98%, FCC, FG;4-(4-Methoxyphenyl)-2-butanone, analytical standard;Q15632756

Chemical Property of 4-(4-Methoxyphenyl)-2-butanone

Chemical Property:

• Appearance/Colour: clear colourless to pale yellow liquid
• Vapor Pressure: 0.00382mmHg at 25°C
• Melting Point: 8 ºC
• Refractive Index: n20/D 1.519(lit.)
• Boiling Point: 280.3 ºC at 760 mmHg
• Flash Point: 112 ºC
• PSA: 26.30000
• Density: 1.01 g/cm³
• LogP: 2.21680
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Not miscible in water.
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 178.099379685
• Heavy Atom Count: 13
• Complexity: 158

Purity/Quality:

99% ^*data from raw suppliers

4-[4- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CCC1=CC=C(C=C1)OC
• Description: 4-(p-Methoxyphenyl)-2-butanone has an intensely sweet, floral, fruity odor and a cherry-raspberry flavor at low concentrations. May be prepared by condensing acetone with anisaldehyde to yield anisylidene acetone and subsequent hydrogenation in the presence of Pd catalyst.
• Uses: 4-(4-Methoxyphenyl)-2-butanone is used as pharmaceutical intermediate. In insect attractants, organic synthesis, flavoring.

Technology Process of 4-(4-Methoxyphenyl)-2-butanone

There total 92 articles about 4-(4-Methoxyphenyl)-2-butanone 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: 91.4%

acetone (67-64-1) + 4-Methoxybenzyl alcohol (105-13-5) → 4-(4-methoxyphenyl)-2-butanone (104-20-1)

Guidance literature:

With potassium phosphate; 5%-palladium/activated carbon; In toluene; at 80 ℃; for 44h; Inert atmosphere;

Reference yield: 88.0%

1-isoprenyloxymethyl-4-methoxybenzene (55831-55-5) → 4-(4-methoxyphenyl)-2-butanone (104-20-1)

Guidance literature:

With Dimethylphenylsilane; C₁₉H₈O₇Ru₃; In 1,4-dioxane; at 50 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2012.02.025

Reference yield: 87.0%

2-hydroxy-3-butene (598-32-3) + para-iodoanisole (696-62-8) → 4-(4-methoxyphenyl)-2-butanone (104-20-1)

Guidance literature:

With tetrabutyl-ammonium chloride; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 100 ℃; for 9h; regioselective reaction; Inert atmosphere;

DOI:10.3184/174751913X13668131126257

upstream raw materials:

2-(4-methoxy-benzyl)-3-oxo-butyric acid ethyl ester

ethyl acetoacetate

4-Methoxybenzyl alcohol

methyl vinyl ketone

Downstream raw materials:

[3-(4-methoxy-phenyl)-1-methyl-propyl]-dimethyl-amine

1-methoxy-4-(3-methylbut-3-en-1-yl)benzene

4-(4-methoxyphenyl)-2-butanone oxime

2-Methoxy-5-(3-oxo-butyl)-benzenesulfonyl chloride

Refernces

• 1、 Ishida, Junko,Kozuka, Mutsuo,Tokuda, Harukuni,Nishino, Hoyoku,Nagumo, Seiji,Lee, Kuo Hsiung,Nagai, Masahiro. "Chemopreventive potential of cyclic diarylheptanoids.". . p. 3361 - 3365. Retrieved 2002.
• 2、 Su, Feifei,Wu, Fulong,Tang, He,Wang, Zhonghua,Wu, Fanhong. "Efficient and facile synthesis of novel stable monodeuterium labeled ractopamine". . p. 479 - 482. Retrieved 2015.
• 3、 Tateiwa, Jun-ichi,Horiuchi, Hiroki,Hashimoto, Keiji,Yamauchi, Takayoshi,Uemura, Sakae. "Cation-Exchanged Montmorillonite-Catalyzed Facile Friedel-Crafts Alkylation of Hydroxy and Methoxy Aromatics with 4-Hydroxybutan-2-one To Produce Raspberry Ketone and Some Pharmaceutically Active Compounds". . p. 5901 - 5904. Retrieved 1994.
• 4、 Yamashita et al.. "-". . p. 835. Retrieved 1978.
• 5、 Kerr, William J.,Mudd, Richard J.,Paterson, Laura C.,Brown, Jack A.. "Iridium(I)-catalyzed regioselective C-H activation and hydrogen-isotope exchange of non-aromatic unsaturated functionality". . p. 14604 - 14607. Retrieved 2014.
• 6、 Hagiwara, Hisahiro,Eda, Yasushi,Morohashi, Kimie,Suzuki, Toshio,Ando, Masayoshi,Ito, Nobuhiko. "Selectivity in palladium catalyzed arylation: Synthetic application leading to aromatized ionone natural products". . p. 4055 - 4058. Retrieved 1998.
• 7、 Musa, Musa M.,Ziegelmann-Fjeld, Karla I.,Vieille, Claire,Zeikus, J. Gregory,Phillips, Robert S.. "Asymmetric reduction and oxidation of aromatic ketones and alcohols using W110A secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus". . p. 30 - 34. Retrieved 2007.
• 8、 Citterio, Attilio,Vismara, Elena. "2-Arylalkyl Ketones and 3-Arylalkanals from Arenediazonium Salts and α,β-Unsaturated Carbonyl Compounds". . p. 291 - 292. Retrieved 1980.
• 9、 Sasson,Blum. "-". . p. 1887,1889. Retrieved 1975.
• 10、 Chandrasekhar, Srivari,Chandrashekar, Gudise,Reddy, Marepally Srinivasa,Srihari, Pabbaraja. "A facile and chemoselective conjugate reduction using polymethylhydrosiloxane (PMHS) and catalytic B(C6F5) 3". . p. 1650 - 1652. Retrieved 2006.