4-Phenyl-3-buten-2-one

Base Information

• Chemical Name: 4-Phenyl-3-buten-2-one
• CAS No.: 122-57-6
• Molecular Formula: C10H10O
• Molecular Weight: 146.189
• Hs Code.: 29143900
• DSSTox Substance ID: DTXSID4025662
• Wikidata: Q27225700
• ChEMBL ID: CHEMBL3187978
• Mol file: 122-57-6.mol

Synonyms:4-Phenyl-but-3-en-2-one;DTXSID4025662;acetylstyrol;trans-Benzylideneacetone;Benzalacetone;BENZAL ACETONE;1-Phenylbut-1-en-3-one;4-phenyl-3 -buten-2-one;CHEMBL3187978;SCHEMBL11470573;AKOS025243640;NCI60_004369;FT-0622620;FT-0633900;FT-0673733;Q27225700;4-Phenyl-3-butene-2-one 100 microg/mL in Acetonitrile

Chemical Property of 4-Phenyl-3-buten-2-one

Chemical Property:

• Appearance/Colour: yellow solid
• Vapor Pressure: 0.01 mm Hg ( 25 °C)
• Melting Point: 39-42 °C(lit.)
• Refractive Index: 1.5836
• Boiling Point: 260.8 °C at 760 mmHg
• Flash Point: 65.6 °C
• PSA: 17.07000
• Density: 1.014 g/cm³
• LogP: 2.28880
• Storage Temp.: Store at
• Sensitive.: Light Sensitive
• Solubility.: Soluble in alcohol, chloroform, diethyl ether.
• Water Solubility.: 1.398g/L(25 oC)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 146.073164938
• Heavy Atom Count: 11
• Complexity: 152

Purity/Quality:

98% ^*data from raw suppliers

Benzylideneacetone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-43-42/43
• Safety Statements: 7-26-36/37/39-45-37/39-24-36/37-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)C=CC1=CC=CC=C1
• Uses: 1. It is used for the preparation of spices and galvanized brightener. 2. GB 2760--1996 allows it used as food with spices. Formulated balm, cherries, grapes, berries, anise-based and other flavors for temporary . 3. This product is used as galvanized additives, coating materials to increase the brightness. The dyeing industry uses it as a mordant in dyeing agent to improve the uniformity and firmness, also it can be used for the preparation of spices and flavoring agents. 4. 4-phenyl-butene (3)one-2 is one rodenticide warfarin intermediates. 5. As an aromatic organic substance, it is the most widely superior light additive in acid zinc plating process , in the potassium chloride, ammonium plating process, it can get bright coating in a very wide current density and the temperature range, play a good effect on the coating of the internal stress, anti-corrosion ability. This product is also available anti volatile agent for spices, mordant and fixing agent in dyeing industry, it can also be used to prepare spices flavoring agent. 6. Organic synthesis intermediates. It can be used as a spice anti propellant. In dyeing industry,it is used as mordant , fixing agent, it is used for the preparation of spices or flavoring agents, and preparation for galvanized credit agent. Benzylideneacetone is used chiefly as a scent in the manufacture of perfume, drugs & electroplating. brightener in acid zinc electroplating,also used as an organic synthesis intermediate in flavor and fragrance, pharmaceutical industries In perfumery, organic syntheses.
• Production method: Using Benzaldehyde for raw materials, and carrying out condensation reaction with acetone . Benzaldehyde and acetone, mixed with water, cooled slowly, added 10% sodium hydroxide solution, the temperature controlled at 25-31°C, After the addition, the stirring was continued for 1h. Then diluted hydrochloric acid was added to pH 6-7, set still for 1h, isolated as a yellow oil. Lower layer was extracted with benzene, the extract and oil were combined, washed twice with water, after the separation the layer of water, recovered benzene, and then dried over calcium chloride, dry decolorizing charcoal was added , filtered and the filtrate vacuum distillation derived products. . Fixed material consumption : benzaldehyde 1700kg/t, acetone 2900kg/t, caustic soda (40%) 500kg/t.

Technology Process of 4-Phenyl-3-buten-2-one

There total 205 articles about 4-Phenyl-3-buten-2-one 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: 96.0%

benzaldehyde (100-52-7) + acetone (67-64-1) → 1-Phenylbut-1-en-3-one (122-57-6)

Guidance literature:

With sodium hydroxide; In water;

DOI:10.1021/acs.orglett.0c00588

Reference yield: 90.0%

bromobenzene (108-86-1,52753-63-6) + methyl vinyl ketone (78-94-4,25038-87-3) → 1-Phenylbut-1-en-3-one (122-57-6)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 110 ℃; for 20h; Green chemistry;

DOI:10.1016/j.materresbull.2015.03.051

Reference yield: 85.0%

4-phenylbut-3-en-2-ol (17488-65-2) → benzaldehyde (100-52-7) + 1-Phenylbut-1-en-3-one (122-57-6)

Guidance literature:

With copper(II) permanganate; In diethyl ether; dichloromethane; for 24h; Heating;

DOI:10.1021/jo00135a024

upstream raw materials:

methyl magnesium iodide

cinnamonitrile

diethyl ether

(E)-3-phenylacrylic acid

Downstream raw materials:

1-(α-furyl)-5-phenylpenta-1,4-dien-3-one

1-(3-hydroxy-2-methyl-4,5-diphenyl-cyclopent-1-enyl)-ethanone

2,4-diethoxycarbonyl-5-hydroxy-5-methyl-3-phenylcyclohexanone

acetone

Refernces

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• 2、 De Souza, Gabriela F. P.,Salles, Airton G.. "Persulfate-mediated synthesis of polyfunctionalized benzenes in water: Via the benzannulation of alkynes and α,β-unsaturated compounds". . p. 5507 - 5511. Retrieved 2019.
• 3、 Cui, Bin,Chen, Li-Zhuang,Hu, Xiao-Lei,Wang, Ming,Han, Guang-Fan. "Synthesis and crystal structure of 4,7-diaryl-5-oxo-4H-benzo[b]pyran derivatives". . p. 900 - 904. Retrieved 2012.
• 4、 Han, Guang-Fan,Cui, Bin,Chen, Li-Zhuang,Wang, Rui-Hua,Jin, Yan. "Green synthesis and crystal structure of 4,7-diaryl-2-oxo(thio)-1,2,3,4,5, 6,7,8-octahydroquinazoline-5-one derivatives". . p. 312 - 316. Retrieved 2011.
• 5、 Karimi, Babak,Behzadnia, Hesam,Bostina, Mihnea,Vali, Hojatollah. "A nano-fibrillated mesoporous carbon as an effective support for palladium nanoparticles in the aerobic oxidation of alcohols "on pure water"". . p. 8634 - 8640. Retrieved 2012.
• 6、 Zhou, Shuai,Liu, Lu,Wang, Bo,Ma, Mingguo,Xu, Feng,Sun, Runcang. "Novel basic ionic liquid based on alkylammonium as efficient catalyst for Knoevenagel reaction". . p. 1384 - 1391. Retrieved 2012.
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• 8、 Wirwis, Anna,Trzeciak, Anna M.. "Ligand-free palladium-catalyzed tandem pathways for the synthesis of 4,4-diarylbutanones and 4,4-diaryl-3-butenones under microwave conditions". . . Retrieved 2019.
• 9、 Gandomkar, Somayyeh,Rocha, Raquel,Sorgenfrei, Frieda A.,Montero, Lía Martínez,Fuchs, Michael,Kroutil, Wolfgang. "PQQ-dependent Dehydrogenase Enables One-pot Bi-enzymatic Enantio-convergent Biocatalytic Amination of Racemic sec-Allylic Alcohols". . p. 1290 - 1293. Retrieved 2021.
• 10、 Fuchibe, Kohei,Aono, Tatsuya,Hu, Ji,Ichikawa, Junji. "Copper(I)-Catalyzed [4 + 1] Cycloaddition of Silyl Dienol Ethers with Sodium Bromodifluoroacetate: Access to β,β-Difluorocyclopentanone Derivatives". . p. 4502 - 4505. Retrieved 2016.