495-41-0

Basic information

• Product Name: 1-PHENYL-2-BUTEN-1-ONE
• Synonyms: PHENYL PROPENYL KETONE;PHENYL 1-PROPENYL KETONE;1-PHENYL-2-BUTEN-1-ONE;1-PHENYL-BUT-2-EN-1-ONE;Phenylpropenylketone80+%;1-Propenylphenyl ketone;2-Butenoylbenzene;Crotonophenone
• CAS NO: 495-41-0
• Molecular Formula: C₁₀H₁₀O
• Molecular Weight: 146.19
• EINECS: 207-800-0
• Mol File: 495-41-0.mol
• Article Data: 133

Chemical Properties

• Melting Point: 20.5°C
• Boiling Point: 122 °C / 12mmHg
• Flash Point: 86.3 °C
• Appearance: /
• Density: 1,03 g/cm3
• Vapor Pressure: 0.0851mmHg at 25°C
• Refractive Index: 1.5600-1.5640
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 1-PHENYL-2-BUTEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PHENYL-2-BUTEN-1-ONE(495-41-0)
• EPA Substance Registry System: 1-PHENYL-2-BUTEN-1-ONE(495-41-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 495-41-0(Hazardous Substances Data)

Usage

Description

1-Phenyl-2-buten-1-one, also known as chalcone, is an organic compound that serves as a key intermediate in the synthesis of various flavonoids, including flavones, aurones, and isoflavonoids. It is characterized by its conjugated carbonyl and phenyl groups, which contribute to its chemical reactivity and diverse applications.

Uses

Used in Pharmaceutical Industry:
1-Phenyl-2-buten-1-one is used as a precursor for the synthesis of chalcone derivatives and analogs, which are known for their antimicrobial activities. These compounds are valuable in the development of new drugs to combat bacterial and fungal infections, as they can inhibit the growth of various pathogenic microorganisms.
Used in Chemical Research:
1-Phenyl-2-buten-1-one is also used as a starting material in the preparation of other organic compounds, such as flavonoids and related compounds, which have a wide range of biological activities. These compounds are of interest in the fields of medicinal chemistry and natural product chemistry, as they can be used to develop new drugs and therapeutic agents.

Synthesis Reference(s)

Journal of the American Chemical Society, 97, p. 5434, 1975 DOI: 10.1021/ja00852a019Tetrahedron Letters, 24, p. 5635, 1983 DOI: 10.1016/S0040-4039(00)94160-1

InChI:InChI=1/C10H10O/c1-2-6-10(11)9-7-4-3-5-8-9/h2-8H,1H3/b6-2+

Upstream product

• 75-07-0 acetaldehyde 
• 98-86-2 acetophenone 
• 495-40-9 propiophenone 
• 6249-80-5 1-phenylbut-3-en-1-one 
• 43058-55-5 Allylphenylketoncyanhydrin 
• 77815-57-7 Trimethyl-(1-phenyl-1-phenylsulfanyl-but-3-enyloxy)-silane 
• 84839-88-3 trimethyl{(1-phenylbut-1-en-1-yl)oxy}silane 
• 4743-74-2 2-phenylpent-4-en-2-ol 
• 100-52-7 benzaldehyde 
• 231609-70-4 N-methoxy-N-methyl-2-(1-methyl-3-oxo-3-phenyl-1-propenylamino)acetamide 
• 7446-70-0 aluminium trichloride 
• 625-35-4 trans-chrotonyl chloride 
• 71-43-2 benzene 
• 83832-76-2 3-methoxy-1-phenylbutane-1-one 

Downstream Products

• 106167-83-3 1-phenyl-3-semicarbazido-butan-1-one semicarbazone 
• 4938-75-4 1-phenyl-but-2ξ-en-1-one-((E)-2,4-dinitro-phenylhydrazone) 
• 1533-20-6 1,3-diphenylbutane-1-one 
• 1008-74-8 5-methyl-3-phenylisoxazole 
• 78664-25-2 N-(1-Hydroxyimino-1-phenyl-3-butyl)hydroxylamine 
• 5050-65-7 3-phenyl-5-methyl-Δ²-isoxazoline 
• 939-04-8 5-methyl-3-phenyl-4,5-dihydro-1H-pyrazole 
• 104-51-8 1-butylbenzene 
• 34880-85-8 3-chloro-1-phenylbutan-1-one 
• 614-14-2 1-Phenyl-1-butanol 
• 1771-65-9 2-methyl-4-oxo-4-phenylbutanoic acid 
• 6072-57-7 3-methylindanone 
• 25552-15-2 3-Methyl-1-phenyl-hexandion-(1,5) 
• 122969-56-6 (3RS,1'RS)-1-methyl-3-(1'-methyl-3'-phenyl-3'-((trimethylsilyl)oxy)-2'-propenyl)-2-pyrrolidinone 

Relevant articles and documents

Solvent responsive self-separation behaviour of Br?nsted acidic ionic liquid-polyoxometalate hybrid catalysts on H2O2 mediated oxidation of alcohols

Two solvent responsive self-separative ionic liquid-based POM hybrids [DEDSA]3[PW12O40] and [DEDSA]3[PMo12O40] were prepared by combination of diethyldisulphoammonium chloride [DEDSA]Cl with Keggin phosphotungstic acid and phosphomolybdic acid. Properties like water tolerance, high activity, high thermal stability and reusability in these POM hybrid compounds facilitate a new type of POM based catalysis used for oxidation of organic alcohols using hydrogen peroxide as oxidizing agent. Due to varied solubility of the hybrid with different solvents, the hybrid can effectively catalyze the oxidation reaction in homogenous condition and then can finally switch back to heterogenous system and convert as self-precipitating catalyst on addition of suitable solvent at the end of the reaction, which made the recovery and reuse of the hybrid very convenient. The catalysts are characterized via different analytical and spectroscopic tools like FT-IR, 1H NMR, 13C NMR, 31P NMR, TGA, UV–Visible, Powder XRD techniques, Raman etc. It was found that the prepared material was highly acidic, thermally stable in nature and was recycled up to 7 times without much loss of catalytic activity.

Modular access to 1,2-allenyl ketones based on a photoredox-catalysed radical-polar crossover process

Herein, a new protocol dealing with the preparation of 1,2-allenyl ketones has been successfully developedviathe reactions of enynes with radicals enabled by dual photoredox/copper catalysis. Based on the results of a deuteration experiment and the competition reaction between cyclopropanation and allenation, the mechanism based on a photoredox-neutral-catalysed radical-polar crossover process has been proposed. Synthetic applications of allenes have also been demonstrated.

Photocatalytic Stoichiometric Oxidant-Free Synthesis of Linear Unsaturated Ketones from 1,2-Disubstituted Cyclopropanols

A one-step catalytic oxidant-free synthesis of unsaturated ketones from 1,2-disubstituted cyclopropanols is reported. Previously for this transformation, only two- and three-step protocols have been developed. The reaction proceeds under irradiation with visible light in the presence of catalytic amounts of both an acridinium photocatalyst and a cobaloxime complex. 2-Aryl-substituted cyclopropanols react giving α,β-unsaturated ketones, while dehydrogenative ring opening of 2-alkyl-substituted substrates affords mixtures of α,β- and β,γ-enones. The reaction starts with one-electron oxidation of a cyclopropanol to cyclopropyloxy radical, presumably, by the photoexcited acridinium catalyst. We also found that Co(dmgBF 2) 2(MeCN) 2complex under an air atmosphere and irradiation with blue LEDs or upon heating can serve as a hydroxycyclopropane oxidant.