1,2-Dibenzoylethane

Base Information

• Chemical Name: 1,2-Dibenzoylethane
• CAS No.: 495-71-6
• Molecular Formula: C16H14O2
• Molecular Weight: 238.286
• Hs Code.: 2914399090
• NSC Number: 402168
• DSSTox Substance ID: DTXSID30197811
• Nikkaji Number: J47.086D
• Wikidata: Q63398457
• ChEMBL ID: CHEMBL4215633
• Mol file: 495-71-6.mol

Synonyms:1,2-Dibenzoylethane;495-71-6;1,4-diphenylbutane-1,4-dione;1,4-Diphenyl-1,4-butanedione;1,4-Butanedione, 1,4-diphenyl-;Diphenacyl;1,4-diphenyl-butane-1,4-dione;MFCD00037818;Succinophenone (Diphenacyl);Biphenacyl;2,2''-Biacetophenone;1,4-Diphenyl-1,4-butadione;NSC402168;NSC 402168;3-Benzoyl propiophenone;Ethane, 1,2-dibenzoyl-;Cambridge id 5102527;Oprea1_385312;CBDivE_002049;SCHEMBL719034;1,4-dipheny-1,4-butanedione;CHEMBL4215633;DTXSID30197811;HMS1577I15;STK328100;1,4-diphenylbutane-1,4-dione (en);AKOS004907792;CS-W012837;NSC-402168;AS-10094;D3179;FT-0606339;A827751;Q63398457

Chemical Property of 1,2-Dibenzoylethane

Chemical Property:

• Vapor Pressure: 7.67E-07mmHg at 25°C
• Melting Point: 144-145 °C
• Refractive Index: 1.574
• Boiling Point: 407.2 °C at 760 mmHg
• Flash Point: 152.5 °C
• PSA: 34.14000
• Density: 1.116 g/cm³
• LogP: 3.53240
• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane (Slightly), DMSO (Slightly), Chloroform (Slightly), Methanol (Sl
• Water Solubility.: Soluble in acetone. Insoluble in water.
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 238.099379685
• Heavy Atom Count: 18
• Complexity: 254

Purity/Quality:

99% ^*data from raw suppliers

1,2-Dibenzoylethane ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)CCC(=O)C2=CC=CC=C2
• General Description: 1,2-Dibenzoylethane (also known as 1,4-diphenyl-1,4-butanedione) is a symmetrical 1,4-diketone that can be efficiently synthesized from α-halo ketones via a Zn-I₂-mediated Wurtz-like condensation. This method offers advantages such as mild reaction conditions (65 °C) and moderate to high yields, making it a practical approach for producing 1,4-diketones, which serve as key intermediates in the synthesis of carbocyclic and heterocyclic compounds.

Technology Process of 1,2-Dibenzoylethane

There total 431 articles about 1,2-Dibenzoylethane 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: 70.0%

O-ethyl S-[2-oxo-2-phenylethyl]carbonodithioate (56817-84-6) → bis-ethoxythiocarbonyldisulfane (502-55-6) + phenacylacetophenone (495-71-6)

Guidance literature:

In acetonitrile; for 15h; Irradiation; Inert atmosphere;

DOI:10.1021/jo201385b

Reference yield: 62.0%

1,1-Dichloroacetone (513-88-2) + 2,2-dichloroacetophenone (2648-61-5) → 1-chloroacetophenone (532-27-4,108321-66-0,164322-25-2) + phenacylacetophenone (495-71-6) + 1-phenylpentane-1,4-dione (583-05-1)

Guidance literature:

With indium(I) bromide; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1055/s-2004-825591

Reference yield: 61.0%

1-chloroacetophenone (532-27-4,108321-66-0,164322-25-2) + phenylboronic acid (98-80-6) → phenyl benzyl ketone (451-40-1) + 1,2,3-tribenzoylcyclopropane (5633-67-0,877469-07-3) + phenacylacetophenone (495-71-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; cesium fluoride; In tetrahydrofuran; at 65 ℃; for 2h; Inert atmosphere;

DOI:10.1002/adsc.201300444

upstream raw materials:

piperidine

2-diazo-acetophenone

morpholine

N-methylsuccinimide

Downstream raw materials:

1-(4-hydroxyphenyl)-2,5-diphenyl-1H-pyrrole

1-(3-methoxy-phenyl)-2,5-diphenyl-pyrrole

1-(4-methoxyphenyl)-2,5-diphenyl-1H-pyrrole

2-(2,5-diphenyl-pyrrol-1-yl)-benzoic acid

Refernces

One-step preparation of symmetrical 1,4-diketones from α-halo ketones in the presence of Zn-I₂ as a condensation agent

10.1055/s-2004-829118

The research aims to develop a new and simple method for synthesizing symmetrical 1,4-diketones from α-halo ketones using zinc and iodine as condensation agents. The study reports the successful preparation of eleven 1,4-diphenylbutane-1,4-diones from corresponding α-halo acetophenones under mild conditions (65 °C) with moderate to high yields. The key chemicals used include various α-halo ketones such as 2-bromo-1-phenyl-ethanone and 2-bromo-4'-chloroacetophenone, along with zinc dust and a small amount of iodine. The reaction mechanism is explained through a Wurtz-like self-condensation pathway, where the initial reduction of α-bromo ketones by zinc forms enolate-like anions, which then attack another α-carbon of the ketone to form the 1,4-diketone products. The study concludes that this method is advantageous due to its mild reaction conditions and higher yields compared to previous methods, making it a useful approach for the preparation of functionalized symmetrical 1,4-diketones, which are important intermediates in the synthesis of five-membered carbocyclic and heterocyclic compounds.

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