1009-61-6

Basic information

• Product Name: 1,4-DIACETYLBENZENE
• Synonyms: 1-(4-Acetyl-phenyl)-ethanone;1,1’-(1,4-phenylene)bis-ethanon;Benzene, p-diacetyl-;P-ACETYL ACETOPHENONE;P-DIACETYLBENZENE;TIMTEC-BB SBB008588;1,4-DIACETYLBENZENE;4'-ACETYLACETOPHENONE
• CAS NO: 1009-61-6
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• EINECS: 213-769-4
• Product Categories: Aromatic Ketones (substituted);C10;Carbonyl Compounds;Ketones
• Mol File: 1009-61-6.mol
• Article Data: 106

Chemical Properties

• Melting Point: 111-113 °C(lit.)
• Boiling Point: 120 °C / 1mmHg
• Flash Point: 112.06 °C
• Appearance: almost white to light brown crystalline powder
• Density: 1.0613 (rough estimate)
• Vapor Pressure: 0.00115mmHg at 25°C
• Refractive Index: 1.5120 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: 6.309mg/L(25 oC)
• BRN: 1907515
• CAS DataBase Reference: 1,4-DIACETYLBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIACETYLBENZENE(1009-61-6)
• EPA Substance Registry System: 1,4-DIACETYLBENZENE(1009-61-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 1009-61-6(Hazardous Substances Data)

Usage

Description

1,4-Diacetylbenzene, also known as 1,1''-(1,4-phenylene)bis-Ethanone, is an organic compound with the chemical formula C16H14O2. It is an almost white to light brown crystalline powder. 1,4-Diacetylbenzene is known for its ability to undergo various chemical reactions, such as oxidative C-C bond cleavage and Suzuki-Miyaura coupling, which makes it a versatile building block in the synthesis of various organic compounds.

Uses

Used in Chemical Synthesis:
1,4-Diacetylbenzene is used as a synthetic intermediate for the production of various organic compounds. Its ability to undergo oxidative C-C bond cleavage allows for the synthesis of aryl carboxylic acids with the aid of an iodine catalyst. This property makes it a valuable component in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
1,4-Diacetylbenzene is also used as a coupling agent in the Suzuki-Miyaura reaction, a widely used method for the formation of carbon-carbon bonds, particularly in the synthesis of biaryl compounds. This reaction is highly applicable in the fields of pharmaceuticals, materials science, and organic synthesis, as it provides a reliable and efficient way to construct complex molecular structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,4-Diacetylbenzene serves as a key building block for the synthesis of various drug candidates. Its unique chemical properties enable the development of novel therapeutic agents with potential applications in the treatment of various diseases and medical conditions.
Used in Materials Science:
1,4-Diacetylbenzene is also utilized in the field of materials science for the development of new materials with specific properties. Its ability to form carbon-carbon bonds through the Suzuki-Miyaura coupling reaction allows for the creation of novel polymers, resins, and other materials with tailored characteristics for various applications, such as electronics, coatings, and adhesives.

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 4308, 1961 DOI: 10.1021/jo01069a031Synthetic Communications, 26, p. 3175, 1996 DOI: 10.1080/00397919608004626

Purification Methods

Crystallise it from EtOH (m 114o) or *benzene and dry it in a vacuum over CaCl2. Also purify it by dissolving it in acetone, treating with Norit, evaporating and recrystallising from MeOH. The dioxime has m 248-259o. [Wagner et al. J Am Chem Soc 108 7727 1986]. [Beilstein 7 H 686, 7 II 624, 7 III 3504, 7 IV 2156.]

InChI:InChI=1/C10H10O2/c1-7(11)9-3-5-10(6-4-9)8(2)12/h3-6H,1-2H3

Upstream product

• 623-26-7 terephthalonitrile 
• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 105-05-5 1,4-diethylbenzene 
• 937-30-4 4-ethylacetophenone 
• 935-14-8 1,4-diethynylbenzene 
• 1600-27-7 mercury(II) diacetate 
• 93-94-7 ethyl 3-(4-(3-ethoxy-3-oxo-propanoyl)phenyl)-3-oxo-propanoate 
• 82-70-2 3,3'-dioxo-2,2'-terephthaloyl-di-butyric acid diethyl ester 
• 1905-26-6 1,4-bis-chloroacetyl-benzene 
• 412034-48-1 terephthaloyl-di-malonic acid tetraethyl ester 
• 64-19-7 acetic acid 
• 636-09-9 diethyl terephthalate 
• 109-65-9 1-bromo-butane 

Downstream Products

• 30038-80-3 phenyl dithioacetomorpholide 
• 34838-67-0 1,4-bis-(3t-[2]furyl-acryloyl)-benzene 
• 95363-42-1 1,4-bis-(5t-phenyl-penta-2t,4-dienoyl)-benzene 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 26279-15-2 1,4-bis-(1-hydroxy-1-methyl-pentyl)-benzene 
• 636-09-9 diethyl terephthalate 
• 221910-24-3 1-(4-(quinolin-2-yl)phenyl)ethan-1-one 
• 2176-75-2 2,2'-p-phenylene-bis-quinoline 
• 2948-46-1 α,α,α',α'-tetramethyl-1,4-benzenedimethanol 
• 101447-97-6 1,4-bis-(1-hydroxy-1-methyl-butyl)-benzene 
• 106596-70-7 1,4-bis-(1-hydroxy-1-methyl-allyl)-benzene 
• 2790-71-8 1,4-bis(trichloroacetyl)benzene 
• 2673-16-7 1,4-dioxoacetyl-benzene 
• 140-50-1 N,N'-diacetyl-1,4-phenylenediamine 

Relevant articles and documents

Development of a Flow Photochemical Aerobic Oxidation of Benzylic C-H Bonds

A continuous mesofluidic process has been developed for benzylic C-H oxidation with moderate to good yields using a photocatalyst (riboflavin tetraacetate, RFT) activated by a UV lamp and an iron additive [Fe(ClO4)2] via incorporation of singlet oxygen (1O2) for the direct formation of oxidized C=O or CH-OH compounds.

Dioxygen-promoted regioselective oxidative Heck arylations of electron-rich olefins with arylboronic acids

Arylations of electron-rich heteroatom-substituted olefins were performed with arylboronic acids. This appears to constitute the first example of palladium(II)-catalyzed internal Heck arylations. The novel protocol exploits oxygen gas for environmentally benign reoxidation and a stable 1,10-phenanthroline bidentate ligand to promote the palladium(II) regeneration and to control the regioselectivity. Internal arylation is strongly favored with electron-rich arylboronic acids. DFT calculations support a charge-driven selectivity rationale, where phenyls substituted with electron-donating groups prefer the electron-poor α-carbon of the olefin. Experiments, verified by calculations, confirm the cationic nature of the catalytic route. This Heck methodology provides a facile and mild access to functionalized enamides. Controlled microwave heating and increased oxygen pressure were used to further reduce the reaction time to 1 h.

Electrochemical Aerobic Oxidative Cleavage of (sp3)C-C(sp3)/H Bonds in Alkylarenes

An electrochemistry-promoted oxidative cleavage of (sp3)C-C(sp3)/H bonds in alkylarenes was developed. Various aryl alkanes can be smoothly converted into ketones/aldehydes under aerobic conditions using a user-friendly undivided cell setup. The features of air as oxidant, scalability, and mild conditions make them attractive in synthetic organic chemistry.

Efficient Aliphatic C-H Oxidation and C═C Epoxidation Catalyzed by Porous Organic Polymer-Supported Single-Site Manganese Catalysts

Bioinspired manganese complexes have emerged over recent decades as attractive catalysts for a number of selective oxidation reactions. However, these catalysts still suffer from oxidative degradation. In the present study, we prepared a series of porous Mn-N4 catalysts in which the catalytic units are embedded in the skeleton of porous organic polymers (POPs). These POP-based manganese catalysts demonstrated high reactivity in the oxidation of aliphatic C-H bonds and the asymmetric epoxidation of olefins. Furthermore, these catalysts could be readily recycled and reused due to their heterogeneous nature. Morphological characterization revealed that the Mn-N4 complex was individually distributed over a porous polymer network. Remarkably, the nature of the single-site catalyst prevented oxidative degradation during the reaction. The present work has thus developed a successful approach for bioinspired single-site manganese catalysts in which the oxidation reaction is confined to a specific channel in an enzyme-like mode.

Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis

A metal- and additive-free methodology for the highly selective, photocatalyzed C-H oxygenation of alkylarenes under air to the corresponding carbonyls is presented. The process is catalyzed by an imide-acridinium that forms an extremely strong photooxidant upon visible light irradiation, which is able to activate inert alkylarenes such as toluene. Hence, this is an easy to perform, sustainable and environmentally friendly oxidation that provides valuable carbonyls from abundant, readily available compounds.