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

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

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

• 105-05-5 1,4-diethylbenzene 
• 935-14-8 1,4-diethynylbenzene 
• 1600-27-7 mercury(II) diacetate 
• 3622-76-2 (2-ethenyloxyethyl)dimethylamine 
• 109613-00-5 4-acetophenyl triflate 
• 13329-40-3 4-Iodoacetophenone 
• 201230-82-2 carbon monoxide 
• 51501-86-1 (p-Methyl-phenyl)-methyl-difluor-silan 
• 35768-36-6 1,4-diacetyl-cyclohexa-1,4-diene 
• 768-93-4 1-iodoadamantane 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 141-78-6 ethyl acetate 
• 35227-78-2 diethyl (ethoxymagnesio)malonate 
• 100-20-9 terephthaloyl chloride 

Downstream Products

• 30038-80-3 phenyl dithioacetomorpholide 
• 26279-15-2 1,4-bis-(1-hydroxy-1-methyl-pentyl)-benzene 
• 908-11-2 1,4-bis(3-phenyl-2-propenoyl)benzene 
• 959-26-2 Bis(2-Hydroxyethyl)terephthalat 
• 109441-89-6 1,4-bis-(3-methoxycarbonyl-2-methyl-oxiranyl)-benzene 
• 143332-36-9 4-(4-Acetylphenyl)-4-hydroxy-2-pentanon 
• 143394-10-9 (S,S)-α,α'-dimethyl-1,4-benzenedimethanol 
• 185144-38-1 (S)-1-(4-(1-hydroxyethyl)phenyl)ethanone 
• 24553-57-9 1,1'‐(1,4‐phenylene)bis(2,2‐dibromoethan‐1‐one) 
• 183060-22-2 1,4-diacetylbenzene bis(trimethylsilyl) enol ether 
• 17658-25-2 2,2'-(1,4-benzenediyl)bis[2-methyl-1,3-dioxolane] 
• 21684-18-4 1,4-bis-(4-methoxy-cinnamoyl)-benzene 
• 473933-46-9 (E)-1-(4-acetylphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 

Relevant articles and documents

Pure acetonitrile as solvent for the efficient electrochemical conversion of aryl bromides in organozinc species and their coupling reaction with acetyl chloride

Conversion of functionalized aryl bromides in an electrochemical cell fitted with a sacrificial anode and in the presence of cobalt bromide without ligand in acetonitrile as solvent affords the corresponding organozinc species in good yields. Their coupling with acetyl chloride is efficient using a palladium catalyst.

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.

TBHP-promoted direct oxidation reaction of benzylic Csp3-H bonds to ketones

A metal-free oxidation system employing tert-butyl hydroperoxide (TBHP) has been developed for selective oxidation of structurally diverse benzylic sp3 C-H bonds. This low-cost methodology allows for rapid generation of synthetically and biologically valued arylketones in good to excellent yields from readily available alkylarenes and diarylmethanes.

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.

Ni-based catalysts derived from a metal-organic framework for selective oxidation of alkanes

Ni nanoparticles embedded in nitrogen-doped carbon (Ni@C-N) materials were prepared by thermolysis of a Ni-containing metal-organic framework (Ni-MOF) under inert atmosphere. The as-synthesized Ni@C-N materials were characterized by powder X-ray diffraction, N2 adsorption-desorption analysis, scanning electron microscopy, transmission electron microscopy, atomic absorption spectroscopy, and X-ray photoelectron spectroscopy. The MOF-derived Ni-based materials were then examined as heterogeneous catalysts for the oxidation of alkanes under mild reaction conditions. The Ni@C-N composites displayed high activity and selectivity toward the oxidation of a variety of saturated C-H bonds, affording the corresponding oxidation products in good-to-excellent yields. Furthermore, the catalysts could be recycled and reused for at least four times without any significant loss in activity and selectivity under the investigated conditions.

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.

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.

Visible-light photocatalytic selective oxidation of C(sp3)-H bonds by anion-cation dual-metal-site nanoscale localized carbon nitride

Selective oxidation of C(sp3)-H bonds to carbonyl groups by abstracting H with a photoinduced highly active oxygen radical is an effective method used to give high value products. Here, we report a heterogeneous photocatalytic alkanes C-H bonds oxidation method under the irradiation of visible light (λ= 425 nm) at ambient temperature using an anion-cation dual-metal-site modulated carbon nitride. The optimized cation (C) of Fe3+or Ni2+, with an anion (A) of phosphotungstate (PW123?) constitutes the nanoscale dual-metal-site (DMS). With a Fe-PW12dual-metal-site as a model (FePW), we demonstrate a A-C DMS nanoscale localized carbon nitride (A-C/g-C3N4) exhibiting a highly enhanced photocatalytic activity with a high product yield (86% conversion), selectivity (up to 99%), and a wide functional group tolerance (52 examples). The carbon nitride performs the roles of both the visible light response, and improves the selectivity for the oxidation of C(sp3)-H bonds to carbonyl groups, along with the function of A-C DMS in promoting product yield. Mechanistic studies indicate that this reaction follows a radical pathway catalyzed by a photogenerated electron and hole on A-C/g-C3N4that is mediated by thetBuO˙ andtBuOO˙ radicals. Notably, a 10 g scale reaction was successfully achieved for alkane photocatalytic oxidation to the corresponding product with a good yield (80% conversion), and high selectivity (95%) under natural sunlight at ambient temperature. In addition, this A-C/g-C3N4photocatalyst is highly robust and can be reused at least six times and the activity is maintained.

HCl-Catalyzed Aerobic Oxidation of Alkylarenes to Carbonyls

The construction of C?O bonds through C?H bond functionalization remains fundamentally challenging. Here, a practical chlorine radical-mediated aerobic oxidation of alkylarenes to carbonyls was developed. This protocol employed commercially available HCl as a hydrogen atom transfer (HAT) reagent and air as a sustainable oxidant. In addition, this process exhibited excellent functional group tolerance and a broad substrate scope without the requirement for external metal and oxidants. The mechanistic hypothesis was supported by radical trapping, 18O labeling, and control experiments.

Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds

A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]