6781-42-6

Basic information

• Product Name: 1,3-DIACETYLBENZENE
• Synonyms: Ethanone, 1,1'-(1,3-phenylene)bis-;1,3-DIACETYLBENZENE;M-DIACETYLBENZENE;M-ACETYL ACETOPHENONE;benzene-1,3-bis(acetyl);1,3-Diacetylbenzene,97%;1,1'-m-Phenylenebisethanone;1,3-Diacetylbenzene,99%
• CAS NO: 6781-42-6
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• EINECS: 229-842-9
• Product Categories: Aromatic Ketones (substituted);C10;Carbonyl Compounds;Ketones;Furans ,Coumarins
• Mol File: 6781-42-6.mol

Chemical Properties

• Melting Point: 28-32 °C(lit.)
• Boiling Point: 150-155 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear slightly yellow/Liquid After Melting
• Density: 1.0613 (rough estimate)
• Vapor Pressure: 0.00382mmHg at 25°C
• Refractive Index: 1.5485-1.5505
• Storage Temp.: 2-8°C
• Solubility: Soluble in ethanol, benzene, chloroform.
• BRN: 2042511
• CAS DataBase Reference: 1,3-DIACETYLBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIACETYLBENZENE(6781-42-6)
• EPA Substance Registry System: 1,3-DIACETYLBENZENE(6781-42-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 6781-42-6(Hazardous Substances Data)

Usage

Uses

1. Used in Organic Synthesis:
1,3-Diacetylbenzene is used as an important raw material and intermediate for the preparation of polyhydroxylated analogs in the field of organic synthesis. Its unique chemical properties allow it to serve as a key component in the creation of various complex organic molecules.
2. Used in Pharmaceutical Industry:
1,3-Diacetylbenzene is used as a starting material for the synthesis of various pharmaceutical compounds. Its ability to induce neuropathological changes in rodents makes it a potential candidate for the development of drugs targeting the central and peripheral nervous systems.
3. Used in Chemical Research:
1,3-Diacetylbenzene is utilized as a research compound in the field of chemistry, particularly in the study of δ-diketone chemistry and its applications. Its unique properties and reactivity make it an interesting subject for further investigation and potential discovery of new chemical reactions and processes.
4. Used in Material Science:
1,3-Diacetylbenzene may also find applications in the development of new materials, such as polymers and composites, due to its chemical structure and properties. Its potential use in material science could lead to the creation of novel materials with specific properties tailored for various industrial applications.

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

Upstream product

• 64-17-5 ethanol 
• 4481-99-6 3,3'-dioxo-3,3'-m-phenylene-di-propionic acid 
• 141-93-5 m-diethylbenzene 
• 143329-81-1 α,α'-dimethyl-1,3-benzenedimethanol 
• 1713-16-2 1,3-bis-chloroacetyl-benzene 
• 860517-17-5 2',3',2'',3''-tetrabromo-m-phenylene-di-propionate dimethyl ester 
• 636-53-3 diethyl isophthalate 
• 64-19-7 acetic acid 
• 71189-76-9 2-(3-{cyano[(trimethylsilyl)oxy]methyl}phenyl)-2-[(trimethylsilyl)oxy]acetonitrile 
• 74-88-4 methyl iodide 
• 1459-93-4 dimethyl Isophthalate 
• 141-78-6 ethyl acetate 
• 107-29-9 Acetaldehyde oxime 
• 22699-70-3 3-ethylacetophenone 

Downstream Products

• 27912-61-4 1,3-diacetylbenzene dioxime 
• 19247-97-3 α,α'-dibromo-1,3-diacetylbenzene 
• 132843-62-0 1,1'-(1,3-phenylene)bis(3-phenyl-2-propen-1-one) 
• 132843-69-7 (2E,2'E)-1,1'-(1,3-phenylene)bis(3-(4-methoxyphenyl)prop-2-en-1-one) 
• 113786-94-0 1,3-bis<1-hydroxy-1-(pyridin-2-yl)ethyl>benzene 
• 86156-17-4 1,3-Bis(3'-dimethylamino-propionyl)-benzol 
• 129005-67-0 1.4-Bis-(4-methyl-cinnamoyl)-benzol 
• 129005-70-5 1.4-Bis-(4-fluor-cinnamoyl)-benzol 
• 55147-57-4 1.4-Bis-(4-chlor-cinnamoyl)-benzol 
• 129005-69-2 (Z)-3-(4-Ethoxy-phenyl)-1-{3-[(Z)-3-(4-ethoxy-phenyl)-acryloyl]-phenyl}-propenone 
• 147428-73-7 1,3-bis(1-(cyclopenta-2,4-dien-1-ylidene)ethyl)benzene 
• 55147-58-5 1,1'-(1,3-phenylene)bis(3-phenyl-2-propen-1-one) 
• 56270-09-8 (E)-3-(4-Methoxy-phenyl)-1-{3-[(E)-3-(4-methoxy-phenyl)-acryloyl]-phenyl}-propenone 
• 56376-45-5 1.4-Bis-(4-brom-cinnamoyl)-benzol 

Relevant articles and documents

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.]

Preparation method 1,3 - diacyl benzene

The preparation method of 1-3 - diacyl benzene comprises the following steps: reacting m-phthalic aldehyde with an alkyl magnesium halide to form an intermediate as shown II. The intermediate shown in Formula II is subjected to an oxidation reaction under the action of an oxidant to generate III, 1 diacyl benzene as shown 3 . In-flight R1 . R2 Alkyl groups from the alkyl magnesium halides, respectively. The method has the advantages of simple process, safety, environmental protection, high target product yield, high purity and the like, and can realize large-scale industrial production.

Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions

A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.

Compartmentalized Nanoreactors for One-Pot Redox-Driven Transformations

This contribution introduces poly(2-oxazoline)-based shell cross-linked micelles (SCMs) as nanoreactors to realize one-pot redox-driven deracemizations of secondary alcohols in aqueous media. TEMPO and Rh-TsDPEN moieties are spatially positioned into the hydrophilic corona and the hydrophobic micelle core, respectively. TEMPO catalyzes the oxidation of racemic secondary alcohols into ketones, while Rh-TsDPEN catalyzes the asymmetric transfer hydrogenation (ATH) of these ketones to afford enantioenriched secondary alcohols. Both catalysts, the Rh-TsDPEN complex and TEMPO, are incompatible with each other and the SCMs are designed to provide indispensable catalyst site isolation. Kinetic studies show that the SCMs enhance the reactivity of the immobilized catalysts, in comparison to those for the unsupported analogues under the same reaction conditions. Our nanoreactors can perform deracemizations on a broad range of secondary alcohol substrates and are reusable in a continuous manner while maintaining high activity.

Method for removing acyl group in diazo of aryl diazonium salt

The invention provides a method for removing an acyl group in diazo of an aryl diazonium salt. The method is characterized in that the aryl diazonium salt and its derivative and an ortho-dicarbonyl compound undergo an illumination reaction to obtain a corresponding arylacyl product. The method has the advantages of high yield of the product, no metal involvement, and simple process.

Efficient Palladium(0) supported on reduced graphene oxide for selective oxidation of olefins using graphene oxide as a ‘solid weak acid’

Selective oxidation of olefin derivatives to ketones has made innovative development over palladium(0) supported on reduced graphene oxide. Compared to traditional Wacker oxidation, the novel method offers an economical and environment-friendly option by using graphene oxide (GO) as a ‘solid weak acid’ instead of classical homogeneous catalysts like H2SO4 and CF3COOH. X-ray diffraction, X-ray photoelectron spectroscopy, scanning electron microscope and transmission electron microscopy images of Pd0/RGO showed that the nanoscaled Pd particles generated at the flake structure of reduced graphene oxide. Under optimized condition, up to 44 kinds of ketones with different structures can be prepared with excellent yields.

Transformation of Alkynes into Chiral Alcohols via TfOH-Catalyzed Hydration and Ru-Catalyzed Tandem Asymmetric Hydrogenation

A novel full atom-economic process for the transformation of alkynes into chiral alcohols by TfOH-catalyzed hydration coupled with Ru-catalyzed tandem asymmetric hydrogenation in TFE under simple conditions has been developed. A range of chiral alcohols was obtained with broad functional group tolerance, good yields, and excellent stereoselectivities.

One-pot synthesis of chiral alcohols from alkynes by CF3SO3H/ruthenium tandem catalysis

A practical one-pot synthesis of chiral alcohols from readily available alkynes via tandem catalysis by the combination of CF3SO3H and a fluorinated chiral diamine Ru(ii) complex in aqueous CF3CH2OH is described. Very interestingly, the combination of fluorinated catalysts and solvent exhibits a positive fluorine effect on the reactivity and enantioselectivity. A range of chiral alcohols with wide functional group tolerance was obtained in high yield and excellent stereoselectivity under simple and mild conditions.

Method for directly oxidizing benzyl-position C-H bond into ketone

The invention discloses a method for directly oxidizing a benzyl-position C-H bond into ketone, wherein aryl ethyl compounds are catalyzed and oxidized by nitrite ester; a synergistic catalytic system of free radical initiator and nitrite ester is adopted, and a catalytic system of non-metallic catalyst and oxygen is adopted, the oxidization of the C-H bond of a free radical-activated aryl side chain is simple in operation; after completing the reaction, petroleum ether/ethyl acetate at a volume ratio of (50-1):1 is used as an eluent; column chromatography separation is performed to obtain a target product. The catalytic system in the invention uses oxygen as an oxygen source and has high atomic economy; the invention is a non-metallic catalytic system and provides a novel method for avoid metal residues in synthetic drugs; for diethyl aromatic hydrocarbon, the method provided by the invention can be adopted to selectively oxidize diethyl aromatic hydrocarbon into monoketone and diketone; the method of the invention can be adopted to efficiently synthesize tranquillizer lenperone, so that a novel method for synthesizing lenperone is provided.

Organopromoted Selectivity-Switchable Synthesis of Polyketones

In this work, an organopromoted metal-free pharmaceutical-oriented selectivity-switchable benzylic oxidation was developed, affording mono-, di-, and trioxygenation products, respectively, using oxygen as the oxidant under mild conditions. This process facilitates dioxygenation of 2,6-benzylic positions of heterocycles, which could be inhibited by heterocycle chelation to the metal cocatalysts. Enantiopure chiral ketones could also be prepared. The noninvolvement of transition metals and toxins avoids metal or hazardous residues, consequently ensuring a final-stage gram-scale synthesis of Lenperone.