704-00-7

Usage

Uses

Used in Chemical Research:
1,2-Diacetylbenzene is used as a research compound for studying its metabolic pathways and potential effects on biological systems, particularly its role as a metabolite of the neurotoxic solvent 1,2-diethylbenzene.
Used in Pharmaceutical Development:
1,2-Diacetylbenzene is used as a starting material or intermediate in the synthesis of pharmaceutical compounds, given its unique chemical structure and reactivity with proteins.
Used in Environmental Monitoring:
1,2-Diacetylbenzene can be used as a biomarker for the presence of neurotoxic solvents in the environment, helping to monitor and control exposure to harmful substances.
Used in Toxicological Studies:
1,2-Diacetylbenzene is used as a subject in toxicological research to understand its potential health risks and to develop methods for mitigating the effects of neurotoxic solvents.

Purification Methods

Purify it by distilling and by recrystallising from pet ether. The bis-2,4-dinitrophenylhydrazone has m 221o (dec). [Halford & Weissmann J Org Chem 17 1646 1952, Riemschneider & Kassahn Chem Ber 92 1705 1959,[Beilstein 7 III 3501, 7 IV 2155.]

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

Upstream product

• 63797-42-2 1,4-epidioxy-1,4-dimethyl-1,2,3,4-tetrahydronaphthalene 
• 2142-64-5 1-(2-ethylphenyl)ethanone 
• 7732-18-5 water 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 4436-75-3 3-hexene-2,5-dione 
• 129849-05-4 trifluoromethanesulfonic acid 2-acetylphenyl ester 
• 104190-22-9 1-(2-ethynylphenyl)ethan-1-one 
• 200957-46-6 (4-methyl-7-oxa-1-benzonorbornenyl)methyl benzoate 
• 10003-76-6 {(E)-N'-[1-(2-hydroxyphenyl)ethylidene]acetohydrazide} 
• 10003-76-6 N′-(1-(2-hydroxyphenyl) ethylidene) acetohydrazide 
• 2717-42-2 1,2,4-trimethylnaphthalene 
• 930-88-1 N-methylmaleimide 
• 91688-22-1 3-Acetoxy-1,2,3,6-tetrahydro-1,2-diacetyl-benzol 
• 68850-07-7 1,2-bis(1-hydroxyethyl)benzene 

Downstream Products

• 164008-15-5 1,2-bis-bromoacetyl-benzene 
• 100255-98-9 1,2-bis-(1-semicarbazono-ethyl)-benzene 
• 823810-77-1 1-acetyl-2-(bromoacetyl)benzene 
• 130766-71-1 1-methyl-2-(p-methoxyphenyl)-3-(p-methoxyphenyliminomethyl)isoindole 
• 130766-72-2 1-formyl-2-(p-methoxyphenyl)-3-(p-methoxyphenyliminomethyl)isoindole 
• 130766-73-3 1,3-bis(p-methoxyphenyliminomethyl)-2-(p-methoxyphenyl)isoindole 
• 130766-68-6 1-methyl-2-phenyl-3-(phenyliminomethyl)isoindole 
• 130766-69-7 1-formyl-2-phenyl-3-(phenyliminomethyl)isoindole 
• 130766-70-0 1,3-bis(phenyliminomethyl)-2-phenylisoindole 
• 1146596-84-0 1,2-bis(4-(4-methoxyphenyl)-6-phenyl-5-(trifluoromethyl)pyridin-2-yl)benzene 
• 1160850-54-3 (E,E)-1,1-[1,2-phenylene]bisethanone-bis(tosylhydrazone) 
• 68850-07-7 1,2-bis(1-hydroxyethyl)benzene 

Relevant academic research and scientific papers

Synthesis of 3-hydroxyindanones via potassium salt of amino acid catalyzed regioselective intramolecular aldolization of ortho-diacylbenzenes

First organocatalytic intramolecular aldolization of ortho-diacylbenzenes to construct highly functionalized 3-hydroxyindanones is described. In this transformation a high trans-selectivity is achieved by the use of metal salt of amino acid. This method allows an easy access to the strained spirocyclic 3-hydroxyindanones related to a number of natural product frameworks. Synthesis of a new class of indole skeleton substituted by 3-hydroxyindanones added an extra essence to this new protocol.

Simple Aza -conjugate addition methodology for the synthesis of isoindole nitrones and 3,4-dihydroisoquinoline nitrones

Aryl-aldehydes containing ortho-substituted α,β-unsaturated carboxylic acid derivatives react with hydroxylamine to afford reactive N-hydroxy-carbinolamine intermediates that undergo intramolecular aza-conjugate addition reactions to afford isoindole nitrones and 3,4-dihydroisoquinoline nitrones in good yield. Conditions have been developed to reduce these isoindole nitrones to their corresponding hydroxylamine, enamine, and amine derivatives. Isoindole nitrones react with dimethyl acetylenedicarboxylate (DMAD) via a [4 + 2]-cycloaddition/deamination pathway to afford substituted naphthalene derivatives, while 3,4-dihydroisoquinoline nitrones react with DMAD via a [1,3]-dipolar cycloaddition pathway to afford tricyclic heteroarenes.

Synthesis of 4,5-Benzotropones by Cyclization of 1,3-Bis-Silyl Enol Ethers with 1,2-Dialdehydes

The cyclization of 1,3-bis-silyl enol ethers or (2,4 -dioxobutylidene)triphenylphosphoranes with phthalic dialdehyde allowed a convenient synthesis of a variety of 4,5-benzotropones. The hydrogenation of benzotropones afforded functionalized benzocycloheptanones which were transformed into tricyclic butenolides.

Preparation of 1,2-diacylbenzenes from o-hydroxyaryl ketone acylhydrazones using cross-linked poly[styrene(iodoso diacetate)]

The 2 percent cross-linked poly[styrene(iodoso diacetate)] was used to synthesis of 1,2-diacylbenzenes, which gave high yields, and could be recycled.

Ultrasound assisted heterogeneous permanganate oxidations

The ultrasound effect on the heterogeneous permanganate oxidation of benzyl alcohol and alkylarenes to the corresponding carbonyl compounds is examined. Application of ultrasonic irradiation leads to shorter reaction times as well as lower reaction temperatures. KMnO4 supported by copper sulfate pentahydrate in CH2Cl2 is possible to use for selective oxidation of benzyl alcohol to benzaldehyde. (C) 2000 Elsevier Science Ltd.

Study of the pyrolytic chemistry of isobenzofurylmethyl benzoates

Pyrolysis of (1-isobenzofuryl)methyl benzoate (9a), produced in situ from flash vacuum pyrolysis of (7-oxa-1-benzonorbornenyl)methyl benzoate (10a), gave methylenebenzocyclobutenone (4), 2-ethynylbenzaldehyde (5) and benzocyclopentadienone (6). The deuterium-labeled study indicated that the mechanism for the formation of these products involved the double migrations of benzoate group in 9a. Pyrolysis of (3-methyl-1-isobenzofuryl)methyl benzoate (9c) gave 1,3-dimethylene-1,3-dihydroisobenzofuran (33), which is stable in benzene and hydrolyzed rapidly in chloroform to give 1,2-diacetylbenzene (35).

Synthesis of 1,2-diacylbenzenes from o-hydroxyaryl ketone acylhydrazones using [(diacetoxy)iodo]benzene

2'-Hydroxyacetophenone and 2'-hydroxypropiophenone acylhydrazones 3 are oxidized to 1,2-diacylbenzenes 4 using [(diacetoxy)iodo]benzene in dichloromethane at room temperature in a synthetically useful and high yield reaction.

α-Regioselectivity in Palladium-Catalyzed Arylation of Acyclic Enol Ethers

Regioselective α-arylation of acyclic enol ethers by aryl trifluoromethanesulfonates, aryl bromide, aryl iodides, and aroyl chlorides is described.The outcome of the reaction proved to be dependent from the relationship between ligand and counterion in the oxidative complex.

OXIDATION OF N-AROYLHYDRAZONES OF o-HYDROXYARYL KETONES WITH LEAD(IV)ACETATE: A FACILE ROUTE TO AROMATIC o-DIKETONES

N-Aroylhydrazones of o-hydroxyaryl ketones are oxidized with lead(IV)acetate to aromatic o-diketones in a synthetically useful reaction.