4693-16-7

Usage

Uses

Used in Pharmaceutical Industry:
2-5-dihydroxybutyrophenone is utilized as an intermediate in the synthesis of medications, specifically for the development of antipsychotic and antiemetic drugs. Its molecular structure and properties make it a valuable component in creating effective treatments for these conditions.
Used in Psychiatric and Neurological Treatments:
2-5-dihydroxybutyrophenone is employed as a potential therapeutic agent for the treatment of certain psychiatric and neurological disorders. Its presence in the synthesis of medications indicates its importance in addressing mental health and neurological conditions.
Used in Natural Product Research:
2-5-dihydroxybutyrophenone, being a natural product of certain plants and microorganisms, is used as a subject of biological activity research. Its potential biological activities warrant further investigation, which could lead to the discovery of new applications in medicine and pharmacology.
Overall, 2-5-dihydroxybutyrophenone holds significant applications in the medical and pharmaceutical fields, with its properties and potential effects being of interest for future research and development.

InChI:InChI=1/C10H12O3/c1-2-3-9(12)8-6-7(11)4-5-10(8)13/h4-6,11,13H,2-3H2,1H3

Upstream product

• 141-75-3 butyryl chloride 
• 123-31-9 hydroquinone 
• 150-78-7 1,4-dimethoxybezene 
• 107-92-6 butyric acid 
• 109-74-0 propyl cyanide 
• 123-72-8 butyraldehyde 
• 106-51-4 p-benzoquinone 
• 83791-03-1 1,4-bis(butanoyloxy)benzene 

Downstream Products

• 65781-65-9 2-Butanoyl-1,4-benzochinon 
• 79521-13-4 5,5'-[[2-(1-hydroxybutyl)-1,4-phenylene]bis(oxy)]bis[2,2-dimethylpentanoic acid] 
• 4197-69-7 4-(2,5-dihydroxyphenyl)butane 
• 79521-12-3 dimethyl 5,5'-[[2-(1-oxobutyl)-1,4-phenylene]bis(oxy)]bis[2,2-dimethylpentanoate] 

Relevant academic research and scientific papers

Half-wave potentials and in vitro cytotoxic evaluation of 3-acylated 2,5-bis(phenylamino)-1,4-benzoquinones on cancer cells

A broad range of 3-acyl-2,5-bis(phenylamino)-1,4-benzoquinones were synthesized and their voltammetric values, as well as in vitro cancer cell cytotoxicities, were assessed. The members of this series were prepared from acylbenzoquinones and phenylamines, in moderate to good yields (47-74%), through a procedure involving a sequence of two in situ regioselective oxidative amination reactions. The cyclic voltammograms of the aminoquinones exhibit two one-electron reduction waves to the corresponding radical-anion and dianion, and two quasi-reversible oxidation peaks. The first and second half-wave potential values (E1/2) of the members of the series were sensitive to the push-pull electronic effects of the substituents around the benzoquinone nucleus. The in vitro cytotoxic activities of the 3-acyl-2,5-bis(phenylamino)-1,4-benzoquinones against human cancer cells (bladder and prostate) and non-tumor human embryonic kidney cells were measured using the MTT colorimetric method. The substitution of both aniline groups, by either methoxy (electron donating effect) or fluorine (electron withdrawal effect), decreased the cytotoxicity in the aminoquinones. Among the members of the unsubstituted phenylamino series, two of the 18 compounds showed interesting anti-cancer activities. A preliminary assay, looking for changes in the expression of selected genes, was performed. In this context, the two compounds increased TNF gene expression, suggesting an association with an inflammatory-like response.

Photochemistry in supercritical carbon dioxide. The benzophenone-mediated addition of aldehydes to α,β-unsaturated carbonyl compounds

The photo-induced addition of aldehydes to α,β-unsaturated carbonyl compounds is an effective, 'environmentally benign' method for the synthesis of 2-acyl-1,4-hydroquinones (from quinones) and 1,4-diketones (from enones). This process has been improved by eliminating benzene as a solvent and replacing it with supercritical carbon dioxide. Highest yields were obtained at higher CO2 pressures, or with the addition of 5% t-butyl alcohol as co-solvent.

The Chemistry of Nitrilium Salts. Part 1. Acylation of Phenols and Phenol Ethers with Nitriles and Trifluoromethanesulphonic Acid

Aliphatic nitriles, RCN (R = Me, n-Pr, CH2Cl, and CCl3), in the presence of trifluoromethanesulphonic acid have been found to react with a number of mono-, di-, and tri-substituted phenols and phenol ethers at room temperature to give ketones after hydrolysis of the reaction mixture.Moderate to good yields of acylation products are obtained in the majority of these reactions.The yield with malononitrile and succinonitrile, which are only slightly soluble in the reaction medium, are generally poor, and reaction involves only one of the available nitrile groups.Attempts to use diethyl ether and dichloromethane as solvents for some of these reactions were unsuccessful, but limited success was achieved with nitromethane.