4390-92-5

Basic information

• Product Name: 2',4'-dihydroxybutyrophenone
• Synonyms: 2',4'-dihydroxybutyrophenone;1-(2,4-dihydroxyphenyl)butan-1-one;1-(2,4-Dihydroxyphenyl)-1-butanone;1-(2,4-Dihydroxyphenyl)
• CAS NO: 4390-92-5
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.20048
• EINECS: 224-508-9
• Mol File: 4390-92-5.mol

Chemical Properties

• Melting Point: 73 °C
• Boiling Point: 338.5 °C at 760 mmHg
• Flash Point: 172.7 °C
• Appearance: /
• Density: 1.194 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 7.72±0.35(Predicted)
• CAS DataBase Reference: 2',4'-dihydroxybutyrophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2',4'-dihydroxybutyrophenone(4390-92-5)
• EPA Substance Registry System: 2',4'-dihydroxybutyrophenone(4390-92-5)

Safety Data

• Hazardous Substances Data: 4390-92-5(Hazardous Substances Data)

Usage

Uses

Used in Research Applications:
2',4'-Dihydroxybutyrophenone is used as a research compound for studying the mechanism of oxidative aromatic substitution and various acylation studies. Its reactivity and chemical properties make it a valuable tool in understanding these processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2',4'-dihydroxybutyrophenone is used as an intermediate in the synthesis of many drugs. Its versatility in chemical reactions allows for the creation of a wide range of pharmaceutical compounds.
Used in Industrial Applications:
2',4'-Dihydroxybutyrophenone is also utilized in various industrial applications due to its reactivity and chemical properties. Its use in these applications is a testament to the compound's versatility and potential for further development.

Upstream product

• 107-92-6 butyric acid 
• 108-46-3 recorcinol 
• 141-75-3 butyryl chloride 
• 4346-18-3 phenyl butanoate 
• 109-74-0 propyl cyanide 
• 106-31-0 butanoic acid anhydride 
• 75175-06-3 1,1'-(4,6-dihydroxy-1,3-phenylene)dibutan-1-one 

Downstream Products

• 20800-24-2 1-(2-hydroxy-4-methoxyphenyl)butan-1-one 
• 128889-92-9 Acetic acid 2-oxo-3-phenyl-4-propyl-2H-chromen-7-yl ester 
• 90919-46-3 1-(5-chloro-2,4-dihydroxyphenyl)butan-1-one 
• 98339-53-8 3-ethyl-7-hydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde 
• 101451-58-5 3-ethyl-7-hydroxy-2-phenyl-chromen-4-one 
• 103274-59-5 1-(3-bromo-2,4-dihydroxy-5-nitro-phenyl)-butan-1-one 
• 143286-57-1 1-(2-Hydroxy-4-methoxy-phenyl)-butan-1-one oxime 
• 81468-73-7 1-(5-butyl-2,4-dihydroxyphenyl)ethan-1-one 
• 230976-83-7 1-(4'-benzyloxy-2'-hydroxyphenyl)-2-ethyl-3-hydroxypropanone 

Relevant articles and documents

Synthesis and evaluation of aromatic methoxime derivatives against five postharvest phytopathogenic fungi of fruits. Main structure–activity relationships

The antifungal activity of a library of twenty-four aromatic methoximes was examined against five representative postharvest phytopathogenic fungi. The panel included Penicillium digitatum, Penicillium italicum, Rhizopus stolonifer, Botrytis cinerea and Monilinia fructicola, all of which cause relevant economic losses worldwide as a result of affecting harvested fruits. The minimum inhibitory concentrations and minimum fungicidal concentrations of each compound were defined and the main structure–activity relationships were determined. Although other congeners were more potent, drug likeliness considerations pointed to the methoxime derived from 2,4-dihydroxypropiophenone as the compound with the most suitable profile. The morphology of the colonies of the fungal strains treated with the methoxime was examined microscopically and the compound was also tested in freshly harvested peaches and oranges, exhibiting promising control profiles in both fruits, similar to those of the commercial agents Imazalil and Carbendazim.

Rational Engineered C-Acyltransferase Transforms Sterically Demanding Acyl Donors

The biocatalytic Friedel-Crafts acylation has been identified recently for the acetylation of resorcinol using activated acetic acid esters for the synthesis of acetophenone derivatives catalyzed by an acyltransferase. Because the wild-type enzyme is limited to acetic and propionic derivatives as the substrate, variants were designed to extend the substrate scope of this enzyme. By rational protein engineering, the key residue in the active site was identified which can be replaced to allow binding of bulkier acyl moieties. The single-point variant F148V enabled the transformation of previously inaccessible medium chain length alkyl and alkoxyalkyl carboxylic esters as donor substrates with up to 99% conversion and up to >99% isolated yield.

Method for synthesizing 4-alkylresorcinol through solvent-free system

The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing 4-alkylresorcinol through a solvent-free system. The method comprises the following stepsthat (1) resorcinol, zinc chloride and alkyl acid are evenly mixed, heated and stirred for a reaction, after cooling, water is added to precipitate a solid, filtering, drying and recrystallization areconducted, and thus 4-acylresorcinol is obtained; (2) the 4-acylresorcinol is dissolved into trifluoroacetic acid, triethyl silicane is added dropwise, heating and stirring are conducted for a reaction, cooling and standing are conducted for layering, an organic layer is extracted and dried, filtration and concentration are conducted to obtain a crude product, recrystallization is conducted, andthe 4-alkylresorcinol is obtained. According to the method, a triethyl silicane/trifluoroacetic acid system is applied to synthesis of the 4-alkylresorcinol for the first time, the reaction conditionis gentler and easier to control, and a post-treatment method is simple; and the system does not contain a solvent, water materials generated during industrial amplification are also greatly reduced,and thus the whole process is more environment friendly.

Preparation method of 4-alkylresorcinol

The invention discloses a preparation method of 4-alkylresorcinol. The preparation method comprises the steps: carrying out a reaction on resorcinol and alkyl acid to prepare acyl resorcinol, and then, catalyzing a hydrogenation reaction to obtain 4-alkylresorcinol. By using the method, the dosages of a catalyst and alkyl groups are controlled in an acylation process, so that the yield is remarkably increased, byproducts are reduced, and the production cost is reduced; and hydrogen reduction is adopted in a reduction process, and a high-toxicity and high-pollution zinc amalgam reducing agent is prevented from being used, so that the preparation method is green and environment-friendly; and the aftertreatment is simple, the prepared product is high in purity, the total yield of the two steps reaches up to 77%, and the preparation method has a remarkable significance for industrial production of 4-alkylresorcinol.

Primulin derivative as well as synthesis method and application of primulin derivative

The invention discloses a primulin derivative with antibacterial activity shown as the structural general formula (I), wherein R is selected from C2-C20 alkyls. The primulin derivative is prepared from raw materials including m-dihydroxybenzene and a fatty acid derivative by the steps: carrying out Friedel-Crafts acylation and methylation to synthesize a paeonol derivative, and carrying out oxidization after carrying out carbonyl reduction. The primulin derivative has good antibacterial activity and can be used as a potential antibacterial agent.

Natural products as sources of new fungicides (II): antiphytopathogenic activity of 2,4-dihydroxyphenyl ethanone derivatives

A series of 17 simple 1-(2,4-dihydroxyphenyl) ethanones were synthesised, and their structures characterised by 1H, 13C NMR and ESI-MS. Their in vitro antifungal activities were evaluated against five phytopathogenic fungi including Glomerella cingulate, Botrytis cirerea, Fusarium graminearum, Curvularia lunata and Fusarium oxysporum f. sp. vasinfectum by the mycelial growth inhibition assay. Compounds 2g and 2h exhibited broad-spectrum inhibitory activity against the mycelial growth of the tested pathogens with IC50 values in the range of 16-36 g/mL, and in particular being more active to G. cingulate, with IC50 values of 16.50 and 19.25 g/mL, respectively, than the other pathogens. Preliminary SAR indicated that an α,β-unsaturated ketone unit of the alkyl chain of the compounds is the structure requirement for fungicidal action. The results suggested that 2g and 2h may be promising leads in the development of new antifungal agents.

Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging

Starting from 7-hydroxyisoflavones, we developed a new class of fluorescent scaffolds, 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs, MW ～ 205.19, λab ～ 350 nm, λem ～ 450 nm) via a trial and error process. AMHCs have the advantages of being a small molecular moiety, having strong fluorescence in basic buffers, reasonable solubility and stability, non-toxicity, and are conveniently linked to pharmacophores. AMHCs were successfully used in fluorescence microscopy imaging of cells and tissues. This journal is

Discovery and SAR study of hydroxyacetophenone derivatives as potent, non-steroidal farnesoid X receptor (FXR) antagonists

Compound 1 (IC50 = 35.2 ± 7.2 μM), a moderate FXR antagonist was discovered via high-throughput screening. Structure-activity relationship studies indicated that the shape and the lipophilicity of the substituents of the aromatic ring affect the activity dramatically, increasing the shape and the lipophilicity of the substituents of the aromatic ring enhances the potency of FXR antagonists. Especially, when the OH at C2 position of the aromatic ring was replaced by the OBn substituent (analog 2b), its activity could be improved to IC50 = 1.1 ± 0.1 μM. Besides, the length of the linker and the tetrazole structure are essential for retaining the activity.

IMIDAZOLE CARBOXAMIDES

The present invention provides certain imidazole carboxamide derivatives, pharmaceutical compositions thereof, methods of using the same and processes for preparing the same.

Ytterbium triflate catalysed Friedel-Crafts reaction using carboxylic acids as acylating reagents under solvent-free conditions

The Friedel-Crafts acylation of 1-naphthol and phenol derivatives with carboxylic acids were investigated by using a catalytic amount of metal-triflate, in particular Yb(OTf)3, under solvent-free conditions. Both aliphatic and aromatic carboxylic acids reacted easily to afford the corresponding hydroxyaryl ketones.