3602-54-8

Basic information

• Product Name: 1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE
• Synonyms: 1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE;2,4-Dihydroxy-6-methoxyacetophene;2,4-Dihydroxy-6-Methoxyacetophenone;2-O-Methylphloroacetophenone;6-O-Methylphloroacetophenone
• CAS NO: 3602-54-8
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.1733
• Mol File: 3602-54-8.mol
• Article Data: 25

Chemical Properties

• Melting Point: 139-140 °C
• Boiling Point: 333.493 °C at 760 mmHg
• Flash Point: 135.5℃
• Appearance: /
• Density: 1.284
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: 2-8°C
• PKA: 7.60±0.23(Predicted)
• CAS DataBase Reference: 1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE(3602-54-8)
• EPA Substance Registry System: 1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE(3602-54-8)

Safety Data

• Hazardous Substances Data: 3602-54-8(Hazardous Substances Data)

Usage

Description

1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE, also known as 2,4-Dihydroxy-6-methoxyacetophenone, is an organic compound with the molecular formula C9H10O4. It is characterized by its aromatic ring structure, featuring two hydroxyl groups at the 2nd and 4th positions, a methoxy group at the 6th position, and an ethanone functional group. 1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE is known for its reactivity and versatility in chemical synthesis, making it a valuable intermediate in the preparation of various organic compounds.

Uses

Used in Pharmaceutical Industry:
1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE is used as a reagent for the preparation of polysubstituted synthetic chalcones. Chalcones are a class of organic compounds that have been extensively studied for their diverse range of biological activities, including anti-inflammatory, antioxidant, and anticancer properties. The synthesis of these chalcones using 2,4-Dihydroxy-6-methoxyacetophenone as a reagent can lead to the development of novel therapeutic agents with potential applications in the treatment of various diseases.
Used in Chemical Synthesis:
1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows for further functionalization and modification, making it a valuable building block in the preparation of complex molecules. 1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE can be utilized in the synthesis of a wide range of products, including pharmaceuticals, agrochemicals, dyes, and other specialty chemicals.
Used in Research and Development:
1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE is also used in research and development for the exploration of new chemical reactions and synthetic pathways. Its reactivity and structural features make it an attractive candidate for studying novel reaction mechanisms and developing innovative synthetic strategies. 1-(2,4-DIHYDROXY-6-METHOXY-PHENYL)-ETHANONE can be employed in academic and industrial research settings to advance the understanding of organic chemistry and contribute to the discovery of new chemical entities with potential applications in various fields.

Preparation

Preparation by reaction of acetonitrile on phloroglucinol monomethyl ether (Hoesch reaction).

InChI:InChI=1/C9H10O4/c1-5(10)9-7(12)3-6(11)4-8(9)13-2/h3-4,11-12H,1-2H3

Upstream product

• 480-66-0 2,4,6-trihydroxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 404597-94-0 1-(2-methoxy-4,6-bis(methoxymethoxy)phenyl)ethan-1-one 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 108-73-6 3,5-dihydroxyphenol 
• 108-22-5 Isopropenyl acetate 
• 2174-64-3 5-methoxyresorcinol 
• 2466-76-4 N-Acetylimidazole 
• 249278-28-2 2,4,6-trihydroxyacetophenone monohydrate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 1393809-20-5 4-acetyl-5-methoxy-1,3-phenylene bis(4-methylbenzenesulfonate) 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 
• 621-23-8 1,2,3-trimethoxybenzene 

Downstream Products

• 103633-31-4 5-C-(o-Benzyloxybenzyl)-4,6-dihydroxy-2-methoxyacetophenone 
• 103633-32-5 3-C-(o-Benzyloxybenzyl)-4,6-dihydroxy-2-methoxyacetophenone 
• 1393809-15-8 (+/-)-3-hydroxy-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-p-tolylpropan-1-one 
• 1393809-16-9 (+/-)-3-hydroxy-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-p-tolylpropan-1-one 
• 1393809-17-0 (+/-)-3-hydroxy-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-methoxyphenyl)propan-1-one 
• 1393809-18-1 (+/-)-3-(3,4-dimethoxyphenyl)-3-hydroxy-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)propan-1-one 
• 1393809-19-2 (+/-)-3-(3,5-dimethoxyphenyl)-3-hydroxy-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)propan-1-one 
• 51703-76-5 obovatachalcone 
• 1393809-14-7 (+/-)-elatadihydrochalcone 
• 119136-14-0 2,4-bis(benzyloxy)-6-methoxyacetophenone 
• 1228673-66-2 (2E)-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one 
• 52117-67-6 2,4-dihydroxy-6-methoxy-3-aldehydoacetophenone 
• 142382-28-3 3,3’-diacetyl-4,4’-dimethoxy-2',2,6,6'-tetrahydroxy diphenylmethane 
• 75679-58-2 2’,4’-dihydroxy-4,6’-dimethoxydihydrochalcone 

Relevant articles and documents

KNIPHOLONE: A UNIQUE ANTHRQUINONE DERIVATIVE FROM KNIPHOFIA FOLIOSA

The roots of Kniphofia foliosa afforded, in addition to chrysophanol, a novel anthraquinone named knipholone, whose structure was determined by spectroscopic methods as well as by degradation to known compounds.Key Word Index - Kniphofia foliosa; Liliaceae; anthraquinone; chrysophanol; knipholone.

Effects of substituent pattern on the intracellular target of antiproliferative benzo[b]thiophenyl chromone derivatives

A new biological scaffold was produced by replacing the 6π-electron phenyl ring-B of a natural flavone skeleton with a 10π-electron benzothiophene (BT). Since aromatic rings are important for ligand protein interactions, this expansion of the π-electron system of ring-B might change the bioactivity profile. One of the resulting novel natural product-inspired compounds, 2-(benzo[b]thiophen-3-yl)-5-hydroxy-7-isopropoxy-6-methoxyflavone (6), effectively arrested the cell cycle at the G2/M phase and displayed significant antiproliferative effects with IC50 values of 0.05–0.08 μM against multiple human tumor cell lines, including a multidrug resistant line. A structure-activity relationship study revealed that a 10π-electron system with high aromaticity, juxtaposed 4-oxo and 5-hydroxy groups, and 7-alkoxy groups were important for potent antimitotic activity. Interestingly, two BT-flavonols (3-hydroxyflavone), 16 and 20, with 3-hydroxy and 5-alkoxy groups, induced distinct biological profiles affecting the cell cycle at the G1/S phase by inhibition of DNA replication through an interaction with topoisomerase I.

Annphenone, a phenolic acetophenone from Artemisia annua

Fractionation of the n-butanol extract of Artemisia annua led to the isolation of a new phenolic acetophenone, the structure of which was elucidated as 2,4-dihydroxy-6-methoxy-acetophenone 40-O-β-D-glucopyranoside on the basis of spectroscopic data.

Construction and Biological Evaluation of Small Libraries Based on the Intermediates within the Total Synthesis of Uvaretin

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Biocatalytic Friedel–Crafts Acylation and Fries Reaction

The Friedel–Crafts acylation is commonly used for the synthesis of aryl ketones, and a biocatalytic version, which may benefit from the chemo- and regioselectivity of enzymes, has not yet been introduced. Described here is a bacterial acyltransferase which can catalyze Friedel–Crafts C-acylation of phenolic substrates in buffer without the need of CoA-activated reagents. Conversions reach up to >99 %, and various C- or O-acyl donors, such as DAPG or isopropenyl acetate, are accepted by this enzyme. Furthermore the enzyme enables a Fries rearrangement-like reaction of resorcinol derivatives. These findings open an avenue for the development of alternative and selective C?C bond formation methods.