3669-41-8

Basic information

• Product Name: 2',4'-Dihydroxy-2-phenylacetophenone
• Synonyms: 1-(2,4-DIHYDROXYPHENYL)-2-PHENYLETHAN-1-ONE;1-(2,4-DIHYDROXYPHENYL)-2-PHENYLETHANONE;2',4'-DIHYDROXY-2-PHENYLACETOPHENONE;ALPHA-PHENYLRESACETOPHENONE;AURORA 15288;BENZYL 2,4-DIHYDROXYPHENYL KETONE;TIMTEC-BB SBB008378;OTAVA-BB BB0107930004
• CAS NO: 3669-41-8
• Molecular Formula: C₁₄H₁₂O₃
• Molecular Weight: 228.24
• Product Categories: Pharmaceutical Intermediates;Building Blocks;C13 to C14;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks
• Mol File: 3669-41-8.mol

Chemical Properties

• Melting Point: 112-116 °C(lit.)
• Boiling Point: 225°C/10mmHg(lit.)
• Flash Point: 227.9 °C
• Appearance: off-white crystalline powder
• Density: 1.278 g/cm³
• Vapor Pressure: 5.41E-08mmHg at 25°C
• Refractive Index: 1.642
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 7.74±0.35(Predicted)
• CAS DataBase Reference: 2',4'-Dihydroxy-2-phenylacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2',4'-Dihydroxy-2-phenylacetophenone(3669-41-8)
• EPA Substance Registry System: 2',4'-Dihydroxy-2-phenylacetophenone(3669-41-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 3669-41-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2',4'-Dihydroxy-2-phenylacetophenone is used as a key intermediate in the synthesis of various substituted pyrazoles, pyrimidines, triazoles, and related heterocycles. These synthesized compounds serve as c-MYC targeting agents, which are crucial in the treatment of cancer and other proliferative diseases. By targeting the c-MYC protein, these agents can potentially inhibit the uncontrolled cell growth associated with cancer, making 2',4'-Dihydroxy-2-phenylacetophenone a valuable component in the development of novel anticancer drugs.
Used in Organic Chemistry:
In the field of organic chemistry, 2',4'-Dihydroxy-2-phenylacetophenone is utilized as a versatile building block for the synthesis of a wide range of complex organic molecules. Its unique structure and reactivity make it a valuable compound for the development of new materials, pharmaceuticals, and other specialty chemicals. Researchers can exploit its chemical properties to create innovative molecules with potential applications in various industries, such as agriculture, materials science, and environmental science.

Preparation

Preparation by Friedel–Crafts acylation of resorcinol with phenylacetyl chloride in the presence of aluminium chloride, ? in methylene chloride (85%) ; ? in nitrobenzene at 70–80° for 15 min (<80%), at r.t. for 24 h (63%) or for 2 days (60%); ? in ethyl ether at r.t. for 24 h (43%).

InChI:InChI=1/C14H12O3/c15-11-6-7-12(14(17)9-11)13(16)8-10-4-2-1-3-5-10/h1-7,9,15,17H,8H2

Upstream product

• 140-29-4 phenylacetonitrile 
• 108-46-3 recorcinol 
• 103-80-0 phenylacetyl chloride 
• 103-82-2 phenylacetic acid 
• 1555-80-2 phenylacetic anhydride 
• 60-29-7 diethyl ether 
• 18439-96-8 1-(2-hydroxy-4-methoxyphenyl)-2-phenylethanone 
• 22665-91-4 1-(2,4-diacetoxyphenyl)-2-phenylethanone 
• 39604-80-3 1-[2-hydroxy-4-(phenylmethoxy)phenyl]-2-phenylethanone 
• 102172-23-6 3-(2,4-dimethoxy-phenyl)-3-oxo-2-phenyl-propionic acid ethyl ester 
• 106821-04-9 ω-phenylresacetophenone imine hydrochloride 

Downstream Products

• 13057-72-2 7-hydroxyisoflavone 
• 108982-03-2 7-hydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylic acid methyl ester 
• 872267-40-8 7-hydroxy-2-(2-nitro-phenyl)-3-phenyl-chromen-4-one 
• 92152-59-5 2,4-dihydroxy-5-bromo-α-phenylacetophenone 
• 787-06-4 1-(2,4,5-trihydroxyphenyl)-2-phenylethanone 
• 19816-40-1 3,5-dibromo-2,4-dihydroxy-deoxybenzoin 
• 112553-03-4 2-hydroxy-4-(4-nitro-benzoyloxy)-deoxybenzoin 
• 22665-91-4 1-(2,4-diacetoxyphenyl)-2-phenylethanone 
• 23596-15-8 5-hydroxy-4-methyl-6-phenylacetyl-coumarin 
• 39604-80-3 1-[2-hydroxy-4-(phenylmethoxy)phenyl]-2-phenylethanone 
• 15485-72-0 ethyl 7-hydroxy-4-oxo-3-phenyl-4H-chromene-2-carboxylate 
• 857567-65-8 2-hydroxy-6-vinyloxy-deoxybenzoin 
• 102478-26-2 2-hydroxy-4-(toluene-4-sulfonyloxy)-deoxybenzoin 
• 59562-17-3 2,4-dihydroxy-deoxybenzoin-(2,4-dinitro-phenylhydrazone) 

Relevant articles and documents

Synthesis, biological evaluation, and molecular docking studies of novel 1,2,3-triazole derivatives as potent anti-inflammatory agents

In the present study, a novel series of 1,2,3-triazole derivatives have been synthesized using click chemistry approach. The structures were confirmed by spectroscopic methods. The products were screened for their in vivo anti-inflammatory activity. The tested compounds 6a, 6f, 6g, 6i, 6j, 6n, and 6p, demonstrated potent anti-inflammatory activity compared to the reference drug ibuprofen. Molecular docking studies of these 1,2,3-triazole derivatives into the active site of human cyclooxygenase-2 (COX-2) (PDB code 4PH9) demonstrated good affinity for the enzyme and suggested binding properties similar to ibuprofen.

Acylation of resorcinol on clay catalysts

Using a series of clay based catalysts (KSF, KSF/0, KP10, K10, K0, KS), resorcinol is acylated in 1,2-dichloroethane by phenylacetyl chloride with a heterogeneous catalytic procedure. The yield of 1-(2,4-dihydroxyphenyl)2- phenyl-ethanone is in correlation with the specific surface area of the catalyst.

A Concise Approach to Oxo-Dehydrorotenoid by Direct Lactonization and the Total Syntheses of Stemonone, Rotenonone, 6-Oxo-dehydroelliptone, and 6-Oxo-6a,12a-dehydrodeguelin

An approach to construct the oxo-dehydrorotenoids via direct lactonization of isoflavone-2-carboxylic acids is reported. The present reaction proceeds smoothly with good substrate scope and an operationally simple protocol. The application of this method

Design, synthesis, and biological evaluation of truncated deguelin derivatives as Hsp90 inhibitors

A series of novel B[sbnd] and C-rings truncated deguelin derivatives have been designed and synthesized in the present study as heat shock protein 90 (Hsp90) inhibitors. The synthesized compounds exhibited micromolar antiproliferative potency toward a pan

Synthesis and biological evaluation of Complex I inhibitor R419 and its derivatives as anticancer agents in HepG2 cells

In this study, Complex I inhibitor R419 was firstly revealed to have significant anticancer activity against HepG2 cells (IC50 = 5.2 ± 0.9 μM). Based on this finding, a series of R419 derivatives were synthesized and biologically evaluated. As results, 9 derivatives were found to have obvious anticancer activity. Among them, H20 exhibited the most potent activity (IC50 = 2.8 ± 0.4 μM). Mechanism study revealed that H20 caused severe depletion of cellular ATP, dose-dependently activated AMPK, decreased Bcl-2/Bax ratio and induced necrotic cell death. Most importantly, H20 displayed definite inhibitory activity against Complex I.

CYTISINE-LINKED ISOFLAVONOID ANTINEOPLASTIC AGENTS FOR THE TREATMENT OF CANCER

Cytisine-linked isoflavonoids, or pharmaceutically acceptable salts thereof or pharmaceutically acceptable compositions thereof, are useful for the treatment of conditions in which cells have a reliance on peroxisomal HSD17B4 to degrade very long chain fatty acids and provide necessary energy for cell proliferation, such as is seen in colorectal cancer and prostate cancer, for example.

A concise synthesis of 2-alkenyl-3-phenyl-4H-chromen-4-ones via novel C-C bond formation using sulfone as potential intermediate

A new methodology has been designed for the synthesis of some non-natural 2-alkenyl-3-phenyl-4H-chromen-4-ones of potential biological importance. The strategy makes use of appropriately substituted heteroaryl sulfone as the potent intermediate. An ambide

Developing antineoplastic agents that target peroxisomal enzymes: Cytisine-linked isoflavonoids as inhibitors of hydroxysteroid 17-beta-dehydrogenase-4 (HSD17B4)

Cytisine-linked isoflavonoids (CLIFs) inhibited PC-3 prostate and LS174T colon cancer cell proliferation by inhibiting a peroxisomal bifunctional enzyme. A pull-down assay using a biologically active, biotin-modified CLIF identified the target of these agents as the bifunctional peroxisomal enzyme, hydroxysteroid 17β-dehydrogenase-4 (HSD17B4). Additional studies with truncated versions of HSD17B4 established that CLIFs specifically bind the C-terminus of HSD17B4 and selectively inhibited the enoyl CoA hydratase but not the d-3-hydroxyacyl CoA dehydrogenase activity. HSD17B4 was overexpressed in prostate and colon cancer tissues, knocking down HSD17B4 inhibited cancer cell proliferation, suggesting that HSD17B4 is a potential biomarker and drug target and that CLIFs are potential probes or therapeutic agents for these cancers.

ANTI-ESTROGENIC COMPOUNDS

The present disclosure provides a compound of Formula I: or a pharmaceutically acceptable salt wherein X, R1-R8, Y1-Y5, m, n, p, and q are defined herein. The novel 2H-chromene compounds are useful for the modul

Synthesis and Aminomethylation of 3-Substituted 6-Hydroxy-1,2-Benzisoxazoles

Oximes of 2,4-dihydroxybenzophenones, 1-(2,4-dihydroxyphenyl)-2-phenylethanones, and 1-(2,4-di-hydroxyphenyl)-2-phenoxyethanones were dehydrated with 1,1'-carbonyldiimidazole, yielding 3-substi-tuted 6-hydroxy-1,2-benzisoxazoles, aminomethylation reactions of which were studied with various reagents.