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
• Article Data: 36

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

Chemical Properties

off-white crystalline powder

Uses

1-(2,4-Dihydroxyphenyl)-2-phenylethanone is used in preparation of substituted pyrazoles, pyrimidines, triazoles and related heterocycles as c-MYC targeting agents for treatment of cancer and other proliferative diseases.

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

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

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.

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

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.

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