1450-72-2

Basic information

• Product Name: 1-(2-Hydroxy-5-methylphenyl)ethanone
• Synonyms: 1-(2-hydroxy-5-methylphenyl)-ethanon;1-Hydroxy-2-acetyl-4-methylbenzene;2’-Hydroxy-5’-methylacetophenon;5’-Methyl-2’-hydroxyacetophenone;Acetophenone, 2'-hydroxy-5'-methyl-;Acetophenone,2’-hydroxy-5’-methyl-;Ethanone,1-(2-hydroxy-5-methylphenyl)-;o-Acetyl-p-cresol
• CAS NO: 1450-72-2
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• EINECS: 215-915-2
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);C9;Carbonyl Compounds;Ketones
• Mol File: 1450-72-2.mol
• Article Data: 88

Chemical Properties

• Melting Point: 45-48 °C(lit.)
• Boiling Point: 112-114°C 12mm
• Flash Point: >230 °F
• Appearance: yellow crystalline powder
• Density: 1.079
• Refractive Index: 1.5369 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.46±0.18(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 1364840
• CAS DataBase Reference: 1-(2-Hydroxy-5-methylphenyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-Hydroxy-5-methylphenyl)ethanone(1450-72-2)
• EPA Substance Registry System: 1-(2-Hydroxy-5-methylphenyl)ethanone(1450-72-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1450-72-2(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystalline powder

Uses

2'-Hydroxy-5'-methylacetophenone is used to produce 2-ethyl-4-methyl-phenol. It is used as an intermediate in organic synthesis.

Preparation

Obtained by treatment of methyl 4-hydroxy-6-methyl-coumarin-3-carboxylate with potassium hydroxide at 200° (82%).

Upstream product

• 25172-54-7 1-(2-hydroxy-5-methylphenyl)ethan-1-one oxime 
• 140-39-6 1-acetoxy-4-methylbenzene 
• 22307-94-4 2-chloroacetyl-4-methylphenol 
• 13252-83-0 4-hydroxy-6-methylcoumarin 
• 56-23-5 tetrachloromethane 
• 59521-07-2 meso-2,3-bis-(2-hydroxy-5-methyl-phenyl)-butane-2,3-diol 
• 585-74-0 3-Methylacetophenone 
• 106-44-5 p-cresol 
• 108-24-7 acetic anhydride 
• 75-77-4 chloro-trimethyl-silane 
• 474353-19-0 N,N-diethyl-2-hydroxy-5-methylbenzamide 
• 132680-48-9 O-4-methylphenyl N,N-diethylcarbamate 
• 108293-71-6 2-(2-propen-1-yloxy)-5-methylacetophenone 
• 64-19-7 acetic acid 

Downstream Products

• 16108-51-3 2,6-dimethyl-chromen-4-one 
• 14002-89-2 4,6-dimethyl-chromen-2-one 
• 34087-19-9 2-acetyl-4-methylphenyl acetate 
• 2164-57-0 2-(3-Chlor-2-hydroxy-propoxy)-5-methyl-acetophenon 
• 108060-43-1 2-<(2-Acetyl-4-methylphenoxy)methyl>benzoesaeure-methylester 
• 112030-36-1 3-(p-bromophenyl)-4,6-dimethyl coumarin 
• 147722-96-1 (E)-3-(6-Chloro-4H-benzo[1,3]dioxin-8-yl)-1-(2-hydroxy-5-methyl-phenyl)-propenone 
• 112030-40-7 4,6-dimethyl-3-(p-methoxyphenyl)coumarin 
• 288087-80-9 (Z)-3-Amino-4,4,4-trichloro-1-(2-hydroxy-5-methyl-phenyl)-but-2-en-1-one 
• 895-05-6 isonicotinic acid [1-(2-hydroxy-5-methyl-phenyl)-ethylidene]hydrazide 
• 83504-95-4 (2-hydroxy-5-methylphenyl)thioacetomorpholide 
• 83504-96-5 (2-hydroxy-5-methylphenyl)thioacetopiperidide 
• 103037-98-5 2-amino-4-(2-hydroxy-5-methylphenyl)thiazole 
• 60121-33-7 3-benzyl-2-(2-hydroxy-5-methyl-phenyl)-2-methyl-thiazolidin-4-one 

Relevant articles and documents

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Dinuclear Metal Complexes. Part 2. Synthesis, Characterisation, and Electrochemical Studies of Macrocyclic Dicopper(II) Complexes

The synthesis, characterisation, and electrochemical studies of dicopper(II) complexes 1>2.nH2O of the macrocycle 7,11;19,23-dimetheno-9,21-dimethyl-tetra-azacycloicosa-5,7,9,12,17,19,21,24-octaene-25,26-diol (H2L1), and of some 6,12,18,24-substituted (Me4; Prn4; Ph4; Ph, Me, Ph, Me) derivatives have been carried out.These compounds undergo sequential one-electron transfers at two different potentials.For all of these compounds, except for 1>2.2H2O, two reversible or almost reversible reduction steps have been observed in acetonitrile medium using a hanging mercury drop electrode.In the case of 1>2.2H2O, the second couple became obscured due to the presence of an adsorption phenomenon or secondary electrode reaction.However, in NN-dimethylformamide (dmf) medium, satisfactory voltammograms have been obtained only with 1>2.2H2O.The mixed-valent complexes are considerably more stable in acetonitrile than is IICuIL1>+ in dmf.The potentials of the first reduction step (E1) remain practically invariant throughout the series and are independent of the extent of magnetic interactions in the dicopper(II) complexes.The potentials of the second reduction step (E2) vary with the alkyl and aryl groups present, and a linear plot has been obtained for E2 vs. the Hammett function ?m.On the basis of previously reported observations and the present study it is inferred that in acetonitrile medium the unpaired electron in the mixed-valent complexes remains localised on one of the copper atoms.

REARRANGEMENT OF DIMETHYLPHENYLACYLATES USING ZEOLITES

The present invention relates to a Fries rearrangement of specific dimethylphenylacylates to form the desired respective hydroxyaryl ketones having two methyl groups bound to the aromatic ring. It has been found that the process is surprisingly very specific in view of the number and position of the methyl group(s) bound to the aromatic ring.

Novel p-functionalized chromen-4-on-3-yl chalcones bearing astonishing boronic acid moiety as MDM2 inhibitor: Synthesis, cytotoxic evaluation and simulation studies

Background: Novel 4-[3-(6/7/8-Substituted 4-Oxo-4H-chromen-3-yl)acryloyl]phenyl-boronic acid derivatives (5a-h) as well as other 6/7/8-substituted-3-(3-oxo-3-(4-substituted-phenyl)prop-1-enyl)-4H-chromen-4-one derivatives (3a-u) have been designed as p53-MDM2 pathway inhibitors and reported to possess significant cytotoxic properties against several cancer cell lines. Objectives: The current project aims to frame the structure-anticancer activity relationship of chromen-4-on-3-yl chalcones (3a-u/5a-h). In addition, docking studies were performed on these chromeno-chalcones in order to have an insight into their interaction possibilities with MDM2 pro-tein. Methods: Twenty-nine chromen-4-on-3-yl chalcone derivatives (3a-u/5a-h) were prepared by utilizing silica supported-HClO4 (green route with magnificent yield) and tested against four cancer cell lines (HCT116, MCF-7, THP-1, NCIH322). Results: Among the series 3a-u, compound 3b exhibited the highest anticancer activity (with IC50 values ranging from 8.6 to 28.4 μM) overall against tested cancer cell lines. Interestingly, para-Boronic acid derivative (5b) showed selective inhibition against colon cancer cell line, HCT-116 with an IC50 value of 2.35 μM. Besides the emblematic hydrophobic interactions of MDM2 inhibi-tors, derivative 5b was found to exhibit extra hydrogen bonding with GLN59 and GLN72 residues of MDM2 in molecular dynamics (MD) simulation. All the compounds were virtually nontoxic against normal fibroblast cells. Conclusion: Novel compounds were obtained with good anticancer activity especially 6-Chlorochromen-4-one substituted boronic acid derivative 5b. The molecular docking study proposed good activity as a MDM-2 inhibitor suggesting hydrophobic as well as hydrogen bonding interactions with MDM2.