5326-42-1

Basic information

• Product Name: 4-HYDROXY-3-METHYLBENZOPHENONE
• Synonyms: 3-Methyl-4-hydroxybenzophenone
• CAS NO: 5326-42-1
• Molecular Formula: C₁₄H₁₂O₂
• Molecular Weight: 212.2505
• Mol File: 5326-42-1.mol

Chemical Properties

• Melting Point: 174–175°C
• Boiling Point: 388°Cat760mmHg
• Flash Point: 165.7°C
• Appearance: /
• Density: 1.164g/cm³
• Vapor Pressure: 1.41E-06mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: 4-HYDROXY-3-METHYLBENZOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-3-METHYLBENZOPHENONE(5326-42-1)
• EPA Substance Registry System: 4-HYDROXY-3-METHYLBENZOPHENONE(5326-42-1)

Safety Data

• Hazardous Substances Data: 5326-42-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H12O2/c1-10-9-12(7-8-13(10)15)14(16)11-5-3-2-4-6-11/h2-9,15H,1H3

Upstream product

• 98-88-4 benzoyl chloride 
• 95-48-7 ortho-cresol 
• 98-07-7 Benzotrichlorid 
• 65-85-0 benzoic acid 
• 4072-08-6 (2-hydroxy-3-methylphenyl)(phenyl)methanone 
• 617-02-7 2-methylphenyl benzoate 
• 15813-38-4 phenyl 2-methylbenzoate 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 536-74-3 phenylacetylene 
• 108-39-4 3-methyl-phenol 
• 30090-97-2 4-methoxy-3-methylbenzophenone 
• 7446-70-0 aluminium trichloride 
• 99821-75-7 4-hydroxy-2-isopropyl-5-methyl-benzophenone 
• 108-90-7 chlorobenzene 

Downstream Products

• 670221-34-8 2-(4-benzoyl-2-methylphenoxy)acetohydrazide 
• 670221-31-5 C₂₄H₂₃N₃O₃S 
• 134994-26-6 4-[(6-bromohexyl)oxy]-3-methylbenzophenone 
• 752952-13-9 4-[[6-(dimethylamino)hexyl]oxy]-3-methylbenzophenone 
• 1150104-99-6 C₂₁H₂₅NO₂ 

Relevant articles and documents

Synthesis, molecular docking, and apoptogenic efficacy of novel N-heterocycle analogs to target B-cell lymphoma 2/X-linked inhibitors of apoptosis proteins to regress melanoma

The novel series of piperidine conjugated benzophenone analogs with amide link 11a–l were synthesized in a multistep process. The structures of these compounds were confirmed by IR, 1H, 13C, NMR, and mass spectra and also by elementa

Visible Light-Mediated [2 + 2] Cycloaddition Reactions of 1,4-Quinones and Terminal Alkynes

A single-step synthesis of 4-hydroxy-functionalized bi-aryl and aryl/alkyl ketones via oxidative coupling of terminal alkynes with benzoquinones is reported. Furthermore, with naphthoquinones, owing to the cross-resonance of carbonyl with the aromatic ring, alkene-alkyne cycloaddition is more favored to give four-membered carbocyclic adducts, thereby precluding the requirement of preactivated alkynes.

Visible Light Copper Photoredox-Catalyzed Aerobic Oxidative Coupling of Phenols and Terminal Alkynes: Regioselective Synthesis of Functionalized Ketones via C C Triple Bond Cleavage

Direct oxidative coupling of phenols and terminal alkynes was achieved at room temperature by a visible-light-mediated copper-catalyzed photoredox process. This method allows regioselective synthesis of hydroxyl-functionalized aryl and alkyl ketones from simple phenols and phenylacetylene via C C triple bond cleavage. 47 examples were presented. From a synthetic perspective, this protocol offers an efficient synthetic route for the preparation of pharmaceutical drugs, such as pitofenone and fenofibrate.

Design and synthesis of diamide-coupled benzophenones as potential anticancer agents

A series of diamide-coupled benzophenone, 2-(4-benzoyl-phenoxy)-N-{2-[2-(4-benzoyl-phenoxy)-acetylamino]-phenyl}-acetamide analogues (9a-l) were synthesized by multistep reactions and all compounds were well characterized. Among the series (9a-l), compound 9k with three methyl groups at ortho position in rings A, B, and D and bromo group at the para position in ring E was selected as a lead compound by screening through multiple cancer cell types by in-vitro cytotoxic and antiproliferative assay systems. Also, the cytotoxic nature of the compound 9k resulted the regression of the tumor growth in-vivo, which could be due to decreased vascularisation in the peritoneum lining of the mice which regress the tumor growth. The results were reconfirmed in-vivo chorioallantoic membrane model which indicates a scope of developing 9k into potent anticancer drug in near future.

TETRAZOLINONE COMPOUND AND APPLICATIONS THEREOF

Disclosed is a tetrazolinone compound having a high pest control effect and represented by the formula (1): wherein R1, R2, R3, and R11 each represent a halogen atom, a C1-C6 alkyl group, or the like; R4 and R5 each represent a hydrogen atom, a halogen atom, a C1-C3 alkyl group, or the like; R6 represents a C1-C3 alkyl group which may have a halogen atom(s) or the like; R7, R8, and R9 each represent a hydrogen atom, a halogen atom, or the like; R10 represents a C1-C3 alkyl group or the like; R12 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, or the like, and R13 represents a C1-C6 alkyl group, a C2-C6 alkenyl group, or the like.

Synthesis and evaluation of novel benzophenone-thiazole derivatives as potent VEGF-A inhibitors

A series of 2-(4-benzoyl-phenoxy)-N-(4-phenyl-thiazol-2-yl)-Acetamides (10a-n) were synthesized by multistep reaction sequence and all the compounds were well characterized for structural elucidation. The in vitro cytotoxicity of compounds 10a-n was evaluated against EAC and DLA cell lines using trypan blue dye exclusion method. Further MTT assay and LDH release assay, followed by in vivo studies on murine model were also evaluated. The compound 10h with a methyl and fluoro groups at benzophenone moiety and methoxy group at phenyl ring was in a leading position to exhibit the promising antiproliferative effect through translational VEGF-A inhibition.

Synthesis, xanthine oxidase inhibition, and antioxidant screening of benzophenone tagged thiazolidinone analogs

A series of novel 2-(diaryl methanone)-N-(4-oxo-2-phenyl-thiazolidin-3-yl)- acetamides were synthesized by various Schiff bases of (4-benzoyl-phenoxy)-aceto hydrazide with thioglycolic acid. The structures of the newly synthesized compounds were confirmed

Design, synthesis, and anticancer properties of novel benzophenone- conjugated coumarin analogs

In the current scenario, development of anticancer drugs with specific targets is of prime importance in modern chemical biology. Observing the importance of benzophenone and coumarin nucleus, it would be worthwhile to design and synthesize novel benzophenone derivatives (8a-o) bearing the coumarin nucleus. Further, they were screened for prospective anticancer activities in vitro against the Michigan Cancer Foundation-7 (MCF-7) and Ehrlich's ascites tumor (EAT) cell lines and their biomarkers, followed by in silico studies regarding phosphoinositide 3-kinase (PI3K) and caspase by molecular docking. Benzophenones have been reported as potential drugs targeting tumor angiogenesis; thus, the formation of neovessels in an in vivo model system like CAM, which is angiogenesis dependent, was observed in the presence of compounds 8a-o. The above findings would help in understanding their putative potential as therapeutic agents for cancer patients. Coumarin-integrated benzophenone conjugates (8a-o) were designed, synthesized, and screened for prospective anticancer activities in vitro against the MCF-7 and EAT cell lines. Molecular docking studies with regard to phosphoinositide 3-kinase and caspase were performed. In addition, neovessel formation was observed in an in vivo model system.

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Polyphosphoric acid (PPA) has been used to synthesize a number of prochiral aryl ketones as well as α,β-unsaturated diaryl ketones by conventional and microwave assisted methods in moderate to good yield. The microwave assisted method is advantageous due to increased yield and high purity of products within incredible short period of time.

Benzophenone-N-ethyl piperidine ether analogues-Synthesis and efficacy as anti-inflammatory agent

A sequence of substituted benzophenone-N-ethyl piperidine ether analogues has been synthesized and evaluated as orally active anti-inflammatory agents with reduced side effects. The anti-inflammatory and ulcerogenic activities of the compounds were compared with naproxen, indomethacin, and phenylbutazone. These analogues showed an interesting anti-inflammatory activity in carrageenan-induced foot pad edema assay. In the air-pouch test, some of the analogues reduced the total number of leukocytes of the exudate, which indicates inhibition of prostaglandin production. Side effects of the compounds were examined on gastric mucosa, in the liver and stomach. None of the compounds illustrated significant side effects compared with standard drugs like indomethacin and naproxen.