163266-02-2

Basic information

• Product Name: 4,4,4-trifluoro-1-(2-methylphenyl)butane-1,3-dione
• Synonyms: 4,4,4-trifluoro-1-(2-methylphenyl)butane-1,3-dione;4,4,4-TRIFLUORO-1-(2-METHYLPHENYL)-1,3-BUTANEDIONE;4,4,4-Trifluoro-1-(o-tolyl)butane-1,3-dione;Celecoxib Impurity 5;Moxifloxacin impurity 13
• CAS NO: 163266-02-2
• Molecular Formula: C₁₁H₉F₃O₂
• Molecular Weight: 230.184
• Mol File: 163266-02-2.mol

Chemical Properties

• Boiling Point: 264.3±35.0 °C(Predicted)
• Appearance: /
• Density: 1.252±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 5.77±0.23(Predicted)
• CAS DataBase Reference: 4,4,4-trifluoro-1-(2-methylphenyl)butane-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4,4-trifluoro-1-(2-methylphenyl)butane-1,3-dione(163266-02-2)
• EPA Substance Registry System: 4,4,4-trifluoro-1-(2-methylphenyl)butane-1,3-dione(163266-02-2)

Safety Data

• Hazardous Substances Data: 163266-02-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4,4,4-Trifluoro-1-(2-methylphenyl)butane-1,3-dione is used as a synthetic intermediate for the production of 4-Desmethyl-2-methyl Celecoxib (D291815), an analog of Celecoxib (C251000). Celecoxib is a well-known cyclooxygenase 2 (COX-2) inhibitor, which is utilized for its anti-inflammatory and analgesic properties. The compound serves as a key building block in the synthesis of D291815, potentially enhancing the development of novel COX-2 inhibitors with improved pharmacological profiles.

Upstream product

• 383-63-1 ethyl trifluoroacetate, 
• 577-16-2 2-Methylacetophenone 
• 407-38-5 2,2,2-trifluoroethyl trifluoroacetate 

Downstream Products

• 170569-99-0 4-[5-(2-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide 
• 703-42-4 2,2-difluoro-1-(o-tolyl)ethan-1-one 
• 41441-74-1 o-methyl-α-diazoacetophenone 

Relevant articles and documents

An SAR study of hydroxy-trifluoromethylpyrazolines as inhibitors of Orai1-mediated store operated Ca2+ entry in MDA-MB-231 breast cancer cells using a convenient Fluorescence Imaging Plate Reader assay

The proteins Orai1 and STIM1 control store-operated Ca2+ entry (SOCE) into cells. SOCE is important for migration, invasion and metastasis of MDA-MB-231 human triple negative breast cancer (TNBC) cells and has been proposed as a target for cancer drug discovery. Two hit compounds from a medium throughput screen, displayed encouraging inhibition of SOCE in MDA-MB-231 cells, as measured by a Fluorescence Imaging Plate Reader (FLIPR) Ca2+ assay. Following NMR spectroscopic analysis of these hits and reassignment of their structures as 5-hydroxy-5-trifluoromethylpyrazolines, a series of analogues was prepared via thermal condensation reactions between substituted acylhydrazones and trifluoromethyl 1,3-dicarbonyl arenes. Structure-activity relationship (SAR) studies showed that small lipophilic substituents at the 2- and 3-positions of the RHS and 2-, 3- and 4-postions of the LHS terminal benzene rings improved activity, resulting in a novel class of potent and selective inhibitors of SOCE.

A Sequential Route to Cyclopentenes from 1,6-Enynes and Diazo Ketones through Gold and Rhodium Catalysis

This work reports the construction of cyclopentene cores from 1,6-enynes and aryl diazo ketones through two new reaction sequences involving initial gold-catalyzed cyclization of 1,6-enynes with diazo species, followed by rhodium-catalyzed skeletal rearrangement of the resulting 3-cyclopropyl-2-en-1-ones. In most instances the rhodium-catalyzed reactions afforded cyclopentene derivatives whereas several n-alkyl- or ortho-substituted phenyl ketones delivered seven-membered oxacycles. A plausible mechanism provides rationales for these two distinct products. (Figure presented.).

Synthesis of 4-[5-(2-methylphenyl)-3-(trifluoromethyl)-1-hydro-pyrazol-1-yl] benzenesulfonamide

The invention discloses a synthesis method of 4-[5-(2-methylphenyl)-3-(trifluoromethyl)-1-hydro-pyrazol-1-yl] benzenesulfonamide. The synthesis method comprises the following steps: with methyl acetophenone as a starting raw material, under a strong alkal

Synthesis, fungicidal activity and mode of action of 4-phenyl-6-trifluoromethyl-2-aminopyrimidines against Botrytis cinerea

Anilinopyrimidines are the main chemical agents for management of Botrytis cinerea. However, the drug resistance in fungi against this kind of compounds is very serious. To explore new potential fungicides against B. cinerea, a series of 4-phenyl-6-trifluoromethyl-2-amino-pyrimidine compounds (compounds III-1 to III-22) were synthesized, and their structures were confirmed by 1H-NMR, IR and MS. Most of these compounds possessed excellent fungicidal activity. The compounds III-3 and III-13 showed higher fungicidal activity than the positive control pyrimethanil on fructose gelatin agar (FGA), and compound III-3 on potato dextrose agar (PDA) indicated high activity compared to the positive control cyprodinil. In vivo greenhouse results indicated that the activity of compounds III-3, III-8, and III-11 was significantly higher than that of the fungicide pyrimethanil. Scanning electron micrography (SEM) and transmission electron micrography (TEM) were applied to illustrate the mechanism of title compounds against B. cinerea. The title compounds, especially those containing a fluorine atom at the ortho-position on the benzene ring, could maintain the antifungal activity against B. cinerea, but their mechanism of action is different from that of cyprodinil. The present study lays a good foundation for us to find more efficient reagents against B. cinerea.

Keto-enol and enol-enol tautomerism in trifluoromethyl-β-diketones

The keto-enol (K?E) and enol-enol (E?E) equilibria of a variety of trifluoromethyl-β-diketones were investigated using 1H, 13C, 19F NMR spectroscopy, infrared spectroscopy and ultraviolet-visible spectrophotometry in nonpolar solvents. In general, NMR, IR and UV spectral evidence indicates that trifluoromethyl-β-diketones exist as mixtures of two chelated cis-enol forms in nonpolar media. Infrared spectroscopy and ultraviolet spectrophotometry show the E?E equilibrium lies in the direction of the enol form which maximizes conjugation in most cases. Exceptions are noted and discussed.

PYRAZOLO AND IMIDAZO-PYRIMIDINE DERIVATIVES

The present invention relates to novel pyrazolo- and imidazo-pyrimidine derivatives of formula (I) wherein A, D, E, L, M, Q, R1, R2 and R3 are as defined in the description and claims and to processes for their preparation, pharmaceutical compositions containing said derivatives and their use in the prevention and treatment of diseases.

Synthesis of fluorinated heterocycles

Selected 1,3-diketones having a trifluoromethyl group and/or a fluorine in the 2-position were condensed with aromatic hydrazines, hydroxylamine, urea, thiourea, guanidine, and substituted anilines producing pyrazoles, isoxazoles, pyrimidines, and quinolines, respectively, in yields ranging from 27 to 87%.

New Heterocyclic compounds for therapeutic use

A class of compounds particularly diaryl pyrazole of general formulas 1 and 2 where R and R′ represents alkyl, hydrogen, halogens, haloalkyl, cyano, nitro, formyl, carboxyl, alkoxycarbonyl, carboxyalkyl, alkoxycarbonylalkyl, hydroxyalkyl, alkylthio, alkylsulfinyl, alkylsulphonyl, N- alkylsulfamyl, N-arylsulfamyl, cyanoamido, amino, amidino, N-monoalkylamido, N-monoarylamido, N,N-dialkylamido, N-alkyl-N-arylamido, N, N-dialkylsulfamyl with the alkyl, or alkyl part of each such group containing 1-3 carbon atoms or mixtures thereof optionally their salts when they exist, and preparation thereof. The compounds of the present invention are antiinflammatory, antipyretic, antirheumatic, antiosteoarthritic agents with antibacterial activity. The particular class of compounds is given below (Formula 1 and Formula 2).

Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)- 3(trifluoromethyl)-1h-pyrazol-1-yl]benzenesulfonamide (sc-58635, celecoxib)

A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC- 236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of 1i (4-[5-(4-methylphenyl)-3- (trifluoromethyl)-1H-pyrazol-1-y1]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.