326-06-7

Basic information

• Product Name: BENZOYL-1,1,1-TRIFLUOROACETONE
• Synonyms: TRIFLUORO-1-PHENYL-1,3-BUTANEDIONE;1,1,1-Trifluoro-4-phenyl-2,4-butanedione;1-Benzoyl-3,3,3-trifluoro-2-propanone;1-Benzoyl-3,3,3-trifluoroacetone;4,4,4-Trifluoro-1-phenylbutane-1,3-dione ,98%;ω-(Trifluoroacetyl)acetophenone;4,4,4-Trifluoro-1-phenyl-1,3-butanedione,99%;4-Phenyl-1,1,1-trifluorobuta
• CAS NO: 326-06-7
• Molecular Formula: C₁₀H₇F₃O₂
• Molecular Weight: 216.16
• EINECS: 206-307-8
• Product Categories: organofluorine compounds;Miscellaneous
• Mol File: 326-06-7.mol
• Article Data: 31

Chemical Properties

• Melting Point: 38-40 °C(lit.)
• Boiling Point: 224 °C(lit.)
• Flash Point: 210 °F
• Appearance: White to yellow/Crystalline Low Melting Solid
• Density: 1,113 g/cm3
• Vapor Pressure: 0.02mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: 95% ethanol: soluble25mg/mL, clear, colorless to yellow
• PKA: pK1: 6.35 (25°C)
• Water Solubility: Sparingly Soluble in water (0.24 g/L) (25°C).
• BRN: 1875083
• CAS DataBase Reference: BENZOYL-1,1,1-TRIFLUOROACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZOYL-1,1,1-TRIFLUOROACETONE(326-06-7)
• EPA Substance Registry System: BENZOYL-1,1,1-TRIFLUOROACETONE(326-06-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 326-06-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
BENZOYL-1,1,1-TRIFLUOROACETONE is used as a synthetic intermediate for the preparation of various organic compounds, particularly those containing trifluoromethyl substituents. Its reactivity and unique structural features make it a valuable building block in the synthesis of complex molecules.
Used in Schiff Base Condensation Reactions:
BENZOYL-1,1,1-TRIFLUOROACETONE is used as a starting material in the synthesis of NNO ketoimines bearing trifluoromethyl substituents via Schiff base condensation reactions. This application takes advantage of the compound's carbonyl group, which can react with amines to form imine linkages, leading to the formation of diverse and potentially bioactive molecules.
Used in Mixed-Ligand Chelate Extraction:
BENZOYL-1,1,1-TRIFLUOROACETONE is used in the mixed-ligand chelate extraction of trivalent lanthanides. Its ability to form stable complexes with these metal ions makes it a useful agent in the separation and purification processes of lanthanide elements.
Used in the Preparation of Ternary Lanthanide Complexes:
BENZOYL-1,1,1-TRIFLUOROACETONE is used as a ligand in the preparation of ternary lanthanide (Ln) complexes. BENZOYL-1,1,1-TRIFLUOROACETONE's ability to form stable complexes with lanthanide ions is exploited in this application, which can be useful in various fields, such as materials science, catalysis, and analytical chemistry.

InChI:InChI=1/C10H7F3O2/c11-10(12,13)9(15)6-8(14)7-4-2-1-3-5-7/h1-6,14H/b8-6-

Upstream product

• 407-38-5 2,2,2-trifluoroethyl trifluoroacetate 
• 98-86-2 acetophenone 
• 1522-22-1 1,1,1,5,5,5-hexafluoroacetylacetone 
• 75840-25-4 (Z)-3-amino-4,4,4-trifluoro-1-phenylbut-2-en-1-one 
• 106578-65-8 (Z)-4-Amino-1,1,1-trifluoro-4-phenyl-but-3-en-2-one 
• 91529-28-1 4,4,4-Trifluoro-1-phenyl-2-(triphenyl-λ⁵-arsanylidene)-butane-1,3-dione 
• 383-63-1 ethyl trifluoroacetate, 

Downstream Products

• 120513-32-8 2-(5-trifluoromethyl-3-phenyl-1H-pyrazol-1-yl)benzimidazole 
• 70594-16-0 5-trifluoromethyl-3,7-diphenylpyrazolo<1,5-a>pyrimidine 
• 65921-31-5 2-acetoxy-4,4,4-trifluoro-1-phenyl-1,3-butanedione 
• 65-85-0 benzoic acid 
• 76-05-1 trifluoroacetic acid 
• 188817-19-8 2,4,4,4-tetrafluoro-1-phenylbutane-1,3-dione 
• 62847-45-4 5-phenyl-3-(trifluoromethyl)isoxazole 

Relevant articles and documents

Further hit optimization of 6-(trifluoromethyl)pyrimidin-2-amine based TLR8 modulators: Synthesis, biological evaluation and structure–activity relationships

Toll-like receptor 8 (TLR8) is an endosomal TLR that has an important role in the innate human immune system, which is involved in numerous pathological conditions. Excessive activation of TLR8 can lead to inflammatory and autoimmune diseases, which highlights the need for development of TLR8 modulators. However, only a few small-molecule modulators that selectively target TLR8 have been developed. Here, we report the synthesis and systematic investigation of the structure–activity relationships of a series of novel TLR8 negative modulators based on previously reported 6-(trifluoromethyl)pyrimidin-2-amine derivatives. Four compounds showed low-micromolar concentration-dependent inhibition of TLR8-mediated signaling in HEK293 cells. These data confirm that the 6-trifluoromethyl group and two other substituents on positions 2 and 4 are important structural elements of pyrimidine-based TLR8 modulators. Substitution of the main scaffold at position 2 with a methylsulfonyl group or para hydroxy/hydroxymethyl substituted benzylamine is essential for potent negative modulation of TLR8. Our best-in-class TLR8-selective modulator 53 with IC50 value of 6.2 μM represents a promising small-molecule chemical probe for further optimization to a lead compound with potent immunomodulatory properties.

Tetrahydropyrimidinones/thiones stabilized by trifluoromethyl-containing β-diketones

A library of new hydropyrimidinone/thione compounds was synthesized via the classical Biginelli reaction using hydrated cerium(III) chloride as the catalyst. The presence of a trifluoromethyl or methyl group in the diketone starting material has been established to selectively control the outcome of the Biginelli reaction where one of the two possible pyrimidinone/thione compounds is formed. The results showed that the electronic effects of substituents of the diketone directly affect the product formation. The synthesized compounds were fully characterized using 1H, 13C, and two dimensional NMR (2D NMR) spectroscopy, single crystal X-ray diffractometry, FT-IR, and ESI-HDMS techniques. We also report on the uncommon one-bond correlations which were observed in the HMBC spectra and the interesting long-range heteronuclear coupling of fluorine to hydrogen and carbon.

An Integrated Continuous Flow Micro-Total Ultrafast Process System (μ-TUFPS) for the Synthesis of Celecoxib and Other Cyclooxygenase Inhibitors

Integrated continuous manufacturing has emerged as a promising device for the rapid manufacturing of active pharmaceutical ingredients (APIs). We herein report a newly designed continuous flow micro-total process system platform for the rapid manufacturing of celecoxib, a selective nonsteroidal anti-inflammatory drug. This approach has been proven generally for the synthesis of several alkyl and aryl substituted pyrazoles. In order to minimize the tedious work-up process of potential reaction intermediates/products, we have developed a continuous flow extraction and separation platform to carry out the entire reaction sequence resulting in a short residence time with good yield. The present process was further extended to gram-scale synthesis of the COX-2-related API, viz. celecoxib, in the continuous flow process.

Ru-Catalyzed Chemo- and Enantioselective Hydrogenation of β-Diketones Assisted by the Neighboring Heteroatoms

A highly chemo- and enantioselective hydrogenation of β-diketones was achieved by using [Ru(benzene)(S)-SunPhosCl]Cl for consistency in THF. The neighboring heteroatoms played important roles in guaranteeing the reactivity and controlling the chemoselectivity. These results suggested a potential approach for the clean and facile synthesis of functionalized chiral β-hydroxy ketones, which could otherwise be prepared through much less step-economic transformations.

Design and synthesis of novel benzenesulfonamide containing 1,2,3-triazoles as potent human carbonic anhydrase isoforms I, II, IV and IX inhibitors

In a quest to discover new biologically active compounds, a series of twenty novel heterocyclic derivatives substituted at position 5 with -H (7a-7j) or -CF3 (8a-8j), bearing benzenesulfonamide at N-1 position and various aroyl groups at position 4 of the 1,2,3-triazole ring was synthesized and screened for their carbonic anhydrase (CA, EC 4.2.1.1) inhibition potential against four human (h) isoforms hCA I, II, IV and IX. All the compounds (7a-7j and 8a-8j) were synthesized via [3+2] cycloaddition reaction from 4-azidobenzenesulfonamide. Interestingly, compounds 7a-7j were prepared in one pot manner via enaminone intermediate using novel methodology. All the newly synthesized compounds (7a-7j & 8a-8j) were found to be excellent inhibitors of edema related isoform hCA I with their inhibition constant (Ki) ranging from 30.1 to 86.8 nM as compared to standard drug acetazolamide (AAZ) with Ki = 250 nM. Further it was found that most of tested compounds were weaker inhibitors of isoform, hCA II although compounds 7b, 7d-7e, 8a, 8d-8f, 8i (mostly with electron withdrawing substituents) have shown better inhibition potential (Ki i = 52.4 nM) than AAZ (Ki = 74 nM) while against tumor associated hCA IX, all the compounds have shown moderate inhibition potential. Present study have added one more step in exploring the 1,2,3-triazlole moiety in the medicinal field.

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.).

Targeting DNA with anti-tumor activity of the naphthalene imide structure biodegradable derivatives, pharmaceutical composition and its preparation method and application

The invention discloses targeted DNA (deoxyribonucleic acid) naphthyldiimide-structure-containing celecoxib derivatives with antitumor activity, of which the structure is disclosed as Formula (I), wherein R is hydrogen, alkyl group or alkoxy group. The invention also discloses a preparation method of the derivatives and application of the derivatives in preparing drugs for resisting mammary cancer, cervical carcinoma and lung adenocarcinoma. The celecoxib structure is modified, and the naphthyldiimide group is used instead of sulfaphenyl group in the celecoxib, thereby designing and synthesizing a series of celecoxib derivatives containing the naphthyldiimide structure unit. The synthesized compounds 5a-5t have certain inhibiting actions on human mammary cancer cells, Hela cells and human lung adenocarcinoma cells. Part of the compounds have excellent antitumor activity, wherein the compounds 5o and 5h have very high selectivity for Hela cells, and the compound 5i has high selectivity for MCF-7 cells. The IC50 value is greatly lower than that of amonafide and higher than that of cis-platinum and celecoxib.

A new series of HCV inhibitors based on a 2-(thieno[2,3B]pyridin-2-yl)-1,3,4-oxadiazole scaffold

A new series of HCV inhibitors based on a 2-(thieno[2,3-b]pyridin-2-yl)-1,3,4-oxadiazole scaffold was developed. Detailed SAR investigations revealed the HCV inhibitory activity was sensitive to the size of C5, the C6-fused ring, and the size and flexibility of C5′ cycloalkane, which led to the identification of several compounds with potent inhibitory activity against HCV genotype 1b replicon. The most potent compound 10d showed ～100-fold improvement in potency compared with compound 1, with an EC50 of 0.039 μM, but without obvious cytotoxicity in vitro.

SMALL MOLECULE INHIBITORS OF LACTATE DEHYDROGENASE AND METHODS OF USE THEREOF

Provided is a compound of formula (I)[Formula (I) should be inserted here], in which Ar1, R1, U, V, W, X, and p are as described herein. Also provided are methods of using a compound of formula (I), including a method of treating cancer, a method of treating a patient with cancer cells resistant to an anti-cancer agent, and a method of inhibiting lactate dehydrogenase A (LDHA) and/ or lactate dehydrogenase B (LDHB) activity in a cell.