785-56-8

Basic information

• Product Name: 3,5-Bis(trifluoromethyl)benzoyl chloride
• Synonyms: 3,5-Bis(trifluoromethyl)benzoylchloride98%;3,5-BIS(TRIFLUOROMETHYL)BENZOYCHLORIDE;Benzoyl chloride, 3,5-bis(trifluoromethyl)-;3,5-Bis(trifluoromethyl)benzoic acid chloride;3,5-Bis(trifluoromethyl)benzoyl chloride,97%;Benzoyl Chloride, 3;3,5-bis(Trifluoromethyl)benzoyl chloride, 95+%;[3,5-bis(trifluoroMethyl)phenyl]carbonylchloranuide
• CAS NO: 785-56-8
• Molecular Formula: C₉H₃ClF₆O
• Molecular Weight: 276.56
• EINECS: 212-322-0
• Product Categories: Miscellaneous;Benzotrifluoride Series;Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 785-56-8.mol

Chemical Properties

• Melting Point: 5-10C
• Boiling Point: 65-67 °C (12 mmHg)
• Flash Point: 162 °F
• Appearance: Clear colorless to very slightly yellow/Liquid
• Density: 1.526 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0865mmHg at 25°C
• Refractive Index: n20/D 1.435(lit.)
• Sensitive: Moisture Sensitive
• BRN: 2593440
• CAS DataBase Reference: 3,5-Bis(trifluoromethyl)benzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Bis(trifluoromethyl)benzoyl chloride(785-56-8)
• EPA Substance Registry System: 3,5-Bis(trifluoromethyl)benzoyl chloride(785-56-8)

Safety Data

• Hazard Codes: C
• Statements: 34-37-36
• Safety Statements: 26-36/37/39-45-27
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 10-19-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 785-56-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Analysis:
3,5-Bis(trifluoromethyl)benzoyl chloride is used as a derivatization agent for the quantitative and selective assay of low levels of clonidine in human plasma. This application is crucial for monitoring the therapeutic levels of clonidine, a medication used to treat high blood pressure and other conditions, ensuring patient safety and effective treatment.
In this context, 3,5-Bis(trifluoromethyl)benzoyl chloride reacts with clonidine to form a derivative that can be easily detected and quantified using analytical techniques such as high-performance liquid chromatography (HPLC) or mass spectrometry. This allows for accurate measurement of clonidine concentrations in patient samples, facilitating optimal dosing and treatment management.

InChI:InChI=1/C10H4Cl3F17Si/c11-31(12,13)2-1-3(14,15)4(16,17)5(18,19)6(20,21)7(22,23)8(24,25)9(26,27)10(28,29)30/h1-2H2

Upstream product

• 725-89-3 3,5-bistrifluoromethylbenzoic acid 
• 402-31-3 1,3-bis(trifluoromethyl)benzene 
• 328-70-1 3,6-bis(trifluoromethyl)bromobenzene 
• 401-96-7 3,5-bis(trifluoromethyl)benzoyl fluoride 
• 1026194-04-6 N-(5-amino-2-methylphenyl)-5-(3-pyridyl)-2-pyrimidinamine 

Downstream Products

• 30071-94-4 3,5-bis(trifluoromethyl)phenyl n-butyl ketone 
• 30071-93-3 3,5-bis(trifluoromethyl)phenyl methyl ketone 
• 863-99-0 Di-<3.5-bis-trifluormethyl-benzoyl>-peroxyd 
• 20929-20-8 3,5-Di-(trifluormethyl)-benzoesaeure-N-methyl-N-<2-dimethylamino-ethyl>-amid 
• 106376-15-2 3,5-Bis-trifluoromethyl-benzoic acid phenyl ester 
• 171112-69-9 C₂₂H₂₄F₆NO₃ 
• 170729-72-3 2-(R)-(3,5-bis(tri-fluoro-methyl)benzoyloxy)-3-(S)-phenyl-4-benzyl morpholine 
• 879507-31-0 3,5-bis(trifluoromethyl)-N-(4-methyl-3-nitro-phenyl)-benzamide 

Relevant articles and documents

Cyano-and ketone-containing selenoesters as multi-target compounds against resistant cancers

Fifteen selenocompounds, comprising of eight ketone-containing selenoesters (K1–K8, also known as oxoselenoesters) and seven cyano-containing selenoesters (N1–N7, known also as cyanoselenoesters), have been designed, synthesized, and evaluated as novel anticancer agents. These compounds are derivatives of previously reported active selenoesters and were prepared following a three-step one-pot synthetic route. The following evaluations were performed in their biological assessment: cytotoxicity determination, selectivity towards cancer cells in respect to non-cancer cells, checkerboard combination assay, ABCB1 inhibition and inhibition of ABCB1 ATPase activity, apoptosis induction, and wound healing assay. As key results, all the compounds showed cytotoxicity against cancer cells at low micromolar concentrations, with cyanoselenoesters being strongly selective. All of the oxoselenoesters, except K4, were potent ABCB1 inhibitors, and two of them, namely K5 and K6, enhanced the activity of doxorubicin in a synergistic manner. The majority of these ketone derivatives modulated the ATPase activity, showed wound healing activity, and induced apoptosis, with K3 being the most potent, with a potency close to that of the reference compound. To summarize, these novel derivatives have promising multi-target activity, and are worthy to be studied more in-depth in future works to gain a greater understanding of their potential applications against cancer.

Nickel-Mediated Photoreductive Cross Coupling of Carboxylic Acid Derivatives for Ketone Synthesis**

A simple visible light photochemical, nickel-catalyzed synthesis of ketones from carboxylic acid-derived precursors is presented. Hantzsch ester (HE) functions as a cheap, green and strong photoreductant to facilitate radical generation and also engages in the Ni-catalytic cycle to restore the reactive species. With this dual role, HE allows for the coupling of a large variety of radicals (1°,2°, benzylic, α-oxy & α-amino) with aroyl and alkanoyl moieties, a new feature in reactions of this type. With both precursors deriving from abundant carboxylic acids, this protocol is a welcome addition to the organic chemistry toolbox. The reaction proceeds under mild conditions without the need for toxic metal reagents or bases and shows a wide scope, including pharmaceuticals and complex molecular architectures.

Isoalantolactone derivative, pharmaceutical composition and application thereof

The invention relates to an isoalantolactone derivative, a pharmaceutical composition and application thereof, especially use of the isoalantolactone derivative shown as formula (I) or a salt pharmaceutical compound thereof in preparation of adjuvant drugs treating cancer, a pharmaceutical composition containing a therapeutically effective amount of isoalantolactone derivative (I) or its salt anda pharmaceutically acceptable carrier or a composition with other anticancer drugs.

Chemo- and Regioselective Functionalization of Isotactic Polypropylene: A Mechanistic and Structure-Property Study

Polyolefins represent a high-volume class of polymers prized for their attractive thermomechanical properties, but the lack of chemical functionality on polyolefins makes them inadequate for many high-performance engineering applications. We report a metal-free postpolymerization modification approach to impart functionality onto branched polyolefins without the deleterious chain-coupling or chain-scission side reactions inherent to previous methods. The identification of conditions for thermally initiated polyolefin C-H functionalization combined with the development of new reagents enabled the addition of xanthates, trithiocarbonates, and dithiocarbamates to a variety of commercially available branched polyolefins. Systematic experimental and kinetic studies led to a mechanistic hypothesis that facilitated the rational design of reagents and reaction conditions for the thermally initiated C-H xanthylation of isotactic polypropylene (iPP) within a twin-screw extruder. A structure-property study showed that the functionalized iPP adheres to polar surfaces twice as strongly as commercial iPP while demonstrating similar tensile properties. The fundamental understanding of the elementary steps in amidyl radical-mediated polyolefin functionalization provided herein reveals key structure-reactivity relationships for the design of improved reagents, while the demonstration of chemoselective and scalable iPP functionalization to realize a material with improved adhesion properties indicates the translational potential of this method.

Production method of fluvoxamine maleate intermediate (5-methoxy-1-(4-trifluoromethyl benzyl)pentanone)

The invention provides a production method of a fluvoxamine maleate intermediate (5-methoxy-1-(4-trifluoromethyl benzyl)pentanone). The production method comprises the following steps of adding 1,2-dichloroethane into 3,5-difluoromethyl benzoic acid, mixing under the low-temperature environment, heating to 60 to 65 DEG C, uniformly stirring, continuing to heat to 80 to 90 DEG C, dripping thionyl chloride, heating and refluxing, stirring to react until no gas overflows, reducing pressure, and distilling, so as to obtain 3,5-bis(trifluoromethyl) benzoyl chloride; adding 1-bromo-4-methyl butyl ether into a solvent, uniformly mixing, adding carbon nanotube-modified magnesium micro-nanoparticle to mix, and dripping benzene diiodide, so as to obtain a Grignard reagent containing the carbon nanotubes; under the ice bath environment, adding the 3,5-bis(trifluoromethyl) benzoyl chloride into a solvent, adding a ferrous chloride catalyst to mix, adding the Grignard reagent containing the carbonnanotubes, and continuing to react, so as to obtain the 5-methoxy-1-(4-trifluoromethyl benzyl)pentanone.

C-H and N-H Bond Annulation of Benzamides with Isonitriles Catalyzed by Cobalt(III)

A simple efficient, atom-economical procedure was developed for the cobalt-catalyzed C-H bond annulation of benzamides with isonitriles under mild conditions. The reaction tolerates a variety of functional group including heterocycles. Diverse 3-(alkylimino)-2-quinolin-8-yl-2,3-dihydro-1 H -isoindol-1-ones were synthesized using isonitriles as the C1 source through C-H and N-H bond annulation via C-H bond activation in a 'green' solvent. Vinylamides were also used similarly with tert -butyl isonitrile to give 3-(tert -butylimino)-1-quinolin-8-yl-1 H -pyrrol-2(5 H)-ones.

Site-Selective Aliphatic C-H Chlorination Using N-Chloroamides Enables a Synthesis of Chlorolissoclimide

Methods for the practical, intermolecular functionalization of aliphatic C-H bonds remain a paramount goal of organic synthesis. Free radical alkane chlorination is an important industrial process for the production of small molecule chloroalkanes from simple hydrocarbons, yet applications to fine chemical synthesis are rare. Herein, we report a site-selective chlorination of aliphatic C-H bonds using readily available N-chloroamides and apply this transformation to a synthesis of chlorolissoclimide, a potently cytotoxic labdane diterpenoid. These reactions deliver alkyl chlorides in useful chemical yields with substrate as the limiting reagent. Notably, this approach tolerates substrate unsaturation that normally poses major challenges in chemoselective, aliphatic C-H functionalization. The sterically and electronically dictated site selectivities of the C-H chlorination are among the most selective alkane functionalizations known, providing a unique tool for chemical synthesis. The short synthesis of chlorolissoclimide features a high yielding, gram-scale radical C-H chlorination of sclareolide and a three-step/two-pot process for the introduction of the β-hydroxysuccinimide that is salient to all the lissoclimides and haterumaimides. Preliminary assays indicate that chlorolissoclimide and analogues are moderately active against aggressive melanoma and prostate cancer cell lines.

From Lead to Drug Candidate: Optimization of 3-(Phenylethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine Derivatives as Agents for the Treatment of Triple Negative Breast Cancer

Herein we report the sophisticated process of structural optimization toward a previously disclosed Src inhibitor, compound 1, which showed high potency in the treatment of triple negative breast cancer (TNBC) both in vitro and in vivo but had considerable toxicity. A series of 3-(phenylethynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine derivatives were synthesized. In vitro cell-based phenotypic screening together with in vivo assays and structure-activity relationship (SAR) studies finally led to the discovery of N-(3-((4-amino-1-(trans-4-hydroxycyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)ethynyl)-4-methylphenyl)-4-methyl-3-(trifluoromethyl)benzamide (13an). 13an is a multikinase inhibitor, which potently inhibited Src (IC50 = 0.003 μM), KDR (IC50 = 0.032 μM), and several kinases involved in the MAPK signal transduction. This compound showed potent anti-TNBC activities both in vitro and in vivo, and good pharmacokinetic properties and low toxicity. Mechanisms of action of anti-TNBC were also investigated. Collectively, the data obtained in this study indicate that 13an could be a promising drug candidate for the treatment of TNBC and hence merits further studies.

C-H Xanthylation: A Synthetic Platform for Alkane Functionalization

Intermolecular functionalizations of aliphatic C-H bonds offer unique strategies for the synthesis and late-stage derivatization of complex molecules, but the chemical space accessible remains limited. Herein, we report a transformation significantly expanding the chemotypes accessible via C-H functionalization. The C-H xanthylation proceeds in useful chemical yields with the substrate as the limiting reagent using blue LEDs and an easily prepared N-xanthylamide. The late-stage functionalizations of complex molecules occur with high levels of site selectivity, and a variety of common functionality is tolerated in the reaction. This approach capitalizes on the versatility of the xanthate functional group via both polar and radical manifolds to unlock a wide array of C-H transformations previously inaccessible in synthesis.

SORAFENIB ANALOGS AND USES THEREOF

The present invention provides, inter alia, compounds according to formula I. Also provided are pharmaceutical compositions and kits containing such compounds. Methods for using such compounds, compositions, and kits for treating a subject having system xc-, dysregulation for activating ferroptosis, for inhibiting system xc- in a cell, and for monitoring treatment of a subject having system xc- dysregulation are provided as well.