832-72-4

Usage

Uses

Used in Pharmaceutical Industry:
(2,3,4,5,6-pentafluorophenyl)acetyl chloride is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical industry, (2,3,4,5,6-pentafluorophenyl)acetyl chloride serves as an essential component in the production of certain agrochemicals. Its reactivity enables the creation of effective compounds for pest control and crop protection.
Used in Specialty Chemicals Manufacturing:
(2,3,4,5,6-pentafluorophenyl)acetyl chloride is utilized in the manufacturing of specialty chemicals, where its reactive nature contributes to the formation of complex and high-value chemical products.
Used in Dye Production:
(2,3,4,5,6-pentafluorophenyl)acetyl chloride also finds application in the dye industry, where it is used in the synthesis of various dyes with specific color properties and stability.
It is important to handle (2,3,4,5,6-pentafluorophenyl)acetyl chloride with care due to its potential to cause irritation and injury, highlighting the need for proper safety measures during its use in various applications.

InChI:InChI=1/C8H2ClF5O/c9-3(15)1-2-4(10)6(12)8(14)7(13)5(2)11/h1H2

Upstream product

• 653-21-4 2,3,4,5,6-pentafluorophenylacetic acid 

Downstream Products

• 34073-32-0 2',3',4',5',6'-Tetrafluor-desoxybenzoin 
• 24043-89-8 1,2-bis(pentafluorophenyl)ethanone 
• 13664-67-0 2-Pentafluorphenyl-1-p-tolyl-ethanon 
• 289477-27-6 N,N'-bis[2-(2,3,4,5,6-pentafluorophenyl)etylamide]-4,13-diaza-18-crown-6 
• 894802-89-2 3-oxo-4-pentafluorophenyl-butyric acid ethyl ester 
• 1382271-38-6 N-(3,6-dioxocyclohexa-1,4-dien-1-yl)-2-(pentafluorophenyl)-N-phenylacetamide 
• 1382271-08-0 N-(2,5-dimethoxyphenyl)-2-(pentafluorophenyl)-N-phenylacetamide 
• 894802-98-3 7-amino-4-pentafluorophenylmethyl-1H-quinolin-2-one 
• 5736-46-9 bis(pentafluorophenyl)methane 
• 19225-85-5 2,3,4,5,6-Pentafluorphenylacetyl-malonsaeurediethylester 

Relevant academic research and scientific papers

Phosphonic acid analogs of fluorophenylalanines as inhibitors of human and porcine aminopeptidases N: Validation of the importance of the substitution of the aromatic ring

A library of phosphonic acid analogs of phenylalanine substituted with fluorine, chlorine and trifluoromethyl moieties on the aromatic ring was synthesized and evaluated for inhibitory activity against human (hAPN) and porcine (pAPN) aminopeptidases. Fluorogenic screening indicated that these analogs are micromolar or submicromolar inhibitors, both enzymes being more active against hAPN. In order to better understand the mode of the action of the most active compounds, molecular modeling was used. It confirmed that aminophosphonic portion of the enzyme is bound nearly identically in the case of all the studied compounds, whereas the difference in activity results from the placement of aromatic side chain of an inhibitor. Interestingly, both enantiomers of the individual compounds are usually bound quite similarly.

Synthesis and biological evaluation of fluorinated N-benzoyl and N-phenylacetoyl derivatives of 3-(4-aminophenyl)-coumarin-7-O-sulfamate as steroid sulfatase inhibitors

In the present work, we report convenient methods for the synthesis of 3-(4-aminophenyl)-coumarin-7-O-sulfamate derivatives N-acylated with fluorinated analogues of benzoic or phenylacetic acid as steroid sulfatase (STS) inhibitors. The design of these potential STS inhibitors was supported by molecular modeling techniques. Additionally, computational docking methods were used to determine the binding modes of the synthesized inhibitors and to identify potential interactions between inhibitors and amino acid residues located in the active site of STS. The inhibitory effects of the synthesized compounds were tested on STS isolated from human placenta and against estrogen receptor-(ER)-positive MCF-7 and T47D cells, as well as ER-negative MDA-MB-231 and SkBr3 cancer cell lines. In the course of our investigation, compounds 6c and 6j demonstrated the highest inhibitory effect in enzymatic STS assays, both with IC50values of 0.18?μM (the IC50value of coumarin-7-O-sulfamate is 1.38?μM, used as a reference). Compound 6j exhibited the highest potency against the MCF-7 and T47D cell lines (15.9?μM and 8.7?μM, respectively). The GI50values of tamoxifen (used as a reference) were 6.8; 10.6; 15.1; 12.5?μM against MCF-7, T47D, MDA-MB-231 and SkBr3 cancer cell lines, respectively. Despite the slightly lower activity of compounds 1 and 2 (both in enzymatic and cell-based experiments) compared to 6g and 6j, analogues 1 and 2 proved to selectively inhibit the growth of ER- and PR-positive cell lines.

Synthesis and biological evaluation of N-acylated tyramine sulfamates containing C–F bonds as steroid sulfatase inhibitors

Steroid sulfatase (STS) is responsible for the hydrolysis of biologically inactive sulfated steroids into their active un-sulfated forms and promotes the growth of various hormone-dependent cancers (e.g., breast cancer). Therefore, the STS enzyme is a promising therapeutic target for the treatment of steroid-sensitive cancers. Herein, we report the synthesis and biological evaluation of sulfamate analogs as potential STS inhibitors based on N-acylated tyramines that contain C–F bonds. The inhibitory effects of the analogs were tested using STS isolated from human placenta. Of the analogs tested, 4-(2-perfluoroundecanoylaminoethyl)-phenyl sulfamate, 5r, demonstrated the greatest inhibitory effect, with an IC50 value of 2.18?μm (IC50 value of 2.13?μm for coumarin-7-O-sulfamate was used as a reference). These findings were supported by the results our computational analyses performed using molecular docking techniques.

Synthesis and Biological Evaluation of Fluorinated 3-Phenylcoumarin-7-O-Sulfamate Derivatives as Steroid Sulfatase Inhibitors

In the present work, we report the initial results of our study on a series of 3-phenylcoumarin sulfamate-based compounds containing C-F bonds as novel inhibitors of steroid sulfatase. The new compounds are potent steroid sulfatase inhibitors, possessing more than 10 times higher inhibitory potency than coumarin-7-O-sulfamate. In the course of our investigation, compounds 2b and 2c demonstrated the highest inhibitory effect on the enzymatic steroid sulfatase assay; both had IC50 values of 0.27 μm (the IC50 value of coumarin-7-O-sulfamate is 3.5 μm, used as a reference).

Redox-responsive conformational alteration of aromatic amides bearing N-quinonyl system

Redox-induced conformational alteration of N-aryl-N-phenylamides, in which the N-aryl group consists of a hydroquinone-p-quinone system, was examined. The reduced form bearing a dihydroxyphenyl or dimethoxyphenyl group exists mainly in the E-form, whereas the oxidized form bearing a N-benzoquinone moiety takes the Z-form both in the crystal and in solution. This redox-induced conformational alteration is associated with a marked change in optical properties. This system appears to have suitable properties for use in external redox stimulus-responsive functional switching.

Modulation of luminescence intensity of lanthanide complexes by photoinduced electron transfer and its application to a long-lived protease probe

Luminescent lanthanide complexes (Tb3+, Eu3+, etc.) have excellent properties for biological applications, including extraordinarily long lifetimes and large Stokes shifts. However, there have been few reports of lanthanide-based functional probes, because of the difficulty in designing suitable complexes with a luminescent on/off switch. Here, we have synthesized a series of complexes which consist of three moieties: a lanthanide chelate, an antenna, and a luminescence off/on switch. The antenna is an aromatic ring which absorbs light and transmits its energy to the metal, and the switch is a benzene derivative with a different HOMO level. If the HOMO level is higher than a certain threshold, the complex emits no luminescence at all, which indicates that the lanthanide luminescence can be modulated by photoinduced electron transfer (PeT) from the switch to the sensitizer. This approach to control lanthanide luminescence makes possible the rational design of functional lanthanide complexes, in which the luminescence property is altered by a biological reaction. To exemplify the utility of our approach to the design of lanthanide complexes with a switch, we have developed a novel protease probe, which undergoes a significant change in luminescence intensity upon enzymatic cleavage of the substrate peptide. This probe, combined with time-resolved measurements, was confirmed in model experiments to be useful for the screening of inhibitors, as well as for clinical diagnosis.

Alkali metal cation - π Interactions observed by using a lariat ether model system

The Na+ or K+ cation - π interaction has been experimentally probed by using synthetic receptors that comprise diaza-18-crown-6 lariat ethers having ethylene sidearms attached to aromatic π-donors. The side chains are 2-(3-indolyl)ethyl (7), 2-(3-(1-methyl)indolyl)ethyl (8), 2-(3-(5-methoxy)indolyl)ethyl (9), 2-(4-hydroxyphenyl)ethyl (10), 2-phenylethyl (11), 2-pentafluorophenylethyl (12), and 2-(1-naphthyl)ethyl (13). Solid-state structures are reported for six examples of alkali metal complexes in which the cation is π-coordinated by phenyl, phenol, or indole. Indole-containing crown, 7, adopts a similar conformation when bound by NaI, KI, KSCN, or KPF6. In each case, the macroring and both arenes coordinate the cation; the counteranion is excluded from the solvation sphere. NMR measurements in acetone-d6 solution confirm the observed solid-state conformations of unbound 7 and 7·NaI. In 7·Na+ and 7·K+, the pyrrolo, rather than benzo, subunit of indole is the π-donor for the alkali metal cation. Cation-π complexes were also observed for 10·KI and 11·KI. In these cases, the orientation of the cation on the aromatic ring is in accord with the binding site predicted by computational studies. In contrast to the phenyl case (11) the pentafluorophenyl group of 12 failed to coordinate K+. Solid-state structures are also reported for 7·NaPF6, 10·NaI, 11·NaI, 13·KI, 13·KPF6, and 9·NaI, in which cation-π complexation is not observed. Steric and electrostatic considerations in the π-complexation of alkali metal cations by these lariat ethers are thought to account for the observed complexation behavior or lack thereof.