653-31-6

Usage

Uses

Used in Organic Chemistry:
2-(PENTAFLUOROPHENYL)ETHANOL is used as a reagent for its ability to influence the reactivity and stability of molecules, which is crucial in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
2-(PENTAFLUOROPHENYL)ETHANOL is used as a building block for the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
2-(PENTAFLUOROPHENYL)ETHANOL is used as a precursor in the production of agrochemicals, aiding in the creation of effective pesticides and other agricultural chemicals.
Used in Fine Chemicals Synthesis:
2-(PENTAFLUOROPHENYL)ETHANOL is used as an intermediate in the synthesis of fine chemicals, which are important in various specialized applications such as fragrances, dyes, and other high-value products.
Used as a Solvent:
2-(PENTAFLUOROPHENYL)ETHANOL is used as a solvent in various chemical processes, taking advantage of its unique properties to dissolve and facilitate reactions with other compounds.
Used in Manufacturing Process of Other Organic Compounds:
2-(PENTAFLUOROPHENYL)ETHANOL is used as an intermediate in the manufacturing process of other organic compounds, playing a key role in the production of a wide range of chemical products.

InChI:InChI=1/C8H5F5O/c9-4-3(1-2-14)5(10)7(12)8(13)6(4)11/h14H,1-2H2

Upstream product

• 784-35-0 ethyl pentafluorophenylacetate 
• 653-34-9 2,3,4,5,6-pentafluorostyrene 
• 344-04-7 bromopentafluorobenzene 
• 75-21-8 oxirane 
• 879-06-1 pentafluorophenylmagnesium chloride 
• 879-05-0 2,3,4,5,6-pentafluorophenylmagnesium bromide 
• 1765-40-8 (bromomethyl)pentafluorobenzene 
• 653-35-0 2,3,4,5,6-pentafluorobenzyl chloride 
• 440-60-8 (2,3,4,5,6-pentafluorophenyl)methanol 
• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 
• 771-56-2 2,3,4,5,6-pentafluorotoluene 
• 653-30-5 (pentafluorophenyl)acetonitrile 
• 653-37-2 perfluorobenzaldehyde 
• 653-21-4 2,3,4,5,6-pentafluorophenylacetic acid 

Downstream Products

• 2412-72-8 2-Pentafluorophenylethyl bromide 
• 201156-98-1 2-Methoxy-5,5-dimethyl-2-(2-pentafluorophenyl-ethoxy)-2,5-dihydro-[1,3,4]oxadiazole 
• 178685-11-5 1,2,3,4,5-Pentafluoro-6-(2-iodo-ethyl)-benzene 
• 1350703-24-0 2-pentafluorophenylethyl β-D-glucopyranoside 
• 653-34-9 2,3,4,5,6-pentafluorostyrene 

Relevant academic research and scientific papers

Direct Ruthenium-Catalyzed Hydrogenation of Carboxylic Acids to Alcohols

The "green" reduction of carboxylic acids to alcohols is a challenging task in organic chemistry. Herein, we describe a general protocol for generation of alcohols by catalytic hydrogenation of carboxylic acids. Key to success is the use of a combination of Ru(acac)3, triphos and Lewis acids. The novel method showed broad substrate tolerance and a variety of aliphatic carboxylic acids including biomass-derived compounds can be smoothly reduced.

Synthesis and neuroprotective effects of the fluorine substituted salidroside analogues in the PC12 cell model exposed to hypoglycemia and serum limitation

Salidroside (Sal) is a natural antioxidant extracted from the root of Rhodiola rosea L., a traditional Chinese medicinal plant, which elicits neuroprotective effects in the treatment of ischemic stroke. In an attempt to improve its neuroprotective effects, fluorine substituted Sal analogues were synthesized and their neuroprotective activities against the hypoglycemia and serum limitation induced cell injury in differentiated PC12 cells were evaluated. The target compounds displayed strong protective effects on the cell viability against the damage caused by hypoglycemia and serum limitation, especially for D1, which had a great potency superior to Sal and efficiently inhibited hypoglycemia and serum limitation induced cell nuclear morphologic changes and the increased apoptotic rate in a dose-dependent manner. These new findings may provide potentially important information for further development of Sal analogues and lay the basis for further studies on the cerebral ischemic stroke and neurodegenerative diseases for human clinical treatment.

Regioselective hydroboration-oxidation and -amination of fluoro-substituted styrenes

Hydroboration of fluorinated styrenes with common hydroborating agents results in polymerization. However, regioselective hydroboration has been achieved by utilizing iodoborane-dimethyl sulfide. A series of fluorinated β-phenethyl alcohols and amines were synthesized via this methodology.

Investigation of the factors controlling the regioselectivity of the hydroboration of fluoroolefins

Either Markovnikov or anti-Markovnikov regioselectivity can be achieved at will during the hydroboration-oxidation of perfluoroalkyl(aryl)ethylenes by varying the hydroborating agent.

Markovnikov hydroboration of perfluoroalkylethylenes

A Markovnikov regioselectivity of 92% or higher is achieved in the hydroboration of a series of perfluoroalkylethylenes and 2',3',4',5',6'- pentafluorostyrene with dichloro- and dibromoborane to provide the corresponding (fluoroalkyl)dihaloboranes (see reaction).

2-substituted (2SR)-2-amino-2-((1SR,2SR)-2-carboxycycloprop-1- yl)glycines as potent and selective antagonists of group II metabotropic glutamate receptors. 2. Effects of aromatic substitution, pharmacological characterization, and bioavailability

In this paper we describe the synthesis of a series of α-substituted analogues of the potent and selective group II metabotropic glutamate receptor (mGluR) agonist (1S,1'S,2'S)-carboxycyclopropylglycine (2, L-CCG 1). Incorporation of a substituent on the amino acid carbon converted the agonist 2 into an antagonist. All of the compounds were prepared and tested as a series of four isomers, i.e., two racemic diastereomers. On the basis of the improvement in affinity realized for the α-phenylethyl analogue 3, in this paper we explored the effects of substitution on the aromatic ring as a strategy to increase the affinity of these compounds for group II mGluRs. Affinity for group II mGluRs was measured using [3H]glutamic acid (Glu) binding in rat forebrain membranes. Antagonist activity was confirmed for these compounds by measuring their ability to antagonize (1S,3R)-1- aminocyclopentane-1,3-dicarboxylic acid-induced inhibition of forskolin stimulated cyclic-AMP in RGT cells transfected with human mGluR2 and mGluR3. Meta substitution on the aromatic ring of 3 with a variety of substituents, both electron donating (e.g., methyl, hydroxy, amino, methoxy, phenyl, phenoxy) and electron withdrawing (e.g., fluorine, chlorine, bromine, carboxy, trifluoromethyl) gave from 1.5- to 4.5-fold increases in affinity. Substitution with p-fluorine, as in 97 (IC50 = 0.022 ± 0.002), was the exception. Here, a greater increase in affinity was realized than for either the ortho- or meta-substituted analogues; 97 was the most potent compound resulting from monosubstitution of the aromatic. At best, only modest increases in affinity were realized for certain compounds bearing either two chlorines or two fluorines, and two methoxy groups gave no improvement in affinity (all examined in a variety of substitution patterns). Three amino acids, 4, 5, and 104, were resolved into their four constituent isomers, and affinity and functional activity for group II mGluRs was found to reside solely in the S,S,S-isomers of each, consistent with 1. With an IC50 = 2.9 ± 0.6 nM, the resolved xanthylmethyl compound 168 was the most potent compound from this SAR. Amino acid 168 demonstrated high plasma levels following intraperitoneal (ip) administration and readily penetrated into the brain. This compound, however, had only limited (~5%) oral bioavailability. Systemic administration of 168 protected mice from limbic seizures produced by the mGluR agonist 3,5-dihydroxyphenylglycine, with an ED50 = 31 mg/kg (ip, 60 min preinjection). Thus, 168 represents a valuable tool to study the role of group II mGluRs in disease.