444-30-4

Usage

Uses

Used in Material Science:
alpha,alpha,alpha-Trifluoro-o-cresol is used as a chemical intermediate for the synthesis of various compounds with potential applications in the material science field. Its unique chemical structure allows for the creation of novel materials with specific properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, alpha,alpha,alpha-Trifluoro-o-cresol is used as a building block for the development of new drugs. Its chemical properties make it a valuable component in the design and synthesis of pharmaceutical compounds.
Used in Research and Development:
alpha,alpha,alpha-Trifluoro-o-cresol is utilized in research and development for the investigation of self-aggregation properties of polyanion-containing cinnamoyl groups with diazoresin (DR). This research contributes to the formation of stable covalent ultrathin films through UV irradiation, which can have potential applications in various industries.
Used in Chemical Synthesis:
alpha,alpha,alpha-Trifluoro-o-cresol is used as a key component in the synthesis of various organic compounds. Its unique fluorinated structure allows for the development of new chemical entities with specific properties and potential applications in different fields.

InChI:InChI=1/C7H5F3O/c8-7(9,10)5-3-1-2-4-6(5)11/h1-4,11H

Upstream product

• 88-17-5 2-(trifluoromethyl)benzenamine 
• 98-08-8 α,α,α-trifluorotoluene 
• 114436-00-9 cis-3-trifluoromethylcyclohexa-3,5-diene-1,2-diol 
• 88-16-4 1-chloro-2-(trifluoromethyl)benzene 
• 75-63-8 Bromotrifluoromethane 
• 108-95-2 phenol 
• 80783-62-6 N-Trifluoromethyl-N-nitrosobenzenesulfonamide 
• 129922-37-8 S-(trifluoromethyl)-3,7-dinitrodibenzothiophenium trifluoromethanesulfonate 
• 384-22-5 2-nitrobenzotrifluoride 
• 351-36-0 N-acetyl-3-trifluoromethylbenzenamine 
• 393-11-3 4-nitro-3-(trifluoromethyl)benzeneamine 
• 392-83-6 o-trifluoromethylphenyl bromide 
• 89466-08-0 2-hydroxyphenyl boronic acid 
• 129946-88-9 Umemoto's reagent 

Downstream Products

• 392-92-7 2,4-dibromo-6-trifluoromethyl-phenol 
• 62489-48-9 4-[6-(2-Trifluoromethylphenoxy)hexyl]-3,5-heptanedione 
• 149209-47-2 2-[2-(trifluoromethyl)phenoxy]tetrahydro-2H-pyrane 
• 136539-10-1 3-(Trifluoromethyl)phenyl 2-Chloro-4-(trifluoromethyl)-5-thiazolylcarbamate 
• 583-59-5 2-Methylcyclohexanol 
• 56734-74-8 2-(trifluoromethyl)cyclohexanone 
• 104282-19-1 cis-, trans-2-(trifluoromethyl)cyclohexanol 
• 150503-14-3 o-(trifluoromethyl)phenyl dodecyl ether 
• 57477-80-2 2-trifluoromethyl-4-(1,1-dimethylethyl)phenol 
• 160725-42-8 O-(2-trifluoromethylphenyl)hydroxylamine 
• 1548-62-5 2-Nitro-6-(trifluoromethyl)phenol 
• 165404-89-7 3-[(tert-butyldimethylsilyloxy)methyl]-6-[(2-trifluoromethylphenyloxy)methyl]-1,2-dithiin 
• 50824-04-9 4-bromo-2-(trifluoromethyl)phenol 
• 69-72-7 salicylic acid 

Relevant academic research and scientific papers

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.

Method for hydrolyzing diarylether compound to generate aryl phenol compound

The invention discloses a method for hydrolyzing a diarylether compound to generate an arylphenol compound. According to the method, visible light is utilized to excite a photosensitizer for catalysis. In a reaction solvent, the raw material in the formula (1) breaks a C (sp2)-O bond under the auxiliary action of acid, and hydrolysis is performed to obtain the bimolecular aryl phenol compounds in the formula (3) and the formula (4). The method can catalyze the reaction at room temperature, is green and environment-friendly, and is easy to operate; the universality is wide, the reaction yield is relatively high, and the tolerance of functional groups is strong; the synthesis method not only can realize small-scale hydrolysis conversion of various diarylether compounds, but also can realize hydrolysis of herbicidal ether, triclosan and a lignin template substrate, and even can realize large-scale hydrolysis of triclosan and the lignin template substrate to realize gram-level degradation. A new strategy is provided for recovering phenol derivatives through lignin hydrolysis, degrading pesticides and purifying wastewater containing a degerming agent or herbicide. The method has wide application prospect and use value.

Aerobic photooxidative hydroxylation of boronic acids catalyzed by anthraquinone-containing polymeric photosensitizer

We report herein the synthesis of a polymeric photosensitizer and its application in aerobic photooxidative hydroxylation of boronic acids. The polymeric photosensitizer was synthesized by the condensation of anthraquinone-2-carbonyl chloride (AQ-2-COCl) with poly (2-hydroxyethyl methacrylate) (PHEMA). The photo-oxidative hydroxylation of boronic acids using anthraquinone-containing-poly (2-hydroxyethyl methacrylate) (AQ-PHEMA) was then explored and shown to exhibit high efficiency and broad scope. Moreover, AQ-PHEMA could be easily recovered and reused for more than 20 times without significant loss of the catalytic activity.

Visible-light-induced Pd-catalyzed: Ortho -trifluoromethylation of acetanilides with CF3SO2Na under ambient conditions in the absence of an external photocatalyst

A visible-light-induced Pd-catalyzed ortho-trifluoromethylation of acetanilides with CF3SO2Na was developed. The reaction proceeded smoothly at room temperature in air without any external photocatalyst or additive, providing the desired products in moderate to good yields with good functional group tolerance and regioselectivity.

Photoinduced Hydroxylation of Organic Halides under Mild Conditions

Presented in this paper is photoinduced hydroxylation of organic halides, providing a mild access to a range of functionalized phenols and aliphatic alcohols. These reactions generally proceed under mild reaction conditions with no need for a photocatalyst or a strong base and show a wide substrate scope as well as excellent functional group tolerance. This work highlights the unique role of NaI that allows a challenging transformation to proceed under mild reaction conditions.

Regioselectivity of Hydroxyl Radical Reactions with Arenes in Nonaqueous Solutions

The regioselectivity of hydroxyl radical addition to arenes was studied using a novel analytical method capable of trapping radicals formed after the first elementary step of reaction, without alteration of the product distributions by secondary oxidation processes. Product analyses of these reactions indicate a preference for o- over p-substitution for electron donating groups, with both favored over m-addition. The observed distributions are qualitatively similar to those observed for the addition of other carbon-centered radicals, although the magnitude of the regioselectivity observed is greater for hydroxyl. The data, reproduced by high accuracy CBS-QB3 computational methods, indicate that both polar and radical stabilization effects play a role in the observed regioselectivities. The application and potential limitations of the analytical method used are discussed.

An efficient and chemoselective deprotection of aryl tert-butyldimethylsilyl (TBDMS) ethers by NaCN

Phenolic tert-butyldimethylsilyl (TBDMS) ethers can be deprotected to yield phenols in excellent yield using sodium cyanide (NaCN) as catalyst in ethanol. The deprotectation of various phenolic TBDMS ethers were found to be very convenient, fast, high yielding and chemoselective.

Selective Aromatic C-H Hydroxylation Enabled by η6-Coordination to Iridium(III)

We report an aromatic C-H hydroxylation protocol in which the arene is activated through η6-coordination to an iridium(III) complex. η6-Coordination of the arene increases its electrophilicity and allows for high positional selectivity of hydroxylation at the site of least electron density. Through investigation of intermediate η5-cyclohexadienyl adducts and arene exchange reactions, we evaluate incorporation of arene π-activation into a catalytic cycle for C-H functionalization.

Solvent-free one-step photochemical hydroxylation of benzene derivatives by the singlet excited state of 2,3-dichloro-5,6-dicyano-p-benzoquinone acting as a super oxidant

Photoinduced hydroxylation of neat deaerated benzene to phenol occurred under visible-light irradiation of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), which acts as a super photooxidant in the presence of water. Photocatalytic solvent-free hydroxylation of benzene derivatives with electron-withdrawing substituents such as benzonitrile, nitrobenzene, and trifluoromethylbenzene used as neat solvents has been achieved for the first time by using DDQ as a super photooxidant to yield the corresponding phenol derivatives and 2,3-dichloro-5,6-dicyanohydroquinone (DDQH2) in the presence of water under deaerated conditions. In the presence of dioxygen and tert-butyl nitrite, the photocatalytic hydroxylation of neat benzene occurred with DDQ as a photocatalyst to produce phenol. The photocatalytic reactions are initiated by oxidation of benzene derivatives with the singlet and triplet excited states of DDQ to form the corresponding radical cations, which associate with benzene derivatives to produce the dimer radical cations, which were detected by the femto- and nanosecond laser flash photolysis measurements to clarify the photocatalytic reaction mechanisms. Radical cations of benzene derivatives react with water to yield the OH-adduct radicals. On the other hand, DDQC?- produced by the photoinduced electron transfer from benzene derivatives reacts with the OH-adduct radicals to yield the corresponding phenol derivatives and DDQH2. DDQ is recovered by the reaction of DDQH2 with tert-butyl nitrite when DDQ acts as a photocatalyst for the hydroxylation of benzene derivatives by dioxygen.

The Hydroxylation of Aromatics with Oxygen by Vanadium Catalysts Supported on N-doped Carbon Materials

Vanadium catalysts supported on N-doped carbon materials (CN) were prepared and the catalyst VOSiW showed high activity for the hydroxylation of various aromatics with O2. Aromatics with electron-withdrawing groups such as CN, NO2, COOH, CF3, COCH3 and aromatic halides (F, Cl and Br) were oxygenated to the corresponding phenols in considerable yields. The CN materials were not only indispensable for the reusability of the vanadium catalyst VOSiW, but also favorable to the high catalytic activity. The VOSiW catalyst is ready for the hydroxylation of aromatics with O2 as both V4+ and V5+ species are coexisted in the VOSiW catalyst.