402-45-9

Basic information

• Product Name: 4-Trifluoromethylphenol
• Synonyms: alpha,alpha,alpha-Trifluoro-p-cresol,loosecrystals;Phenol, 4-(trifluoromethyl)-;P-HYDROXYBENZOTRIFLUORIDE;P-(TRIFLUOROMETHYL)PHENOL;ALPHA,ALPHA,ALPHA-TRIFLUORO-4-CRESOL;ALPHA,ALPHA,ALPHA-TRIFLUORO-P-CRESOL;4-(TRIFLUOROMETHYL)PHENOL;4-HYDROXYBENZOTRIFLUORIDE
• CAS NO: 402-45-9
• Molecular Formula: C₇H₅F₃O
• Molecular Weight: 162.11
• EINECS: 206-945-7
• Product Categories: Trifluoromethylbenzene serise;Aromatic Phenols;Phenol&Thiophenol&Mercaptan;Fluorochemicals
• Mol File: 402-45-9.mol

Chemical Properties

• Melting Point: 45-47 °C(lit.)
• Boiling Point: 71.5-72 °C (8 mmHg)
• Flash Point: 183 °F
• Appearance: White to yellow-brown/Crystals
• Density: 1.3226 (estimate)
• Vapor Pressure: 0.506mmHg at 25°C
• Refractive Index: 1.457
• Storage Temp.: 0-6°C
• PKA: pK1:8.675 (25°C)
• Water Solubility: Insoluble in water
• BRN: 1637019
• CAS DataBase Reference: 4-Trifluoromethylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Trifluoromethylphenol(402-45-9)
• EPA Substance Registry System: 4-Trifluoromethylphenol(402-45-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-36/37/38
• Safety Statements: 26-39-24/25
• RIDADR: UN 2926 4.1/PG 2
• WGK Germany: 3
• PackingGroup: Ⅱ
• Hazardous Substances Data: 402-45-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Trifluoromethylphenol is used as an intermediate for the synthesis of various medicinal compounds. Its unique chemical structure allows it to be a key component in the development of new drugs, contributing to the advancement of pharmaceutical research and innovation.
Used in Pesticide Industry:
In the pesticide industry, 4-Trifluoromethylphenol serves as an intermediate for the production of various pesticides. Its chemical properties make it a valuable component in the formulation of effective and targeted pest control solutions.
Used in Diaryl Ether Synthesis:
4-Trifluoromethylphenol is used in the synthesis of diaryl ethers, which are important compounds in various chemical and material applications. Its presence in the synthesis process contributes to the development of new materials with specific properties and potential uses.
Used in Liquid Crystals Industry:
As an intermediate for the production of liquid crystals, 4-Trifluoromethylphenol plays a crucial role in the development of advanced display technologies. Its chemical properties enable the creation of liquid crystal compounds with improved performance characteristics, such as enhanced color reproduction and faster response times.

Preparation method

Chlorosilane and bromotrifluoromethane at-59℃form trifluoromethylsilane. Trifluoromethylsilane and benzoquinone in the presence of catalyst form 4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-ketone which is reduced by zinc powder to p-trifluoromethylphenol with a yield of 71%. This method avoids the use of? hydrofluoric acid in the traditional process but? should be carried out under anhydrous conditions.If there were water trifluoromethyl silane would rapidly become silanol under the effect of water and alkali. The catalyst used in the reaction is alkali of which the strength has nothing to do with the catalytic activity. By now the role of catalyst is still unknown but the reaction can not proceed without catalyst.

Chemical Characteristics

Off-white crystal

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 2873, 1989 DOI: 10.1021/jo00273a020

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

Upstream product

• 455-14-1 4-trifluoromethylphenylamine 
• 124-38-9 carbon dioxide 
• 146397-87-7 p-(trifluoromethyl)phenyl trifluoromethanesulfonate 
• 98-08-8 α,α,α-trifluorotoluene 
• 120120-29-8 4-(tri-n-butylsiloxy)-4-(trifluoromethyl)-2,5-cyclohexadien-1-one 
• 75-63-8 Bromotrifluoromethane 
• 108-95-2 phenol 
• 80783-62-6 N-Trifluoromethyl-N-nitrosobenzenesulfonamide 
• 40161-45-3 4-trifluoromethyl-1-(diethoxymethylsilyl)benzene 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 16222-44-9 para-trifluoromethylphenyl tert-butyl ether 
• 402-52-8 methyl 4-(trifluoromethyl)phenyl ether 
• 70097-65-3 1-(benzyloxy)-4-(trifluoromethyl)benzene 
• 104614-27-9 1-(prop-2-en-1-yloxy)-4-(trifluoromethyl)benzene 

Downstream Products

• 35852-57-4 2,6-dibromo-4-(trifluoromethyl)phenol 
• 132586-45-9 4-hydroxybenzoic acid 4'-trifluoromethylphenyl ester 
• 69183-42-2 {4-[2-(4-Chloro-phenoxy)-propoxy]-phenyl}-(4-trifluoromethyl-phenoxy)-acetic acid 
• 69183-23-9 {4-[2-(4-Chloro-phenoxy)-ethoxy]-phenyl}-(4-trifluoromethyl-phenoxy)-acetic acid methyl ester 
• 69183-21-7 {4-[3-(4-Chloro-phenoxy)-propoxy]-phenyl}-(4-trifluoromethyl-phenoxy)-acetic acid methyl ester 
• 69182-79-2 [4-(4-Chloro-phenoxymethoxy)-phenyl]-(4-trifluoromethyl-phenoxy)-acetic acid 
• 35852-58-5 2-chloro-4-trifluoromethylphenol 
• 75091-92-8 4-(trifluoromethyl)cyclohexan-1-ol 
• 34961-98-3 (4-Chloro-phenyl)-carbamic acid 4-trifluoromethyl-phenyl ester 
• 34857-78-8 (3,4-Dichloro-phenyl)-carbamic acid 4-trifluoromethyl-phenyl ester 
• 41571-86-2 1-trifluoromethyl-4-trimethylsilyloxybenzene 
• 134142-88-4 2-[(4-trifluoromethyl)phenoxy]tetrahydro-2H-pyrane 
• 120281-22-3 1-[(2-methylbut-3-yn-2-yl)oxy]-4-(trifluoromethyl)benzene 
• 97209-47-7 5-(4-trifluoromethylphenoxy)-1-tetrazole 

Relevant articles and documents

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Different carboxy-functionalized imidazolium salts have been considered as components of low transition temperature mixtures (LTTMs) in combination with urea. Among them, a novel LTTM based on 1-(methoxycarbonyl)methyl-3-methylimidazolium chloride and urea has been prepared and characterized by differential scanning calorimetry throughout its entire composition range. This LTTM has been employed for the oxidation of boron reagents using urea-hydrogen peroxide adduct (UHP) as the oxidizer, thus avoiding the use of aqueous H2O2, which is dangerous to handle. This metal-free protocol affords the corresponding alcohols in good to quantitative yields in up to 5 mmol scale without the need of further purification. The broad composition range of the LTTM allows for the reaction to be carried out up to three consecutive times with a single imidazolium salt loading offering remarkable sustainability with an E-factor of 7.9, which can be reduced to 3.2 by the threefold reuse of the system.

Radical-anion coupling through reagent design: hydroxylation of aryl halides

The design and development of an oxime-based hydroxylation reagent, which can chemoselectively convert aryl halides (X = F, Cl, Br, I) into phenols under operationally simple, transition-metal-free conditions is described. Key to the success of this approach was the identification of a reducing oxime anion which can interact and couple with open-shell aryl radicals. Experimental and computational studies support the proposed radical-nucleophilic substitution chain mechanism.

Biocatalytic Cross-Coupling of Aryl Halides with a Genetically Engineered Photosensitizer Artificial Dehalogenase

Devising artificial photoenzymes for abiological bond-forming reactions is of high synthetic value but also a tremendous challenge. Disclosed herein is the first photobiocatalytic cross-coupling of aryl halides enabled by a designer artificial dehalogenase, which features a genetically encoded benzophenone chromophore and site-specifically modified synthetic NiII(bpy) cofactor with tunable proximity to streamline the dual catalysis. Transient absorption studies suggest the likelihood of energy transfer activation in the elementary organometallic event. This design strategy is viable to significantly expand the catalytic repertoire of artificial photoenzymes for useful organic transformations.

Decarboxylative Hydroxylation of Benzoic Acids

Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35 °C via photoinduced ligand-to-metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late-stage applications.

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.

Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes

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