320-42-3

Basic information

• Product Name: 4-HYDROXY-2-(TRIFLUOROMETHYL)BENZONITRILE
• Synonyms: 4-HYDROXY-2-(TRIFLUOROMETHYL)BENZONITRILE;4-Cyano-3-(trifluoromethyl)phenol, 2-Cyano-5-hydroxybenzotrifluoride;4-Hydroxy-2-(trifluoroeMthyl)benzonitrile;4-Hydroxy-2-(trifluoromethyl)
• CAS NO: 320-42-3
• Molecular Formula: C₈H₄F₃NO
• Molecular Weight: 187.12
• Product Categories: Aromatic Nitriles
• Mol File: 320-42-3.mol

Chemical Properties

• Melting Point: 120-124℃
• Boiling Point: 297.9 °C at 760 mmHg
• Flash Point: 134 °C
• Appearance: /
• Density: 1.44 g/cm³
• Vapor Pressure: 0.00074mmHg at 25°C
• Refractive Index: 1.495
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.84±0.18(Predicted)
• CAS DataBase Reference: 4-HYDROXY-2-(TRIFLUOROMETHYL)BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-2-(TRIFLUOROMETHYL)BENZONITRILE(320-42-3)
• EPA Substance Registry System: 4-HYDROXY-2-(TRIFLUOROMETHYL)BENZONITRILE(320-42-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 320-42-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-2-(trifluoromethyl)benzonitrile is used as a key intermediate in the synthesis of pharmaceuticals for its ability to be incorporated into the molecular structures of various drugs. Its unique chemical properties allow for the creation of novel therapeutic agents with improved pharmacological profiles.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Hydroxy-2-(trifluoromethyl)benzonitrile is utilized as a precursor in the development of new agrochemicals, such as pesticides and herbicides. Its structural features contribute to the design of more effective and targeted agrochemicals, enhancing crop protection and yield.
Used in Organic Synthesis:
4-Hydroxy-2-(trifluoromethyl)benzonitrile is employed as a versatile building block in organic synthesis for the production of a wide range of functionalized molecules. Its unique structure allows for the formation of various chemical bonds, facilitating the synthesis of complex organic compounds with diverse applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 4-Hydroxy-2-(trifluoromethyl)benzonitrile is used as a starting material for the development of new pharmaceutical agents. Its chemical properties enable the design of innovative drug candidates with potential therapeutic benefits in various medical conditions.

InChI:InChI=1/C8H4F3NO/c9-8(10,11)7-3-6(13)2-1-5(7)4-12/h1-3,13H

Upstream product

• 194853-86-6 4-fluoro-2-(trifluoromethyl)benzonitrile 
• 767-00-0 4-cyanophenol 
• 320-41-2 4-chloro-2-(trifluoromethyl)benzonitrile 

Downstream Products

• 1146401-69-5 dimethylthiocarbamid acid O-(4-cyano-3-trifluoromethylphenyl) ester 
• 1076225-23-4 4-cyclohex-1-enyl-2-trifluoromethyl-benzonitrile 
• 1233244-19-3 p-cyano-m-trifluoromethylphenyl triflate 
• 1417782-28-5 1-(4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl)ethan-1-one 
• 1096960-88-1 C₁₄H₇ClF₃NO 
• 876760-39-3 4-(2,4-difluorophenoxy)-2-(trifluoromethyl)benzonitrile 

Relevant articles and documents

Cu and hydroquinone for the trifluoromethylation of unprotected phenols

Fluorination and trifluoromethylation are indispensable tools in the preparation of modern pharmaceuticals and APIs. Herein we present a concept for the introduction of a trifluoromethyl group into unprotected phenols employing catalytic copper(I) iodide

Synergistic Photo-Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides with Molecular Oxygen

Photoredox-mediated copper-catalyzed hydroxylation of (hetero)aryl halides (including chlorides, bromides, and iodides) with O2 at room temperature has been developed. Preliminary mechanistic studies indicate no arylcopper intermediate and that aryl radicals are involved in this procedure. 18O-labeling experiments confirm the hydroxyl oxygen atom originated from molecular oxygen.

A chemoenzymatic synthesis of an androgen receptor antagonist

A new scalable enzymatic resolution approach to both enantiomers of trans-2-hydroxycyclohexanecarbonitrile (9 and 11) was developed. Treatment of the racemic mixture (4) with succinic anhydride in the presence of Novozym 435 led to selective acylation of one enantiomer to the corresponding hemisuccinate, which was separated from the unreacted enantiomer by a simple basic extraction. This procedure produced the desired enantiomer in high ee, while obviating the need for chromatography or expensive catalysts and ligands. The application of this protocol to the large-scale synthesis of an androgen receptor antagonist (1) is described.

Process for producing trifluoromethylbenzylamines

The invention relates to a process for producing a trifluotomethylbenzylamine represented by the following general formula (1), 1where each R independently represents a halogen selected from the group consisting of fluorine, chlorine, bromine and iodine, an alkyl group having a carbon atom number of 1-4, an alkoxy group having a carbon atom number of 1-4, an amino group, a hydroxyl group or a trifluoromethyl group, and n represents an integer from 0 to 4. The process includes hydrogenating a trifluoromethylbenzonitrile by hydrogen in an organic solvent in the presence of ammonia and a catalyst containing a platinum group element. This trifluoromethylbenzonitrile is represented by the following general formula (2), 2where R and n are defined as above. With this process, it is possible to obtain the trifluoromethylbenzylamine at an extremely high yield.

Process for producing trifluoromethylbenzylamines

The invention relates to a process for producing a trifluoromethylbenzylamine represented by the following general formula (1). This process includes hydrogenating a trifliuoromethylbenzonitrile represented by the following general formula (2) by hydrogen in an organic solvent in the presence of ammonia, using a Raney catalyst, where each R independently represents a halogen selected from the group consisting of fluorine, chlorine, bromine and iodine, an alkyl group having a carbon atom number of 1-4, an alkoxy group having a carbon atom number of 1-4, an amino group, a hydroxyl group or a trifluoromethyl group, and n represents an integer from 0 to 4, where R and n are defined as above. With this process, it is possible to obtain the trifluoromethylbenzylamine easily and inexpensively at an extremely high yield.