142738-94-1

Basic information

• Product Name: 3-(TRIFLUOROMETHOXY)ANISOLE
• Synonyms: 1-METHOXY-3-(TRIFLUOROMETHOXY)BENZENE;3-(TRIFLUOROMETHOXY)ANISOLE
• CAS NO: 142738-94-1
• Molecular Formula: C₈H₇F₃O₂
• Molecular Weight: 192.14
• Mol File: 142738-94-1.mol

Chemical Properties

• Boiling Point: 162℃
• Flash Point: 58℃
• Appearance: /
• Density: 1.249
• Vapor Pressure: 2.82mmHg at 25°C
• Refractive Index: 1.434
• Storage Temp.: Room temperature.
• CAS DataBase Reference: 3-(TRIFLUOROMETHOXY)ANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(TRIFLUOROMETHOXY)ANISOLE(142738-94-1)
• EPA Substance Registry System: 3-(TRIFLUOROMETHOXY)ANISOLE(142738-94-1)

Safety Data

• Hazard Codes: F,Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 1993
• HazardClass: IRRITANT, FLAMMABLE
• PackingGroup: III
• Hazardous Substances Data: 142738-94-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(TRIFLUOROMETHOXY)ANISOLE is used as an intermediate in the synthesis of various pharmaceuticals for its ability to improve the bioavailability and metabolic stability of drug molecules. The introduction of fluorine atoms, facilitated by the trifluoromethoxy group, can significantly impact the pharmacokinetic and pharmacodynamic properties of the resulting compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 3-(TRIFLUOROMETHOXY)ANISOLE serves as an intermediate in the production of agrochemicals, contributing to the development of more effective and stable pesticides and other agricultural chemicals.
Used in Organic Synthesis:
3-(TRIFLUOROMETHOXY)ANISOLE is utilized as a solvent in organic reactions, providing a medium that facilitates the progress of various chemical transformations, thereby enhancing the efficiency of synthetic processes.
Used in Medicinal Chemistry Research:
As a reagent in organic synthesis, 3-(TRIFLUOROMETHOXY)ANISOLE is employed in the development of new chemical entities and the modification of existing compounds in medicinal chemistry research, allowing for the exploration of novel therapeutic agents and drug candidates.

InChI:InChI=1/C8H7F3O2/c1-12-6-3-2-4-7(5-6)13-8(9,10)11/h2-5H,1H3

Upstream product

• 512-56-1 trimethyl phosphite 
• 827-99-6 3-(trifluoromethoxy)phenol 
• 1006904-72-8 silver(I) trifluoromethoxide 
• 536-90-3 m-Anisidine 
• 217813-03-1 3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate 
• 74-88-4 methyl iodide 

Downstream Products

• 905077-14-7 potassium 4-methoxy-2-(trifluoromethoxy)benzenesulfonate 
• 905077-18-1 potassium 2-methoxy-4-(trifluoromethoxy)benzenesulfonate 
• 142739-14-8 2-Methoxy-4-trifluoromethoxy-benzenesulfonic acid 
• 142739-13-7 4-Methoxy-2-trifluoromethoxy-benzenesulfonic acid 

Relevant articles and documents

A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination

A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.

Silver-Mediated Trifluoromethoxylation of (Hetero)aryldiazonium Tetrafluoroborates

Here we report a silver-mediated trifluoromethoxylation of (hetero)aryldiazonium tetrafluoroborates by converting an aromatic amino group into an OCF3 group. This method, which can be considered to be a trifluoromethoxylation variation of the classic Sandmeyer-type reaction, uses readily available aryl and heteroaromatic amines as starting materials and AgOCF3 as trifluoromethoxylating reagents. The broad substrate scope and simple, mild reaction condition made this transformation a valuable method in constructing aryl-OCF3 bonds.

Method for trifluoro methoxylation of arylamine

The invention provides a method for synthesizing an aryltrifluoromethoxy compound from an arylamine compound. The method comprises the steps of: performing a diazotization reaction on arylamine, and performing a one-pot reaction between the obtained aryl diazonium salt and trifluoromethoxy silver in an acetonitrile solvent so as to obtain the corresponding aryltrifluoromethoxy product. The obtained product has a high yield, and the process is simple.

Trifluoromethyl Benzoate: A Versatile Trifluoromethoxylation Reagent

Trifluoromethyl benzoate (TFBz) is developed as a new shelf-stable trifluoromethoxylation reagent, which can be easily prepared from inexpensive starting materials using KF as the only fluorine source. The synthetic potency of TFBz is demonstrated by trifluoromethoxylation-halogenation of arynes, nucleophilic substitution of alkyl (pseudo)halides, cross-coupling with aryl stannanes, and asymmetric difunctionalization of alkenes. The unprecedented trifluoromethoxylation-halogenation of arynes proceeds smoothly at room temperature with the aid of a crown ether-complexed potassium cation, which significantly stabilizes the trifluoromethoxide anion derived from TFBz.

1,3-Dihydro-2H-Indole-2-One Compound and Pyrrolidine-2-One Compound Fused With Aromatic Heterocycle

It is intended to provide a drug which is efficacious against pathological conditions relating to arginine-vasopressin V1b receptor. More particularly speaking, it is intended to provide a drug which has a therapeutic or preventive effect on depression, anxiety, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorders, hypertension, digestive diseases, drug addiction, epilepsy, brain infarction, brain ischemia, brain edema, head injury, inflammation, immune diseases, alopecia and so on. As the results of intensive studies, a novel 1,3-dihydro-2H-indol-2-one compound and a pyrrolidin-2-one compound fused with a heteroaromatic ring, which are highly selective antagonists of arginine-vasopressin V1b receptor, have high metabolic stabilities and show favorable brain penetration and high plasma concentrations, are found, thereby achieving the above objective.

The trifluoromethoxy group: A long-range electron-withdrawing substituent

Judged by its capacity to promote a hydrogen/metal permutation at an ortho position, the trifluoromethoxy group is superior to both the methoxy and trifluoromethyl groups. Moreover, like CF3 and unlike OCH3, OCF3 exerts a long-range effect that still considerably lowers the basicity of arylmetal compounds when located in a more remote meta or even para position. As a consequence, 4-(trifluoromethoxy)-anisole is deprotonated by sec-butyllithium mainly, and by tert-butyllithium exclusively, at a position adjacent to the OCH3 group rather than next to the strongly electron-withdrawing CF3O group. 1,3-Benzodioxole undergoes ortho lithiation only six times faster than anisole, whereas 2,2-difluoro-1,3-benzodioxole reacts about 5000 times faster, as evidenced by competition experiments. The structure and distance dependence of substituent effects can be rationalized by assuming superposing σ- and π-polarizing interactions.