1535-73-5

Usage

Uses

Used in Pharmaceutical Industry:
3-(Trifluoromethoxy)aniline is used as a reactant in the synthesis of pyrazolone-quinazolone hybrids, which serve as human hydroxyphenylpyruvate dioxygenase inhibitors. These inhibitors are a potential treatment for type I tyrosinemia, a rare genetic disorder that affects the body's ability to break down the amino acid tyrosine.

InChI:InChI=1/C7H6F3NO/c8-7(9,10)12-6-3-1-2-5(11)4-6/h1-4H,11H2

Upstream product

• 95-57-8 2-monochlorophenol 
• 39065-91-3 3-(chlorodifluoromethoxy) aniline 
• 450-96-4 o-chloro-α,α,α-trifluoromethoxybenzene 
• 914636-35-4 3-bromo-5-(trifluoromethoxy)aniline 
• 461-81-4 1-chloro-4-(trifluoromethoxy)benzene 
• 97608-46-3 2-chloro-trichloromethoxybenzene 
• 766-51-8 2-Chloroanisole 

Downstream Products

• 2402-59-7 m-Trifluormethoxy-N_.N-dimethylanilin 
• 51679-40-4 2-(3-Trifluoromethoxy-phenylamino)-benzoic acid 
• 886792-81-0 2-chloro-N-(3-(trifluoromethoxy)phenyl)acetamide 
• 235101-42-5 N-<3-(trifluoromethoxy)phenyl>thiourea 
• 1026798-34-4 {1-[(3-trifluoromethoxy-phenylamino)-methyl]-pentyl}-carbamic acid tert-butyl ester 
• 561304-42-5 tert-butyl N-[3-(trifluoromethoxy)phenyl]carbamate 
• 57330-49-1 2-methyl-6-(trifluoromethoxy)-1H-indole 

Relevant academic research and scientific papers

Co-production preparation method of o-amino trifluoromethoxy benzene and m-amino trifluoromethoxy benzene

The invention discloses a co-production preparation method of o-amino trifluoromethoxybenzene and m-amino trifluoromethoxybenzene, and belongs to the technical field of fine chemical engineering. Thepreparation method comprises the following steps: (1) nitration reaction: carrying out nitration reaction on 4-chlorine-trifluoromethoxybenzene to obtain a mixture of 4-chlorine-2-nitro- trifluoromethoxy benzene and 4-chlorine-3-nitro-trifluoromethoxybenzene; (2) reduction and dechlorination: carrying out reduction and dechlorination on the mixture of the 4-chloro-2-nitro-trifluoromethoxybenzene and the 4-chloro-3-nitro-trifluoromethoxybenzene to obtain o-amino trifluoromethoxybenzene and m-amino trifluoromethoxybenzene; and (3) rectification separation: separating the o-amino trifluoromethoxybenzene from the m-amino trifluoromethoxybenzene through rectification so as to realize co-production. The method is low in cost and high in yield, two useful chemical products are obtained at the same time, the process is simple, and industrial production is easy to achieve.

A divergent SAR study allows optimization of a potent 5-HT2c inhibitor to a promising antimalarial scaffold

From the 13-533 chemical structures published by GlaxoSmithKline in 2010, we identified 47 quality starting points for lead optimization. One of the most promising hits was the TCMDC-139046, a molecule presenting an indoline core, which is well-known for its anxiolytic properties by interacting with serotonin antagonist receptors 5-HT2. The inhibition of this target will complicate the clinical development of these compounds as antimalarials. Herein, we present the antimalarial profile of this series and our efforts to avoid interaction with this receptor, while maintaining a good antiparasitic potency. By using a double-divergent structure-activity relationship analysis, we have obtained a novel lead compound harboring an indoline core.

Insecticidal heterolignans-Tubuline polymerization inhibitors with activity against chewing pests

Starting from natural product podophyllotoxin 1 substituted heterolignans were identified with promising insecticidal in vivo activity. The impact of substitution in each segment of the core structure was investigated in a detailed SAR study, and variation of substituents in both aromatic moieties afforded derivatives 5 and 43 with broad insecticidal activity against lepidopteran and coleopteran species. In vitro measurements supported by modeling studies indicate that heterolignans 3-134 act as tubuline polymerization inhibitors interacting with the colchicine-binding site. Insect specific structure-activity effects were observed showing that the insecticidal SAR described herein differs from reported cytotoxicity studies.

Preparation of alkyl and aryl chlorodifluoromethyl ethers using BrF 3

Both alkyl and aryl chlorothioformates could readily be obtained from the corresponding alcohols and thiophosgene. These families of compounds were treated with BrF3 to form the corresponding alkyl and aryl chlorodifluoromethyl ethers in 60-85% yields. The method is suitable for constructing a variety of aliphatic as well as electron-deficient aromatic chlorodifluoromethyl ethers. The reactions proceed under mild conditions and short reaction times. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

A safe and economical synthesis of 3-(trifluoromethoxy) aniline from 2-chlorophenol

A simple, safe and realistic synthesis of 3-(trifluoromethoxy) aniline from 2-chlorophenol is proposed, the key step being a regiospecific arynic amination of 2-chloro (trifluoromethoxy) benzene.This method has been extended to the synthesis of 4-chloro-3-(trifluoromethoxy) aniline from 2,6-dichlorophenol.Some unusual products are obtained during the reaction between sodium amide and 2-chloro (chlorodifluoromethoxy) benzene, the formation of which is discussed.