445-03-4

Basic information

• Product Name: 2-Amino-5-chlorobenzotrifluoride
• Synonyms: 4-chloro-2-(trifluoromethyl)-benzenamin;5-Chloro-2-aminobenzotrifluoride;Aniline,4-chloro-2-trifluoromethyl-;Benzenamine,4-chloro-2-(trifluoromethyl)-;C.I. 37055;C.I. Azoic Diazo Component 17;Diazo Fast Scarlet VD;Fast Scarlet Salt VD
• CAS NO: 445-03-4
• Molecular Formula: C₇H₅ClF₃N
• Molecular Weight: 195.57
• EINECS: 207-151-3
• Product Categories: Aromatic Halides (substituted);API Intermediate
• Mol File: 445-03-4.mol
• Article Data: 18

Chemical Properties

• Melting Point: 8.8 °C
• Boiling Point: 66-67 °C3 mm Hg(lit.)
• Flash Point: 203 °F
• Appearance: Clear yellow liquid
• Density: 1.386 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0145mmHg at 25°C
• Refractive Index: n20/D 1.507(lit.)
• Storage Temp.: 0-6°C
• PKA: 0.83±0.10(Predicted)
• BRN: 2366801
• CAS DataBase Reference: 2-Amino-5-chlorobenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-chlorobenzotrifluoride(445-03-4)
• EPA Substance Registry System: 2-Amino-5-chlorobenzotrifluoride(445-03-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-33-36/37/38-41-22
• Safety Statements: 26-36-37/39
• RIDADR: UN 2810
• WGK Germany: 2
• TSCA: T
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 445-03-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5-chlorobenzotrifluoride is used as a building block for the synthesis of various pharmaceutical compounds due to its biological activity and versatility in chemical reactions. It can be transformed into a range of valuable molecules, making it a promising candidate for the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
2-Amino-5-chlorobenzotrifluoride is used as a key intermediate in the synthesis of 2-amino-5-chloro 3-(trifluoromethyl)benzenethiol, which is an important compound in the chemical industry. Its ability to form a variety of fluorine-containing molecules and heterocyclic compounds makes it a valuable asset in the development of new chemical products and materials.
Used in Research and Development:
As a biologically active compound, 2-Amino-5-chlorobenzotrifluoride is used in research and development for studying its potential applications in various fields, including pharmaceuticals, materials science, and chemical synthesis. Its unique properties and reactivity make it an interesting subject for further investigation and potential commercialization.

Preparation

Preparation?of?the?chromophore : 4-Chloro-2-(trifluoromethyl)benzenamme?and 4-Chloro-1-nitro-2-(trifluoromethyl)benzene? reduction.

InChI:InChI=1/C7H6ClFO2S/c1-5-2-3-6(9)4-7(5)12(8,10)11/h2-4H,1H3

Upstream product

• 2926-30-9 sodium triflate 
• 100-00-5 4-chlorobenzonitrile 
• 14547-72-9 N-(4-chlorophenyl)-2-pyridinecarboxaminde 
• 2314-97-8 iodotrifluoromethane 
• 106-47-8 4-chloro-aniline 
• 75-63-8 Bromotrifluoromethane 
• 887144-94-7 Togni's reagent II 
• 74383-34-9 4-chlorobenzen-2-d-amine 
• 2926-29-6 Langlois reagent 
• 112359-25-8 5-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate 
• 887144-97-0 Togni's reagent 
• 35749-94-1 4-chloro-2,6-dideuteroaniline 
• 88-17-5 2-(trifluoromethyl)benzenamine 
• 393-11-3 4-nitro-3-(trifluoromethyl)benzeneamine 

Downstream Products

• 344-53-6 N-<4-chloro-2-(trifluoromethyl)phenyl>acetamide 
• 57729-87-0 (4-Chloro-2-trifluoromethyl-phenyl)-(2,4-dinitro-6-trifluoromethyl-phenyl)-amine 
• 72773-26-3 (4-Chloro-2-trifluoromethyl-phenyl)-(2-nitro-4,6-bis-trifluoromethyl-phenyl)-amine 
• 18904-34-2 4-chloro-2-(trifluoromethyl)benzenethiol 
• 39886-30-1 5-methyl-oxazolidine-3-carboxylic acid (4-chloro-2-trifluoromethyl-phenylcarbamoyl)-amide 
• 32935-40-3 N-(4-Chlor-2-trifluormethyl-phenyl)-2-oxo-cyclopentan-carbonsaeure-⁽¹⁾-amid 
• 35566-96-2 N,N'-Bis-(4-chlor-2-trifluormethyl-phenyl)-2-imino-cyclopentan-carbonsaeure-⁽¹⁾-amid 
• 76616-18-7 C₁₃H₈Cl₃F₃NP 
• 76616-06-3 2,2,2,4,4,4-Hexachloro-1,3-bis-(4-chloro-2-trifluoromethyl-phenyl)-2λ⁵,4λ⁵-[1,3,2,4]diazadiphosphetidine 
• 128924-39-0 C₁₅H₁₂ClF₃N₂O₃S 
• 76616-22-3 C₁₉H₁₃Cl₂F₃NP 
• 17128-18-6 4-Dimethylamino-4'-chlor-2'-trifluormethyl-azobenzol 
• 51679-39-1 2-(4-Chloro-2-trifluoromethyl-phenylamino)-benzoic acid 
• 892496-63-8 bis(N-(4-chloro-2-trifluoromethylphenyl)-1,4,5,8-naphthalimide) 

Relevant articles and documents

Mechanistic study of visible light-driven CdS or g-C3N4-catalyzed C–H direct trifluoromethylation of (hetero)arenes using CF3SO2Na as the trifluoromethyl source

The mild and sustainable methods for C–H direct trifluoromethylation of (hetero)arenes without any base or strong oxidants are in extremely high demand. Here, we report that the photo-generated electron-hole pairs of classical semiconductors (CdS or g-C3N4) under visible light excitation are effective to drive C–H trifluoromethylation of (hetero)arenes with stable and inexpensive CF3SO2Na as the trifluoromethyl (TFM) source via radical pathway. Either CdS or g-C3N4 propagated reaction can efficiently transform CF3SO2Na to [rad]CF3 radical and further afford the desired benzotrifluoride derivatives in moderate to good yields. After visible light initiated photocatalytic process, the key elements (such as F, S and C) derived from the starting TFM source of CF3SO2Na exhibited differential chemical forms as compared to those in other oxidative reactions. The photogenerated electron was trapped by chemisorbed O2 on photocatalysts to form superoxide radical anion (O2[rad]?) which will further attack [rad]CF3 radical with the generation of inorganic product F? and CO2. This resulted in a low utilization efficiency of [rad]CF3 (3SO2Na served as the starting materials in inert atmosphere, the photoexcited electrons can be directed to reduce the nitro group to amino group rather than being trapped by O2. Meanwhile, the photogenerated holes oxidize SO2CF3? into [rad]CF3. Both the photogenerated electrons and holes were engaged in reductive and oxidative paths, respectively. The desired product, trifluoromethylated aniline, was obtained successfully via one-pot free-radical synthesis.

Ruthenium-Catalyzed Site-Selective Trifluoromethylations and (Per)Fluoroalkylations of Anilines and Indoles

Introducing (per)fluoroalkyl groups into arenes continues to be an interesting, but challenging area in organofluorine chemistry. We herein report an ortho-selective C?H perfluoroalkylation including trifluoromethylations of anilines and indoles without the need of protecting groups using RfI and RfBr as commercially available reagents. The availability and price of the starting materials and the inherent selectivity make this novel methodology attractive for the synthesis of diverse (per)fluoroalkylated building blocks, for example, for bioactive compounds and materials.

Transition metal-free direct C–H trifluoromethyltion of (hetero)arenes with Togni's reagent

A new transition-metal-free direct C–H trifluoromethylation reaction of (hetero)arenes with Togni's reagent was developed. This transformation proceeded smoothly under mild conditions and exhibited good tolerance of many synthetically relevant functional groups. It provided an alternative approach for the synthesis of trifluoromethylated (hetero)arenes.

Preparation method of trifluoromethylated aniline compound

The invention provides a preparation method of a trifluoromethylated aniline compound shown in a formula (IIA) or a formula (IIB). The method comprises the following steps: by taking a mixed solvent of DMF and water in a volume ratio of 1:(1-4) as a reaction medium, adding an aniline compound shown in a formula (IA) or a formula (IB), 1-(trifluoromethyl)-1,2-benziodoxol-3-(1H)-one and a photocatalyst, and reacting for 2-6 hours at room temperature under blue light; and carrying out post-treatment on the obtained reaction mixture to obtain the trifluoromethylated aniline compound as shown in the formula (IIA) or the formula (IIB). According to the method, by the photocatalyst, the reaction is driven to be carried out under the irradiation of visible light, the reaction conditions are mild,the site selectivity is high, the reaction is efficient, green and environment-friendly, the reaction yield can reach 90%, and the product can be prepared by only one step.

Synthetic method of aminobenzotrifluoride and derivant thereof

The invention discloses a synthetic method of aminobenzotrifluoride and a derivant thereof. By adopting a method for performing amino-ortho-position trifluoromethylation on an amino-benzene compound,trifluoromethyl trimethylsilane is used a reaction reagent, free radical substitution reaction is carried out on an amino-ortho-position of the amino-benzene compound and then trifluoromethylation isdirectly carried out, so that a target product is obtained. The method disclosed by the invention has the advantages that raw materials are cheap and easy to obtain, the production is convenient, precious metal is not needed, environmental protection and safety are achieved, and purification is easy to carry out; the method can be developed into an industrial production method. Based on that, according to the synthetic method disclosed by the invention, screening and optimization on synthetic conditions of the compound are also carried out, so that the reaction yield is further improved.

Coordinating Activation Strategy-Induced Selective C?H Trifluoromethylation of Anilines

A simple protocol for the synthesis of 2-(trifluoromethyl)aniline derivatives through a coordinating activation strategy was developed. The reaction showed good reactivity and gave the target products in moderate to good yields. Pleasingly, the directing group could be recovered in excellent yield. Furthermore, this strategy allowed efficient access to the synthesis of floctafenine. A single-electron-transfer mechanism was proposed to be responsible for this trifluoromethylation reaction.

Nickel-Catalyzed Direct C-H Trifluoromethylation of Free Anilines with Togni's Reagent

An efficient nickel-catalyzed C-H trifluoromethylation for the synthesis of trifluoromethylated free anilines using Togni's reagent has been developed. This approach exhibits a good functional group tolerance, good regioselectivity, and chemoselectivity under mild conditions. The newly developed economical one-step method is a better alternative to synthesize trifluoromethylated free anilines.

Preparation method of trifluoromethylamine

The invention relates to a preparation method of trifluoromethylamine. The method includes the following steps that aromatic amine shown in the formula (1) and a trifluoromethyl reagent shown in the formula (2) react in a solvent under the condition that an alkali and/or nickel compound exists, and the trifluoromethylamine compound shown in the formula (3) is generated. According to the preparation method of trifluoromethylamine, aromatic amine and 1-trifluoromethyl-1,2-iodobenzoyl-3(H)-ketone serve as raw materials and react under the condition that the alkali and/or nickel compound exists through the amino positioning effect on aromatic nucleus. The synthesis steps of the method are simple, the cost of the raw materials is low, the production cost of trifluoromethylamine can be greatly reduced, and large-scale industrialized production is promoted.

Iron(III)-Catalyzed Chlorination of Activated Arenes

A general and regioselective method for the chlorination of activated arenes has been developed. The transformation uses iron(III) triflimide as a powerful Lewis acid for the activation of N-chlorosuccinimide and the subsequent chlorination of a wide range of anisole, aniline, acetanilide, and phenol derivatives. The reaction was utilized for the late-stage mono- and dichlorination of a range of target compounds such as the natural product nitrofungin, the antibacterial agent chloroxylenol, and the herbicide chloroxynil. The facile nature of this transformation was demonstrated with the development of one-pot, tandem, iron-catalyzed dihalogenation processes allowing highly regioselective formation of different carbon-halogen bonds. The synthetic utility of the resulting dihalogenated aryl compounds as building blocks was established with the synthesis of natural products and pharmaceutically relevant targets.

Nickel(II)-Catalyzed Site-Selective C-H Bond Trifluoromethylation of Arylamine in Water through a Coordinating Activation Strategy

The first example of nickel(II)-catalyzed site-selective C-H bond trifluoromethylation of arylamine in water is established. In this transformation, a coordinating activation strategy is performed by the utilization of picolinamide as a directing group, and target products are obtained in moderate to good yields. In addition, the catalyst-in-water system can be reutilized eight times with a slight loss of catalytic activity and applied in the green, concise synthesis of acid red 266. Furthermore, a series of control experiments verify that a single-electron transfer mechanism is responsible for this reaction.