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

Description

2-Amino-5-chlorobenzotrifluoride is a chemical compound characterized by its clear yellow liquid appearance. It is a biologically active compound and serves as a useful building block in the synthesis of various valuable fluorine-containing molecules and heterocyclic compounds. Its Fourier-transform (FT) infrared and FT-Raman spectra have been studied, providing insights into its chemical properties.

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

• 118-83-2 5-chloro-2-nitrotrifluoromethylbenzene 
• 436-20-4 N-(4-chloro-2-trifluoromethyl-phenyl)-phthalimide 
• 393-11-3 4-nitro-3-(trifluoromethyl)benzeneamine 
• 88-17-5 2-(trifluoromethyl)benzenamine 
• 887144-94-7 Togni's reagent II 
• 106-47-8 4-chloro-aniline 
• 35749-94-1 4-chloro-2,6-dideuteroaniline 
• 887144-97-0 Togni's reagent 
• 112359-25-8 5-(trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate 
• 2926-29-6 Langlois reagent 
• 74383-34-9 4-chlorobenzen-2-d-amine 
• 75-63-8 Bromotrifluoromethane 
• 2314-97-8 iodotrifluoromethane 
• 14547-72-9 N-(4-chlorophenyl)-2-pyridinecarboxaminde 

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 
• 68105-73-7 (4-Chloro-2-trifluoromethyl-phenyl)-(2,4-dinitro-naphthalen-1-yl)-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 
• 58140-13-9 C₁₆H₇Cl₂F₆N₅ 
• 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 
• 155793-50-3 2-(benzo[d]oxazol-2-yl)-4-chloroaniline 
• 155793-48-9 2-(2'-amino-5'-chlorophenyl)benzothiazole 

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.

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.

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.