24279-39-8

Basic information

• Product Name: 4-Amino-3,5-dichlorobenzotrifluoride
• Synonyms: 3,5-DICHLORO-4-AMINO BENZOTRIFLUORIDE;2,6-DICHLORO-4-(TRIFLUOROMETHYL)ANILINE;BUTTPARK 29\06-100;TIMTEC-BB SBB003283;2,6-dichloro-4-Trifluoromethyllaniline;4-Amino-3,5-dichlorobenzotrifluoride,97% (2,6-Dichloro-4-trifluoromethylaniline);2,6-dichloro-(trifluoromethyl)aniline;2,6-Dichloro-4-(trifluoromethyl)aniline 99%
• CAS NO: 24279-39-8
• Molecular Formula: C₇H₄Cl₂F₃N
• Molecular Weight: 230.01
• EINECS: 416-430-0
• Product Categories: Trifluoromethylbenzene serise;Anilines, Aromatic Amines and Nitro Compounds;Aromatic Halides (substituted);Aniline;Fluorochemicals;API intermediates;Pesticide Intermediate;Benzenes;Amines;C7;Nitrogen Compounds;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;amine| alkyl chloride
• Mol File: 24279-39-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 34-36 °C(lit.)
• Boiling Point: 60-62 °C1 mm Hg(lit.)
• Flash Point: 190 °F
• Appearance: light yellow low melting crystalline mass
• Density: 1.532 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.241mmHg at 25°C
• Refractive Index: 1.518
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: -1.13±0.10(Predicted)
• BRN: 2838819
• CAS DataBase Reference: 4-Amino-3,5-dichlorobenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-3,5-dichlorobenzotrifluoride(24279-39-8)
• EPA Substance Registry System: 4-Amino-3,5-dichlorobenzotrifluoride(24279-39-8)

Safety Data

• Hazard Codes: Xn,N,T
• Statements: 20/22-38-43-50/53
• Safety Statements: 24-37-60-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• HazardClass: TOXIC
• PackingGroup: III
• Hazardous Substances Data: 24279-39-8(Hazardous Substances Data)

Usage

Description

4-Amino-3,5-dichlorobenzotrifluoride is an organic compound characterized by its amino group attached to a benzene ring, which is substituted with two chlorine atoms at the 3rd and 5th positions, and a trifluoromethyl group at the 4th position. 4-Amino-3,5-dichlorobenzotrifluoride is known for its reactivity and is commonly utilized in the synthesis of various pharmaceuticals and agrochemicals due to its unique structural features.

Uses

Used in Pharmaceutical Industry:
4-Amino-3,5-dichlorobenzotrifluoride is used as an intermediate in the synthesis of GABA receptor antagonists. It plays a crucial role in the development of medications targeting neurological disorders by modulating the activity of GABA receptors in the brain.
Used in Agrochemical Industry:
4-Amino-3,5-dichlorobenzotrifluoride is used as a key component in the production of insecticides. Its chemical structure allows for the creation of compounds that can effectively control and manage insect populations, thereby protecting crops and reducing agricultural losses.
Used in Organic Synthesis:
4-Amino-3,5-dichlorobenzotrifluoride may be employed for the synthesis of complex organic molecules, such as 1-[2,6-di-chloro-4-(tri-fluoro-methyl)-phenyl]-5-[(4-nitro-phenyl)-methyl-ene-imino]-1H-pyrazole-3-carbo-nitrile. 4-Amino-3,5-dichlorobenzotrifluoride has potential applications in various fields, including pharmaceuticals and materials science, due to its unique chemical properties and reactivity.

preparation

Using 4-chlorotrifluoromethylbenzene as raw material, 2,6-dichloro-4-trifluoromethylaniline was prepared through two-step reaction of amination and chlorination.

InChI:InChI=1/C7H4Cl2F3N/c8-4-1-3(7(10,11)12)2-5(9)6(4)13/h1-2H,13H2

Upstream product

• 2926-29-6 Langlois reagent 
• 608-31-1 2,6-Dichloroaniline 
• 86398-94-9 2,6-dichloro-4-(trifluoromethyl)phenyl hydrazine 
• 455-14-1 4-trifluoromethylphenylamine 
• 56148-83-5 2,4,5-trichloro-1-(trifluoromethyl)benzene 
• 50594-82-6 1-trifluoromethyl-3,4,5-trichlorobenzene 
• 2314-97-8 iodotrifluoromethane 
• 39885-50-2 2-chloro-4-(trifluoromethyl)aniline 
• 328-84-7 1,2-dichloro-4-(trifluoromethyl)benzene 
• 689300-85-4 (2-chloro-4-trifluoromethyl-phenyl)-methyl-amine 
• 156639-47-3 2,6-dichloro-4-trifluoromethyl-N-methylaniline 
• 106-43-4 para-chlorotoluene 
• 5216-25-1 4-chlorotrichloromethylbenzene 
• 57729-79-0 2-chloro-6-nitro-4-(trifluoromethyl)aniline 

Downstream Products

• 68105-63-5 (2,6-Dichloro-4-trifluoromethyl-phenyl)-(2,4-dinitro-naphthalen-1-yl)-amine 
• 72773-08-1 (2,6-Dichloro-4-trifluoromethyl-phenyl)-(4-nitro-2,6-bis-trifluoromethyl-phenyl)-amine 
• 28313-69-1 Cyano-[(2,6-dichloro-4-trifluoromethyl-phenyl)-hydrazono]-acetic acid methyl ester 
• 120068-79-3 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole 
• 133152-04-2 2-azido-1,3-dichloro-5-(trifluoromethyl)benzene 

Relevant articles and documents

New synthesis method of 2,6-dichloro-4-trifluoromethylaniline

The invention discloses a new synthesis method of 2,6-dichloro-4-trifluoromethylaniline, wherein p-trifluoromethylaniline is usedas a raw material, and is added with a certain amount of sulfonyl chloride in a dropwise manner, and chlorination, water washing and pressure reducing rectification are performed to obtain the target compound. Compared with the method in the prior art, the method of theinvention has characteristics of simple process, easy operation, short reaction time, high yield and low production cost, is suitable for industrial production, is an environmentally-friendly chemicalprocess, and has good industrial application prospect.

Continuous Flow Homolytic Aromatic Substitution with Electrophilic Radicals: A Fast and Scalable Protocol for Trifluoromethylation

We report an operationally simple and rapid continuous flow radical C?C bond formation under Minisci-type reaction conditions. The transformations are performed at or below room temperature employing hydrogen peroxide (H2O2) and dimethylsulfoxide (DMSO) as reagents in the presence of an FeIIcatalyst. For electron-rich aromatic and heteroaromatic substrates, C?C bond formation proceeds satisfactorily with electrophilic radicals including.CF3,.C4F9,.CH2CN, and.CH2CO2Et. In contrast, electron-poor substrates exhibit minimal reactivity. Importantly, trifluoromethylations and nonafluororobutylations using CF3I and C4F9I as reagents proceed exceedingly fast with high conversion for selected substrates in residence times of a few seconds. The attractive features of the present process are the low cost of the reagents and the extraordinarily high reaction rates. The direct application of the protocol to dihydroergotamine, a complex ergot alkaloid, yielded the corresponding trifluoromethyl ergoline derivative within 12 seconds in a continuous flow microreactor on a 0.6 kg scale. The trifluoromethyl derivative of dihydroergotamine is a promising therapeutic agent for the treatment of migraines.

Method for preparing 99 percent of 2,6-dichloro-4-trifluoromethyl phenylamine

The invention relates to a method for preparing 99 percent of 2,6-dichloro-4-trifluoromethyl phenylamine, which includes the following two steps of reaction: (1) amination reaction: 3,4-dichloro-5-nitrobenzotrifluoride reacts with ammonia to generate 3--chloro-4-amino-5-nitrobenzotrifluoride; (2) chlorination reaction: 3--chloro-4-amino-5-nitrobenzotrifluoride reacts with chlorine to generate 2,6-dichloro-4-trifluoromethyl phenylamine. The advantages of the invention are as follows: the target product 2,6-dichloro-4-trifluoromethyl phenylamine is prepared with 3,4-dichloro-5-nitrobenzotrifluoride as a material; the specific implementation route includes amination and chlorination, only simple distillation or steam distillation is needed, 99 percent of target product can be obtained without rectification, and the method has the advantages of mild reaction conditions, high safety and high product content; the process is suitable for mass industrial production, pollution is little, energy is saved, and the environment is protected.