328-84-7

Basic information

• Product Name: 3,4-Dichlorobenzotrifluoride
• Synonyms: 1,2-DICHLORO-4-(TRIFLUOROMETHYL)BENZENE;3,4-DICHLORO-ALPHA,ALPHA,ALPHA-TRIFLUOROTOLUENE;3,4-DICHLOROBENZOTRIFLUORIDE;3,4-DICHLORO TRIFLUORO METHYL BENZENE;3,4-DICHLORO-1-(TRIFLUOROMETHYL)BENZENE;3,4-DCBTE;1,2-dichloro-4-(trifluoromethyl)-benzen;3,4-dichloro-alpha,alpha,alpha-trifluoro-toluen
• CAS NO: 328-84-7
• Molecular Formula: C₇H₃Cl₂F₃
• Molecular Weight: 215
• EINECS: 206-337-1
• Product Categories: Chlorine Compounds;Fluorine Compounds;Aryl;Building Blocks;C7;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks;alkyl chloride
• Mol File: 328-84-7.mol

Chemical Properties

• Melting Point: −13-−12 °C(lit.)
• Boiling Point: 173-174 °C(lit.)
• Flash Point: 150 °F
• Appearance: clear colourless to slightly yellow liquid
• Density: 1.478 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.6 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.475(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• BRN: 1950151
• CAS DataBase Reference: 3,4-Dichlorobenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dichlorobenzotrifluoride(328-84-7)
• EPA Substance Registry System: 3,4-Dichlorobenzotrifluoride(328-84-7)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38-34-22
• Safety Statements: 26-36/37/39-45-60-20
• RIDADR: 1760
• WGK Germany: 2
• RTECS: CZ5527510
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 328-84-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3,4-Dichlorobenzotrifluoride is used as a key intermediate in the chemical synthesis process for creating a range of products. Its unique molecular structure allows it to participate in various chemical reactions, making it a versatile compound in the field of organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,4-Dichlorobenzotrifluoride is used as a building block for the development of new drugs. Its chemical properties enable it to be modified and incorporated into drug molecules, potentially leading to the discovery of novel therapeutic agents.
Used in Dye Manufacturing:
3,4-Dichlorobenzotrifluoride is also employed in the production of dyes. Its chemical structure contributes to the formation of vibrant and stable colorants, which are essential in various industries such as textiles, plastics, and printing.
Used in Solvent Applications:
Due to its solubility properties, 3,4-Dichlorobenzotrifluoride is used as a solvent in various industrial processes. It can dissolve a wide range of substances, making it a valuable component in the manufacturing of chemicals, resins, and other materials.
Used in the Preparation of 3,4-Difluorobenzotrifluoride:
3,4-Dichlorobenzotrifluoride is used as a starting material in the preparation of 3,4-difluorobenzotrifluoride through a KF exchange reaction. 3,4-Dichlorobenzotrifluoride has potential applications in various fields, including pharmaceuticals and materials science.
Used in the Synthesis of 2-Chloro-4-Trifluoromethylphenyl 4-Nitrophenylether (RH-2512):
3,4-Dichlorobenzotrifluoride is utilized in the synthesis of 2-chloro-4-trifluoromethylphenyl 4-nitrophenylether (RH-2512), a potential diphenyl ether herbicide. This herbicide candidate could be used in the agricultural industry to control the growth of unwanted plants and improve crop yields.

Air & Water Reactions

Flammable. Slightly soluble in water.

Reactivity Profile

Simple aromatic halogenated organic compounds are very unreactive; halogenated aliphatic compounds are moderately or very reactive. For both subgroups, reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C7H3Cl2F3/c8-5-2-1-4(3-6(5)9)7(10,11)12/h1-3H

Upstream product

• 50594-82-6 1-trifluoromethyl-3,4,5-trichlorobenzene 
• 98-08-8 α,α,α-trifluorotoluene 
• 121-17-5 2-chloro-3-nitro-5-trifluoromethylbenzene 
• 95-75-0 3,4-Dichlorotoluene 
• 95-50-1 1,2-dichloro-benzene 
• 3376-24-7 N-tert-butyl-α-phenylnitrone 
• 2926-29-6 Langlois reagent 
• 20555-91-3 3,4-dichloroiodobenzene 
• 289706-46-3 4-[2,2,2-trifluoro-1-(trimethylsilyloxy)ethyl]morpholine 
• 98-56-6 4-chlorobenzotrifluoride 
• 32137-19-2 1,2-difluoro-4-(trifluoromethyl)benzene 
• 584-08-7 potassium carbonate 
• 66682-07-3 3,4,5-trichlorotrichlorotoluene 
• 2136-87-0 2,3,4,5-tetrachloro-1-(trichloromethyl)benzene 

Downstream Products

• 50594-76-8 3-(2'-chloro-4'-trifluoromethyl-phenoxy)-phenol 
• 42874-63-5 5-(o-chloro-p-trifluoromethyl-phenoxy)-2-nitrophenol 
• 50594-44-0 2-Chlor-4-trifluormethyl-3'-acetoxy-4'-nitrodiphenylether 
• 50594-49-5 2-[5-(2-Chloro-4-trifluoromethyl-phenoxy)-2-nitro-phenoxy]-propionic acid ethyl ester 
• 169159-43-7 2,3-dichloro-5-trifluoromethylbenzaldehyde 
• 101463-63-2 4-(2-chloro-4-(trifluoromethyl)-phenoxy)-2-fluoroaniline 
• 42874-96-4 5-[2-chloro-4-(trifluoromethyl)phenoxy]toluene 
• 63734-62-3 3-(2-chloro-4-(trifluoromethyl)phenoxy)benzoic acid 
• 71980-08-0 (2'-chloro-4'-trifluoromethylphenoxy)-3,4-dinitrobenzene 
• 75795-07-2 3,3',4,4'-tetrachlorobenzophenone 
• 150172-63-7 1-(2-chloro-4-trifluoromethylphenyl)-5-nitroindazole 
• 186517-27-1 2,3-dichloro-6-(trifluoromethyl)benzaldehyde 
• 86398-98-3 2-chloro-4-trifluoromethylphenyl hydrazine 
• 1869-22-3 [2-Chloro-5-(trifluoromethyl)phenyl]hydrazine 

Relevant articles and documents

Novel process for synthesizing 3,4-dichlorobenzotrifluoride

The invention discloses a novel process for synthesizing 3,4-dichlorobenzotrifluoride, wherein the target compound is obtained by using 3,4-dichlorotoluene as a raw material and using a mixture of cuprous chloride and copper powder as a catalyst through a two-step reaction of chlorination and fluorination. Compared with the method in the prior art, the method of the invention has the following characteristics that the chlorination side reaction is less, the product purity is high, the 3,4-dichlorobenzotrifluorideis produced by using the byproduct 3,4-dichlorotoluene as the raw material so as to achieve the advantages of wide raw material source, low price, turning of byproduct into treasure and target compound production cost reducing, and the catalyst has characteristics of low price andconvenient recovery so as to reduce the production cost of the target compound, increase the economic benefit and avoid environmental pollution.

Efficient chlorination process of dichlorobenzotrifluoride

The invention discloses an efficient chlorination process of dichlorobenzotrifluoride, and belongs to the field of organic synthesis. According to the method, dichlorotoluene is used as a raw material, a mixture catalyst of cuprous chloride and copper powder is added, a target compound is obtained through two-step reaction of chlorination and fluorination, the raw materials applied in the reactionprocess are convenient to purchase, the production cost is low, after-treatment is simple, reaction conditions are mild, and good economic benefits and social benefits are achieved.

Efficient chlorination process of 3,4-dichlorobenzotrifluoride

The invention discloses an efficient chlorination process of 3,4-dichlorobenzotrifluoride, and belongs to the field of organic synthesis. According to the method, 3,4-dichlorotoluene is used as a rawmaterial, a mixture catalyst of cuprous chloride and copper powder is added, a target compound is obtained through two-step reaction of chlorination and fluorination, the raw materials applied in thereaction process are convenient to purchase, the production cost is low, after-treatment is simple, reaction conditions are mild, and good economic benefits and social benefits are achieved.

C?H Bond Trifluoromethylation of Arenes Enabled by a Robust, High-Valent Nickel(IV) Complex

The robust, high-valent NiIV complex [(Py)2NiIVF2(CF3)2] (Py=pyridine) was synthesized and fully characterized by NMR spectroscopy, X-ray diffraction, and elemental analysis. It reacts with aromatic compounds at 25 °C to form the corresponding benzotrifluorides in nearly quantitative yield. The monomeric and dimeric NiIIICF3 complexes 2?Py and 2 were identified as key intermediates, and their structures were unambiguously determined by EPR spectroscopy and X-ray diffraction. Preliminary kinetic studies in combination with the isolation of reaction intermediates confirmed that the C?H bond-breaking/C?CF3 bond-forming sequence can occur both at NiIVCF3 and NiIIICF3 centers.

Phosphovanadomolybdic acid catalyzed direct C-H trifluoromethylation of (hetero)arenes using NaSO2CF3 as the CF3 source and O2 as the terminal oxidant

A direct C-H trifluoromethylation of (hetero)arenes using NaSO2CF3 (Langlois' reagent) as the CF3 source and O2 as the terminal oxidant has been developed. In the presence of catalytic amounts of phosphovanadomolybdic acids, such as H6PV3Mo9O40, various kinds of substituted benzenes and heteroaromatic compounds could be converted into the corresponding trifluoromethylated products.

Continuous synthesis method of aromatic fluorine-containing compound and synthesis equipment thereof

The invention discloses a continuous synthesis method of aromatic fluorine-containing compound and synthesis equipment thereof. The synthesis method comprises the following steps: the aromatic chloride enters from the top of a fluorinationreaction tower, and anhydrous hydrogen fluoride liquid enters from the bottom so as to perform the backward fluorination reaction in the fluorination reaction tower; the tail gas is mixed with the anhydrous hydrogen fluoride liquid so as to commonly enter from the top of the fluorinationreaction tower after orderly passing through a condenser and an acid mist eliminator; and the bottom of the fluorination reaction tower obtains the aromatic fluorine-containing compound. The continuous synthesis equipment comprises the fluorination reaction tower, a chloride inlet of thefluorination reaction tower is communicated with a chloride storage tank; the lower part and the middle part of the fluorination reaction tower are respectively provided with a hydrogen fluoride inlet; the tail gas outlet of the fluorination reaction tower is orderly communicated withthe condenser, the acid mist eliminator and a mixer; the outlet of the mixer is communicated with the chloride inlet; and an aromatic fluorine-containing compound outlet is arranged at the bottom of the fluorination reaction tower. Through the synthesis method and synthesis equipmentdisclosed by theinvention, the continuous reaction is realized, and the process flow is short, the production security is high, and the product quality is stability.

Trifluoromethylation of (hetero)aryl iodides and bromides with copper(i) chlorodifluoroacetate complexes

A new copper-mediated trifluoromethylation reaction using copper(i) chlorodifluoroacetate complexes as reagents is reported. The complex [L2Cu][O2CCF2Cl] (L = bpy, dmbpy, phen) reacted with (hetero)aryl iodides and bromides in the presence of CsF in DMF at 75 °C to afford the trifluoromethylarenes in good to excellent yields. High compatibility with various chemical functions or (hetero)cycles was also observed in the reaction. A reaction mechanism involving a difluorocarbene intermediate, along with a subsequent formation of a -CF3 anion was proposed.

Decarboxylative Trifluoromethylating Reagent [Cu(O2CCF3)(phen)] and Difluorocarbene Precursor [Cu(phen)2][O2CCF2Cl]

This article describes the new economic decarboxylative trifluoromethylating reagent [Cu(phen)(O2CCF3)] (1; phen=1,10-phenanthroline) and the efficient difluorocarbene precursor [Cu(phen)2][O2CCF2Cl] (2). Treatment of copper tert-butoxide with phen and subsequent addition of trifluoroacetic acid or chlorodifluoroacetic acid afforded air-stable complexes 1 and 2, respectively, which were characterized by X-ray crystallography. The copper(I) ion in 1 is coordinated by a bidentate phen ligand, a monodentate trifluoroacetate group, and a molecule of CH3CN in a distorted tetrahedral coordination geometry. The molecular structure of 2 adopts an ionic form that consists of a [Cu(phen)2]+ cation and a chlorodifluoroacetate anion. Complex 1 reacted with a variety of aryl and heteroaryl halides to form trifluoromethyl (hetero)arenes in good yields. The corresponding Hammett plot exhibited a linear relationship and a reaction parameter (ρ)=+0.56±0.02, which indicated that the trifluoromethylation reaction proceeded via a nucleophilic reactive species. Complex 2 reacts with phenols to produce aryl difluoromethyl ethers in modest-to-excellent yields. Mechanistic investigations revealed that the difluoromethylation reaction proceeds by initial copper-mediated formation of difluorocarbene and subsequent concerted addition of difluorocarbene to the phenol to form a three-center transition state.

Copper-catalyzed aromatic trifluoromethylation via group transfer from fluoral derivatives

Starting from a readily available fluoral derivative, catalytic aromatic trifluoromethylation has been successfully achieved. A small amount of copper(I) iodide-phenanthroline complex catalyzed the cross-coupling reactions of aryl/heteroaryl iodides with the O-silylated hemiaminal of fluoral (trifluoroacetaldehyde) to provide trifluoromethylated arenes in moderate to high yields.

Preparation Method of 2, 6-Dichlor-4-Trifluoromethyl Aniline

This invention is involved with a preparation method of 2,6-dichlor-4-trifluoromethyl aniline. With this process, 4-chlorotrifluoromethyl benzene is used as the starting material and subjected to halogenation reaction and ammoniation reaction and through separation of reaction products the desired 2,6-dichlor-4-trifluoromethyl aniline is obtained. In addition, ammonia is recovered from the surplus ammonia water in ammoniation reaction. This applied invention in characterized by simple process, cheap and easy-available raw materials, high reaction yield and friendly environment.