2629-68-7

Usage

Uses

Used in Pharmaceutical Industry:
1,4-Bis(chlorodifluoromethyl)benzene is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique molecular structure allows for the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 1,4-Bis(chlorodifluoromethyl)benzene serves as an intermediate in the production of agrochemicals, contributing to the development of effective pesticides and other agricultural chemicals.
Used in Polymer Production:
1,4-Bis(chlorodifluoromethyl)benzene is utilized in the manufacture of polymers, where its properties can enhance the performance characteristics of the resulting materials, such as durability, stability, and resistance to environmental factors.
Used as a Solvent in Industrial Processes:
This chemical compound also functions as a solvent in various industrial applications, where its ability to dissolve other substances is leveraged to facilitate chemical reactions or material processing.
Proper handling and disposal of 1,4-Bis(chlorodifluoromethyl)benzene are crucial due to its potential toxicity and environmental impact, ensuring the safety of workers and the preservation of the environment.

InChI:InChI=1/C8H4Cl2F4/c9-7(11,12)5-1-2-6(4-3-5)8(10,13)14/h1-4H

Synthetic route

p-bis(difluoromethyl)benzene (369-54-0) → 1,4-bis-(difluorochloromethyl)-benzene (2629-68-7)

Conditions	Yield
With chlorine at 60℃; under 760.051 Torr; for 1.66667h; Time; Temperature; Reagent/catalyst; Irradiation;	99.49%
With chlorine In tetrachloromethane Irradiation;
With chlorine; dibenzoyl peroxide In tetrachloromethane at 80℃; for 9h; Reagent/catalyst; Solvent; Temperature;

1,4-bis(trichloromethyl)benzene (68-36-0) → 1-(chlorodifluoromethyl)-4-(trifluoromethyl)benzene (13947-94-9) + 1,4-bis-(difluorochloromethyl)-benzene (2629-68-7) + 1-fluorodichloromethyl-4-difluorochloromethyl-benzene (13947-95-0)

Conditions	Yield
With hydrogen fluoride In 1,2-dichloro-ethane at 45℃; under 2280.15 Torr; for 10h;	A 3.3% B n/a C 4%

p-bis(difluoromethyl)benzene (369-54-0) → dichloro-tetrafluoro-p-xylene + 1,4-bis-(difluorochloromethyl)-benzene (2629-68-7)

Conditions	Yield
With chlorine In tetrachloromethane

1,4-bis-(difluorochloromethyl)-benzene (2629-68-7) + thiophenol (108-98-5) → C20H14F4S2 (3200-14-4)

Conditions	Yield
Stage #1: thiophenol With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride Stage #2: 1,4-bis-(difluorochloromethyl)-benzene	70%

1,4-bis-(difluorochloromethyl)-benzene (2629-68-7) + phenol (108-95-2) → 1,4-bis(difluorophenoxymethyl)benzene (1154741-12-4)

Conditions	Yield
Stage #1: phenol With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride Stage #2: 1,4-bis-(difluorochloromethyl)-benzene	65%
With 1-methyl-pyrrolidin-2-one; sodium methylate at 100℃; for 8h; Reagent/catalyst; Temperature; Inert atmosphere;	48.7%

1,4-bis-(difluorochloromethyl)-benzene (2629-68-7) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + (Z)-2,3,8,8,9,9-Hexafluoro-tricyclo[8.2.2.24,7]hexadeca-1(13),2,4(16),5,7(15),10(14),11-heptaene

Conditions	Yield
With zinc In N,N-dimethyl acetamide at 100℃; for 4h; Substitution;	A 60.5% B 6%

1,4-bis-(difluorochloromethyl)-benzene (2629-68-7) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
With potassium iodide; zinc In N,N-dimethyl acetamide at 120 - 142℃; for 6h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature;	45.7%
With lithium aluminium tetrahydride; titanium tetrachloride In tetrahydrofuran Heating;	22%

1,4-bis-(difluorochloromethyl)-benzene (2629-68-7) + α,α'-dibromo-α,α,α',α'-tetrafluoro-p-xylene (651-12-7) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7)

Conditions	Yield
With calcium chloride; zinc In N,N-dimethyl acetamide at 120 - 140℃; for 4h; Catalytic behavior; Reagent/catalyst;	31.4%

1,4-bis-(difluorochloromethyl)-benzene (2629-68-7) → 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (3345-29-7) + dodecafluoro[2,2]paracyclophane

Conditions	Yield
With aluminium In N,N-dimethyl-formamide at 0 - 20℃; for 50h;	A 22% B 20%

Upstream product

• 369-54-0 p-bis(difluoromethyl)benzene 
• 68-36-0 1,4-bis(trichloromethyl)benzene 

Downstream Products

• 3345-29-7 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane 
• 3200-14-4 C₂₀H₁₄F₄S₂ 
• 1154741-12-4 1,4-bis(difluorophenoxymethyl)benzene 

Relevant academic research and scientific papers

Method for synthesizing 1,4-di(difluoro phenoxy methyl) benzene

The invention provides a method for synthesizing 1,4-di(difluoro phenoxy methyl) benzene. The method comprises the following steps: (1) by taking 1,4-di(difluoro methyl) benzene as an initial raw material, and carrying out a free radical substation reaction with chlorine in the presence of a free radical initiator so as to obtain 1,4-di(chlorine difluoro methyl) benzene; (2) without refining of the intermittent, namely the 1,4-di(chlorine difluoro methyl) benzene, directly carrying out a unimolecule free radical nucleophilic substitution reaction on the intermittent with an alkali and phenol in an organic solvent, and carrying out recrystallization on a crude product, thereby obtaining the 1,4-di(difluoro phenoxy methyl) benzene. The method is gentle in reaction condition, and the obtainedproduct is high in both yield and purity and is applicable to large-scale production.

FACILE AND EFFECTIVE METHOD OF PREPARING 1,4-BIS(CHLORODIFLUOROMETHYL)BENZENE

The present invention relates to a facile method of preparing 1,4-bis(chlorodifluoromethyl)benzene, comprising the steps of: (A) providing a reactant liquid of 1,4-bis(difluoromethyl)benzene; optionally (B) providing a light source for UV radiation; and (C) introducing chlorine gas into the reactant liquid at a temperature of 50-90° C. under a pressure above 1 atm to obtain 1,4-Bis(chlorodifluoromethyl)benzene. The invented facile method can be utilized in a batch process or a continuous process for effective production of 1,4-bis(chlorodifluoromethyl)benzene.

Efficient synthesis of p-bis-(chlorodifluoromethyl)benzene

Selective, high yield partial fluorination of p-bis-(trichloromethyl)benzene to p-bis-(chlorodifluoromethyl)benzene has been accomplished by warming a slurry of the p-bis-(trichloromethyl)benzene in anhydrous HF which also contains a small quantity of inert solvent, such as 1,2-dichloroethane.

Processes for the preparation of octafluoro-[2,2]paracyclophane

Processes are disclosed for the preparation of octafluoro-[2,2]paracyclophane which utilize a low temperature, e.g., less than about 200° C., and a reducing agent comprising titanium to promote the dimerization of dihalo-tetrafluoro-p-xylenes. One suitable reducing agent is prepared by combining TiCl4 with LiAlH4 in an organic solvent.