2629-68-7

Basic information

• Product Name: 1,4-BIS(CHLORODIFLUOROMETHYL)BENZENE
• Synonyms: ALPHA,ALPHA'-DICHLORO-ALPHA,ALPHA,ALPHA',ALPHA'-TETRAFLUORO-P-XYLENE;1,4-BIS(CHLORODIFLUOROMETHYL)BENZENE;1,4-Bis(chlorodifluoromethyl)benzene98%;Benzene,1,4-bis(chlorodifluoromethyl)-
• CAS NO: 2629-68-7
• Molecular Formula: C8H4Cl2F4
• Molecular Weight: 247.02
• EINECS: 1312995-182-4
• Mol File: 2629-68-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 11-12°C
• Boiling Point: 55.5/3.8mm
• Flash Point: >150°C
• Appearance: /
• Density: 1,46 g/cm3
• Vapor Pressure: 0.313mmHg at 25°C
• Refractive Index: 1.453
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,4-BIS(CHLORODIFLUOROMETHYL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-BIS(CHLORODIFLUOROMETHYL)BENZENE(2629-68-7)
• EPA Substance Registry System: 1,4-BIS(CHLORODIFLUOROMETHYL)BENZENE(2629-68-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 2629-68-7(Hazardous Substances Data)

Usage

General Description

1,4-Bis(chlorodifluoromethyl)benzene, also known as bischlorodifluoromethylbenzene, is a chemical compound with the molecular formula C8H6Cl2F4. It is a colorless liquid at room temperature and is used as an intermediate in the production of pharmaceuticals and agrochemicals. 1,4-Bis(chlorodifluoromethyl)benzene is also used in the manufacture of polymers and as a solvent in various industrial processes. Due to its potential toxicity and environmental impact, proper handling and disposal procedures are necessary when working with this chemical.

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 
• 1154741-12-4 1,4-bis(difluorophenoxymethyl)benzene 
• 3200-14-4 C₂₀H₁₄F₄S₂ 

Relevant articles and documents

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.

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.