68-36-0

Basic information

• Product Name: 1,4-BIS(TRICHLOROMETHYL)BENZENE
• Synonyms: 2,2-Hexachloro-p-xylene;alpha,alpha,alpha,alpha’,alpha’,alpha’-hexachloro-p-xylen;alpha,alpha’-hexachloro-p-xylen;alpha,alpha’-hexachloro-p-xylene;alpha,alpha’-hexachloroxylene;alpha,alpha'-Hexachloro-p-xylene;alpha,alpha'-Hexachloroxylene;Benzene, 1,4-bis(trichloromethyl)-
• CAS NO: 68-36-0
• Molecular Formula: C₈H₄Cl₆
• Molecular Weight: 312.84
• EINECS: 200-686-3
• Mol File: 68-36-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 106-110 °C
• Boiling Point: 312 °C
• Flash Point: 153 °C
• Appearance: Light yellow/Crystalline Powder and Chunks
• Density: 1.6957 (rough estimate)
• Vapor Pressure: 0.000334mmHg at 25°C
• Refractive Index: 1.5840 (estimate)
• Solubility: soluble in Methanol
• Merck: 1303
• CAS DataBase Reference: 1,4-BIS(TRICHLOROMETHYL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-BIS(TRICHLOROMETHYL)BENZENE(68-36-0)
• EPA Substance Registry System: 1,4-BIS(TRICHLOROMETHYL)BENZENE(68-36-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 45-36/37/39-26
• RTECS: ZE4655000
• Hazardous Substances Data: 68-36-0(Hazardous Substances Data)

Usage

Chemical Properties

light yellow crystalline powder and chunks

Uses

1,4-Bis(trichloromethyl)benzene is one of the potential environmental pollutant being studied.

InChI:InChI=1/C8H4Cl6/c9-7(10,11)5-1-2-6(4-3-5)8(12,13)14/h1-4H

Synthetic route

para-xylene (106-42-3) → 1,4-bis(trichloromethyl)benzene (68-36-0)

Conditions	Yield
With chlorine at 60 - 180℃; for 13.5h; Temperature;	95.2%
With chlorine at 80 - 180℃; Irradiation;	87.6%
With chlorine at 150℃; Irradiation;

4-Methylbenzyl chloride (104-82-5) → 1,4-bis(trichloromethyl)benzene (68-36-0)

Conditions	Yield
With chlorine at 100℃; Irradiation;

formaldehyd (50-00-0) + toluene (108-88-3) → 1,4-bis(trichloromethyl)benzene (68-36-0)

Conditions	Yield
With hydrogenchloride; zinc(II) chloride

formaldehyd (50-00-0) + toluene (108-88-3) → 1,4-bis(trichloromethyl)benzene (68-36-0) + o-dichloromethyltrichloromethylbenzene (2741-57-3)

Conditions	Yield
With hydrogenchloride; zinc(II) chloride at 75℃;

1,4-bis(trifluoromethyl)benzene (433-19-2) → 1,4-bis(trichloromethyl)benzene (68-36-0)

Conditions	Yield
With aluminium trichloride

para-xylene (106-42-3) + chlorine (7782-50-5) → 1,4-bis(trichloromethyl)benzene (68-36-0)

Conditions	Yield
Licht;

para-xylene (106-42-3) + chlorine (7782-50-5) + charcoal → 1,4-bis(trichloromethyl)benzene (68-36-0)

methanol (67-56-1) + 1,4-bis(trichloromethyl)benzene (68-36-0) → 1,4-benzenedicarboxylic acid dimethyl ester (120-61-6)

Conditions	Yield
at 20℃; for 6h; UV-irradiation;	99%
With zinc(II) chloride

1,4-bis(trichloromethyl)benzene (68-36-0) + 2-amino-phenol (95-55-6) → 1,4-bis(2-benzoxazolyl)benzene (904-39-2)

Conditions	Yield
With PPA at 100 - 150℃; for 6h; Addition;	94%

1,4-bis(trichloromethyl)benzene (68-36-0) + 2-amino-benzenethiol (137-07-5) → 1,4-bis(benzothiazol-2-yl)benzene (5153-65-1)

Conditions	Yield
With PPA at 100 - 150℃; for 6h; Addition;	94%

1,4-bis(trichloromethyl)benzene (68-36-0) → 1,4-bis(trifluoromethyl)benzene (433-19-2)

Conditions	Yield
With hydrogen fluoride at 150℃; under 77574.3 Torr; for 7h;	75%
With hydrogen fluoride at 150 - 210℃;
With hydrogen fluoride; antimonypentachloride at 20℃;
With hydrogen fluoride at 150 - 210℃;

1,4-bis(trichloromethyl)benzene (68-36-0) → 4-trichloromethylbenzoyl chloride (14815-86-2)

Conditions	Yield
With isophthalic acid; zinc(II) chloride at 185℃; for 4.5h;	56%
With iron(III) chloride
With antimonypentachloride; water at 125 - 135℃;
With water; iron(III) chloride at 125 - 135℃;

1,4-bis(trichloromethyl)benzene (68-36-0) + formic acid hydrazide (624-84-0) → p-phenylene-2,2′-bis-1,3,4-oxadiazole (23571-78-0)

Conditions	Yield
With pyridine In ethanol for 34h; Heating;	47%

isoniazid (54-85-3) + 1,4-bis(trichloromethyl)benzene (68-36-0) → 5,5'-di(4-pyridyl)-1,4-phenylenebis-1,3,4-oxadiazole

Conditions	Yield
With pyridine In ethanol for 27h; Heating;	41%

1,4-bis(trichloromethyl)benzene (68-36-0) + triethylamine (121-44-8) → N1,N1,N4,N4-tetraethylterephthalamide (15394-30-6)

Conditions	Yield
With heptamethyl Coβ-perchlorato-cob(II)yrinate; tetrabutylammonium perchlorate In acetonitrile at 20℃; for 3h; Electrolysis;	41%

1,4-bis(trichloromethyl)benzene (68-36-0) + 2-Hydroxybenzoylhydrazine (936-02-7) → 5,5'-di(2-hydroxyphenyl)-1,4-phenylenebis-1,3,4-oxadiazole

Conditions	Yield
With pyridine In ethanol for 19h; Heating;	38%

1,4-bis(trichloromethyl)benzene (68-36-0) + N-amino-(4-nitrophenyl)carboxamide (636-97-5) → 5,5'-di(4-nitrophenyl)-1,4-phenylenebis-1,3,4-oxadiazole (22915-82-8)

Conditions	Yield
With pyridine In ethanol for 20h; Heating;	36%

1,4-bis(trichloromethyl)benzene (68-36-0) + benzoic acid hydrazide (613-94-5) → 5,5'-diphenyl-1,4-phenylenebis-1,3,4-oxadiazole (5888-97-1)

Conditions	Yield
With pyridine In ethanol for 21h; Heating;	35%

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + 1,4-bis(trichloromethyl)benzene (68-36-0) → {Co3(CO)9C}2C6H4

Conditions	Yield
In tetrahydrofuran thermal react. of p-(Cl3C)2C6H4 with Co2(CO)8 in THF; ppt. is washed with CH2Cl2, dried in vac., elem. anal.;	10%

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%

maleic anhydride (108-31-6) + 1,4-bis(trichloromethyl)benzene (68-36-0) + (E)-3-Ureido-but-2-enoic acid ethyl ester (5435-44-9, 22243-66-9) → terephthaloyl chloride (100-20-9)

Conditions	Yield
at 140℃;

propan-1-ol (71-23-8) + 1,4-bis(trichloromethyl)benzene (68-36-0) → terephthalic acid dipropyl ester (1962-74-9)

Conditions	Yield
With zinc(II) chloride

ethanol (64-17-5) + 1,4-bis(trichloromethyl)benzene (68-36-0) → diethyl terephthalate (636-09-9)

Conditions	Yield
With zinc(II) chloride

2-methyl-propan-1-ol (78-83-1) + 1,4-bis(trichloromethyl)benzene (68-36-0) → diisobutyl terephthalate (18699-48-4)

Conditions	Yield
With zinc(II) chloride

1,4-bis(trichloromethyl)benzene (68-36-0) + furan-2,3,5(4H)-trione pyridine (1:1) → terephthalic acid (100-21-0)

1,4-bis(trichloromethyl)benzene (68-36-0) → terephthaloyl chloride (100-20-9)

Conditions	Yield
With titanium(IV) oxide
With maleic acid; zinc(II) chloride
With water; iron(III) chloride at 125 - 140℃;
With aluminium trichloride; water at 125 - 140℃;
at 125℃; for 1h; Temperature;

1,4-bis(trichloromethyl)benzene (68-36-0) + hexan-1-ol (111-27-3) → dihexyl terephthalate (1818-96-8)

Conditions	Yield
With zinc(II) chloride

chloro-trimethyl-silane (75-77-4) + 1,4-bis(trichloromethyl)benzene (68-36-0) → α,α,α,α',α',α'-hexakis(trimethylsilyl)-1,4-xylol (17557-11-8)

Conditions	Yield
With magnesium
With magnesium 1.) THF, 2.) THF, reflux, 70 h; Yield given. Multistep reaction;

terephthalic acid (100-21-0) + 1,4-bis(trichloromethyl)benzene (68-36-0) → terephthaloyl chloride (100-20-9)

Conditions	Yield
iron(III) chloride In chlorobenzene at 115℃; Rate constant; Kinetics; Mechanism; activation energy, reaction order;

1,4-bis(trichloromethyl)benzene (68-36-0) → 1,1,2,2-Tetrachlor-1,2-bis-<4-trichlormethyl-phenyl>-aethan (92967-63-0)

Conditions	Yield
With pyridine; copper

Upstream product

• 106-42-3 para-xylene 
• 104-82-5 4-Methylbenzyl chloride 
• 50-00-0 formaldehyd 
• 108-88-3 toluene 
• 433-19-2 1,4-bis(trifluoromethyl)benzene 
• 7782-50-5 chlorine 

Downstream Products

• 100-20-9 terephthaloyl chloride 
• 636-09-9 diethyl terephthalate 
• 433-19-2 1,4-bis(trifluoromethyl)benzene 
• 15394-30-6 N₁,N₁,N₄,N₄-tetraethylterephthalamide 
• 2142-29-2 2,5-dichloro-1,4-bis-(trichloromethyl)-benzene 
• 92967-54-9 1,1,2,2-Tetrachlor-1,2-bis-(4-isocyanatophenyl)-ethan 
• 1691-62-9 1,1,2,2-Tetrafluor-1,2-bis-(4-isocyanatophenyl)-ethan 
• 94428-86-1 1.1.2.2-Tetrachlor-1.2-bis-<4-azidocarbonyl-phenyl>-aethan 
• 2793-42-2 1.1.2.2-Tetrafluor-1.2-bis-<4-azidocarbonyl-phenyl>-aethan 
• 856-69-9 1.1.2.2-Tetrafluor-1.2-bis-<4-methoxycarbonyl-phenyl>-aethan 
• 1547-61-1 1.1.2.2-Tetrafluor-1.2-bis-<4-carbamoyl-phenyl>-aethan 
• 2821-14-9 1.1.2.2-Tetrafluor-1.2-bis-<4-chlorcarbonyl-phenyl>-aethan 
• 94298-27-8 1.1.2.2-Tetrachlor-1.2-bis-<4-carbamoyl-phenyl>-aethan 
• 853-15-6 α,α,α',α'-Tetrafluor-bibenzyl-4,4'-dicarbonsaeure 

Relevant articles and documents

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A second (trichloromethyl) benzene and two (chloroformyl) benzenetrisamide preparation method

The present invention relates to a method for preparing bis(trichloromethyl)benzene through a photochemical reaction and preparing bis(chloroformyl)benzene through the further reaction of the bis(trichloromethyl)benzene. According to the present invention, di(methyl)benzene is added to a reactor, chlorine gas is introduced under the control of the illuminance of an incident light source and the reaction temperature, the obtained reaction mixture is subjected to a simple treatment so as to obtain the high purity bis(trichloromethyl)benzene; with the bis(trichloromethyl)benzene of the present invention, the high purity bis(chloroformyl)benzene, one of the aramid fiber production raw materials, can be conveniently obtained; and the preparation method of the present invention has the following advantages that the solvent, the free radical initiator, the photosensitizer and other third components can not be inproduced, and only the stage-control of the reaction condition and the wavelength and the intensity of the light source are required so as to improve the product purity.

METHOD FOR THE PREPARATION OF TRICHLOROMETHYL-GROUP-SUBSTITUTED BENZENE

The present application relates to a method for photochlorination, and specifically to photochlorination by a photochemical reaction of an aromatic compound with gaseous chlorine so as to prepare a trichloromethyl-substituted benzene, and to a method using bis-(trichloromethyl)-benzene as the trichloromethyl-substituted benzene to prepare by further reaction bis-(chloroformyl)-benzene. Through the control of temperature, illuminance and consumption of gaseous chlorine, the method of this application can greatly improve the purity of trichloromethyl-substituted benzene and further prepare polymer-grade bis-(chloroformyl)-benzene with low cost. The present application also relates to a method for purifying trichloromethyl-substituted benzene, and specifically to a method for purifying trichloromethyl-substituted benzene via molecular distillation. The present application further relates to a photochlorination reactor for use in photochlorination reactions (such as those of the present application).