106-46-7

Hazards Identification

Pictogram(s):

Signal:

Warning

GHS Hazard Statements:

H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H351: Suspected of causing cancer [Warning Carcinogenicity]
H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes:

P203, P264+P265, P273, P280, P305+P351+P338, P318, P337+P317, P391, P405, and P501

Hazard Classes and Categories:

Carc. 2
Eye Irrit. 2
Aquatic Acute 1
Aquatic Chronic 1
Eye Irrit. 2 (100%)
Carc. 2 (100%)
Aquatic Acute 1 (93.06%)
Aquatic Chronic 1 (100%)
Carcinogenicity - category 2
Eye irritation - category 2
Hazardous to the aquatic environment (acute) - category 1
Hazardous to the aquatic environment (chronic) - category 1
Serious eye damage/eye irritation - Category 2
Skin sensitization - Category 1
Carcinogenicity - Category 2
Reproductive toxicity - Category 2
Specific target organ toxicity - Single exposure - Category 1 (central nervous system, blood system, liver), Category 3 (respiratory tract irritation)
Specific target organ toxicity - Repeated exposure - Category 1 (nervous system, liver, blood system), Category 2 (respiratory system, kidney)
Hazardous to the aquatic environment (Acute) - Category 1
Hazardous to the aquatic environment (Long-term) - Category 1
Reproductive toxicity - Category 1B
Specific target organ toxicity - Single exposure - Category 1 (blood, liver), Category 3 (respiratory tract irritation)
Specific target organ toxicity - Repeated exposure - Category 1 (respiratory system, liver, nervous system, blood), Category 2 (kidney)
Acute toxicity (Oral) - Category 5
Skin corrosion/irritation - Category 3
Serious eye damage/eye irritation - Category 2B
Germ cell mutagenicity - Category 2
Specific target organ toxicity - Single exposure - Category 1 (blood system, liver)
Specific target organ toxicity - Repeated exposure - Category 1 (respiratory system, liver, nervous system), Category 2 (kidney)
Carcinogens, Flammable - 2nd degree

Hazards Summary:

The primary exposure to 1,4-dichlorobenzene is from breathing contaminated indoor air. Acute (short- term) exposure to 1,4-dichlorobenzene, via inhalation in humans, results in irritation of the skin, throat, and eyes. Chronic (long-term) 1,4-dichlorobenzene inhalation exposure in humans results in effects on the liver, skin, and central nervous system (CNS). No information is available on the reproductive, developmental, or carcinogenic effects of 1,4-dichlorobenzene in humans. A National Toxicology Program (NTP) study reported that 1,4-dichlorobenzene caused kidney tumors in male rats and liver tumors in both sexes of mice by gavage (experimentally placing the chemical in their stomachs). EPA has classified 1,4- dichlorobenzene as a Group C, possible human carcinogen.

Usage

Uses

1,4-Dichlorobenzene is used in various applications across different industries due to its properties and characteristics. Some of its primary uses include:
Used in Pest Control:
1,4-Dichlorobenzene is used as a moth repellent, making it a common ingredient in mothballs and deodorant cakes. It is used to protect stored clothes, fabrics, and other materials from damage caused by moths and other insects.
Used in Deodorization:
1,4-Dichlorobenzene is used as a space deodorant in various products, such as room deodorizers, toilet bowl blocks, and diaper pail deodorizers. Its strong odor helps to mask and neutralize unpleasant smells in these environments.
Used in Agriculture:
1,4-Dichlorobenzene is used as an insecticide on fruit, helping to protect crops from damage caused by insects. It is also used to control mold and mildew growth on tobacco seeds, leather, and certain fabrics.
Used in Beekeeping:
1,4-Dichlorobenzene is approved for controlling wax moths in empty, stored beehives, helping to protect the hives from infestation and damage.
Used in Chemical Production:
1,4-Dichlorobenzene serves as an intermediate in the production of various chemicals, including those used in the manufacturing of plastics for electronic components.
Used in Fumigation:
As a fumigant, 1,4-dichlorobenzene is used to control pests in various settings, such as agricultural storage facilities and other areas where pests may be a problem.

Preparation

1,4-Dichlorobenzene was first produced commercially in the United States in 1915 (IARC 1982). It is produced by reacting liquid benzene with gaseous chlorine in the presence of a catalyst at moderate temperature and atmospheric pressure. 1,4-Dichlorobenzene is used mainly as a fumigant for the control of moths, molds, and mildews, and as a space deodorant for toilets and refuse containers.

Synthesis Reference(s)

Chemistry Letters, 8, p. 939, 1979The Journal of Organic Chemistry, 48, p. 250, 1983 DOI: 10.1021/jo00150a020Tetrahedron Letters, 23, p. 371, 1982 DOI: 10.1016/S0040-4039(00)86833-1

Air & Water Reactions

Insoluble in water.

Reactivity Profile

1,4-Dichlorobenzene is incompatible with oxidizing agents. 1,4-Dichlorobenzene is also incompatible with aluminum and its alloys. 1,4-Dichlorobenzene liquefies when mixed with camphor, phenol and salol. 1,4-Dichlorobenzene will attack some forms of plastics, rubber and coatings. .

Health Hazard

Toxic symptoms are headache, weakness,dizziness, nausea, vomiting, diarrhea, loss ofweight, and injury to liver and kidney. Thesesymptoms occur from repeated inhalationof high concentrations of vapors or fromingestion. The vapors are an irritant to theeyes, throat, and skin. Chronic exposure maycause jaundice and cirrhosis. The oral LD50value in mice is in the range 3000 mg/kg.The fatal oral dose in humans is estimated tobe 40–50 g. Carcinogenic studies on animalshave not produced adequate evidence of anycancer-causing action.

Fire Hazard

Special Hazards of Combustion Products: Vapors are irritating. Toxic chlorine, hydrogen chloride, and phosgene gases may be generated in fires.

Trade name

DowTHERM?; EVOLA; PARACIDE?; PARA CRYSTALS?; PARADI?; PARADOW?; PARAMOTH?; PARANUGGETS?; PARAZENE?; PERSIA-PERAZOL?; SANTOCHLOR?; Mixed isomers: DILATIN DBI?; MOTTENSCHUTZMITTEL EVAU P?; MOTT-EX?; TOTAMOTT?

Safety Profile

There is limited evidence that 1,4-dichlorobenzene can damage a developing fetus. Exposure can damage the lungs, liver, kidneys, and blood cells, causing anemia; it can also cause swelling of the eyes, hands, and feet. It can damage the nervous system, causing weakness, trembling, and numbness in the arms and legs. It may cause a skin allergy, which when developed can cause itching and a skin rash. Higher levels of the chemical in air, such as the levels that are sometimes associated with industrial exposure, can cause headaches, nausea, clumsiness, slurred speech, and dizziness. Levels that would result in death would be associated with an odor so intense that it would be very unpleasant, if not intolerable, and would serve as a danger warning. In industrial situations, workers exposed to 1,4-dichlorobenzene at high levels are usually directed to wear respirators. Workers involved in the production of the chemical may be exposed to concentrations significantly higher than those encountered by the general population. High exposure levels may result from some consumer products of moth repellents and room deodorizers. Approximately 95% of the environmental release of 1,4-dichlorobenzene occurs during its use, rather than during its manufacture or processing.

Potential Exposure

The major uses of o-DCB are as a process solvent in the manufacturing of toluene diisocyanate and as an intermediate in the synthesis of dyestuffs, herbicides, and degreasers. p-Dichlorbenzene is used primarily as a moth repellant, a mildew control agent; space deodorant; and in insecticides, which accounts for 90% of the total production of this isomer. Information is not available concerning the production and use of m-DCB. However, it may occur as a contaminant of o-or p-DCB formulations. Both o-and p-isomers are produced almost entirely as by-products during the production of monochlorobenzene

Carcinogenicity

1,4-Dichlorobenzene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

Metabolic pathway

1,4-Dichlorobenzene undergoes degradation by the Xanthobacter flavus 14p1 isolated from river sludge by selective enrichment with 1,4-dichlorobenzene, resulting in the degradation products 3,6-dichloro-cis- 1,2-dihydroxycyclohexa-3,5-diene and 3,6- dichlorocatechol. 2,5-Dichloromuconic acid and 2- chloromaleylacetic acid, as well as the decarboxylation product 2-chloroacetoacrylic acid, are identified after enzymatic conversion of 3,6-dichlorocatechol.

Shipping

m-DCB: UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. United States DOT Regulated Marine Pollutant. UN3077 Environmentally hazardous substances, solis, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical NameRequired. UN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required

Purification Methods

o-Dichlorobenzene is a common impurity. The p-isomer has been purified by steam distillation, crystallisation from EtOH or boiling MeOH, air-dried and dried in the dark under vacuum. It has also been purified by zone refining. [Beilstein 5 IV 658.]

Incompatibilities

For o-DCB and m-DCB: acid fumes, chlorides, strong oxidizers; hot aluminum, or aluminum alloys. For p-DCB: Strong oxidizers; although, incompatibilities for this chemical may also include other materials listed for o-DCB.

Waste Disposal

Incineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal

Synthetic route

1-Chloro-4-iodobenzene (637-87-6) → para-dichlorobenzene (106-46-7)

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; hypochlorite In dichloromethane other iodoaromatics, intermediacy of iodyl compounds at short reaction times;	100%
With tetra(n-butyl)ammonium hydrogensulfate; hypochlorite In dichloromethane 23-28 h; Yield given;
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid 2: copper(l) chloride / acetonitrile / 2 h / 80 °C View Scheme

1,2,4,5-tetrachlorobenzene (95-94-3) → para-dichlorobenzene (106-46-7) + 1,2-dichloro-benzene (95-50-1) + 1,3-Dichlorobenzene (541-73-1) + benzene (71-43-2)

Conditions	Yield
With potassium hydroxide; hydrogen; palladium on activated charcoal In water at 50℃; for 0.92h; Yields of byproduct given;	A n/a B n/a C n/a D 98%

4-chloro-benzoyl chloride (122-01-0) → para-dichlorobenzene (106-46-7)

Conditions	Yield
palladium on activated charcoal In gas at 360℃;	98%

bromochlorobenzene (106-39-8) → para-dichlorobenzene (106-46-7)

Conditions	Yield
With trans-bis(glycinato)copper(II) monohydrate; tetramethlyammonium chloride In ethanol at 100℃; for 24h; Finkelstein Reaction; Schlenk technique; Inert atmosphere;	95%
With sodium hypochlorite; (tetraphenylporphyrinato)nickel(II); benzyl tri-n-butylammonium bromide In chloroform at 25℃; for 0.5h;	75%
With tetrachloromethane; chlorine Photolysis;
With tetrachloromethane at 250℃; for 21h; Inert atmosphere; Autoclave;	13 %Spectr.
With iron(III) chloride; sodium chloride In acetonitrile for 10h; Kinetics; Irradiation; Green chemistry; regioselective reaction;

4-chlorobenzenesulfonyl chloride (98-60-2) → para-dichlorobenzene (106-46-7)

Conditions	Yield
With sulfuryl dichloride; 2,2'-azobis(isobutyronitrile); hexamethylenetetramine at 54.9 - 64.9℃; for 2h; Thermodynamic data; Kinetics; Mechanism; activation energy;	95%
With sulfuryl dichloride; 2,2'-azobis(isobutyronitrile); hexamethylenetetramine at 54.9 - 64.9℃;	95%

1,2,4-Trichlorobenzene (120-82-1) → para-dichlorobenzene (106-46-7) + 1,2-dichloro-benzene (95-50-1) + 1,3-Dichlorobenzene (541-73-1)

Conditions	Yield
With radical anion of p,p'-di-tert-butylbiphenyl In tetrahydrofuran at -60℃; Product distribution; Rate constant; Mechanism; Irradiation; radical anion of naphthalene, different temperatures;	A 87.2% B 2.79% C 9.96%
With radical anion of p,p'-di-tert-butylbiphenyl In tetrahydrofuran at -70℃; Irradiation;	A 87.7% B 2.97% C 9.32%
With radical anion of p,p'-di-tert-butylbiphenyl In tetrahydrofuran at 45℃; Irradiation;	A 75.3% B 9.89% C 13.7%

potassium (4-chlorophenyl)trifluoroborate → para-dichlorobenzene (106-46-7)

Conditions	Yield
With trichloroisocyanuric acid In water; ethyl acetate at 20℃; for 1h; Open flask;	86%

(4-chlorophenyl)(mesityl)iodonium trifluoromethanesulfonate (1204518-00-2) → para-dichlorobenzene (106-46-7)

Conditions	Yield
With copper(l) chloride In acetonitrile at 80℃; for 2h;	83%

benzene (71-43-2) → para-dichlorobenzene (106-46-7) + chlorobenzene (108-90-7) + 1,2-dichloro-benzene (95-50-1)

Conditions	Yield
With iron sulfide; antimony(III) sulfide; chlorine at 35 - 55℃; under 760.051 Torr; Reagent/catalyst; Temperature;	A 7.2% B 80.7% C 3.1%
With hydrogenchloride; sodium peroxide In acetic acid at 78 - 80℃; for 3h;	A 12% B 79% C 6%
With chlorine at 40 - 60℃; under 760.051 Torr; for 1.75h; Reagent/catalyst; Temperature;	A 72.4% B 5.1% C 22%

4-chloro-aniline (106-47-8) → para-dichlorobenzene (106-46-7)

Conditions	Yield
With N-chloro-succinimide; sodium nitrite In N,N-dimethyl-formamide at 20℃; for 6h;	80%
With tetrachloromethane; tert-Butyl thionitrate for 1h; Heating;	40%
With tert.-butylnitrite; N-benzyl-N,N,N-triethylammonium chloride; copper dichloride; 10-camphorsulfonic acid In neat (no solvent) Time; Solvent;	10%

Benzophenon-O-(p-chlorbenzoyl)-oxim (14688-34-7) → benzophenone (119-61-9) + para-dichlorobenzene (106-46-7) + hexachloroethane (67-72-1) + benzophenone azine (983-79-9)

Conditions	Yield
With tetrachloromethane Ambient temperature; Irradiation; Yields of byproduct given;	A n/a B 80% C n/a D n/a

4-chlorophenyldiazonium salt (17333-85-6) → para-dichlorobenzene (106-46-7)

Conditions	Yield
With bromide; copper(II) nitrate; ascorbic acid In water for 0.5h; Ambient temperature;	76%
With hydrogenchloride; acetic acid; copper(l) chloride at 0 - 5℃;

4-chlorobenzonitrile (100-00-5) → para-dichlorobenzene (106-46-7)

Conditions	Yield
With Dichlorophenylphosphine In various solvent(s) at 170℃; for 5h;	73%
With thionyl chloride at 160 - 200℃;
With hydrogenchloride at 270℃;

1,2,4,5-tetrachlorobenzene (95-94-3) → para-dichlorobenzene (106-46-7) + chlorobenzene (108-90-7) + 1,2-dichloro-benzene (95-50-1) + 1,3-Dichlorobenzene (541-73-1) + 1,2,4-Trichlorobenzene (120-82-1) + benzene (71-43-2)

Conditions	Yield
With potassium hydroxide; hydrogen; palladium on activated charcoal In water at 50℃; for 0.5h; Product distribution; Aliquat 336 and other phase-transfer catalysts, different multiphase systems, different time and solvents;	A n/a B 4% C n/a D n/a E 4% F 73%
With potassium hydroxide; sodium hypophosphite; cetyltributylphosphonium bromide; isobutyric Acid; palladium on activated charcoal In 2,2,4-trimethylpentane at 50℃; for 2h; Product distribution; varying conditions (solvent, aqueous phase, hydrogen source, phase-transfer agent, time), other aromatic halides, competitive hydrodehalogenations;
With potassium hydroxide; hydrogen; palladium on activated charcoal In 2,2,4-trimethylpentane at 50℃; for 0.5h; Product distribution; add. of Aliquat 336, var. phase-transfer cat.; var. base: Ca(OH)2; add. of polyethylene glycol monomethyl ether; add of NaBO3*H2O or KF; var. solv. and time;	A n/a B 4 % Chromat. C n/a D n/a E 4 % Chromat. F 73 % Chromat.

benzene (71-43-2) → para-dichlorobenzene (106-46-7) + 1,2-dichloro-benzene (95-50-1)

Conditions	Yield
With chlorine at 50 - 60℃; under 760.051 Torr; for 1.83333h; Reagent/catalyst; Temperature;	A 72.2% B 22.4%
Multi-step reaction with 2 steps 1: dipotassium peroxodisulfate; sodium chloride / [D3]acetonitrile; water / 1 h / 100 °C 2: dipotassium peroxodisulfate; sodium chloride / [D3]acetonitrile; water / 2 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: trichloroisocyanuric acid; acetic acid / 1,2-dichloro-ethane / 0.5 h / 80 °C / Green chemistry 2: trichloroisocyanuric acid; acetic acid / 1,2-dichloro-ethane / 0.5 h / 80 °C / Green chemistry View Scheme
With chlorine

chlorobenzene (108-90-7) → para-dichlorobenzene (106-46-7) + 1,2-dichloro-benzene (95-50-1)

Conditions	Yield
With chlorine; natural kaolinitic clay In tetrachloromethane for 2h; Heating;	A 71% B 25%
With N-chloro-succinimide; iron(III) chloride In acetonitrile for 7h;	A 35% B 45%
With lead(IV) acetate; C6F13COOH; lithium chloride at 80℃; for 14h;	A 43.9% B 14.9%

2,5-dichlorbenzenethiol (5858-18-4) → para-dichlorobenzene (106-46-7) + S-(2,5-dichlorophenyl) thioacetate (91772-67-7)

Conditions	Yield
With hexacarbonyl molybdenum In acetic acid at 115 - 120℃; for 3h;	A 71% B 20%

2,5-dichlorbenzenethiol (5858-18-4) + acetic acid (64-19-7) → para-dichlorobenzene (106-46-7) + S-(2,5-dichlorophenyl) thioacetate (91772-67-7)

Conditions	Yield
With hexacarbonyl molybdenum at 115 - 120℃; for 3h;	A 71% B 20%

1-(p-chlorophenyl)-3,3-dimethyl-1-triazene (7203-90-9) → para-dichlorobenzene (106-46-7)

Conditions	Yield
With methanesulfonic acid; N-benzyl-N,N,N-triethylammonium chloride; copper In acetonitrile at 40℃; for 0.25h;	71%

4-(chloro)benzenediazonium benzo[d][1,3,2]dithiazol-2-ide-1,1,3,3-tetraoxide → para-dichlorobenzene (106-46-7)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; copper In acetonitrile at 20℃; for 0.75h; Substitution;	70%
Multi-step reaction with 2 steps 1: 90 percent / aq. NaOH / 0.5 h / 0 - 5 °C 2: 71 percent / Et3PhCH2N(+)Cl(-); MeSO3H; Cu / acetonitrile / 0.25 h / 40 °C View Scheme

2,5-dichlorbenzenethiol (5858-18-4) → para-dichlorobenzene (106-46-7)

Conditions	Yield
With aluminum oxide; sodium triethylborohydride; iron(II) chloride In tetrahydrofuran; benzene Ambient temperature;	67%

p-chlorobenzenediazonium chloride (2028-74-2) → para-dichlorobenzene (106-46-7) + 4-chloro-phenol (106-48-9)

Conditions	Yield
With copper(II) sulfate; sodium chloride; ascorbic acid In water Product distribution; Rate constant; Mechanism; other substrates; competitive reaction with NaBr;	A 20.5% B 67%

1,2,4-Trichlorobenzene (120-82-1) → para-dichlorobenzene (106-46-7) + chlorobenzene (108-90-7) + 1,2-dichloro-benzene (95-50-1) + 1,3-Dichlorobenzene (541-73-1) + benzene (71-43-2)

Conditions	Yield
With hydrogen; palladium diacetate; sodium hydrogencarbonate In water at 25℃; under 760.051 Torr;	A n/a B 6% C n/a D n/a E 60%
With sodium tetrahydroborate In water; acetonitrile Quantum yield; Product distribution; Irradiation; effect of scavengers and quenchers;	A 37 % Chromat. B 18 % Chromat. C 2 % Chromat. D 43 % Chromat. E 1 % Chromat.
With potassium hydroxide; hydrogen; palladium on activated charcoal In 2,2,4-trimethylpentane at 50℃; for 0.333333h; Product distribution; add. of Aliquat 336, var. cat.: Raney-Ni; var. temp.;	A 1 % Chromat. B 9 % Chromat. C 7 % Chromat. D 2 % Chromat. E 81 % Chromat.

pyridine (110-86-1) + (2,5-dichlorophenyl)hydrazine (305-15-7) → 2,5 dichloroaniline (95-82-9) + para-dichlorobenzene (106-46-7) + 2-(2,5-dichlorophenyl)pyridine (4381-30-0) + 4-(2,5-Dichloro-phenyl)-pyridine (4467-14-5)

Conditions	Yield
With KO2 for 10h; Ambient temperature; Yield given. Further byproducts given;	A 6% B 59% C n/a D n/a

(2,5-dichlorophenyl)hydrazine (305-15-7) → 2,5 dichloroaniline (95-82-9) + para-dichlorobenzene (106-46-7) + 2-(2,5-dichlorophenyl)pyridine (4381-30-0) + 4-(2,5-Dichloro-phenyl)-pyridine (4467-14-5)

Conditions	Yield
With KO2 In pyridine for 10h; Ambient temperature; Further byproducts given;	A 6% B 59% C n/a D n/a

(2,5-dichlorophenyl)hydrazine (305-15-7) → para-dichlorobenzene (106-46-7) + 2,5-dichlorophenol (583-78-8) + 2-(2,5-dichlorophenyl)pyridine (4381-30-0) + 4-(2,5-Dichloro-phenyl)-pyridine (4467-14-5)

Conditions	Yield
With KO2 In pyridine for 10h; Ambient temperature; Further byproducts given;	A 59% B 2% C n/a D n/a

(2,5-dichlorophenyl)hydrazine (305-15-7) → para-dichlorobenzene (106-46-7) + 2,2',5,5'-Tetrachlorobiphenyl (35693-99-3) + 2-(2,5-dichlorophenyl)pyridine (4381-30-0) + 4-(2,5-Dichloro-phenyl)-pyridine (4467-14-5)

Conditions	Yield
With KO2 In pyridine for 10h; Ambient temperature; Further byproducts given;	A 59% B 4% C n/a D n/a

4-chloro-aniline (106-47-8) → para-dichlorobenzene (106-46-7) + 3,4'-dichlorobiphenyl (2974-90-5) + 4,4'-dichlorobiphenyl (2050-68-2) + chlorobenzene (108-90-7)

Conditions	Yield
With tetrachloromethane; n-Butyl nitrite at 60℃; for 1h;	A 53% B n/a C n/a D 38%

Trichloroethylene (79-01-6) + p-chlorobenzenediazonium chloride (2028-74-2) → para-dichlorobenzene (106-46-7) + 1-chloro-4-(1,2,2,2-tetrachloro-ethyl)-benzene (4714-30-1)

Conditions	Yield
With potassium chloride; copper dichloride In water; acetone	A n/a B 50%

para-dichlorobenzene (106-46-7) + pentan-1-ol (71-41-0) → 1-chloro-4-(pentyloxy)benzene (51241-40-8)

Conditions	Yield
With potassium hydroxide; ethylene glycol; poly(ethylene glycol) at 140 - 150℃; for 6h; Product distribution; Investigation of the reactions of p-dichlorobenzene and o-dichlorobenzene with n-pentylalcohol in the presence of poly(ethylene glycol) catalysts with various molecular weight.;	100%
With potassium hydroxide; PEG-6000 at 150℃; for 6h;	100%

para-dichlorobenzene (106-46-7) → benzene (71-43-2)

Conditions	Yield
With hydrogen; palladium on activated charcoal In water at 50℃; for 0.25h;	100%
With sodium hydroxide; ethanol; hydrogen; PdCl2-poly(N-vinyl-2-pyrrolidone); palladium dichloride at 65℃; under 760 Torr; for 6h;	100%
With Ni[1,10-phenanthroline]2(PF6)2; water; zinc at 70℃; for 7h; Ionic liquid;	51.2%

para-dichlorobenzene (106-46-7) + phenylboronic acid (98-80-6) → [1,1';4',1'']terphenyl (92-94-4)

Conditions	Yield
With potassium phosphate; SP-4-[1,3-bis[2,6-diisopropylphenyl]-1,3-dihydro-2H-imidazol-2-ylidene]chloro[2-(1-methyl-1H-imidazol-2-yl-κN3)phenyl-κC]palladium(II) In ethanol at 60℃; for 6h; Suzuki-Miyaura Coupling; Inert atmosphere;	100%
With potassium phosphate; tetrabutylammomium bromide In water at 95℃; for 40h; Suzuki-Miyaura Coupling;	96%
With C27H39Br2N3Pd; potassium hydroxide In isopropyl alcohol at 82℃; for 0.5h; Suzuki-Miyaura Coupling;	95%

para-dichlorobenzene (106-46-7) + (5,10,15,20-tetrakis(p-tolyl)porphyrinato)carbonyliridium(III) chloride (872415-81-1) → (p-chlorophenyl)(5,10,15,20-tetrakis(p-tolyl)porphyrinato)iridium(III) (1280227-58-8)

Conditions	Yield
With K2CO3 In benzene heating of Ir(C20H8N4(p-tol)4)(CO)Cl, K2CO3 (20 equiv.), 1,4-dichlorobenzene (200 equiv.) and benzene in Teflon screw capped Schlenk tube at 150°C under N2 for 3.5 ds;	100%

para-dichlorobenzene (106-46-7) + (5,10,15,20-tetrakis(p-tolyl)porphyrinato)carbonyliridium(III) chloride (872415-81-1) → C54H40ClIrN4

Conditions	Yield
With potassium carbonate In benzene at 150℃; for 84h; Inert atmosphere;	100%

para-dichlorobenzene (106-46-7) + n-hexylmagnesium bromide (3761-92-0) → 1,4-dihexylbenzene (22588-73-4)

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether at 0℃; for 17h; Reflux;	99%
With 1,3-bis(triphenylphosphanyl)propanenickel(II) chloride In diethyl ether Heating;	98%
1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether for 24h; Heating;	87%

para-dichlorobenzene (106-46-7) + 1-bromo-hexane (111-25-1) → 1,4-dihexylbenzene (22588-73-4)

Conditions	Yield
Stage #1: 1-bromo-hexane With magnesium In diethyl ether for 5h; Inert atmosphere; Reflux; Stage #2: para-dichlorobenzene With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether at 0℃; for 24h; Reflux; Inert atmosphere;	99%
Stage #1: 1-bromo-hexane With magnesium Stage #2: para-dichlorobenzene With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether Kumada coupling;	95%
Stage #1: 1-bromo-hexane With magnesium In diethyl ether for 5h; Inert atmosphere; Reflux; Stage #2: para-dichlorobenzene With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether for 15.5h; Inert atmosphere; Reflux;	89%

para-dichlorobenzene (106-46-7) + para-methylphenylmagnesium bromide (4294-57-9) → 1,4-bis(p-tolyl)benzene (97295-31-3)

Conditions	Yield
With C36H32ClN4NiP In tetrahydrofuran at 70℃; for 20h; Reagent/catalyst; Kumada Cross-Coupling; Schlenk technique; Inert atmosphere;	99%
With N-heterocyclic carbene-based nickel(II) complex In tetrahydrofuran at 20℃; for 12h; Kumada reaction;	89%
With C20H23BrN4Ni In tetrahydrofuran at 25℃; for 24h; Kumada Cross-Coupling; Inert atmosphere;	89%

para-dichlorobenzene (106-46-7) + bis(ethylenediamine)palladium nitrate + 4,3′:5′,4″-terpyridine (106047-37-4) → [(C2H8N2Pd)6(C15H11N3)4](12+)*12NO3(1-)*C6H4Cl2=[(C2H8N2Pd)6(C15H11N3)4](NO3)12*C6H4Cl2

Conditions	Yield
In water-d2 C5H3N(C5H4N)2 suspended in D2O soln. of Pd complex; the mixt. heated at 80°C for 15 min; C6H4Cl2 added to the soln., stirred at room. temp. for 9 h; the excess of C6H4Cl2 filtered; not isolated; monitored by NMR;	99%

para-dichlorobenzene (106-46-7) + boron trifluoride dihydrate + Ir(η5-C5(CH3)5)(acetone)3(CF3SO3)2 → [η6-(C5Me5)(iridium)(1,4-dichlorobenzene)3][BF4]2

Conditions	Yield
In further solvent(s) Ar, Schlenk technique; reaction of Ir-complex with excess of dichlorobenzene in BF3*2H2O soln.;	99%

para-dichlorobenzene (106-46-7) + (4-fluoro-2,6-dimethylphenyl)boronic acid (1392512-54-7) → C22H20F2 (1392512-46-7)

Conditions	Yield
With Pd-PEPPSI-IPrAn; potassium tert-butylate In toluene at 80℃; for 24h; Suzuki coupling; Inert atmosphere;	99%

styrene (292638-84-7) + para-dichlorobenzene (106-46-7) → (E)-1-(4-chlorophenyl)-2-phenylethene (1657-50-7)

Conditions	Yield
With tetrakis[μ-1-[(3-methoxyphenyl)methyl]-2-phenyl-3-[2-oxo-2-[(2-phenolato-kO)aminokN]ethyl]-1H-imidazoliumato-kC4]tetrapalladium; tetrabutylammomium bromide; sodium acetate at 140℃; for 12h; Heck Reaction;	99%
With tetrabutylammomium bromide; sodium acetate; C84H60N12O8Pd4 at 140℃; for 12h; Heck Reaction; Inert atmosphere; Schlenk technique;	72%

para-dichlorobenzene (106-46-7) + isooctyl glycolate → isooctyl 4-chlorophenoxyacetate

Conditions	Yield
Stage #1: isooctyl glycolate With magnesium 2-methylpropan-2-olate at 80℃; Stage #2: para-dichlorobenzene at 110℃; Temperature;	98.8%

para-dichlorobenzene (106-46-7) + C9H7Li(1+) → 1,4-bis(1-indenyl)benzene

Conditions	Yield
In tetrahydrofuran at -78 - 60℃; for 48h;	98.25%

para-dichlorobenzene (106-46-7) → 1,2,4,5-tetrabromo-3,6-dichlorobenzene (31604-30-5)

Conditions	Yield
With aluminum tri-bromide; bromine for 3h; Heating;	98%
With sulfuric acid; sulfur trioxide; bromine; iodine; iron at 60 - 70℃; for 6h;	92%
With bromine; iodine; nitric acid; iron at 60 - 70℃; for 6h;	92%

para-dichlorobenzene (106-46-7) + phenol (108-95-2) → 4-chlorodiphenyl ether (7005-72-3)

Conditions	Yield
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 20 - 110℃;	98%
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 12h;	98%
With 2-acetonylpyridine; caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; chemoselective reaction;

para-dichlorobenzene (106-46-7) + para-tert-butylphenol (98-54-4) → 1-(tert-butyl)-4-(4-chlorophenoxy)benzene

Conditions	Yield
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 20 - 110℃;	98%

para-dichlorobenzene (106-46-7) + C8H10MgO → 4,4-dimethoxy-1,1':4',1-terphenyl (13021-19-7)

Conditions	Yield
With C36H32ClN4NiP In tetrahydrofuran at 30℃; for 12h; Temperature; Reagent/catalyst; Kumada Cross-Coupling; Schlenk technique; Inert atmosphere;	98%

para-dichlorobenzene (106-46-7) + C120H132Ag2Cl8N8O16Rh8(6+)*6CF3O3S(1-) → C120H132Ag2Cl8N8O16Rh8(6+)*6CF3O3S(1-)*C6H4Cl2

Conditions	Yield
In methanol at 20℃; for 0.0833333h; Solvent; Inert atmosphere; Schlenk technique;	98%

para-dichlorobenzene (106-46-7) + sodium diphenylphosphide (4376-01-6) → 1,4-Bis(diphenylphosphino)benzene (1179-06-2)

Conditions	Yield
With 15-crown-5 In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere;	98%

para-dichlorobenzene (106-46-7) + benzoyl chloride (98-88-4) → (2,5-dichlorophenyl)(phenyl)methanone (16611-67-9)

Conditions	Yield
With sodium hydroxide; aluminium trichloride In water; toluene	97%
aluminium trichloride	64%
With aluminium trichloride at 150 - 170℃;

morpholine (110-91-8) + para-dichlorobenzene (106-46-7) → N-(4-chlorophenyl)morpholine (70291-67-7)

Conditions	Yield
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 20 - 110℃;	97%
With C31H43Cl2N3OPd; potassium tert-butylate In toluene at 70℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; chemoselective reaction;	92%
Yield given. Multistep reaction;

para-dichlorobenzene (106-46-7) + 4-formylphenylboronic acid, (87199-17-5) → [1,1′:4′,1″-terphenyl]-4,4″-dicarbaldehyde (62940-38-9)

Conditions	Yield
With C27H39Br2N3Pd; potassium hydroxide In isopropyl alcohol at 82℃; for 0.5h; Suzuki-Miyaura Coupling;	97%

para-dichlorobenzene (106-46-7) + (2-tert-butoxy-2-oxoethyl)zinc(II) bromide (51656-70-3) → tert-butyl 2-[4-(2-tert-butoxy-2-oxoethyl)phenyl]acetate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); N,N,N,N,-tetramethylethylenediamine; C38H62P2 In tetrahydrofuran at 20℃; for 16h; Negishi Coupling; Inert atmosphere;	97%

para-dichlorobenzene (106-46-7) → 2,5-dichloronitrobenzene (89-61-2)

Conditions	Yield
With ortho-difluorobenzene; sulfuric acid; nitric acid at 35℃; Temperature;	96.7%
With sulfuric acid; nitric acid at 0 - 23℃; for 0.283333h; Inert atmosphere;	93%
With nitric acid

para-dichlorobenzene (106-46-7) + chromium(0) hexacarbonyl (199620-14-9, 13007-92-6) → tricarbonyl(1,4-dichlorobenzene)chromium(0) (86409-62-3)

Conditions	Yield
boiling;;	96.5%
boiling;;	96.5%
In 1,4-dioxane Stirring and refluxing under a cover of dry N2 gas.; Cooling, filtn., evapn., sublimation.;
In 1,4-dioxane in anaerobic and anhydrous conditions; Cr(CO)6, C6H4(NMe2)2, and dioxane were mixed, suspension was refluxed;

Upstream product

• 98-67-9 p-hydoroxybenzenesulfonic acid 
• 106-37-6 1.4-dibromobenzene 
• 98-66-8 4-chloro-benzenesulfonic acid 
• 29682-41-5 2,5-dichloroiodobenzene 
• 124-41-4 sodium methylate 
• 1623-92-3 4-phenoxyphenylsulfonyl chloride 
• 108-24-7 acetic anhydride 
• 106-47-8 4-chloro-aniline 
• 106-48-9 4-chloro-phenol 
• 100-00-5 4-chlorobenzonitrile 
• 88-42-6 2,5-dichlorobenzenesulfonic acid 
• 108-38-3 m-xylene 
• 71-43-2 benzene 
• 110-86-1 pyridine 

Downstream Products

• 855152-60-2 4-(2,5-dichloro-phenyl)-butyric acid 
• 825-93-4 4-chlorophenyl-methyl-dichlorosilane 
• 830-45-5 Si,Si,Si',Si'-tetrachloro-Si,Si'-dimethyl-Si,Si'-p-phenylene-bis-silane 
• 106263-50-7 4-(2-chlorophenyl)-4-oxobutanoic acid 
• 106-48-9 4-chloro-phenol 
• 108-90-7 chlorobenzene 
• 106022-00-8 2-(2,5-dichloro-benzoyl)-benzoic acid 
• 10541-64-7 bis-(2,5-dichloro-phenyl)-methane 
• 35599-92-9 2,5-dichloro-mandelic acid 
• 107915-92-4 6-(2,5-dichloro-phenyl)-2-methyl-benzothiazole 
• 4132-70-1 1,4-dichloro-2-isopropylbenzene 
• 623-26-7 terephthalonitrile 
• 54484-63-8 2,5-dichloroethylbenzene 
• 55191-17-8 1,4-dichloro-2,3,5-triethylbenzene 

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Relevant academic research and scientific papers

Facile Hydrodehalogenation with Hydrogen and Pd/C Catalyst under Multiphase Conditions

A multiphase system consisting of a hydrocarbon solvent, a strong alkaline solution, and a quaternary onium salt, in the presence of a Pd/C catalyst with hydrogen at atmospheric pressure, allows the rapid and progressive displacement of the chlorine atoms from polyhalogenated benzenes.The onium salt in this case constitutes a third liquid phase in which the reaction takes place.At 50 deg C, 1,2,4,5-tetrachlorobenzene is reduced to benzene in 30 min using a Pd/Cl molar ratio of 1/130.Halogenated compounds are partitioned between the hydrocarbon solution and the liquid phase of the phase-transfer agent; rapid removal of HCl adsorbed on Pd/C is effected by neutralization with the alkaline solution.The enhancement of the reaction rate compared with the known methods might be attributed to the facile adsorption of H2 by the catalyst under the reaction conditions.Different reaction rates result in the reduction of the three isomeric chlorotoluenes, whether the reaction is carried out in the presence or absence of the onium salt.

The Photochemistry of Polyhaloarenes. 5. Fragmentation Pathways in Polychlorobenzene Radical Anions

Negative chemical ionization mass spectroscopy of polychlorobenzenes reveals that parent radical anion undergoes fission by two pathways--(a) cleavage to aryl radical plus Cl- (kCl-) and (b) fission to aryl carbanion plus chlorine atom (kCl*)--and that there is a Hammett relationship between log(kCl*/kCl-) and Σ?.The dependence of the reciprocal of the quantum yield for photochemical dechlorination of trichlorobenzenes through pentachlorobenzene upon the reciprocal of the concentration of the electron donor, triethylamine, was analyzed in order to establish the optimum concentration for radical anion formation.The regiochemistries for the photodechlorination of trichlorobenzenes through pentachlorobenzene in the presence of triethylamine, with and without acetophenone sensitizer, were determined and found to be very similar and quite different from those observed for the direct photolysis in the absence of triethylamine for the comparison cases of 1,2,3,5-tetrachloro- and pentachlorobenzene.The regiochemistry of the fragmentation of polychlorobenzene radical anion to aryl radical plus chloride ion is rationalized in terms of a bent transition state.

Photolyses of Polychloro- and Polybromobenzenes. Novel Isomerization in Solvents Resisting against Hydrogen Abstraction

Polychloro- and polybromobenzenes were photolyzed in acetonitrile and perfluorohexane.Photolyses of polychlorobenzenes in acetonitrile gave isomerized products in addition to dechlorinated products, which appeared exclusively in the photolyses in hexane and other solvents carrying hydrogen atoms active to hydrogen abstraction.The photolyses in perfluorohexane gave isomerized products to a lesser extent.The reaction in this solvent gave predominantly polyhalobiphenyls which are assumed to be produced through coupling.Without exception the isomerized products have the structure which can be expected to be formed via 1,3-migration of chlorine atom, though it is not sure at present whether it takes place actually.The isomerization was shown to proceed intramolecularly.Some evidence and theoretical rationalization in favor of the 1.3-chlorine migration mechanism are given.

Zeolite ZSM-5 and related materials as catalyst in benzene chlorination

ZSM-5 type zeolites and related high siliceous materials induce addition of chlorine to benzene yielding hexachlorocyclohexanes, whereas Y-type zeolites favour substitution to yield chlorobenzenes.

Photo-Rearrangement of Polychlorobenzenes meta-Migration of Chlorine Atom

Several polychlorobenzenes were irradiated by ultraviolet light (254 nm) in acetonitrile and the products were determined by gas chromatography.In addition to the abstraction of hydrogen atom from the solvent, photo-isomerization was shown to proceed giving isomeric polychlorobenzenes one of which chlorine atoms migrated to meta to the original position.The meta-rearrangement was rationalized by an MNDO calculation on o-chlorophenyl free radical.

Chlorination of Benzene with L-Zeolite Catalyst in the Presence of Oxygen and Various Solvents

Benzene was chlorinated by using L type zeolite into p-dichlorobenzene (p-DCB) in a high yield in the presence of 1,2-dichloroethane (EDC) and oxygen.

Dechlorination of Polychlorobenzenes over Triiron Tetraoxide in the Presence of Hydrogen Donating Solvents

Dechlorination of polychlorobenzenes over Fe3O4 was investigated by a pulse micro-reactor technique.Dechlorinations of various polychlorobenzenes in hexane and cyclohexane were carried out in the gas phase at the temperatures ranging from 498 to 623 K.In the presence of such hydrogen donating solvents, dechlorination was shown to proceed almost exclusively.The relative rates of dechlorination were measured by gas chromatography.It was found that the solvents used to dissolve polychlorobenzenes plays a role of a hydrogen donor in this reaction.The different rates among unequivalent chlorine atoms in a molecule were interpreted by the effect of steric acceleration caused by the neighboring chlorine atom(s).The reaction will probably proceed via hydrogenolytic cleavage of C-Cl bonds.

A Desirable Route to Heterodimers of 1,4-Dihalobenzenes and Anthracene and Their Photoproperties and Thermal Properties

Electronic oxidative bisdecarboxylation of photoadducts of 2,5-dihalo-1,2-dihydrophthalic anhydride and anthracene gave the corresponding energy-rich heterodimers 12 and 13.The quantum yields of the formation of the excited anthracene from 12 and 13 by the irradiation of 280-nm light were 0.65 and 0.25, respectively.We assumed that the heterodimers of 12 and 13 form biradicaloid intermediates during thermal retro cycloaddition and consumed their stored energy without any visible light.However, we observed emission light from 340 to 460 nm through a glass filter and the formation of anthracene using Nd-YAG laser IR light (1.06 μm) by the multiphoton absorption, when fine powders of 12 and 13 were used.

Dechlorination of lindane, dieldrin, tetrachloroethane, trichloroethene, and PVC in subcritical water

Pure water has been used to dechlorinate aliphatic organics without the need for catalysts or other additives. Dehydrohalogenation (loss of HCl with the formation of a double bond) occurred at temperatures as low as 105-200 °C for 1,1,2,2-tetrachloroethane, lindane (1,2,3,4,5,6-hexachlorocyclohexane, γ-isomer), and dieldrin (1,2,3,4,10,10-hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-endo, exo-1,4:5,8-dimethanonaphthalene). Complete loss of the parent compounds was achieved in less than 1 h at 150, 200, and 300 °C for 1,1,2,2-tetrachloroethane, lindane, and dieldrin, respectively. The initial dechlorination of lindane had an activation energy of 84 kJ mol-1 with an Arrhenius pre-exponential factor of 1.5 x 106 s-1. Dehydrohalogenation of lindane formed trichlorobenzenes, followed by subsequent hydrolysis and hydride/chloride exchange to form chlorophenols, lower chlorobenzenes, and phenol as the major final product. Reaction of poly(vinyl chloride) at 300 °C for 1 h formed aromatic hydrocarbons ranging from benzene to anthracene and a char residue with a ca. 1:1 carbon-to-hydrogen ratio (mol/mol). The residue contained 1 wt % of chlorine compared to 57 wt % chlorine in the original polymer. All compounds tested yielded chloride ion as the major product (at higher temperatures), indicating that complete dechlorination of some aliphatic organochlorines may be feasible.

Nickel Complexes as Soluble Catalysts for Reductive Dehalogenation of Aromatic Halides

Nickel(II) complexes 1 and 2 are soluble catalysts for reductive dehalogenation of aromatic bromides and polychlorobenzenes by sodium borohydride at 25-45 deg C in aqueous ethanol, aqueous acetonitrile, or ethanol-acetonitrile.Deuterium incorporation experiments, and rate retardation by added cumene, point to a radical-chain mechanism.Hydrazine can replace borohydride as a source of reducing power.Reactivity toward this reducing system increases with increasing halogen content of the substrate, a finding that parallels prior observations of dechlorination in natural sediments.