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106-46-7 Usage

Description

1,4-Dichlorobenzene (also known as p-dichlorobenzene) is a chlorinated aromatic compound with a distinctive aromatic odor that is very strong at high concentrations. It is a white or colorless crystal at room temperature (Akron 2009, HSDB 2009). 1,4-Dichlorobenzene is practically insoluble in water; soluble in chloroform, carbon disulfide, benzene, and ether; and very soluble in ethanol and acetone. 1,4-Dichlorobenzene is noncorrosive, volatile, and combustible, and it is flammable when exposed to heat, flame, or oxidizers. When it is heated to decomposition, toxic gases and vapors (such as hydrochloric acid and carbon monoxide) are released (HSDB 2009). It is stable at room temperature under normal handling and storage in closed containers (Akron 2009).1,4-Dichlorobenzene is the primary ingredient in mothballs and deodorant cakes placed in toilet bowls, urinals, and animal holding facilities. People may also use it to control lice and mites in and around birdcages. 1,4-Dichlorobenzene is used as an insecticide on fruit and is used to control mold and mildew growth on tobacco seeds, leather, and certain fabrics. It is also approved for controlling wax moths in empty, stored beehives.

Chemical Properties

There are three isomeric forms of dichlorobenzene (DCB): m-DCB is a flammable liquid and vapor.

Physical properties

Colorless to white crystals with a penetrating, sweet, mothball or almond-like odor. At 40 °C, the average odor threshold concentration and the lowest concentration at which an odor was detected were 18 and 4.5 μg/L, respectively. Similarly, at 25 °C, the average taste threshold concentration and the lowest concentration at which a taste was detected were 32 and 11 μg/L, respectively (Young et al., 1996). A detection odor threshold concentration of 73 μg/m3 (121 ppbv) was reported by Punter (1983).

Uses

1,4-Dichlorobenzene is used to make mothballs and solid deodorant blocks for garbage cans and restrooms. It is also used to control odors in places where animals are held. It has been used as an insecticide on fruit, and to control mold and mildew on tobacco seeds, leather and some fabrics. 1,4-Dichlorobenzene is sent into the air by plants that make or use it and a small amount is released to soil and water. This chemical can also be detected in indoor air where products containing 1,4-Dichlorobenzene are used.

Application

1,4-Dichlorobenzene is used as a fumigantand as an insecticide. For domestic use against clothes moths; as space deodorant in room deodorizers, toilet bowl blocks and diaper pail deodorizers. Intermediate in production of plastics for electronic components.

Definition

ChEBI: 1,4-dichlorobenzene is a dichlorobenzene carrying chloro groups at positions 1 and 4. It has a role as an insecticide.

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

General Description

A white colored liquid with the odor of moth balls. Denser than water and insoluble in water. Flash point below 200°F. Used as a moth repellent, to make other chemicals, as a fumigant, and for many other uses.

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

Check Digit Verification of cas no

The CAS Registry Mumber 106-46-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 106-46:
(5*1)+(4*0)+(3*6)+(2*4)+(1*6)=37
37 % 10 = 7
So 106-46-7 is a valid CAS Registry Number.

106-46-7 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (D0687)  1,4-Dichlorobenzene  >99.0%(GC)

  • 106-46-7

  • 25g

  • 190.00CNY

  • Detail
  • TCI America

  • (D0687)  1,4-Dichlorobenzene  >99.0%(GC)

  • 106-46-7

  • 500g

  • 490.00CNY

  • Detail
  • Alfa Aesar

  • (A16290)  1,4-Dichlorobenzene, 99+%   

  • 106-46-7

  • 100g

  • 203.0CNY

  • Detail
  • Alfa Aesar

  • (A16290)  1,4-Dichlorobenzene, 99+%   

  • 106-46-7

  • 500g

  • 245.0CNY

  • Detail
  • Alfa Aesar

  • (A16290)  1,4-Dichlorobenzene, 99+%   

  • 106-46-7

  • 2500g

  • 627.0CNY

  • Detail
  • Supelco

  • (40025)  1,4-Dichlorobenzenesolution  certified reference material, 5000 μg/mL in methanol

  • 106-46-7

  • 000000000000040025

  • 545.22CNY

  • Detail
  • Supelco

  • (48627)  1,4-Dichlorobenzenesolution  certified reference material, 200 μg/mL in methanol

  • 106-46-7

  • 000000000000048627

  • 272.61CNY

  • Detail

106-46-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,4-dichlorobenzene

1.2 Other means of identification

Product number -
Other names Benzene, 1,4-dichloro-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Volatile organic compounds
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:106-46-7 SDS

106-46-7Synthetic route

1-Chloro-4-iodobenzene
637-87-6

1-Chloro-4-iodobenzene

para-dichlorobenzene
106-46-7

para-dichlorobenzene

Conditions
ConditionsYield
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

1,2,4,5-tetrachlorobenzene

A

para-dichlorobenzene
106-46-7

para-dichlorobenzene

B

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

C

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

D

benzene
71-43-2

benzene

Conditions
ConditionsYield
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

4-chloro-benzoyl chloride

para-dichlorobenzene
106-46-7

para-dichlorobenzene

Conditions
ConditionsYield
palladium on activated charcoal In gas at 360℃;98%
bromochlorobenzene
106-39-8

bromochlorobenzene

para-dichlorobenzene
106-46-7

para-dichlorobenzene

Conditions
ConditionsYield
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

4-chlorobenzenesulfonyl chloride

para-dichlorobenzene
106-46-7

para-dichlorobenzene

Conditions
ConditionsYield
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

1,2,4-Trichlorobenzene

A

para-dichlorobenzene
106-46-7

para-dichlorobenzene

B

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

C

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
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

potassium (4-chlorophenyl)trifluoroborate

para-dichlorobenzene
106-46-7

para-dichlorobenzene

Conditions
ConditionsYield
With trichloroisocyanuric acid In water; ethyl acetate at 20℃; for 1h; Open flask;86%
(4-chlorophenyl)(mesityl)iodonium trifluoromethanesulfonate
1204518-00-2

(4-chlorophenyl)(mesityl)iodonium trifluoromethanesulfonate

para-dichlorobenzene
106-46-7

para-dichlorobenzene

Conditions
ConditionsYield
With copper(l) chloride In acetonitrile at 80℃; for 2h;83%
benzene
71-43-2

benzene

A

para-dichlorobenzene
106-46-7

para-dichlorobenzene

B

chlorobenzene
108-90-7

chlorobenzene

C

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

Conditions
ConditionsYield
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

4-chloro-aniline

para-dichlorobenzene
106-46-7

para-dichlorobenzene

Conditions
ConditionsYield
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

Benzophenon-O-(p-chlorbenzoyl)-oxim

A

benzophenone
119-61-9

benzophenone

B

para-dichlorobenzene
106-46-7

para-dichlorobenzene

C

hexachloroethane
67-72-1

hexachloroethane

D

benzophenone azine
983-79-9

benzophenone azine

Conditions
ConditionsYield
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

4-chlorophenyldiazonium salt

para-dichlorobenzene
106-46-7

para-dichlorobenzene

Conditions
ConditionsYield
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

4-chlorobenzonitrile

para-dichlorobenzene
106-46-7

para-dichlorobenzene

Conditions
ConditionsYield
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

1,2,4,5-tetrachlorobenzene

A

para-dichlorobenzene
106-46-7

para-dichlorobenzene

B

chlorobenzene
108-90-7

chlorobenzene

C

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

D

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

E

1,2,4-Trichlorobenzene
120-82-1

1,2,4-Trichlorobenzene

F

benzene
71-43-2

benzene

Conditions
ConditionsYield
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

benzene

A

para-dichlorobenzene
106-46-7

para-dichlorobenzene

B

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

Conditions
ConditionsYield
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

chlorobenzene

A

para-dichlorobenzene
106-46-7

para-dichlorobenzene

B

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

Conditions
ConditionsYield
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

2,5-dichlorbenzenethiol

A

para-dichlorobenzene
106-46-7

para-dichlorobenzene

B

S-(2,5-dichlorophenyl) thioacetate
91772-67-7

S-(2,5-dichlorophenyl) thioacetate

Conditions
ConditionsYield
With hexacarbonyl molybdenum In acetic acid at 115 - 120℃; for 3h;A 71%
B 20%
2,5-dichlorbenzenethiol
5858-18-4

2,5-dichlorbenzenethiol

acetic acid
64-19-7

acetic acid

A

para-dichlorobenzene
106-46-7

para-dichlorobenzene

B

S-(2,5-dichlorophenyl) thioacetate
91772-67-7

S-(2,5-dichlorophenyl) thioacetate

Conditions
ConditionsYield
With hexacarbonyl molybdenum at 115 - 120℃; for 3h;A 71%
B 20%
1-(p-chlorophenyl)-3,3-dimethyl-1-triazene
7203-90-9

1-(p-chlorophenyl)-3,3-dimethyl-1-triazene

para-dichlorobenzene
106-46-7

para-dichlorobenzene

Conditions
ConditionsYield
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

4-(chloro)benzenediazonium benzo[d][1,3,2]dithiazol-2-ide-1,1,3,3-tetraoxide

para-dichlorobenzene
106-46-7

para-dichlorobenzene

Conditions
ConditionsYield
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

2,5-dichlorbenzenethiol

para-dichlorobenzene
106-46-7

para-dichlorobenzene

Conditions
ConditionsYield
With aluminum oxide; sodium triethylborohydride; iron(II) chloride In tetrahydrofuran; benzene Ambient temperature;67%
p-chlorobenzenediazonium chloride
2028-74-2

p-chlorobenzenediazonium chloride

A

para-dichlorobenzene
106-46-7

para-dichlorobenzene

B

4-chloro-phenol
106-48-9

4-chloro-phenol

Conditions
ConditionsYield
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

1,2,4-Trichlorobenzene

A

para-dichlorobenzene
106-46-7

para-dichlorobenzene

B

chlorobenzene
108-90-7

chlorobenzene

C

1,2-dichloro-benzene
95-50-1

1,2-dichloro-benzene

D

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

E

benzene
71-43-2

benzene

Conditions
ConditionsYield
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

pyridine

(2,5-dichlorophenyl)hydrazine
305-15-7

(2,5-dichlorophenyl)hydrazine

A

2,5 dichloroaniline
95-82-9

2,5 dichloroaniline

B

para-dichlorobenzene
106-46-7

para-dichlorobenzene

C

2-(2,5-dichlorophenyl)pyridine
4381-30-0

2-(2,5-dichlorophenyl)pyridine

D

4-(2,5-Dichloro-phenyl)-pyridine
4467-14-5

4-(2,5-Dichloro-phenyl)-pyridine

Conditions
ConditionsYield
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-dichlorophenyl)hydrazine

A

2,5 dichloroaniline
95-82-9

2,5 dichloroaniline

B

para-dichlorobenzene
106-46-7

para-dichlorobenzene

C

2-(2,5-dichlorophenyl)pyridine
4381-30-0

2-(2,5-dichlorophenyl)pyridine

D

4-(2,5-Dichloro-phenyl)-pyridine
4467-14-5

4-(2,5-Dichloro-phenyl)-pyridine

Conditions
ConditionsYield
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

(2,5-dichlorophenyl)hydrazine

A

para-dichlorobenzene
106-46-7

para-dichlorobenzene

B

2,5-dichlorophenol
583-78-8

2,5-dichlorophenol

C

2-(2,5-dichlorophenyl)pyridine
4381-30-0

2-(2,5-dichlorophenyl)pyridine

D

4-(2,5-Dichloro-phenyl)-pyridine
4467-14-5

4-(2,5-Dichloro-phenyl)-pyridine

Conditions
ConditionsYield
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

(2,5-dichlorophenyl)hydrazine

A

para-dichlorobenzene
106-46-7

para-dichlorobenzene

B

2,2',5,5'-Tetrachlorobiphenyl
35693-99-3

2,2',5,5'-Tetrachlorobiphenyl

C

2-(2,5-dichlorophenyl)pyridine
4381-30-0

2-(2,5-dichlorophenyl)pyridine

D

4-(2,5-Dichloro-phenyl)-pyridine
4467-14-5

4-(2,5-Dichloro-phenyl)-pyridine

Conditions
ConditionsYield
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

4-chloro-aniline

A

para-dichlorobenzene
106-46-7

para-dichlorobenzene

B

3,4'-dichlorobiphenyl
2974-90-5

3,4'-dichlorobiphenyl

C

4,4'-dichlorobiphenyl
2050-68-2

4,4'-dichlorobiphenyl

D

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With tetrachloromethane; n-Butyl nitrite at 60℃; for 1h;A 53%
B n/a
C n/a
D 38%
Trichloroethylene
79-01-6

Trichloroethylene

p-chlorobenzenediazonium chloride
2028-74-2

p-chlorobenzenediazonium chloride

A

para-dichlorobenzene
106-46-7

para-dichlorobenzene

B

1-chloro-4-(1,2,2,2-tetrachloro-ethyl)-benzene
4714-30-1

1-chloro-4-(1,2,2,2-tetrachloro-ethyl)-benzene

Conditions
ConditionsYield
With potassium chloride; copper dichloride In water; acetoneA n/a
B 50%
para-dichlorobenzene
106-46-7

para-dichlorobenzene

pentan-1-ol
71-41-0

pentan-1-ol

1-chloro-4-(pentyloxy)benzene
51241-40-8

1-chloro-4-(pentyloxy)benzene

Conditions
ConditionsYield
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

para-dichlorobenzene

benzene
71-43-2

benzene

Conditions
ConditionsYield
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

para-dichlorobenzene

phenylboronic acid
98-80-6

phenylboronic acid

[1,1';4',1'']terphenyl
92-94-4

[1,1';4',1'']terphenyl

Conditions
ConditionsYield
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

para-dichlorobenzene

(5,10,15,20-tetrakis(p-tolyl)porphyrinato)carbonyliridium(III) chloride
872415-81-1

(5,10,15,20-tetrakis(p-tolyl)porphyrinato)carbonyliridium(III) chloride

(p-chlorophenyl)(5,10,15,20-tetrakis(p-tolyl)porphyrinato)iridium(III)
1280227-58-8

(p-chlorophenyl)(5,10,15,20-tetrakis(p-tolyl)porphyrinato)iridium(III)

Conditions
ConditionsYield
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

para-dichlorobenzene

(5,10,15,20-tetrakis(p-tolyl)porphyrinato)carbonyliridium(III) chloride
872415-81-1

(5,10,15,20-tetrakis(p-tolyl)porphyrinato)carbonyliridium(III) chloride

C54H40ClIrN4

C54H40ClIrN4

Conditions
ConditionsYield
With potassium carbonate In benzene at 150℃; for 84h; Inert atmosphere;100%
para-dichlorobenzene
106-46-7

para-dichlorobenzene

n-hexylmagnesium bromide
3761-92-0

n-hexylmagnesium bromide

1,4-dihexylbenzene
22588-73-4

1,4-dihexylbenzene

Conditions
ConditionsYield
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

para-dichlorobenzene

1-bromo-hexane
111-25-1

1-bromo-hexane

1,4-dihexylbenzene
22588-73-4

1,4-dihexylbenzene

Conditions
ConditionsYield
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-dichlorobenzene

para-methylphenylmagnesium bromide
4294-57-9

para-methylphenylmagnesium bromide

1,4-bis(p-tolyl)benzene
97295-31-3

1,4-bis(p-tolyl)benzene

Conditions
ConditionsYield
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

para-dichlorobenzene

bis(ethylenediamine)palladium nitrate

bis(ethylenediamine)palladium nitrate

4,3′:5′,4″-terpyridine
106047-37-4

4,3′:5′,4″-terpyridine

[(C2H8N2Pd)6(C15H11N3)4](12+)*12NO3(1-)*C6H4Cl2=[(C2H8N2Pd)6(C15H11N3)4](NO3)12*C6H4Cl2

[(C2H8N2Pd)6(C15H11N3)4](12+)*12NO3(1-)*C6H4Cl2=[(C2H8N2Pd)6(C15H11N3)4](NO3)12*C6H4Cl2

Conditions
ConditionsYield
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

para-dichlorobenzene

boron trifluoride dihydrate

boron trifluoride dihydrate

Ir(η5-C5(CH3)5)(acetone)3(CF3SO3)2

Ir(η5-C5(CH3)5)(acetone)3(CF3SO3)2

[η6-(C5Me5)(iridium)(1,4-dichlorobenzene)3][BF4]2

[η6-(C5Me5)(iridium)(1,4-dichlorobenzene)3][BF4]2

Conditions
ConditionsYield
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

para-dichlorobenzene

(4-fluoro-2,6-dimethylphenyl)boronic acid
1392512-54-7

(4-fluoro-2,6-dimethylphenyl)boronic acid

C22H20F2
1392512-46-7

C22H20F2

Conditions
ConditionsYield
With Pd-PEPPSI-IPrAn; potassium tert-butylate In toluene at 80℃; for 24h; Suzuki coupling; Inert atmosphere;99%
styrene
292638-84-7

styrene

para-dichlorobenzene
106-46-7

para-dichlorobenzene

(E)-1-(4-chlorophenyl)-2-phenylethene
1657-50-7

(E)-1-(4-chlorophenyl)-2-phenylethene

Conditions
ConditionsYield
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

para-dichlorobenzene

isooctyl glycolate

isooctyl glycolate

isooctyl 4-chlorophenoxyacetate

isooctyl 4-chlorophenoxyacetate

Conditions
ConditionsYield
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

para-dichlorobenzene

C9H7Li(1+)

C9H7Li(1+)

1,4-bis(1-indenyl)benzene

1,4-bis(1-indenyl)benzene

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 60℃; for 48h;98.25%
para-dichlorobenzene
106-46-7

para-dichlorobenzene

1,2,4,5-tetrabromo-3,6-dichlorobenzene
31604-30-5

1,2,4,5-tetrabromo-3,6-dichlorobenzene

Conditions
ConditionsYield
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

para-dichlorobenzene

phenol
108-95-2

phenol

4-chlorodiphenyl ether
7005-72-3

4-chlorodiphenyl ether

Conditions
ConditionsYield
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-dichlorobenzene

para-tert-butylphenol
98-54-4

para-tert-butylphenol

1-(tert-butyl)-4-(4-chlorophenoxy)benzene

1-(tert-butyl)-4-(4-chlorophenoxy)benzene

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 20 - 110℃;98%
para-dichlorobenzene
106-46-7

para-dichlorobenzene

C8H10MgO

C8H10MgO

4,4-dimethoxy-1,1':4',1-terphenyl
13021-19-7

4,4-dimethoxy-1,1':4',1-terphenyl

Conditions
ConditionsYield
With C36H32ClN4NiP In tetrahydrofuran at 30℃; for 12h; Temperature; Reagent/catalyst; Kumada Cross-Coupling; Schlenk technique; Inert atmosphere;98%
para-dichlorobenzene
106-46-7

para-dichlorobenzene

C120H132Ag2Cl8N8O16Rh8(6+)*6CF3O3S(1-)

C120H132Ag2Cl8N8O16Rh8(6+)*6CF3O3S(1-)

C120H132Ag2Cl8N8O16Rh8(6+)*6CF3O3S(1-)*C6H4Cl2

C120H132Ag2Cl8N8O16Rh8(6+)*6CF3O3S(1-)*C6H4Cl2

Conditions
ConditionsYield
In methanol at 20℃; for 0.0833333h; Solvent; Inert atmosphere; Schlenk technique;98%
para-dichlorobenzene
106-46-7

para-dichlorobenzene

sodium diphenylphosphide
4376-01-6

sodium diphenylphosphide

1,4-Bis(diphenylphosphino)benzene
1179-06-2

1,4-Bis(diphenylphosphino)benzene

Conditions
ConditionsYield
With 15-crown-5 In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere;98%
para-dichlorobenzene
106-46-7

para-dichlorobenzene

benzoyl chloride
98-88-4

benzoyl chloride

(2,5-dichlorophenyl)(phenyl)methanone
16611-67-9

(2,5-dichlorophenyl)(phenyl)methanone

Conditions
ConditionsYield
With sodium hydroxide; aluminium trichloride In water; toluene97%
aluminium trichloride64%
With aluminium trichloride at 150 - 170℃;
morpholine
110-91-8

morpholine

para-dichlorobenzene
106-46-7

para-dichlorobenzene

N-(4-chlorophenyl)morpholine
70291-67-7

N-(4-chlorophenyl)morpholine

Conditions
ConditionsYield
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

para-dichlorobenzene

4-formylphenylboronic acid,
87199-17-5

4-formylphenylboronic acid,

[1,1′:4′,1″-terphenyl]-4,4″-dicarbaldehyde
62940-38-9

[1,1′:4′,1″-terphenyl]-4,4″-dicarbaldehyde

Conditions
ConditionsYield
With C27H39Br2N3Pd; potassium hydroxide In isopropyl alcohol at 82℃; for 0.5h; Suzuki-Miyaura Coupling;97%
para-dichlorobenzene
106-46-7

para-dichlorobenzene

(2-tert-butoxy-2-oxoethyl)zinc(II) bromide
51656-70-3

(2-tert-butoxy-2-oxoethyl)zinc(II) bromide

tert-butyl 2-[4-(2-tert-butoxy-2-oxoethyl)phenyl]acetate

tert-butyl 2-[4-(2-tert-butoxy-2-oxoethyl)phenyl]acetate

Conditions
ConditionsYield
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

para-dichlorobenzene

2,5-dichloronitrobenzene
89-61-2

2,5-dichloronitrobenzene

Conditions
ConditionsYield
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

para-dichlorobenzene

chromium(0) hexacarbonyl
199620-14-9, 13007-92-6

chromium(0) hexacarbonyl

tricarbonyl(1,4-dichlorobenzene)chromium(0)
86409-62-3

tricarbonyl(1,4-dichlorobenzene)chromium(0)

Conditions
ConditionsYield
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;

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106-46-7Relevant articles and documents

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

Marques, Carlos Alberto,Selva, Maurizio,Tundo, Pietro

, p. 5256 - 5260 (1993)

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.

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

Hirota, Minoru,Nakada, Masahiro

, p. 2926 - 2933 (1992)

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.

Photo-Rearrangement of Polychlorobenzenes meta-Migration of Chlorine Atom

Morisaki, Kenji,Miura, Yasuki,Abe, Kazuhisa,Hirota, Minoru,Nakada, Masahiro

, p. 1589 - 1592 (1987)

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.

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

Hao, Cui Xiang,Nakada, Masahiro,Yamaguchi, Tatsuaki,Fukushi, Sachio,Hirota, Minoru

, p. 1707 - 1710 (1985)

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.

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

Kubatova, Alena,Lagadec, Arnaud J. M.,Hawthorne, Steven B.

, p. 1337 - 1343 (2002)

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.

Campaigne,Leal

, p. 230 (1953)

-

Mathes

, p. 591 (1939)

-

Transchlorination of o-Dichlorobenzene and Benzene into Chlorobenzene

Shinoda, Kiyonori

, p. 2051 - 2052 (1987)

The transchlorination of o-dichlorobenzene (o-DCB) and benzene into chlorobenzene (CB) was carried out in the presence of catalyst at 400 degC. o-C6H4Cl2 + C6H6 = 2 C6H5Cl Noble metal chloride supported on activated charcoal promoted remarkably the transchlorination.

Photodechlorination of polychlorobenzene congeners in surfactant micelle solutions

Wei Chu,Jafvert

, p. 2415 - 2422 (1994)

Photochemical reactions of polychlorobenzene congeners in aqueous solutions containing surfactant micelles have been investigated. Photoreduction through photodechlorination was shown to be the main decay pathway in which lesser chlorinated congeners and benzene were formed as intermediates. Final products included H+ and Cl- in approximately stoichiometric amounts. Several hydrogen sources were investigated with sodium borohyride shown to be a promising rate enhancer at elevated concentrations. -Authors

-

Tamai,Othsuka

, p. 1996,1997, 1998, 1999 (1973)

-

-

Prud'homme,Rabaut

, p. 223 (1892)

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Photochemistry of Polyhaloarenes. 9. Characterization of the Radical Anion Intermediate in the Photodehalogenation of Polyhalobenzenes

Freeman, P. K.,Ramnath, N.

, p. 3646 - 3651 (1991)

The product-determining intermediate in the photodehalogenation of polyhalobenzenes has been characterized by generating excimers and radical anions within a micellar core and by formation of corresponding radical anions by electron transfer from lithium p,p'-di-tert-butylbiphenyl radical anion (LiDBB).The photodechlorination of pentachlorobenzene (1; 254 nm, CH3CN) produces 1,2,3,5-tetrachloro- (2), 1,2,4,5-tetrachloro- (3), and 1,2,3,4-tetrachlorobenzene (4).The regiochemistry of this reaction is compared with that observed in the photodechlorination of 1 in a micellar solution of hexadecyltrimethylammonium bromide (CTAB) with occupancy numbers (n) principally /=2.Further comparisons with photodechlorination of 1 in a micellar CTAB solution (n 2) in the presence of triethylamine, as well as photodechlorination in CH3CN in the presence of triethylamine, were used to characterize unencumbered radical anions.The regiochemistries observed in photolytic dehalogenations of 1, 2, 1,2,4-trichlorobenzene, and pentafluorobenzene in the presence of triethylamine are in good agreement with those realized in the radical anion fragmentations induced by electron transfer from LiDBB.

Novel catalysts for dechlorination of polychlorinated biphenyls (PCBs) and other chlorinated aromatics

Fletcher, Andrew E. D.,Moss, James,Cowley, Andrew R.,O'Hare, Dermot

, p. 2971 - 2973 (2007)

Diiron complexes of fluorene and fluorene* (1,2,3,4,5,6,7,8,9- nonamethylfluorene) have been found to be catalysts for the dechlorination of chlorinated aromatics, such as PCBs. The Royal Society of Chemistry.

Rate of Reaction of Phenyl Radicals with Oxygen in Solution and in the Gas Phase

Sommeling, Paul M.,Mulder, Peter,Louw, Robert,Avila, David V.,Lusztyk, Janusz,Ingold, K. U.

, p. 8361 - 8364 (1993)

The rate constant for the title reaction, k1, is 3.8 X 109 M-1 s-1 in water at 298 K and is >/= 108 M-1 s-1 in the gas phase at 603 K.It is concluded that two reports that this reaction is very slow in the gas phase, k1 >/= 1.2 X 104 and ca.2.3 X 106 M-1 s-1, are in error.

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Orloff,Kolka

, p. 5484,5487 (1954)

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Electrochemical reductive dehalogenation of chlorobenzenes

Plekhanov, V. P.,Tsyganok, A. I.,Kulikov, S. M.

, p. 1091 - 1095 (1995)

Electrochemical dechlorination of 1,2,3,5-tetrachlorobenzene in methanol and chlorobenzene in dimethylsulfoxide with tetraalkylammonium salts as supporting electrolytes was carried out.The extent of dechlorination depends significantly on the electrode composition. - Key words: electrochemical dechlorination, cathodic materials, polychlorobenzenes.

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Aronheim

, p. 1400 (1875)

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MFI-type zeolite nanosheets for gas-phase aromatics chlorination: A strategy to overcome mass transfer limitations

Boltz, Marilyne,Losch, Pit,Louis, Benoit,Rioland, Guillaume,Tzanis, Lydie,Daou, T. Jean

, p. 27242 - 27249 (2014)

The continuous gas-solid (environmentally-friendly) chlorination of deactivated arenes using trichloroisocyanuric acid (TCCA, C3N 3O3Cl3) as a chlorination agent was chosen to compare the catalytic performances of various MFI-type catalysts in a reaction demanding a strong acidity. Mass transfer limitations were also evaluated by reacting either chloro- or nitrobenzene through a ZSM-5 zeolite porous network having different crystal sizes and morphologies. Whereas, the reaction rate was completely controlled by internal diffusion in 10-15 μm-sized big ZSM-5 zeolite crystals (Weisz modulus, big crystals ~ 10), the impact of internal diffusion could be ruled out for ZSM-5 nanocrystals (200-400 nm) and in stacked ZSM-5 nanosheets (thickness 2 nm). Based on reactivity differences in arene halogenation between the two nano-sized ZSM-5 zeolites, we were able to estimate the quantity of mild acidic silanol groups in ZSM-5 nanosheets to roughly 1/3 of the total amount of Brnsted acid sites.

Highly active polymer anchored palladium catalyst for the hydrodehalogenation of organic halides under mild conditions

Zhang, Yiping,Liao, Shijian,Xu, Yun

, p. 4599 - 4602 (1994)

Palladium anchored on poly(N-vinyl-2-pyrrolidone) (PVP-PdCl2) exhibits very high catalytic activity for the hydrodehalogenation of organic halides under atmospheric pressure in the presence of a base.

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Voegtli et al.

, p. 1627,1633 (1954)

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Kinetic study of the hydrogenolysis of polychlorobenzenes over a Pd/C catalyst in an alkaline aqueous-n-hexane system

Anusiewicz, Iwona,Janiak, Tadeusz,Okal, Janina

, p. 797 - 801 (2010)

The kinetics of the hydrogenolysis of chlorobenzene, dichlorobenzenes and some trichlorobenzenes over a 10% Pd/C catalyst was studied using a multiphase system. The reactions were carried out in a batch reactor with an aqueous NaOH/n-hexane solution of chloroaromatic compound as the liquid phase. Benzene was the final product of the hydrogenolysis of all the compounds studied. Hydrogenolysis was more effective in the presence of in situ generated hydrogen than gaseous hydrogen. The initial reaction rates and TOFs of dichlorobenzenes and trichlorobenzenes were slightly lower than those of chlorobenzene. The position of the chlorine atoms in trichlorobenzenes affects the kinetics of the removal of the first chlorine from these molecules. The differences in chlorine reactivity were explained by the inductive and steric effects induced by the benzene-Cl bonds.

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Hodgson,Walker

, p. 530 (1935)

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Blum

, p. 1605 (1966)

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The graphite-catalyzed: ipso -functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes

Badgoti, Ranveer Singh,Dandia, Anshu,Parewa, Vijay,Rathore, Kuldeep S.,Saini, Pratibha,Sharma, Ruchi

, p. 18040 - 18049 (2021/05/29)

An efficient, metal-free, and sustainable strategy has been described for the ipso-functionalization of phenylboronic acids using air as an oxidant in an aqueous medium. A range of carbon materials has been tested as carbocatalysts. To our surprise, graphite was found to be the best catalyst in terms of the turnover frequency. A broad range of valuable substituted aromatic compounds, i.e., phenols, anilines, nitroarenes, and haloarenes, has been prepared via the functionalization of the C-B bond into C-N, C-O, and many other C-X bonds. The vital role of the aromatic π-conjugation system of graphite in this protocol has been established and was observed via numerous analytic techniques. The heterogeneous nature of graphite facilitates the high recyclability of the carbocatalyst. This effective and easy system provides a multipurpose approach for the production of valuable substituted aromatic compounds without using any metals, ligands, bases, or harsh oxidants.

Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide

Mukhopadhyay, Sushobhan,Batra, Sanjay

supporting information, p. 14622 - 14626 (2018/09/21)

A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.

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