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541-73-1

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541-73-1 Usage

Physical properties

1,3-Dichlorobenzene is a clear, colorless liquid with a disinfectant or musty-type odor. Soluble in alcohol, ether, insoluble in water. At 40 °C, the average odor threshold concentration and the lowest concentration at which an odor was detected were 170 and 177 μg/L, respectively. At 25 °C, the lowest concentration at which a taste was detected was 190 μg/L, respectively (Young et al., 1996).

Uses

Different sources of media describe the Uses of 541-73-1 differently. You can refer to the following data:
1. 1,3-Dichlorobenzene is used in medicine, and dyes. And it is also used to study the effect of solvent vapor pressure on the vertical nanowire of C60 molecules1. 1,3-Dichlorobenzene, a chlorinated aromatic hydrocarbon, can be detected in environmental samples using an advanced Fourier transform infrared spectroscopy-attenuated total reflectance (FTIR-ATR) sensor.
2. 1,3-Dichlorobenzene is used in organic synthesis that can synthesize fungicides imazalil, propiconazole, epiconazole, and insecticides insectaphos. It is also used in the synthesis of 1,2-diaminobenzene, in addition, it is also used as a solvent in the fields of dyes, medicine, resin, rubber and so on.

Application

1,3-Dichlorobenzene was used to study the effect of solvent vapor pressure on the vertical nanowire of C60 molecules. 1,3-Dichlorobenzene, a chlorinated aromatic hydrocarbon, can be detected in environmental samples using an advanced Fourier transform infrared spectroscopy-attenuated total reflectance (FTIR-ATR) sensor.

Preparation

1,3-Dichlorobenzene is prepared from o-chloroaniline through diazotization and displacement reaction. Add o-chloroaniline and hydrochloric acid into the reaction pot, mix evenly below 25°C, cool to 0°C, drop in sodium nitrite solution, control the temperature at 0-5°C, stop adding when the potassium iodide starch indicator turns blue, and obtain diazonium salt solution. Then add the diazonium salt solution into the hydrochloric acid solution of cuprous chloride at 0~5℃, stir well, heat up to 60~70℃ and react for 1h, after cooling, let stand for stratification, and use 5% sodium hydroxide for the oil layer. Repeated washing with water, dehydration with anhydrous calcium chloride, fractional distillation, and collection of fractions at 177-183 °C to obtain the product 1,3-dichlorobenzene.

Definition

ChEBI: 1,3-dichlorobenzene is a dichlorobenzene carrying chloro substituents at positions 1 and 3. Used as a fumigant, insecticide, and chemical intermediate.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 250, 1983 DOI: 10.1021/jo00150a020

General Description

Colorless liquid. Sinks in water.

Air & Water Reactions

1,3-Dichlorobenzene is sensitive to moisture. Insoluble in water.

Reactivity Profile

1,3-Dichlorobenzene is incompatible with oxidizing agents and aluminum and its alloys. Above the flash point, explosive vapor-air mixtures may be formed.

Health Hazard

INHALATION: Causes headache, drousiness, unsteadiness. Irritating to mucous membranes. EYES: Severe irritation. SKIN: Severe irritation. INGESTION: Irritation of gastric mucosa, nausea, vomiting, diarrhea, abdominal cramps and cyanosis.

Fire Hazard

Special Hazards of Combustion Products: Irritating vapors including hydrogen chloride are produced.

Flammability and Explosibility

Flammable

Safety Profile

Moderately toxic by intraperitoneal route. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl-. See also oDICHLOROBENZENE and p DICHLOROBENZENE.

Environmental fate

Biological. When 1,3-dichlorobenzene was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, significant biodegradation with gradual acclimation was followed by a deadaptive process in subsequent subcultures. At a concentration of 5 mg/L, 59, 69, 39, and 35% losses were observed after 7, 14, 21, and 28-d incubation periods, respectively. At a concentration of 10 mg/L, percent losses were virtually unchanged. After 7, 14, 21, and 28-d incubation periods, percent losses were 58, 67, 31, and 33, respectively (Tabak et al., 1981). Photolytic. The sunlight irradiation of 1,3-dichlorobenzene (20 g) in a 100-mL borosilicate glass-stoppered Erlenmeyer flask for 56 d yielded 520 ppm trichlorobiphenyl (Uyeta et al., 1976).Chemical/Physical. Anticipated products from the reaction of 1,3-dichlorobenzene with atmospheric ozone or OH radicals are chlorinated phenols, ring cleavage products, and nitro compounds (Cupitt, 1980). Based on an assumed base-mediated 1% disappearance after 16 d at 85 oC and pH 9.70 (pH 11.26 at 25 oC), the hydrolysis half-life was estimated to be >900 yr (Ellington et al., 1988). 1,3-Dichlorobenzene (0.17–0.23 mM) reacted with OH radicals in water (pH 8.7) at a rate of 5.0 x 109/M·sec (Haag and Yao, 1992).

Purification Methods

Wash it with aqueous 10% NaOH, then with water until neutral, dry and distil it. Conductivity material (ca 10-10 mhos) has been prepared by refluxing over P2O5 for 8hours, then fractionally distilling, and storing with activated alumina. m-Dichlorobenzene dissolves rubber stoppers. [Beilstein 5 IV 657.]

Check Digit Verification of cas no

The CAS Registry Mumber 541-73-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 1 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 541-73:
(5*5)+(4*4)+(3*1)+(2*7)+(1*3)=61
61 % 10 = 1
So 541-73-1 is a valid CAS Registry Number.

541-73-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A13688)  1,3-Dichlorobenzene, 98%   

  • 541-73-1

  • 250g

  • 459.0CNY

  • Detail
  • Alfa Aesar

  • (A13688)  1,3-Dichlorobenzene, 98%   

  • 541-73-1

  • 500g

  • 501.0CNY

  • Detail
  • Alfa Aesar

  • (A13688)  1,3-Dichlorobenzene, 98%   

  • 541-73-1

  • 1000g

  • 920.0CNY

  • Detail
  • Sigma-Aldrich

  • (36708)  1,3-Dichlorobenzene  PESTANAL®, analytical standard

  • 541-73-1

  • 36708-1G

  • 196.56CNY

  • Detail

541-73-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3-dichlorobenzene

1.2 Other means of identification

Product number -
Other names iazine

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:541-73-1 SDS

541-73-1Synthetic route

Reaxys ID: 15739021

Reaxys ID: 15739021

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With triethyl phosphate at 50 - 60℃; under 7.50075 - 22.5023 Torr; Product distribution / selectivity;99%
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-benzene sulphonyl chloride

4-chloro-benzene sulphonyl chloride

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
98%
2,4 dichlorobenzoic acid
50-84-0

2,4 dichlorobenzoic acid

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With [Au(1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)(O2CAd)] In toluene at 140℃; for 20h;93%
With silver(I) acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 16h; Inert atmosphere;74%
With C38H53AuN2O2 at 120℃;
1-bromo-3,5-dichlorobenzene
19752-55-7

1-bromo-3,5-dichlorobenzene

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With methanol; gold; hydrogen; caesium carbonate at 100℃; under 3800.26 Torr; for 72h;89%
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%
1,3-dichloro-2-iodobenzene
19230-28-5

1,3-dichloro-2-iodobenzene

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With hydrogen; triethylamine In methanol; water at 120℃; under 22502.3 Torr;87%
With 2-(2-methoxyethoxy)ethyl alcohol; oxygen; sodium hydride In 1,4-dioxane at 20℃; for 18h; Schlenk technique; chemoselective reaction;73%
With sodium methylate In methanol; dimethyl sulfoxide at 50.1℃; Rate constant;
With potassium cyanide; Pd(PPh2(C6H4-p-SO3K))2Cl2; zinc In n-heptane; water at 100℃; for 1h; Inert atmosphere;38 %Chromat.
With hydrogen; triethylamine In methanol; water at 120℃; under 22502.3 Torr; for 44h; Autoclave;87 %Chromat.
2,6-dichlorobenzoic acid
50-30-6

2,6-dichlorobenzoic acid

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With silver(I) acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 120℃; for 16h; Inert atmosphere;76%
With acetamide at 225 - 235℃;
With silver carbonate In dimethylsulfoxide-d6 at 120℃; for 16h; Sealed vessel;96 %Spectr.
With silver carbonate In 1,4-dioxane at 130℃; for 24h;
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.
3-monochlorophenol
108-43-0

3-monochlorophenol

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With phenylphosphorus tetrachloride at 160℃;71%
2,6-dichloro-benzonitrile
1194-65-6

2,6-dichloro-benzonitrile

phenylmagnesium bromide

phenylmagnesium bromide

A

2,6-Dichlorbenzophenonimin
65231-41-6

2,6-Dichlorbenzophenonimin

B

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
In diethyl ether for 6h; Addition; Heating;A 70%
B 4%
C10H13Cl2N3
401631-85-4

C10H13Cl2N3

A

1-bromo-2,6-dichlorobenzene
19393-92-1

1-bromo-2,6-dichlorobenzene

B

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With hydrogen bromide; copper In acetonitrile at 20 - 25℃; for 0.25h;A 70%
B 15%
C6H4ClN2(1+)*C6H4NO4S2(1-)

C6H4ClN2(1+)*C6H4NO4S2(1-)

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; copper In acetonitrile at 20℃; for 0.75h; Substitution;68%
para-dichlorobenzene
106-46-7

para-dichlorobenzene

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
at 170℃; for 4h; Temperature; Inert atmosphere;64.7%
With aluminium trichloride at 160℃;
With aluminum (III) chloride; lithium chloride In melt at 170℃; for 4h; Inert atmosphere;
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.
sodium thiophenolate
930-69-8

sodium thiophenolate

2,6-dichlorobenzenediazonium o-benzenedisulfonimide

2,6-dichlorobenzenediazonium o-benzenedisulfonimide

A

diphenyldisulfane
882-33-7

diphenyldisulfane

B

sodium o-benzenedisulfonimide

sodium o-benzenedisulfonimide

C

(2,6-dichlorophenyl)(phenyl)sulfane

(2,6-dichlorophenyl)(phenyl)sulfane

D

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
In methanol at 20 - 25℃; Dimerization; arylthiodediazoniation; hydrodediazoniation;A 40%
B n/a
C 47%
D 35%
para-dichlorobenzene
106-46-7

para-dichlorobenzene

A

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

1,2-dichloro-benzene

B

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With aluminum (III) chloride; lithium chloride In melt at 170℃; for 4h; Catalytic behavior; Reagent/catalyst; Time; Autoclave; Inert atmosphere;A n/a
B 45%
With Zeolite β at 339.9℃; under 1 Torr; Mechanism; Thermodynamic data; Product distribution; activation energy; relative rate constants; different temperatures;
ZSM-5 type zeolite at 399.9℃; under 26252.1 Torr; Product distribution; various catalysts; further temperatures;
With aluminum (III) chloride; lithium chloride; sodium chloride at 150℃; for 16.5h; Reagent/catalyst; Temperature;
styrene
292638-84-7

styrene

m-phenylenebisdiazonium tetrafluoroborate

m-phenylenebisdiazonium tetrafluoroborate

A

(E,E)-1,3-distyrylbenzene
1725-76-4

(E,E)-1,3-distyrylbenzene

B

1-phenyl-1-chloro-2-(3-chlorophenyl)ethane
146736-38-1

1-phenyl-1-chloro-2-(3-chlorophenyl)ethane

C

1,3-Bis-(2-chloro-2-phenyl-ethyl)-benzene

1,3-Bis-(2-chloro-2-phenyl-ethyl)-benzene

D

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With sodium chloride; copper dichloride In acetone at 5 - 50℃;A 7%
B 45%
C n/a
D n/a
acrylic acid n-butyl ester
141-32-2

acrylic acid n-butyl ester

m-phenylenebisdiazonium tetrafluoroborate

m-phenylenebisdiazonium tetrafluoroborate

A

2-Chloro-3-(3-chloro-phenyl)-propionic acid butyl ester

2-Chloro-3-(3-chloro-phenyl)-propionic acid butyl ester

B

3-[3-(2-Butoxycarbonyl-2-chloro-ethyl)-phenyl]-2-chloro-propionic acid butyl ester

3-[3-(2-Butoxycarbonyl-2-chloro-ethyl)-phenyl]-2-chloro-propionic acid butyl ester

C

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With sodium chloride; copper dichloride In acetone at 5 - 50℃;A 39%
B n/a
C n/a
ethyl 2,6-dichlorobenzoate
81055-73-4

ethyl 2,6-dichlorobenzoate

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With potassium fluoride; 18-crown-6 ether; tetraphenylphosphonium bromide at 210℃; for 3h;37%
m-phenylenebisdiazonium tetrafluoroborate

m-phenylenebisdiazonium tetrafluoroborate

ethyl acrylate
140-88-5

ethyl acrylate

A

2-Chloro-3-(3-chloro-phenyl)-propionic acid ethyl ester

2-Chloro-3-(3-chloro-phenyl)-propionic acid ethyl ester

B

2-Chloro-3-[3-(2-chloro-2-ethoxycarbonyl-ethyl)-phenyl]-propionic acid ethyl ester

2-Chloro-3-[3-(2-chloro-2-ethoxycarbonyl-ethyl)-phenyl]-propionic acid ethyl ester

C

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With sodium chloride; copper dichloride In acetone at 5 - 50℃;A 36%
B 5%
C n/a
m-phenylenebisdiazonium tetrafluoroborate

m-phenylenebisdiazonium tetrafluoroborate

acrylonitrile
107-13-1

acrylonitrile

A

2-chloro-3-(3-chlorophenyl)propanenitrile
18826-39-6

2-chloro-3-(3-chlorophenyl)propanenitrile

B

2-Chloro-3-[3-(2-chloro-2-cyano-ethyl)-phenyl]-propionitrile

2-Chloro-3-[3-(2-chloro-2-cyano-ethyl)-phenyl]-propionitrile

C

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With sodium chloride; copper dichloride In acetone at 5 - 50℃;A 32%
B n/a
C n/a
m-phenylenebisdiazonium tetrafluoroborate

m-phenylenebisdiazonium tetrafluoroborate

methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

A

2-Chloro-3-(3-chloro-phenyl)-2-methyl-propionic acid methyl ester

2-Chloro-3-(3-chloro-phenyl)-2-methyl-propionic acid methyl ester

B

2-Chloro-3-[3-(2-chloro-2-methoxycarbonyl-propyl)-phenyl]-2-methyl-propionic acid methyl ester

2-Chloro-3-[3-(2-chloro-2-methoxycarbonyl-propyl)-phenyl]-2-methyl-propionic acid methyl ester

C

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With sodium chloride; copper dichloride In acetone at 5 - 50℃;A 32%
B 4%
C n/a
2-methoxyacrylic acid ethyl ester
36997-05-4

2-methoxyacrylic acid ethyl ester

2,6-dichlorobenzoic acid
50-30-6

2,6-dichlorobenzoic acid

A

(Z)-ethyl 3-(2,6-dichlorophenyl)-2-methoxyacrylate

(Z)-ethyl 3-(2,6-dichlorophenyl)-2-methoxyacrylate

B

diethyl 2,5-dimethoxyhexa-2,4-dienedioate

diethyl 2,5-dimethoxyhexa-2,4-dienedioate

C

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane; dimethyl sulfoxide at 130℃; for 24h; Solvent; Sealed tube; Inert atmosphere; stereoselective reaction;A 27%
B n/a
C n/a
1,3,5-trichlorobenzene
108-70-3

1,3,5-trichlorobenzene

isopropyl alcohol
67-63-0

isopropyl alcohol

A

acetone
67-64-1

acetone

B

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

C

benzene
71-43-2

benzene

Conditions
ConditionsYield
With sodium hydroxide; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In water; toluene for 48h; Conversion of starting material; Alkaline conditions; Heating / reflux;A n/a
B 24%
C 36 %Chromat.
With sodium hydroxide; nickel dihydroxide; 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In water; toluene for 72h; Conversion of starting material; Alkaline conditions; Heating / reflux;A n/a
B 16%
C 50 %Chromat.
tetrachloromethane
56-23-5

tetrachloromethane

3-chloro-benzenecarboperoxoic acid
937-14-4

3-chloro-benzenecarboperoxoic acid

A

hexachloroethane
67-72-1

hexachloroethane

B

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With cyclohexane In 1,2-dichloro-ethane at 65℃; for 24h; Product distribution; Mechanism;A 3.2%
B 15.5%
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

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

1,2,4-Trichlorobenzene

Conditions
ConditionsYield
With carbon dioxide; tetrabutylammomium bromide In N,N-dimethyl-formamide at -5 - 0℃; Dehalogenation; Electrochemical reaction; Further byproducts given;A 9%
B 1%
C 2%
D 8%
With [2,2]bipyridinyl; nickel dichloride; zinc In water; N,N-dimethyl-formamide at 80℃; for 6h; Title compound not separated from byproducts;A 15.2 % Spectr.
B 5.8 % Spectr.
C 3.9 % Spectr.
D 66.0 % Spectr.
meta-dinitrobenzene
99-65-0

meta-dinitrobenzene

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With chlorine at 220℃; Ausschluss von Wasser und Eisen;
With tetrachloromethane at 260 - 310℃;
With chlorine at 230 - 250℃;
With chlorine at 230℃; Temperature;
1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

Conditions
ConditionsYield
With tetrachloromethane; chlorine Photolysis;
With iron(III) chloride; sodium chloride In acetonitrile for 10h; Irradiation; Green chemistry; regioselective reaction;
pentan-1-ol
71-41-0

pentan-1-ol

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

m-pentoxychlorobenzene
51241-38-4

m-pentoxychlorobenzene

Conditions
ConditionsYield
With potassium hydroxide; PEG-6000 at 150℃; for 6h;100%
1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

benzene
71-43-2

benzene

Conditions
ConditionsYield
With sodium hydroxide; ethanol; hydrogen; PdCl2-poly(N-vinyl-2-pyrrolidone); palladium dichloride at 65℃; under 760 Torr; for 2h;100%
With Ni[1,10-phenanthroline]2(PF6)2; water; zinc at 70℃; for 7h; Ionic liquid;46%
With Ni-Al clusters In tetrahydrofuran for 1.5h; Dehalogenation; reduction; hydrogenolysis; dechlorination; Heating;
1-fluoro-2-trifluoromethylbenzene
392-85-8

1-fluoro-2-trifluoromethylbenzene

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

2,4-dichloro-1-[dichloro-(2-fluorophenyl)methyl]benzene
917751-97-4

2,4-dichloro-1-[dichloro-(2-fluorophenyl)methyl]benzene

Conditions
ConditionsYield
With aluminum (III) chloride In 1,2-dichloro-ethane at 0 - 5℃; for 3h;100%
With aluminium trichloride In 1,2-dichloro-ethane at 0℃; for 3h; Friedel-Crafts alkylation;92.4%
laurylmagnesium bromide
15890-72-9

laurylmagnesium bromide

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

1,3-Didodecyl-benzol
52066-87-2

1,3-Didodecyl-benzol

Conditions
ConditionsYield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether; hexane at 50℃; Kumada Cross-Coupling; Inert atmosphere; Schlenk technique;100%
dimethyl amine
124-40-3

dimethyl amine

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

N,N,N',N'-tetramethyl-m-phenylenediamine
22440-93-3

N,N,N',N'-tetramethyl-m-phenylenediamine

Conditions
ConditionsYield
With (R)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; palladium dichloride; lithium hexamethyldisilazane In tetrahydrofuran; 1,2-dimethoxyethane at 0 - 20℃; for 16h; Inert atmosphere; Glovebox;99.9%
With C8H11N*C33H50ClPPd; lithium hexamethyldisilazane In tetrahydrofuran at 0 - 20℃; Inert atmosphere;94%
With phenyllithium In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;
1,1,1,3,5,5,5-heptamethyltrisiloxan
1873-88-7

1,1,1,3,5,5,5-heptamethyltrisiloxan

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

1,1,1,3,5,5,5-heptamethyl-3-(3,5-dichlorophenyl)trisiloxane

1,1,1,3,5,5,5-heptamethyl-3-(3,5-dichlorophenyl)trisiloxane

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 2.9-dimethyl-1,10-phenanthroline In 1,4-dioxane at 100℃; for 6h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Sealed tube; regioselective reaction;99%
With IrH3{κ3-P,O,P-[9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene]} In cyclohexene at 110℃; for 18h; Inert atmosphere; Glovebox;94%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 2,4,7-trimethyl-1,10-phenanthroline In tetrahydrofuran at 120℃; for 40h; Inert atmosphere; Sealed tube;66%
1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

1-bromo-2,4-dichlorobenzene
1193-72-2

1-bromo-2,4-dichlorobenzene

Conditions
ConditionsYield
With bromine; iron(III) chloride98.5%
With methanesulfonic acid; monobromoisocynaurate In diethyl ether for 6h; Heating;65%
1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

1,3-dichloro-2-iodobenzene
19230-28-5

1,3-dichloro-2-iodobenzene

Conditions
ConditionsYield
Stage #1: 1,3-Dichlorobenzene With n-butyllithium In tetrahydrofuran; hexane at -75℃; for 2h;
Stage #2: With iodine In tetrahydrofuran; hexane
98%
Stage #1: 1,3-Dichlorobenzene With sodium; diisopropylamine; isoprene In tetrahydrofuran at -20℃; for 0.000138889h; Flow reactor;
Stage #2: With iodine In tetrahydrofuran Temperature; Flow reactor;
84%
Stage #1: 1,3-Dichlorobenzene With Li(2,2,6,6-tetramethylpiperidide)*Al(iBu)3 In tetrahydrofuran; hexane at -78℃; for 12h;
Stage #2: With iodine In tetrahydrofuran; hexane at 0℃; for 1h;
74%
9H-carbazole
86-74-8

9H-carbazole

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

1,3-bis(9H-carbazol-9-yl)benzene

1,3-bis(9H-carbazol-9-yl)benzene

Conditions
ConditionsYield
Stage #1: 9H-carbazole With methylmagnesium chloride In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene for 0.25h; Inert atmosphere; Schlenk technique;
Stage #2: 1,3-Dichlorobenzene With [2,6-bis(2,4,6-triisopropylphenyl)phenyl(dicyclohexylphosphine)](allyl-η3)palladium(II) chloride; 2,6-bis(2,4,6-triisopropylphenyl)phenyl(dicyclohexylphosphine) In 5,5-dimethyl-1,3-cyclohexadiene at 145℃; for 3h; Reagent/catalyst; Temperature; Glovebox; Schlenk technique; Inert atmosphere;
98%
Stage #1: 9H-carbazole With methylmagnesium chloride In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 5 - 20℃; for 0.166667h; Inert atmosphere;
Stage #2: 1,3-Dichlorobenzene With PdCl(π-allyl)(cyclohexyl-(1-methyl-2,2-diphenylcyclopropylphophine)) In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 108 - 112℃; for 0.25h; Inert atmosphere;
97%
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)); methylmagnesium chloride In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 5℃; Buchwald-Hartwig Coupling; Inert atmosphere; Reflux;96.8%
acetic anhydride
108-24-7

acetic anhydride

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

1-(2,4-dichlorophenyl)ethan-1-one
2234-16-4

1-(2,4-dichlorophenyl)ethan-1-one

Conditions
ConditionsYield
With aluminum (III) chloride at 40 - 55℃;97.9%
Stage #1: acetic anhydride; 1,3-Dichlorobenzene With aluminum (III) chloride at 40 - 55℃; under 637.564 Torr;
Stage #2: With hydrogenchloride In water
95%
With aluminum (III) chloride at 50℃; for 4h; Reagent/catalyst; Temperature;70.9%
Stage #1: acetic anhydride With aluminum (III) chloride In 1,2-dichloro-benzene for 0.333333h;
Stage #2: 1,3-Dichlorobenzene With hydrogenchloride In water; 1,2-dichloro-benzene Cooling with ice;
55.46%
With hydrogenchloride; aluminum (III) chloride; calcium chloride In water for 0.833333h;55.46%
1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

2,4-dichloronitrobenzene
611-06-3

2,4-dichloronitrobenzene

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 10 - 15℃; for 3h; Temperature;97.2%
With sulfuric acid; nitric acid at 60℃; for 1h;95.4%
With nitric acid; acetic anhydride In tetrachloromethane65.3%
succinic acid anhydride
108-30-5

succinic acid anhydride

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

4-(2,4-dichlorophenyl)-4-oxobutanoic acid
58457-57-1

4-(2,4-dichlorophenyl)-4-oxobutanoic acid

Conditions
ConditionsYield
With aluminium trichloride at 80℃; for 1h;96%
With aluminium trichloride
acetyl chloride
75-36-5

acetyl chloride

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

1-(2,4-dichlorophenyl)ethan-1-one
2234-16-4

1-(2,4-dichlorophenyl)ethan-1-one

Conditions
ConditionsYield
at 60℃; for 4h; Ionic liquid; Green chemistry;96%
at 60℃; for 4h; Temperature; Ionic liquid;96%
With aluminium trichloride
carbon dioxide
124-38-9

carbon dioxide

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

2,6-dichlorobenzoic acid
50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide With AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); potassium hydroxide In tetrahydrofuran at 20℃; under 1125.11 Torr; for 0.25h;
Stage #2: 1,3-Dichlorobenzene In tetrahydrofuran at 20℃; under 1125.11 Torr; for 12h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water regioselective reaction;
96%
With n-butyllithium In tetrahydrofuran; hexane for 0.75h; cooling;95%
Stage #1: 1,3-Dichlorobenzene With n-butyllithium In tetrahydrofuran at -75℃; for 2h;
Stage #2: carbon dioxide In tetrahydrofuran
95%
Stage #1: 1,3-Dichlorobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Inert atmosphere;
Stage #2: carbon dioxide In tetrahydrofuran; hexane at -78℃; for 0.166667h; Inert atmosphere;
437 mg
ortho-methylphenyl iodide
615-37-2

ortho-methylphenyl iodide

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

2,6-dichloro-2'-methyl-1,1'-biphenyl

2,6-dichloro-2'-methyl-1,1'-biphenyl

Conditions
ConditionsYield
Stage #1: 1,3-Dichlorobenzene With n-butyllithium
Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at 0 - 20℃;
Stage #3: ortho-methylphenyl iodide With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 10h; Negishi coupling reaction; Inert atmosphere; Reflux;
96%
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

m-chlorobiphenyl
2051-61-8

m-chlorobiphenyl

Conditions
ConditionsYield
With Ni(N,N'-bis(diphenylphosphino)-1,3-benzenediamine(-1H))Cl In tetrahydrofuran at 40℃; for 18h; Kumada Cross-Coupling; Schlenk technique; Inert atmosphere;95.7%
benzaldehyde
100-52-7

benzaldehyde

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

(2,6-dichlorophenyl)(phenyl)methanol
22543-77-7

(2,6-dichlorophenyl)(phenyl)methanol

Conditions
ConditionsYield
Stage #1: 1,3-Dichlorobenzene With sodium; diisopropylamine; isoprene In tetrahydrofuran at -20℃; for 0.000138889h; Flow reactor;
Stage #2: benzaldehyde In tetrahydrofuran Flow reactor;
95%
With n-butyllithium 1.) hexane,THF, -65 to -70 deg C, 45 min, 2.) THF, -70 deg C, 45 min; Yield given. Multistep reaction;
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

2-(3,5-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
68716-51-8

2-(3,5-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
Stage #1: bis(pinacol)diborane With C24H28ClIrN2O In n-heptane; isopropyl alcohol at 75℃; for 1h; Sealed tube; Inert atmosphere;
Stage #2: 1,3-Dichlorobenzene In n-heptane; isopropyl alcohol Sealed tube; Inert atmosphere;
95%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tert-butyl methyl ether at 80℃; for 1h; Microwave irradiation;94%
With [Ir(OMe)(1,5-cyclooctadiene)]2; C88H164N2 In n-heptane at 25℃; for 18h; Inert atmosphere;84%
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

2-(3,5-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
68716-51-8

2-(3,5-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With IrH2(Bpin){κ3-P,O,P-[9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene]}; cyclohexene at 110℃; for 18h; Inert atmosphere; Glovebox;95%
With iridium-bipyridine periodic mesoporous organosilica In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique;94%
With 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer In hexane at 25℃; for 8h;86%
bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex

bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

C15H21Cl2MgN

C15H21Cl2MgN

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Schlenk technique; regioselective reaction;95%
2-methoxyphenyllithium
31600-86-9

2-methoxyphenyllithium

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

2,2”-dimethoxy-1,1’:3’,1”-terphenyl
103068-14-0

2,2”-dimethoxy-1,1’:3’,1”-terphenyl

Conditions
ConditionsYield
In diethyl ether for 15h; Ambient temperature;94%
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

2-(2,6-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
69807-92-7

2-(2,6-dichlorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
ConditionsYield
With bis(2,2,6,6-tetramethylpiperidin-1-yl)magnesium-bis(lithium chloride) complex In tetrahydrofuran at 0 - 25℃; for 2h; Inert atmosphere; Schlenk technique;94%
(triethylphosphine)chlorogold(I)
15529-90-5

(triethylphosphine)chlorogold(I)

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

2,6-dichlorophenyl(triethylphosphine)gold(I)

2,6-dichlorophenyl(triethylphosphine)gold(I)

Conditions
ConditionsYield
With sodium t-butanolate In N,N-dimethyl-formamide at 50℃; for 15h;94%
With potassium tert-butylate In neat (no solvent) for 1.5h; Reagent/catalyst; Time; Milling;92%
triethylsilane
617-86-7

triethylsilane

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

(3,5-dichlorophenyl)triethylsilane

(3,5-dichlorophenyl)triethylsilane

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; tert-butylethylene; 3,4,7,8-Tetramethyl-o-phenanthrolin In cyclohexane at 100℃; for 4h; Time; Inert atmosphere; Sealed tube; chemoselective reaction;94%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

2,2',4'-trichloroacetophenone
4252-78-2

2,2',4'-trichloroacetophenone

Conditions
ConditionsYield
With aluminum (III) chloride at 30℃; for 3h; Friedel-Crafts Acylation;93.1%
With aluminum (III) chloride In dichloromethane at 20℃;90%
With aluminum (III) chloride In dichloromethane for 3h; Reflux;86%
4-methoxyphenyl magnesium bromide
13139-86-1

4-methoxyphenyl magnesium bromide

1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

4,4’’-dimethoxy-1,1′:3′,1’’-terphenyl
1568-74-7

4,4’’-dimethoxy-1,1′:3′,1’’-terphenyl

Conditions
ConditionsYield
With C20H23BrN4Ni In tetrahydrofuran at 25℃; for 24h; Kumada Cross-Coupling; Inert atmosphere;93%
Stage #1: 1,3-Dichlorobenzene With Ni(PPh3)(1,3-di-tert-butylimidazol-2-ylidene)Br2 In tetrahydrofuran at 0℃; for 0.0333333h; Inert atmosphere; Schlenk technique;
Stage #2: 4-methoxyphenyl magnesium bromide In tetrahydrofuran at 0 - 25℃; for 5h; Inert atmosphere; Schlenk technique;
79%

541-73-1Relevant articles and documents

-

Lobry de Bruyn

, (1894)

-

Exploiting a silver-bismuth hybrid material as heterogeneous noble metal catalyst for decarboxylations and decarboxylative deuterations of carboxylic acids under batch and continuous flow conditions

?tv?s, Sándor B.,Fül?p, Ferenc,Kónya, Zoltán,Kukovecz, ákos,Márton, András,Mészáros, Rebeka,Pálinkó, István,Szabados, Márton,Varga, Gábor

, p. 4685 - 4696 (2021/07/12)

Herein, we report novel catalytic methodologies for protodecarboxylations and decarboxylative deuterations of carboxylic acids utilizing a silver-containing hybrid material as a heterogeneous noble metal catalyst. After an initial batch method development, a chemically intensified continuous flow process was established in a simple packed-bed system which enabled gram-scale protodecarboxlyations without detectable structural degradation of the catalyst. The scope and applicability of the batch and flow processes were demonstrated through decarboxylations of a diverse set of aromatic carboxylic acids. Catalytic decarboxylative deuterations were achieved on the basis of the reaction conditions developed for the protodecarboxylations using D2O as a readily available deuterium source.

Controllable synthesis of ultrasmall Pd nanocatalysts templated by supramolecular coordination cages for highly efficient reductive dehalogenation

Jiang, Wei-Ling,Peng, Zhiyong,Shen, Ji-Chuang,Shi, Xueliang,Wu, Gui-Yuan,Yang, Hai-Bo,Yin, Guang-Qiang

supporting information, p. 12097 - 12105 (2020/07/09)

Supported ultrasmall noble metal nanocatalysts (UNMNs) are one of the most important classes of solid materials for heterogeneous catalysis. Herein, a simple and efficient supramolecular coordination cage (SCC) template-strategy has been developed to synthesize UNMNs with controllable size and size distribution. A series of SCCs, including M2L4, M4L2, M6L4 and M12L24, with well-defined sizes and shapes as well as different numbers of Pd ions were designed and synthesized as templates. Subsequently, the corresponding Pd nanocatalysts M2&at;CMC, M4&at;CMC, M6&at;CMC and M12&at;CMC were prepared by an impregnation-reduction method on carboxymethylcellulose (CMC) hydrogel supports. It was found that the employment of SCCs as templates could not only significantly reduce the aggregation tendency of Pd nanoparticles but also play an important role in regulating their size and size distribution. For example, the analysis of the catalyst size distribution indicated that the greater the number of Pd ions the cage possesses, the bigger the size of the catalyst. Moreover, with the decrease of the concentration of the template, the size of the Pd nanocatalyst also decreased obviously. Particularly, the resultant catalyst with a nano-Pd loading as high as 12.63percent could still maintain a narrow size distribution. Furthermore, the as-prepared Pd nanocatalyst could serve as a highly efficient polychlorinated biphenyl (PCB) degrader both in a stirred vessel and a continuous flow reactor because of its excellent catalytic efficiency in the reductive dehalogenation reaction under mild conditions. In a word, the SCC template-strategy employed in this study provides new guidelines for the preparation of size-controllable UNMNs on a variety of supports, along with high noble metal loading and catalytic activity. This journal is

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