34883-43-7

Basic information

• Product Name: 2,4'-DICHLOROBIPHENYL
• Synonyms: 1,1'-Biphenyhl, 2,4'-dichloro-;2,4’-dichloro-1,1’-biphenyl;2,4’-dichloro-1’-biphenyl;2,4’-dichloro-bipheny;2,4'-Dichloro-1,1'-biphenyl;Biphenyl, 2,4'-dichloro-;PCB 8;PCB NO 8
• CAS NO: 34883-43-7
• Molecular Formula: C₁₂H₈Cl₂
• Molecular Weight: 223.1
• EINECS: 215-648-1
• Product Categories: DIA - DIC;Alphabetic;D
• Mol File: 34883-43-7.mol
• Article Data: 17

Chemical Properties

• Melting Point: 46°C
• Boiling Point: 289.78°C (rough estimate)
• Flash Point: 133.6°C
• Appearance: /
• Density: 1.2490 (rough estimate)
• Refractive Index: 1.5940 (rough estimate)
• Storage Temp.: 2-8°C
• Water Solubility: 0.62mg/L(25 oC)
• BRN: 1946417
• CAS DataBase Reference: 2,4'-DICHLOROBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4'-DICHLOROBIPHENYL(34883-43-7)
• EPA Substance Registry System: 2,4'-DICHLOROBIPHENYL(34883-43-7)

Safety Data

• Hazard Codes: N,Xn
• Statements: 33-50/53
• Safety Statements: 35-60-61
• RIDADR: UN 3432 9/PG 2
• WGK Germany: 3
• RTECS: DV3905000
• Hazardous Substances Data: 34883-43-7(Hazardous Substances Data)

Usage

Uses

2,4''-Dichlorobiphenyl is a polychlorinated biphenyl (PCB) congeners.

Definition

ChEBI: A dichlorobiphenyl that is chlorobenzene in which the hydrogen at position 2 has been replaced by a 4-chlorophenyl group.

Synthetic route

biphenyl (92-52-4) → 2-chloro-1,1'-biphenyl (2051-60-7) + 2,4'-dichlorobiphenyl (34883-43-7) + 4,4'-dichlorobiphenyl (2050-68-2) + 4'-biphenyl chloride (2051-62-9)

Conditions	Yield
With chlorine; K-Zeolith L In dichloromethane at 20℃; for 6h; Product distribution; further zeolithes; further solvents and reaction conditions;	A 1.9% B 4.9% C 89% D 3%
With chlorine; K-Zeolith L In dichloromethane at 20℃; for 6h;	A 1.9% B 4.9% C 89% D 3%
With chlorine; K-Zeolith L In tetrachloromethane at 20℃; for 6h; Title compound not separated from byproducts;	A 10% B 14.7% C 66.5% D 5.7%
With chlorine; K-Zeolith L In various solvent(s) at 20℃; for 6h; Title compound not separated from byproducts;	A 10.1% B 5.4% C 39.7% D 35.9%
With chlorine; K-Zeolith L In acetic acid at 40℃; for 6h; Title compound not separated from byproducts;	A 28.9% B 8.8% C 13% D 31.9%

4-Chlorophenylboronic acid (1679-18-1) + 1,2-dichloro-benzene (95-50-1) → 2,4'-dichlorobiphenyl (34883-43-7)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In toluene at 70℃; Suzuki coupling; Inert atmosphere; chemoselective reaction;	64%

1-Bromo-2-iodobenzene (583-55-1) + 4-chlorophenyl lithium (14774-78-8) → 2,4'-dichlorobiphenyl (34883-43-7)

Conditions	Yield
Stage #1: 1-Bromo-2-iodobenzene With n-butyllithium In tetrahydrofuran; hexane at -70℃; Flow reactor; Stage #2: 4-chlorophenyl lithium In tetrahydrofuran at 0℃; Flow reactor; Stage #3: With hexachloroethane In tetrahydrofuran; hexane at -30℃; Flow reactor;	64%

chlorobenzene (108-90-7) + phenol (108-95-2) → 2,3'-dichloro-1,1'-biphenyl (25569-80-6) + 2,4'-dichlorobiphenyl (34883-43-7) + 3,4'-dichlorobiphenyl (2974-90-5) + 4,4'-dichlorobiphenyl (2050-68-2) + PCB 11 (2050-67-1) + 2,2'-Dichlorobiphenyl (13029-08-8)

Conditions	Yield
With tert.-butylhydroperoxide; iodine at 289.9℃; for 0.0272222h; Product distribution;	A 34.4% B 18.7% C 15.5% D 3.9% E 13.1% F 14.4%

2,4'-diaminobiphenyl (492-17-1) → 2,4'-dichlorobiphenyl (34883-43-7)

Conditions	Yield
With sulfuric acid Diazotization.Behandlung der Diazoniumsalz-Loesung mit Hg(NO3)2 und KCl und Erhitzen des erhaltenen Diazonium-tetrachloromercurats(II) mit KCl bis auf 120grad;

3-chloro-4-(4-chlorophenyl)benzenamine (138588-57-5) → 2,4'-dichlorobiphenyl (34883-43-7)

Conditions	Yield
With sulfuric acid Diazotization.Behandlung der Diazoniumsalz-Loesung mit H3PO2;

p-chlorobenzenediazonium tetrafluoroborate (673-41-6) → 2,4'-dichlorobiphenyl (34883-43-7) + 3,4'-dichlorobiphenyl (2974-90-5) + (4-chloro-phenyl)-(5,4'-dichloro-biphenyl-2-yl)-diazene (141320-17-4) + chlorobenzene (108-90-7) + bis-(4-chloro-phenyl)-diazene (1602-00-2)

Conditions	Yield
With titanium(III) sulphate In water; acetonitrile at 0 - 5℃; Mechanism; Product distribution; other solvents, p-chlorobenzenediazonium sulfate and benzenediazonium salts;	A 0.7 % Chromat. B 6.5 % Chromat. C 63.5 % Chromat. D 5.8 % Chromat. E 5.3 % Chromat.

4-chloro-aniline (106-47-8) + chlorobenzene (108-90-7) → 2,4'-dichlorobiphenyl (34883-43-7) + 3,4'-dichlorobiphenyl (2974-90-5) + 4,4'-dichlorobiphenyl (2050-68-2)

Conditions	Yield
With sodium nitrite; trichloroacetic acid; copper(l) chloride at 85℃; for 2h; Yield given. Yields of byproduct given;

1,6-bis-(4-chlorophenyl)-3,4-diacetyl-1,5-hexazadiene (10312-71-7) + chlorobenzene (108-90-7) → Diacetylhydrazin (3148-73-0) + 2,4'-dichlorobiphenyl (34883-43-7) + 3,4'-dichlorobiphenyl (2974-90-5) + 4,4'-dichlorobiphenyl (2050-68-2) + 1-acetyl-1-p-chlorophenylhydrazine (82408-82-0)

Conditions	Yield
at 131℃; Product distribution; Mechanism; thermolysis, var.: photolysis;
at 10℃; for 6h; Product distribution; Mechanism; Irradiation;

p-chlorobenzenediazonium tetrafluoroborate (673-41-6) + chlorobenzene (108-90-7) → 2,4'-dichlorobiphenyl (34883-43-7) + 3,4'-dichlorobiphenyl (2974-90-5) + 4,4'-dichlorobiphenyl (2050-68-2)

Conditions	Yield
With potassium acetate; 18-crown-6 ether for 1.5h; Ambient temperature; Yield given. Yields of byproduct given;
With potassium acetate; 18-crown-6 ether for 1.5h; Product distribution; Ambient temperature; other catalysts and reaction conditions; other aromatic reactants;
With pyridine at 23℃; for 18h; Gomberg-Bachman Arylation; Inert atmosphere; Irradiation; Overall yield = 94 percent; Overall yield = 126 mg;

1-p-chlorophenyl-3,4-diacetyl-1-tetrazene (79991-27-8) + chlorobenzene (108-90-7) → Diacetylhydrazin (3148-73-0) + 2,4'-dichlorobiphenyl (34883-43-7) + 3,4'-dichlorobiphenyl (2974-90-5) + 4,4'-dichlorobiphenyl (2050-68-2) + 1-acetyl-1-p-chlorophenylhydrazine (82408-82-0)

Conditions	Yield
Product distribution; Mechanism; thermolysis, var.: photolysis, 10 degC;
at 10℃; for 2h; Product distribution; Mechanism; Irradiation;

1,6-bis-(4-chlorophenyl)-3,4-diacetyl-1,5-hexazadiene (10312-71-7) + chlorobenzene (108-90-7) + isopropyl alcohol (67-63-0) → Dimethyl ether (115-10-6) + diacetyl diazene (10465-77-7) + Diacetylhydrazin (3148-73-0) + 2,4'-dichlorobiphenyl (34883-43-7) + 3,4'-dichlorobiphenyl (2974-90-5) + 4,4'-dichlorobiphenyl (2050-68-2)

Conditions	Yield
at 83℃; Product distribution; Mechanism;

...Expand

chlorobenzene (108-90-7) → 2,3'-dichloro-1,1'-biphenyl (25569-80-6) + 2,4'-dichlorobiphenyl (34883-43-7) + 3,4'-dichlorobiphenyl (2974-90-5) + 4,4'-dichlorobiphenyl (2050-68-2)

Conditions	Yield
With thallium(III) trifluoroacetate; palladium diacetate at 135℃; for 50h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
With thallium(III) trifluoroacetate; palladium diacetate at 70℃; for 50h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;
With thallium(III) trifluoroacetate; palladium diacetate at 70℃; for 50h; Yield given. Further byproducts given. Yields of byproduct given;

chlorobenzene (108-90-7) → 2,4'-dichlorobiphenyl (34883-43-7) + 3,4'-dichlorobiphenyl (2974-90-5) + 4,4'-dichlorobiphenyl (2050-68-2) + PCB 11 (2050-67-1)

Conditions	Yield
With palladium diacetate; thallium(III) trifluoroacetate at 60 - 70℃; Yield given. Further byproducts given. Yields of byproduct given;

chlorobenzene (108-90-7) → 2,3'-dichloro-1,1'-biphenyl (25569-80-6) + 2,4'-dichlorobiphenyl (34883-43-7) + 3,4'-dichlorobiphenyl (2974-90-5) + 4,4'-dichlorobiphenyl (2050-68-2) + PCB 11 (2050-67-1) + 2,2'-Dichlorobiphenyl (13029-08-8)

Conditions	Yield
With thallium(III) trifluoroacetate; palladium diacetate at 70℃; for 50h; Product distribution; Rate constant; variation of amount of Pd(II) and temperature;
With palladium diacetate; thallium(III) trifluoroacetate at 60 - 70℃; Product distribution; selectivity in the oxidative coupling;

chlorobenzene (108-90-7) → 2,4'-dichlorobiphenyl (34883-43-7) + 3,4'-dichlorobiphenyl (2974-90-5) + 4,4'-dichlorobiphenyl (2050-68-2) + 2,2'-Dichlorobiphenyl (13029-08-8)

Conditions	Yield
With thallium(III) trifluoroacetate; palladium diacetate at 135℃; for 50h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

1-Chloro-4-iodobenzene (637-87-6) + 2-iodochlorobenzene (615-41-8) → 2,4'-dichlorobiphenyl (34883-43-7)

Conditions	Yield
With copper In N,N-dimethyl-formamide Ulman reaction; Heating;

2′-chlorobiphenyl-4-amine (1204-42-8) → 2,4'-dichlorobiphenyl (34883-43-7)

Conditions	Yield
With copper(I) chloride; cis-nitrous acid Sandmeyer reaction;

4-chloro-aniline (106-47-8) + chlorobenzene (108-90-7) → 2,4'-dichlorobiphenyl (34883-43-7)

Conditions	Yield
With sodium acetate; cis-nitrous acid Arylation; Gomberg-Bachman reaction;

chlorobenzene (108-90-7) → 2,3'-dichloro-1,1'-biphenyl (25569-80-6) + 2,4'-dichlorobiphenyl (34883-43-7) + 3,4'-dichlorobiphenyl (2974-90-5) + PCB 11 (2050-67-1) + phenol (108-95-2) + 2,2'-Dichlorobiphenyl (13029-08-8) + chlorobiphenyls, chlorophenols

Conditions	Yield
With tert.-butylhydroperoxide at 212℃; Product distribution; Mechanism; various temperatures;

4-chloro-aniline (106-47-8) + 2-hydroxy-9-methyl-carbazole-3(?)-carboxylic acid → 2,4'-dichlorobiphenyl (34883-43-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaNO2, 10percent H2SO4, 2.) TiCl3 / 1.) H2O, 0-2 deg C, 2.) H2O, MeOH, 0-5 deg C 2: NaNO2, CCl3COOH / CuCl / 2 h / 85 °C View Scheme

2,4'-dichloro-4-nitro-biphenyl (138588-58-6) → 2,4'-dichlorobiphenyl (34883-43-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: tin; aqueous hydrochloric acid; ethanol 2: aqueous H2SO4 / Diazotization.Behandlung der Diazoniumsalz-Loesung mit H3PO2 View Scheme

2-iodochlorobenzene (615-41-8) + 4-Chlorophenylboronic acid (1679-18-1) → 2,4'-dichlorobiphenyl (34883-43-7)

Conditions	Yield
With palladium diacetate; sodium carbonate In water; acetone at 25℃; for 12h;
With palladium diacetate; sodium carbonate In water; acetone at 20℃; for 10h;

2,5-dichloroiodobenzene (29682-41-5) → 2,4'-dichlorobiphenyl (34883-43-7) + 3,4'-dichlorobiphenyl (2974-90-5) + 2,5-dichlorobiphenyl (34883-39-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; C20H29Cl2N5O2Pd / ethanol / 2.5 h / 78 - 83 °C 2: isopropyl alcohol; sodium hydroxide; palladium 10% on activated carbon / 1 h / 83 °C View Scheme

2,5-dichloroiodobenzene (29682-41-5) → biphenyl (92-52-4) + 2,4'-dichlorobiphenyl (34883-43-7) + 2,5-dichlorobiphenyl (34883-39-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; C20H29Cl2N5O2Pd / ethanol / 2.5 h / 78 - 83 °C 2: isopropyl alcohol; sodium hydroxide; palladium 10% on activated carbon / 83 °C View Scheme

2-bromo-1-chlorobenzene (694-80-4) + 4-Chlorophenylboronic acid (1679-18-1) → 2,4'-dichlorobiphenyl (34883-43-7)

Conditions	Yield
With C20H29Cl2N5O2Pd; potassium carbonate In ethanol at 78 - 83℃; for 2.5h;

2,4,4'-Trichlorobiphenyl (7012-37-5) → 2,4'-dichlorobiphenyl (34883-43-7) + 4,4'-dichlorobiphenyl (2050-68-2) + PCB 7 (33284-50-3)

Conditions	Yield
With palladium 10% on activated carbon; isopropyl alcohol; sodium hydroxide at 83℃; for 1h; regioselective reaction;

1-bromo-2,4-dichlorobenzene (1193-72-2) + 4-Chlorophenylboronic acid (1679-18-1) → 2,4'-dichlorobiphenyl (34883-43-7) + 4,4'-dichlorobiphenyl (2050-68-2) + PCB 7 (33284-50-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; C20H29Cl2N5O2Pd / ethanol / 2.5 h / 78 - 83 °C 2: isopropyl alcohol; sodium hydroxide; palladium 10% on activated carbon / 1 h / 83 °C View Scheme

4-Chlorophenylboronic acid (1679-18-1) → 2,4'-dichlorobiphenyl (34883-43-7) + 3,4'-dichlorobiphenyl (2974-90-5) + 2,5-dichlorobiphenyl (34883-39-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; C20H29Cl2N5O2Pd / ethanol / 2.5 h / 78 - 83 °C 2: isopropyl alcohol; sodium hydroxide; palladium 10% on activated carbon / 1 h / 83 °C View Scheme

2,4'-dichlorobiphenyl (34883-43-7) + acetonitrile (75-05-8) → 4-chloro-2'-hydroxybiphenyl (64181-76-6) + N-[4’-chloro-(1,1’-biphenyl)-2-yl]acetamide

Conditions	Yield
With water Photolysis;	A 10% B 90%

2,4'-dichlorobiphenyl (34883-43-7) → 2,4'-Dichloro-biphenyl

Conditions	Yield
In gas Irradiation; study of resonance enhanced two-photon ionization spectra using a time-of-flight mass spectrometer;

2,4'-dichlorobiphenyl (34883-43-7) → biphenyl (92-52-4)

Conditions	Yield
With potassium hydroxide In isopropyl alcohol at 45℃; for 20h; Inert atmosphere;	98 %Chromat.

Upstream product

• 492-17-1 2,4'-diaminobiphenyl 
• 637-87-6 1-Chloro-4-iodobenzene 
• 615-41-8 2-iodochlorobenzene 
• 1204-42-8 2′-chlorobiphenyl-4-amine 
• 16606-02-3 2,4',5-Trichlorobiphenyl 
• 1679-18-1 4-Chlorophenylboronic acid 
• 1193-72-2 1-bromo-2,4-dichlorobenzene 
• 7012-37-5 2,4,4'-Trichlorobiphenyl 
• 694-80-4 2-bromo-1-chlorobenzene 
• 29682-41-5 2,5-dichloroiodobenzene 
• 583-55-1 1-Bromo-2-iodobenzene 
• 14774-78-8 4-chlorophenyl lithium 
• 95-50-1 1,2-dichloro-benzene 
• 138588-58-6 2,4'-dichloro-4-nitro-biphenyl 

Downstream Products

• 92-52-4 biphenyl 

Relevant articles and documents

Pd-Catalysed Suzuki-Miyaura cross-coupling of aryl chlorides at low catalyst loadings in water for the synthesis of industrially important fungicides

The Suzuki-Miyaura coupling reaction of electron-poor aryl chlorides in the synthesis of crop protection-relevant active ingredients in water is disclosed. Optimisation of the reaction conditions allowed running the reaction with 50 ppm of Pd-catalyst loading without an additional organic solvent in the cross-coupling reaction step in short reaction times. The system was optimised for the initial cross-coupling step of the large scale produced fungicides Boscalid, Fluxapyroxad and Bixafen up to 97% yield. It is also shown that the Suzuki-Miyaura reaction can be easily scaled up to 50 g using a simple product separation and purification using environmentally benign solvents in the work-up. To show the usability of this method, it was additionally applied in the three-step synthesis of the desired active ingredients.

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Biaryls were synthesized via a novel visible-light-promoted Gomberg-Bachmann reaction that does not require a photosensitizer or any metal reagents. The formation of an electron donor-acceptor complex between aryl diazonium salts and pyridine allows, under visible-light irradiation, the synthesis of biaryls in moderate-to-high yields.

Significant stabilization of palladium by gold in the bimetallic nanocatalyst leading to an enhanced activity in the hydrodechlorination of aryl chlorides

The stabilization effect of Au towards Pd changed the reactivity of Pd in Au/Pd bimetallic nanoclusters, altering the reaction mechanism from homogeneous to heterogeneous in dechlorination reaction of aryl chlorides. This phenomenon was illustrated by the observed enhancement of the rate of reaction by in situ generated Au-rich bimetallic Au/Pd nanoclusters.