1591-31-7

Basic information

• Product Name: 4-Iodobiphenyl
• Synonyms: MONOIODOBIPHENYL;P-IODODIPHENYL;4-IODOBIPHENYL;4-IODO-1,1'-BIPHENYL;1,1’-Biphenyl,4-iodo-;4-iodo-1’-biphenyl;1-Iodo-4-phenylbenzene;4-Phenyliodobenzene
• CAS NO: 1591-31-7
• Molecular Formula: C₁₂H₉I
• Molecular Weight: 280.1
• EINECS: 216-469-1
• Product Categories: Biphenyl derivatives;pharmacetical;Halides;Phenyls & Phenyl-Het;White to yellow crystalline powder;Phenyls & Phenyl-Het;Aryl;C9 to C12;Halogenated Hydrocarbons
• Mol File: 1591-31-7.mol
• Article Data: 129

Chemical Properties

• Melting Point: 110-114 °C
• Boiling Point: 320°C(lit.)
• Flash Point: 145.8 °C
• Appearance: Off-white/Crystalline Powder
• Density: 1.6696 (rough estimate)
• Vapor Pressure: 0.000517mmHg at 25°C
• Refractive Index: 1.7600 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Slightly soluble in water.
• Sensitive: Light Sensitive
• CAS DataBase Reference: 4-Iodobiphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Iodobiphenyl(1591-31-7)
• EPA Substance Registry System: 4-Iodobiphenyl(1591-31-7)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 22-41-50/53-36/37/38
• Safety Statements: 26-39-60-61-37/39
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 1591-31-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Iodobiphenyl is used as a starting material for the preparation of p-terphenyl derivatives, which are important compounds in the field of organic chemistry. These derivatives have a wide range of applications, including pharmaceuticals, agrochemicals, and advanced materials.
Used in the Suzuki Reaction:
4-Iodobiphenyl is also utilized in the Suzuki reaction, a widely employed cross-coupling reaction in organic chemistry. This reaction allows for the formation of carbon-carbon bonds, which are crucial for the synthesis of complex organic molecules. The use of 4-Iodobiphenyl in the Suzuki reaction contributes to the development of new compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Iodobiphenyl is used as a key intermediate in the synthesis of various therapeutic agents. Its unique chemical properties enable the development of novel drugs with improved efficacy and reduced side effects.
Used in Material Science:
In the field of material science, 4-Iodobiphenyl is used in the development of advanced materials with specific properties, such as optoelectronic materials, polymers, and coatings. Its incorporation into these materials can enhance their performance and expand their potential applications.

Purification Methods

Crystallise 4-iodobiphenyl from EtOH/*C6H6, and dry it in vacuo over P2O5. [Beilstein 5 H 581, 5 I 273, 5 II 486, 5 III 1748, 5 IV 1821.]

InChI:InChI=1/C12H9I/c13-12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H

Synthetic route

biphenyl (92-52-4) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With dicloroiodoisocyanuric acid In acetonitrile at 20℃; for 2.5h; Darkness; regioselective reaction;	99%
With sulfuric acid; iodine; periodic acid; H-β zeolite In water; acetic acid at 20 - 118℃; for 6h; Heating / reflux;	92%
With tetramethylammonium dibromoiodate(I) at 20℃; for 0.333333h;	90%

para-diiodobenzene (624-38-4) + phenylboronic acid (98-80-6) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With potassium phosphate In ethanol; water at 28℃; for 24h; Catalytic behavior; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere; Green chemistry;	99%
With 5%-palladium/activated carbon; sodium carbonate In water at 60℃; for 6h; Reagent/catalyst; Temperature;	95%
With sodium hydroxide In ethanol at 25℃; for 1.5h; Suzuki-Miyaura Coupling; Irradiation; Sealed tube; Green chemistry;	92%
With potassium carbonate In water at 90℃; for 5h; Suzuki Coupling; Green chemistry;	91%
With 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide; tetrabutylammomium bromide; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 24h; Catalytic behavior; Reagent/catalyst; Suzuki Coupling;	80%

4-biphenylboronic acid (5122-94-1) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With sodium nitrite In acetonitrile at 80℃; for 0.5h; Sealed tube;	99%
With N-iodo-succinimide; potassium acetate In acetonitrile at 50℃; for 4h;	97%
With potassium fluoride; iodine In 1,4-dioxane at 80℃; for 1h;	93%
With perfluoroisopropyl iodide; copper; hydroquinone In N,N-dimethyl-formamide at 20℃; for 24h;	88%
With iodine; potassium carbonate In toluene at 70℃; under 750.075 Torr; for 7h; Inert atmosphere;	50.8%

4-iodoxybiphenyl (91493-19-5) + diphenyl acetylene (501-65-5) → 4-iodo-biphenyl (1591-31-7) + benzil (134-81-6)

Conditions	Yield
In nitrobenzene at 170℃; for 5h;	A 98% B 34.5%

4-iodobenzenediazonium tetrafluoroborate (1514-50-7) + phenylboronic acid (98-80-6) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With polystyrene-supported-diiodobis(theophylline)palladium(II) complex In methanol at 25℃; for 3h; Suzuki-Miyaura Coupling; chemoselective reaction;	98%
With 5% Pd/BaCO3 In methanol at 25℃; for 12h;	87%
polystyrene-supported N-heterocyclic carbene-Pd complex In ethanol at 20℃; for 12h; Suzuki-Miyaura cross-coupling;	65%

4-biphenyldiazonium tetrafluoroborate → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With trimethylsilyl iodide; methyl iodide In N,N-dimethyl-formamide for 1h; Ambient temperature;	97%

4-bromo-1,1'-biphenyl (92-66-0) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With copper(l) iodide; Trimethylenediamine; sodium iodide In pentan-1-ol at 130℃; for 22h; aromatic Finkelstein reaction;	96%
Stage #1: 4-bromo-1,1'-biphenyl With Trimethylenediamine; sodium iodide; copper(l) iodide In pentan-1-ol at 130℃; for 22h; Stage #2: With ammonia	96%
With copper(l) iodide; trans-N,N'-dimethylcyclohexane-1,2-diamine; sodium iodide In acetonitrile at 100℃; for 1h; Buchwald's halogen exchange reaction; Inert atmosphere; Microwave irradiation;	96%

para-diiodobenzene (624-38-4) + triethoxyphenylsilane (780-69-8) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With sodium hydroxide In water at 90℃; for 6h; Hiyama Coupling; Green chemistry;	93%
With sodium hydroxide In ethanol at 25℃; for 5h; Hiyama Coupling; Irradiation; Sealed tube; Green chemistry;	88%

tributylphenylstannane (960-16-7) + 4-Iodobenzenediazonium o-benzenedisulfonimide → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
palladium diacetate In tetrahydrofuran at 20℃; for 0.5h; Stille reaction;	90%

potassium biphenyl-4-yltrifluoroborate → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With 2-iodo-propane; dimethylglyoxal In water at 23℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; Green chemistry;	90%
With acetic acid; lithium iodide In dimethyl sulfoxide at 100℃; for 8h; Schlenk technique;	71%
With tetra-(n-butyl)ammonium iodide; copper(II) bis(trifluoromethanesulfonate) In acetonitrile at 25℃; for 16h; Sealed tube;	68%
With caesium tribromide In water; N,N-dimethyl-formamide at 80℃; for 6h; chemoselective reaction;	45%

triethoxyphenylsilane (780-69-8) + 4-iodophenylhydrazine (13116-27-3) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride In tetrahydrofuran at 50℃; for 3h; Hiyama Coupling;	89%

(4-iodophenyl)(phenyl)iodonium trifluoromethanesulfonate (144930-55-2) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With palladium diacetate at 50℃; for 0.166667h; Microwave irradiation;	89%

4-iodobenzenediazonium tetrafluoroborate (1514-50-7) + 8-phenylhexahydro-1,3,2-oxazaborolo[2,3-b]-1,3,2-oxazaborol-4-ium-8-uide → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With 1% Pd/C In methanol at 50℃; for 0.5h; Suzuki-Miyaura reaction; Inert atmosphere;	88%

potassium (4-iodophenyl)trifluoroborate + phenylhydrazine hydrochloride (59-88-1) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With diamminedichloropalladium(II); copper(II) choride dihydrate; potassium carbonate In water at 25℃; for 12h; Suzuki Coupling; Green chemistry;	88%

biphenyl (92-52-4) → 4-iodo-biphenyl (1591-31-7) + 4,4'-diiodobiphenyl (3001-15-8)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; iodine In ethyl acetate at 60℃; for 16h;	A 12% B 87%
With [bis(acetoxy)iodo]benzene; iodine In ethyl acetate at 60℃; for 16h; Iodination;	A 12% B 87%
With poly; iodine In ethyl acetate at 60℃; for 16h;	A 43% B 2%

triphenylindium (3958-47-2) + 4-Iodobenzenediazonium o-benzenedisulfonimide → biphenyl (92-52-4) + (E)-1-(4-iodophenyl)-2-phenyldiazene (21650-47-5) + 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 20℃; for 0.0833333h;	A 6% B 3% C 85%

4-iodobenzenesulfonyl hydrazide (2751-27-1) + phenylboronic acid (98-80-6) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tert-butyl methyl ether at 60℃; for 6h; Suzuki Coupling;	84%

potassium (4-iodophenyl)trifluoroborate + benzenesulfonyl chloride (98-09-9) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; potassium acetate; palladium dichloride In dimethyl sulfoxide at 60℃; for 6h; Suzuki-Miyaura Coupling;	83%

4-Aminobiphenyl (92-67-1) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
Stage #1: 4-phenylalanine With sulfuric acid; silica gel; sodium nitrite at 20℃; grinding; Neat (no solvent); Stage #2: With water at 20℃; grinding; Neat (no solvent); Stage #3: With potassium iodide at 20℃; for 0.166667h; Sandmeyer reaction; grinding; Neat (no solvent);	82%
With toluene-4-sulfonic acid; potassium iodide; sodium nitrite In acetonitrile at 20℃; for 0.5h;	80%
Stage #1: 4-phenylalanine With nicotinic acid sulfate; sodium nitrite In water at 20℃; for 0.333333h; Grinding; Stage #2: With sodium iodide In water at 20℃;	80%

4-biphenylboronic acid (5122-94-1) + phenylacetonitrile (140-29-4) → 4-cyano-1,1'-biphenyl (2920-38-9) + 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With tert.-butylhydroperoxide; copper(l) iodide In N,N-dimethyl acetamide; water at 130℃; for 16h; Reagent/catalyst; Solvent; Temperature; Time;	A 82% B 13%
With tert.-butylhydroperoxide; copper(l) iodide In N,N-dimethyl acetamide; water at 130℃; for 4h; Concentration; Time;	A 29% B 61%

4-iodophenylboronic acid (5122-99-6) + benzenediazonium tetrafluoroborate (369-57-3) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With chloro[tris(para-trifluoromethylphenyl)phosphine]gold (I) In methanol at 20℃; Irradiation; Inert atmosphere;	81%

potassium biphenyl-4-yltriolborate → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With chloroamine-T; sodium iodide In tetrahydrofuran; water at 20℃; for 0.333333h;	80%

4-tolyl iodide (624-31-7) + benzene (71-43-2) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With dipotassium peroxodisulfate; silver nitrate In acetonitrile at 120℃; for 20h; Sealed tube; Schlenk technique; Inert atmosphere;	80%

[1,1'-biphenyl-4-yl]triethylsilane (18057-71-1) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With N-iodo-succinimide In acetonitrile at 20℃; for 24h; Inert atmosphere;	79%

formic acid (64-18-6) + 4-Phenylbenzaldehyde (3218-36-8) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 80℃; for 3h; Catalytic behavior; Schlenk technique; Green chemistry;	78%

para-diiodobenzene (624-38-4) + phenylboronic acid (98-80-6) → [1,1';4',1'']terphenyl (92-94-4) + 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With potassium carbonate; copper-palladium In N,N-dimethyl-formamide at 110℃; for 24h; Suzuki cross-coupling;	A 75% B 25%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; methanol at 95℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere;	A < 10 %Spectr. B 64%

[1,1'-biphenyl]-4-diazonium trifluoromethanesulfonate → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With potassium iodide In water at 20℃;	75%

para-diiodobenzene (624-38-4) + benzene (71-43-2) → [1,1';4',1'']terphenyl (92-94-4) + 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
With potassium tert-butylate; N,N`-dimethylethylenediamine at 80℃; sealed tube; Inert atmosphere;	A 74% B 8%
With 1-(2-hydroxyethyl)piperazine; potassium tert-butylate at 100℃; for 24h; Sealed tube; Inert atmosphere;	A 69% B 7%
With potassium tert-butylate; vasicine at 20 - 110℃; for 48h; Schlenk technique; Inert atmosphere;	A 55% B 29%
With potassium tert-butylate for 6h; Inert atmosphere; Heating; High pressure;	A 21% B 30%

4-iodoxybiphenyl (91493-19-5) → 4-iodo-biphenyl (1591-31-7)

Conditions	Yield
In nitrobenzene at 170℃; for 5h;	72%

4-iodo-biphenyl (1591-31-7) → biphenyl (92-52-4)

Conditions	Yield
With LiCrH4*2LiCl*2THF In tetrahydrofuran at 25℃; for 12h;	100%
With potassium tert-butylate; benzyl alcohol In N,N-dimethyl-formamide at 90℃; for 2h; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere;	98%
With potassium tert-butylate; benzaldehyde In N,N-dimethyl-formamide at 90℃; for 2h; Schlenk technique; Inert atmosphere;	96%

4-iodo-biphenyl (1591-31-7) + C18H17CuF4N2O → (2-tert-butoxy-1,1,2,2-tetrafluoroethyl)-4-phenylbenzene

Conditions	Yield
In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;	100%

4-iodo-biphenyl (1591-31-7) + ethylenediamine (107-15-3) → N1-([1,1'-biphenyl]-4-yl)ethane-1,2-diamine

Conditions	Yield
With copper(l) chloride; potassium hydroxide at 50℃; for 3h;	100%
With copper(l) chloride; potassium hydroxide at 50℃; for 3h; Ullmann Condensation; Inert atmosphere;	100%

ethanol (64-17-5) + carbon monoxide (201230-82-2) + 4-iodo-biphenyl (1591-31-7) → ethyl 4-phenylbenzoate (6301-56-0)

Conditions	Yield
With triethylamine; dichloro bis(acetonitrile) palladium(II) at 70℃; for 24h;	99%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; [(Ph2CH=NOH)PdCl]2 In benzene at 120℃; for 3h;	90%

4-iodo-biphenyl (1591-31-7) + phenylboronic acid (98-80-6) → [1,1';4',1'']terphenyl (92-94-4)

Conditions	Yield
With caesium carbonate In water; N,N-dimethyl-formamide at 20℃; for 50h; Suzuki Coupling; Inert atmosphere;	99%
With sodium acetate In water; N,N-dimethyl-formamide at 80℃; for 1h; Suzuki coupling;	90%
With C33H48Cl2N4O9Pd; oxygen; potassium carbonate In water at 80℃; Suzuki-Miyaura Coupling;	90%

4-iodo-biphenyl (1591-31-7) → 4-biphenylthiol (19813-90-2)

Conditions	Yield
With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; dimethyl sulfoxide at 90℃; for 20h; Inert atmosphere;	99%
With sodiumsulfide nonahydrate; ethane-1,2-dithiol; copper(II) oxide In dimethyl sulfoxide at 120℃; for 20h; Inert atmosphere; Sealed tube;	97%
With sodiumsulfide nonahydrate; copper; ethane-1,2-dithiol In dimethyl sulfoxide at 100℃; for 20h; Inert atmosphere; Green chemistry;	97%
Stage #1: 4-iodo-biphenyl With copper(l) iodide; potassium carbonate; sulfur In N,N-dimethyl-formamide at 90℃; for 12h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In N,N-dimethyl-formamide at 40℃; Inert atmosphere; Cooling with ice;	84%
With copper(l) iodide; thiourea; L-proline; sodium t-butanolate In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere;	83%

4-iodo-biphenyl (1591-31-7) → 4-Phenylphenol (92-69-3)

Conditions	Yield
With water; ethylene glycol; potassium hydroxide; copper dichloride In dimethyl sulfoxide at 120℃; for 24h; Reagent/catalyst; Temperature; Inert atmosphere;	99%
Stage #1: 4-iodo-biphenyl With copper(l) iodide; cesiumhydroxide monohydrate; 1,3-diphenylpropanedione In water; dimethyl sulfoxide at 130℃; for 24h; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane; water; dimethyl sulfoxide at 20℃; Inert atmosphere; chemoselective reaction;	95%
Stage #1: 4-iodo-biphenyl With copper(l) iodide; 8-Hydroxyquinoline-N-oxide In dimethyl sulfoxide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With cesiumhydroxide monohydrate In water; dimethyl sulfoxide at 100℃; for 36h; Inert atmosphere;	93%

4-iodo-biphenyl (1591-31-7) + (1,10-phenanthroline)(perfluoropropyl)copper(l) → 4-(perfluoropropyl)-1,1′-biphenyl (87415-24-5)

Conditions	Yield
In N,N-dimethyl-formamide at 50℃; for 18h; Product distribution / selectivity; Inert atmosphere;	99%

4-iodo-biphenyl (1591-31-7) + tetramethylammonium trifluoromethylselenate(0) (75264-92-5) → 4-[(trifluoromethyl)selanyl]-1,1′-biphenyl (1447204-44-5)

Conditions	Yield
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0) In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	99%
With C54H76I2N4Ni2 In benzene at 45℃; Inert atmosphere; Glovebox; chemoselective reaction;	99%
With palladium(l) tri-tert-butylphosphine iodide dimer In toluene at 40℃; for 24h; Glovebox; Inert atmosphere;	96%

ethene (74-85-1) + 4-iodo-biphenyl (1591-31-7) → p-vinylbiphenyl (2350-89-2)

Conditions	Yield
With tri-tert-butylphosphonium tetrafluoroborate; N-Methyldicyclohexylamine; palladium diacetate In methanol; toluene at 120℃; under 11251.1 Torr; for 0.333333h; Wacker Oxidation; Flow reactor;	99%
With N-Methyldicyclohexylamine; palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate In methanol; toluene at 120℃; under 11251.1 Torr; Flow reactor;	99%

4-iodo-biphenyl (1591-31-7) + 1-cyclopentyl-2,4,6-triphenylpyridin-1-ium tetrafluoroborate salt → 4-cyclopentyl-1,1'-biphenyl

Conditions	Yield
With [2,2]bipyridinyl; manganese; (1,2-dimethoxyethane)dichloronickel(II) In N,N-dimethyl acetamide at 20℃;	99%

4-iodo-biphenyl (1591-31-7) + trifluoromethyl-(3-chlorophenyl) bis(carbomethoxy)methylide → 1-phenyl-4-(trifluoromethyl)benzene (398-36-7)

Conditions	Yield
With copper In N,N-dimethyl-formamide at 60℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;	99%

p-nitrobenzene iodide (636-98-6) + 4-iodo-biphenyl (1591-31-7) + 1,4-Phenyldiboronic acid (4612-26-4) → 4-nitro-1,1':4',1'':4'',1'''-quaterphenyl (25627-14-9)

Conditions	Yield
Stage #1: p-nitrobenzene iodide; 1,4-Phenyldiboronic acid With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; water; toluene Suzuki cross-coupling; Stage #2: 4-iodo-biphenyl With tetrakis(triphenylphosphine) palladium(0) In methanol; water; toluene for 32h; Reflux;	98%

4-iodo-biphenyl (1591-31-7) + phenylacetylene (536-74-3) → 4-(phenylethynyl)-1,1'-biphenyl (15784-39-1)

Conditions	Yield
With copper(l) iodide; triethylamine; triphenylphosphine In water at 60℃; for 24h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere;	98%
With palladium diacetate; potassium carbonate In ethanol at 80℃; for 24h;	88%
With copper(l) iodide; tetrakis(triphenylphosphine)palladium dichloride; triethylamine In tetrahydrofuran at 80℃; for 12h; Inert atmosphere;	84%

4-iodo-biphenyl (1591-31-7) + [1-methoxyprop-1-enyloxy]trimethylsilane (34880-70-1) → C16H16O2

Conditions	Yield
With (R)-1-(bis(4-methoxy-3,5-dimethylphenyl)phosphano)-2-((S)-1-(dicyclohexylphosphano)ethyl)ferrocene; palladium diacetate; thallium(I) acetate In toluene at 70℃; for 6h; optical yield given as %ee; enantioselective reaction;	98%

4-iodo-biphenyl (1591-31-7) + p-Chlorothiophenol (106-54-7) → biphenyl-4-yl(4-chlorophenyl)sulfane (1361124-61-9)

Conditions	Yield
With tetra(n-butyl)ammonium hydroxide In water at 50℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;	98%

pyrrole (109-97-7) + 4-iodo-biphenyl (1591-31-7) → 1-([1,1'-biphenyl]-4-yl)-1H-pyrrole

Conditions	Yield
With 4.5Cu(2+)*4.5Ni(2+)*9C16H12N2*6C2O4(2-)*6H2O*P2W18O62(6-); sodium hydroxide In dimethyl sulfoxide at 120℃; for 12h;	98%
With MOF-199; sodium hydroxide In dimethyl sulfoxide at 120℃; for 12h; Sealed tube;	95%
With copper(ll) sulfate pentahydrate; sodium hydroxide In dimethyl sulfoxide at 110℃; for 12h; Sealed tube;	86%
With copper(II) acetate monohydrate; caesium carbonate In N,N-dimethyl-formamide at 20 - 110℃; for 24h; Inert atmosphere; Schlenk technique;	82%

tert-butylisonitrile (119072-55-8, 7188-38-7) + 4-iodo-biphenyl (1591-31-7) → 4-cyano-1,1'-biphenyl (2920-38-9)

Conditions	Yield
With copper (II) trifluoroacetate hydrate; palladium diacetate In dimethyl sulfoxide at 130℃; for 12h; Reagent/catalyst; Solvent; Sealed tube; Inert atmosphere;	98%

4-iodo-biphenyl (1591-31-7) + (N-heterocyclic carbene)Ag(SCF2H) → [1,1'-biphenyl]-4-yl(difluoromethyl)thioether

Conditions	Yield
With bis[2-(diphenylphosphino)phenyl] ether; bis(dibenzylideneacetone)-palladium(0) In toluene at 50℃; for 12h;	98%

tert-Butyl acrylate (1663-39-4) + 4-iodo-biphenyl (1591-31-7) → tert-butyl(E)-3-([1,1′-biphenyl]-4-yl)acrylate (910574-67-3)

Conditions	Yield
With di-μ-iodobis(tri-t-butylphosphino)dipalladium(l); N-ethyl-N,N-diisopropylamine In toluene at 100℃; for 15h; Heck Reaction; Inert atmosphere; Sealed tube; Glovebox;	98%

ethyl bromofluoroacetate (401-55-8) + 4-iodo-biphenyl (1591-31-7) → ethyl 2-(biphenyl-4-yl)-2-fluoroacetate (1234908-38-3)

Conditions	Yield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; tetrabutylammomium bromide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; zinc In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;	98%

4-iodo-biphenyl (1591-31-7) + trimethylsilylacetylene (1066-54-2) → ([1,1'-biphenyl]-4-ylethynyl)trimethylsilane (75867-42-4)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 1h;	97%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In triethylamine for 4h; Ambient temperature;	86%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 20℃; for 24h; Sonogashira Cross-Coupling; Schlenk technique; Inert atmosphere;	86%

4-iodo-biphenyl (1591-31-7) + tetramethylammonium trifluoromethanethiolate → [1,1′-biphenyl]-4-yl(trifluoromethyl)sulfane (177551-63-2)

Conditions	Yield
With palladium(l) tri-tert-butylphosphine iodide dimer In toluene at 80℃;	97%
With bis(1,5-cyclooctadiene)nickel(0); 4,4'-Dimethoxy-2,2'-bipyridin In tetrahydrofuran at 20℃; for 22h; Inert atmosphere;	92%

1,3-Benzothiazole (95-16-9) + 4-iodo-biphenyl (1591-31-7) → 2-([1,1'-biphenyl]-4-ylthio)benzenamine (403517-20-4)

Conditions	Yield
With tetra(n-butyl)ammonium hydroxide; water; copper(l) chloride at 50℃; for 12h; Inert atmosphere;	97%

Upstream product

• 3001-15-8 4,4'-diiodobiphenyl 
• 591-50-4 iodobenzene 
• 98-95-3 nitrobenzene 
• 94-36-0 dibenzoyl peroxide 
• 66003-76-7 Diphenyliodonium triflate 
• 75-05-8 acetonitrile 
• 58109-40-3 diphenyliodonium hexafluorophosphate 
• 177490-72-1 (4-Bromo-phenyl)-chloromethoxymethyl-dimethyl-silane 
• 98-80-6 phenylboronic acid 
• 92-52-4 biphenyl 
• 624-38-4 para-diiodobenzene 
• 106-37-6 1.4-dibromobenzene 
• 96379-66-7 (cyclo-C₆H₁₁)3SnC₆H₄-p-C₆H₅ 
• 7553-56-2 iodine 

Downstream Products

• 122215-84-3 N-([1,1'-biphenyl]-4-yl)-N-phenyl-[1,1'-biphenyl]-4-amine 
• 1165-58-8 o,p-quaterphenyl 
• 5080-61-5 4,4?-diphenyl-o-quaterphenyl 
• 135-70-6 p-quaterphenyl 
• 97388-37-9 4,4'''-dinitro-o-quaterphenyl 
• 78487-04-4 2-(4-biphenylyl)-4'-nitrobiphenyl 
• 2436-96-6 1-nitro-2-(2-nitrophenyl)benzene 
• 10355-51-8 2-nitro-[1,1'; 4',1'']terphenyl 
• 73178-11-7 1-[hydroxy(tosyloxy)iodo]-4-phenylbenzene 
• 84-15-1 o-terphenyl 
• 7104-67-8 2,2'''-diphenyl-p-quaterphenyl 
• 77036-62-5 2-phenyl-p-quaterphenyl 
• 92-52-4 biphenyl 
• 78626-79-6 3-(4-biphenylyl)-3'-nitrobiphenyl 

Relevant articles and documents

Organocatalysis in cross-coupling: DMEDA-catalyzed direct C-H arylation of unactivated benzene

A striking breakthrough to the frame of traditional cross-couplings/C-H functionalizations using an organocatalyst remains unprecedented. We uncovered a conceptually different approach toward the biaryl syntheses by using DMEDA as the catalyst to promote the direct C-H arylation of unactivated benzene in the presence of potassium tert-butoxide. The arylation of unactivated benzene with aryl iodides, or aryl bromides and even chlorides under the assistance of an iodo-group, could simply take place at 80 °C. The new methodology presumably involves an aryl radical anion as an intermediate. This finding offers an option toward establishing a new horizon for direct C-H/cross-coupling reactions.

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The Suzuki-Miyaura cross-coupling of arenediazonium salts with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene-Pd complex catalyst has been achieved for the first time. The reaction was performed at room temperature under aerobic conditions to give biaryls in good to excellent yields in the absence of a base. The supported catalyst could be reused several times and still retained its high activity. Georg Thieme Verlag Stuttgart.

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Halogen Exchange Between Aryl Grignarg Reagents and Aryl Halides in the Presence of Nickel(II) Chloride

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Biaryl Coupling of Aryldiazonium Salts and Arylboronic Acids Catalysed by Gold

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