2113-57-7

Basic information

• Product Name: 3-Bromobiphenyl
• Synonyms: 3-BROMODIPHENYL;3-BROMOBIPHENYL;BROMOBIPHENYL(3-);PBB NO 2;1,1’-(biphenyl,3-bromo-;1,1’-biphenyl,3-bromo-(3-bromobiphenyl);3-Bromo-1,1'-biphenyl;3-bromo-1’-biphenyl
• CAS NO: 2113-57-7
• Molecular Formula: C₁₂H₉Br
• Molecular Weight: 233.1
• EINECS: 218-304-9
• Product Categories: Biphenyl derivatives;Biphenyl & Diphenyl ether;Aryl;C9 to C12;Halogenated Hydrocarbons
• Mol File: 2113-57-7.mol
• Article Data: 65

Chemical Properties

• Melting Point: 93-94 °C
• Boiling Point: 300 °C
• Flash Point: 110 °C
• Appearance: Light yellow to gray-beige/Powder
• Density: 1.398 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00205mmHg at 25°C
• Refractive Index: 1.637-1.641
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Insoluble
• Merck: 14,4188
• BRN: 2043191
• CAS DataBase Reference: 3-Bromobiphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromobiphenyl(2113-57-7)
• EPA Substance Registry System: 3-Bromobiphenyl(2113-57-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36
• WGK Germany: 3
• RTECS: DV1750000
• TSCA: Yes
• Hazardous Substances Data: 2113-57-7(Hazardous Substances Data)

Usage

Description

3-Bromobiphenyl is an important industrial raw material, but also a very widely used organic synthesis intermediates, it is widely used in pharmaceutical, liquid crystal industry and other fields. In recent years, the export volume of 3-Bromobiphenyl in our country is increasing day by day, the main export object is some liquid crystal display production enterprises in Japan and South Korea.

synthesis

Add 1-bromo-3-iodobenzene (4.67 g, 16.5mmol), phenylboronic acid (1.83 g, 15.0 mmol), Pd (OAc)2 (101 mg, 0.450 mmol), PPh3 (239 mg, 0.911 mmol), and K2CO3 (6.23 g, 45.1 mmol) to a 200 mL twonecked round-bottom flask. Add toluene (40 mL) and water (40 mL) via syringe and reflux the mixture (bath temp. 100°C) for 24 h. Extract the resulting mixture with ethyl acetate (30 mL x 3). Dry the combined organic layer over Na2SO4 and concentrate in vacuo. Purify the residue to silica gel column chromatography (eluent:hexane).

Chemical Properties

Colorless to pale yellow liquid

Uses

3-Bromobiphenyl is utilized as an electrochemical immunosensor based on poly(dopamine) coated gold nanocluster for brominated flame retardants.

Synthesis Reference(s)

The Journal of Organic Chemistry, 41, p. 24, 1976 DOI: 10.1021/jo00863a005

General Description

Clear yellow viscous liquid. Insoluble in water.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

3-Bromobiphenyl may be sensitive to light. 3-Bromobiphenyl may react with oxidizing materials.

Fire Hazard

Flash point data for 3-Bromobiphenyl are not available. 3-Bromobiphenyl is probably combustible.

InChI:InChI=1/C12H9Br/c13-12-8-4-7-11(9-12)10-5-2-1-3-6-10/h1-9H

Synthetic route

1-Bromo-3-iodobenzene (591-18-4) + phenylboronic acid (98-80-6) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With palladium diacetate; potassium carbonate; triphenylphosphine In water; toluene at 100℃; for 24h;	98%
With barium dihydroxide; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water for 6h; Suzuki coupling; Heating;	92%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water for 8h; Inert atmosphere; Reflux;	80%

1,3-dibromobenzene (108-36-1) + phenylboronic acid (98-80-6) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With C27H23ClNO3PPd; potassium carbonate In ethanol; water at 50℃; for 7h; Temperature; Suzuki-Miyaura Coupling; Schlenk technique;	94%
With palladium diacetate In ethanol at 20℃; for 0.25h; Suzuki-Miyaura Coupling; chemoselective reaction;	86%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 90℃; for 3h;	70%

(3-bromophenyl)boronic acid (89598-96-9) + benzene (71-43-2) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
Stage #1: benzene With potassium permanganate; acetic acid Microwave irradiation; Stage #2: (3-bromophenyl)boronic acid for 0.5h; Microwave irradiation;	91%
With potassium permanganate; acetic acid Heating;	90%
With manganese triacetate for 0.5h; Heating;	89%
With iron(III) trifluoromethanesulfonate; di-tert-butyl peroxide; 4,7-bis[4-(trifluoromethyl)phenyl]-1,10-phenanthroline at 80℃; for 24h;	76%
With NH-pyrazole; potassium phosphate; iron(III) sulphate heptahydrate; 1,4,7,10-tetraazacyclododecan at 80℃; for 48h;	55%

3-bromophenylhydrazine hydrochloride (27246-81-7) + benzene (71-43-2) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With potassium permanganate; acetic acid Heating;	90%
With manganese triacetate Heating;	73%

3-bromophenyl trifluoromethanesulfonate (66107-31-1) + phenylzinc(II) bromide (38111-44-3) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
bis(diphenylphosphino)propanepalladium(II) dichloride In tetrahydrofuran at 60℃; for 11h; Negishi cross-coupling reaction;	90%

3-bromobenzene-1-diazonium tetrafluoroborate + 8-phenylhexahydro-1,3,2-oxazaborolo[2,3-b]-1,3,2-oxazaborol-4-ium-8-uide → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With 1% Pd/C In methanol at 50℃; for 0.5h; Suzuki-Miyaura reaction; Inert atmosphere;	90%

bis-(3-bromo-benzoyl)-peroxide (1829-88-5) + benzene (71-43-2) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
at 100℃; for 12h; Sealed tube;	89%
With meta-dinitrobenzene

bromobenzene (108-86-1) + 1-Bromo-3-iodobenzene (591-18-4) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
Stage #1: bromobenzene; 1-Bromo-3-iodobenzene With magnesium In tetrahydrofuran for 1h; Inert atmosphere; Reflux; Green chemistry; Stage #2: In tetrahydrofuran at 50 - 85℃; for 8h; Green chemistry;	84.69%

m-bromobenzoic acid (585-76-2) + benzene (71-43-2) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With diethyl bromomethylmalonate; [4,4′-di-tert-butyl-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C}iridium(III) hexafluorophosphate; caesium carbonate at 80℃; for 22h; Irradiation;	82%
With dipotassium peroxodisulfate; silver nitrate In acetonitrile at 120℃; for 24h; Glovebox; Schlenk technique; Sealed tube; Inert atmosphere;	55%

3-bromobenzylamine (10269-01-9) + benzene (71-43-2) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With dipotassium peroxodisulfate; silver nitrate In acetonitrile at 120℃; for 10h; Inert atmosphere; Sealed tube; Green chemistry;	82%

1-Bromo-3-iodobenzene (591-18-4) + chlorobenzene (108-90-7) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
Stage #1: 1-Bromo-3-iodobenzene; chlorobenzene With magnesium In tetrahydrofuran for 1h; Inert atmosphere; Reflux; Green chemistry; Stage #2: In tetrahydrofuran; water; toluene at 50 - 85℃; for 8h; Inert atmosphere; Reflux; Green chemistry;	81.37%

iodobenzene (591-50-4) + 1-Bromo-3-iodobenzene (591-18-4) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
Stage #1: iodobenzene; 1-Bromo-3-iodobenzene With magnesium In tetrahydrofuran for 1h; Inert atmosphere; Reflux; Green chemistry; Stage #2: In tetrahydrofuran at 50 - 85℃; for 8h; Green chemistry;	80.61%

meta-bromotoluene (591-17-3) + benzene (71-43-2) → 3-bromobiphenyl (2113-57-7)

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

2-Phenyl-1,3,2-dioxaborinane (4406-77-3) + 1-Bromo-3-iodobenzene (591-18-4) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With potassium phosphate In 1,4-dioxane at 115℃; for 30h; Suzuki-Miyaura Coupling; Inert atmosphere;	77%

1,3-dibromobenzene (108-36-1) + C19H16NS(1+)*F6P(1-) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
Stage #1: 1,3-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: C19H16NS(1+)*F6P(1-) In tetrahydrofuran; hexane at -78 - 23℃; for 1.5h; Inert atmosphere;	71%

1-Bromo-3-iodobenzene (591-18-4) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
	70%

1,3-dibromobenzene (108-36-1) + phenylboronic acid (98-80-6) → 1,3-diphenylbenzene (92-06-8) + 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With disodium[(N,N’-bis(2-hydroxy-5-sulfonatobenzyl)-1,2-diphenyl-1,2-diaminoethano)palladate(II)]; caesium carbonate In water at 80℃; for 1h; Suzuki-Miyaura Coupling;	A 68% B 24%
With potassium phosphate; {1,3-di(NHP(piperidinyl)2)C6H3}PdCl In toluene at 100℃; for 0.0833333h; Suzuki reaction;	A 76 % Chromat. B 24 % Chromat.
With potassium carbonate; [{P(NC4H8NMe)3}2PdCl2] In methanol at 20℃; for 2h; Suzuki-Miyaura coupling reaction;

1-Bromo-3-iodobenzene (591-18-4) + benzene (71-43-2) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With 1,10-Phenanthroline; potassium 2-methylbutan-2-olate at 80℃; for 24h; Inert atmosphere;	65%

3-bromophenyl trifluoromethanesulfonate (66107-31-1) + phenylmagnesium bromide → 1,3-diphenylbenzene (92-06-8) + 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With lithium bromide; bis(diphenylphosphino)propanepalladium(II) dichloride In diethyl ether at 0℃; for 2h; Kumada cross-coupling reaction;	A 20% B 60%

(3-Bromophenyl)methanol (15852-73-0) + benzene (71-43-2) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With tert.-butylhydroperoxide; 1,2-Dinitrobenzene In decane at 150℃; for 12h; Inert atmosphere; Sealed tube;	59%

bromobenzene (108-86-1) + phenol (108-95-2) → 2-Bromobiphenyl (2052-07-5) + 4-bromo-1,1'-biphenyl (92-66-0) + 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With tert.-butylhydroperoxide; iodine at 289.9℃; for 0.0272222h; Product distribution;	A 22.7% B 18.4% C 58.9%

3-bromostyrene (2039-86-3) + benzene (71-43-2) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With tert.-butylhydroperoxide; 1,2-Dinitrobenzene In decane at 150℃; for 12h; Inert atmosphere; Sealed tube;	56%

1-Bromo-3-iodobenzene (591-18-4) + benzene (71-43-2) → 1,3-diphenylbenzene (92-06-8) + 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With 1-(2-hydroxyethyl)piperazine; potassium tert-butylate at 100℃; for 24h; Sealed tube; Inert atmosphere;	A 50% B 25%

3-bromobenzene-1-diazonium tetrafluoroborate + tributylphenylstannane (960-16-7) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With (triphenylphosphine)gold(I) chloride In acetonitrile at 20℃; for 16h; Inert atmosphere;	44%

1-(3-bromophenyl)cyclohexanol (19920-85-5) → 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With copper; Selectfluor In acetonitrile at 80℃; for 24h; chemoselective reaction;	41%

1,3-dibromobenzene (108-36-1) + benzene (71-43-2) → 1,3-diphenylbenzene (92-06-8) + 3-bromobiphenyl (2113-57-7)

Conditions	Yield
With potassium tert-butylate; vasicine at 20 - 110℃; for 72h; Schlenk technique; Inert atmosphere;	A 24% B 19%

bromobenzene (108-86-1) + N-sulphinylphenylhydrazine (17420-03-0) → 2-Bromobiphenyl (2052-07-5) + 4-bromo-1,1'-biphenyl (92-66-0) + 3-bromobiphenyl (2113-57-7) + diphenyldisulfane (882-33-7) + S, SO2

Conditions	Yield
at 135℃; for 72h; Further byproducts given;	A 20.9% B 6.9% C 12.7% D 1.1% E n/a
at 135℃; for 72h; Further byproducts given;	A 19.5% B 8.1% C 12.9% D 1.1% E n/a

bromobenzene (108-86-1) + N-sulphinylphenylhydrazine (17420-03-0) → S-Phenyl benzenethiosulfonate (1212-08-4) + 2-Bromobiphenyl (2052-07-5) + 4-bromo-1,1'-biphenyl (92-66-0) + 3-bromobiphenyl (2113-57-7) + S, SO2

Conditions	Yield
at 135℃; for 72h; Further byproducts given;	A 0.2% B 20.9% C 6.9% D 12.7% E n/a

bromobenzene (108-86-1) + N-sulphinylphenylhydrazine (17420-03-0) → 2-Bromobiphenyl (2052-07-5) + 4-bromo-1,1'-biphenyl (92-66-0) + diphenyl sulfide (139-66-2) + 3-bromobiphenyl (2113-57-7) + S, SO2

Conditions	Yield
at 135℃; for 72h; Further byproducts given;	A 20.9% B 6.9% C 0.8% D 12.7% E n/a

pyridine (110-86-1) + bromobenzene (108-86-1) + dibenzoyl peroxide (94-36-0) → 2-phenylpyridine (1008-89-5) + 2-Bromobiphenyl (2052-07-5) + 4-bromo-1,1'-biphenyl (92-66-0) + 3-bromobiphenyl (2113-57-7)

Conditions	Yield
at 70℃;

2-ethylhexyl 3-sulfanylpropanoate (50448-95-8) + 3-bromobiphenyl (2113-57-7) → 2-ethylhexyl 3-([1,1'-biphenyl]-3-ylthio)propanoate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 110℃; for 18h; Inert atmosphere;	100%

(3-bromophenyl)(pyridin-2-yl)methanone (206357-82-6) + 3-bromobiphenyl (2113-57-7) → [1,1‘-biphenyl]-2-yl(3-bromophenyl)(pyridin-2-yl)methanol

Conditions	Yield
Stage #1: 3-bromobiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Stage #2: (3-bromophenyl)(pyridin-2-yl)methanone In tetrahydrofuran; hexane at -78 - 20℃; for 16h;	99%

3-Ethoxycyclohex-2-en-1-one (5323-87-5) + 3-bromobiphenyl (2113-57-7) → 4''-ethoxy-5'',6''-dihydro-2''H-[1,1':3',1'':1'',1''':3''',1''''-quinquephenyl]-2''-one

Conditions	Yield
With tris(1-adamantyl)phosphine; palladium diacetate; lithium hexamethyldisilazane In toluene at 70℃; for 0.55h; Inert atmosphere;	99%

3-bromobiphenyl (2113-57-7) + m-nitrobenzene boronic acid (13331-27-6) → 1‐(3‐nitrophenyl)‐3‐phenylbenzene (78626-53-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane; water for 16h; Suzuki Coupling; Inert atmosphere; Reflux;	98%

2,5-dichloro-2,5-dimethyl hexane (6223-78-5) + 3-bromobiphenyl (2113-57-7) → 6-(3-bromophenyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene (288259-76-7)

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-ethane at 0℃; Condensation;	97%

3-bromobiphenyl (2113-57-7) + 3-methoxyphenylboronic acid (10365-98-7) → 3-methoxy-[1,1';3',1'']terphenyl (156941-81-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene for 3h; Suzuki coupling; Heating;	97%

3-bromobiphenyl (2113-57-7) + phenylmethanethiol (100-53-8) → [1,1'-biphenyl]-3-yl(benzyl)sulfane (94306-39-5)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; Inert atmosphere; Sealed tube;	97%
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; Inert atmosphere; Sealed tube;	97%

3-bromobiphenyl (2113-57-7) + 9-(4-biphenylyl)-3,3'-bicarbazole (1346669-48-4) → 9-([1,1'-biphenyl]-3-yl)-9’-([1,1'-biphenyl]-4-yl)-9H,9'H-3,3'-bicarbazole

Conditions	Yield
Stage #1: 3-bromobiphenyl; 9-(4-biphenylyl)-3,3'-bicarbazole With potassium tert-butylate In toluene for 0.5h; Inert atmosphere; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; XPhos In toluene for 10h; Reflux;	97%

3-bromobiphenyl (2113-57-7) + aniline (62-53-3) → N-phenyl-[1,1′-biphenyl]-3-amine (198275-79-5)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene for 2h; Inert atmosphere; Reflux;	95%
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 100℃; for 24h;	85%

3-bromobiphenyl (2113-57-7) + benzamide (55-21-0) → N-biphenyl-3-yl-benzamide

Conditions	Yield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In toluene for 120h; Reflux;	95%

2,2,2-trifluoroethanol (75-89-8) + 3-bromobiphenyl (2113-57-7) → 3-(2,2,2-trifluoroethoxy)-1,1'-biphenyl

Conditions	Yield
With C43H59NO2PPd(1+)*CH3O3S(1-); caesium carbonate In toluene at 80℃; Schlenk technique; Inert atmosphere;	95%

3-bromobiphenyl (2113-57-7) + 2-(4-aminophenyl)-10H-chromeno[3,2-b]pyridin-10-one → 2(4-([1,1'-biphenyl]-3-ylamino)phenyl)-10H-chromeno[3,2-b]pyridin-10-one

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 12h;	95%

(R)-2,2'-(2,2'-bis(methoxymethoxy)-1,1'-binaphthyl-3,3'-diyl)bis(4,4',5,5'-tetramethyl-1,3,2-dioxaborolane) + 3-bromobiphenyl (2113-57-7) → (R)-3,3'-di([1,1'-biphenyl]-3-yl)-[1,1'-binaphthalene]-2,2'-diol

Conditions	Yield
Stage #1: (R)-2,2'-(2,2'-bis(methoxymethoxy)-1,1'-binaphthyl-3,3'-diyl)bis(4,4',5,5'-tetramethyl-1,3,2-dioxaborolane); 3-bromobiphenyl With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 120℃; Alkaline conditions; Stage #2: With hydrogenchloride In 1,4-dioxane; methanol; dichloromethane; water at 80℃;	95%

3-bromobiphenyl (2113-57-7) + phenylacetylene (536-74-3) → 1-(m-biphenylyl)-2-phenylethyne (263916-95-6)

Conditions	Yield
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) at 80℃; for 5h; Hagihara coupling;	94%

3-bromobiphenyl (2113-57-7) + 2-(diisopropylsilyl)pyridine (1232692-92-0) → C23H27NSi (1232692-97-5)

Conditions	Yield
Stage #1: 3-bromobiphenyl With n-butyllithium In tetrahydrofuran; hexanes at -78℃; Inert atmosphere; Stage #2: 2-(diisopropylsilyl)pyridine In tetrahydrofuran; hexanes at -78 - -30℃; Inert atmosphere;	93%
Stage #1: 3-bromobiphenyl With n-butyllithium In tetrahydrofuran; hexanes at -78℃; Inert atmosphere; Stage #2: 2-(diisopropylsilyl)pyridine In tetrahydrofuran; hexanes at -78 - 30℃; Inert atmosphere;	93%

3-bromobiphenyl (2113-57-7) → C12H6(2)H3Br

Conditions	Yield
With water-d2; potassium carbonate; silver carbonate; cyclohexyldiphenylphosphine In toluene at 120℃; for 12h;	93%

3-bromobiphenyl (2113-57-7) → 3-iodo-1,1'-biphenyl (20442-79-9)

Conditions	Yield
With copper(l) iodide; cis-N,N'-dimethyl-1,2-diaminocyclohexane; sodium iodide In 1,4-dioxane Reflux; Inert atmosphere;	92%
With iodine; sodium iodide In acetonitrile at 20℃; for 36h; Inert atmosphere; UV-irradiation; Green chemistry;	87%

3-bromobiphenyl (2113-57-7) + chlorodicyclohexylphosphane (16523-54-9) → [1,1'-biphenyl]-3-yldicyclohexylphosphane (640735-28-0)

Conditions	Yield
Stage #1: 3-bromobiphenyl With n-butyllithium In diethyl ether; hexane at -20℃; for 2h; Inert atmosphere; Stage #2: chlorodicyclohexylphosphane In diethyl ether; hexane at 20℃; for 6h; Cooling;	92%

3-bromobiphenyl (2113-57-7) + 4-tert-butyl-dimethylsilyloxyphenylboronic acid anhydride (123088-32-4) → [1,1’:3’,1’’-terphenyl]-4-ol (139265-73-9)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 95℃; Suzuki reaction;	91%

3-bromobiphenyl (2113-57-7) → biphenyl (92-52-4)

Conditions	Yield
With methanol; magnesium at 20℃;	91%
With 2-H-1,3-di-tert-butyl-1,3,2-diazaphosphorinane; 2,2'-azobis(isobutyronitrile) In toluene at 90℃; for 5h;	83%
With sodium formate In water; isopropyl alcohol at 50℃; for 0.00222222h; microflow reactor;	99 %Chromat.

3-bromobiphenyl (2113-57-7) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) → 6,9,12,15,18-pentakis(3'-biphenylyl)-1-hydro[60]fullerene

Conditions	Yield
Stage #1: 3-bromobiphenyl With iodine; magnesium In tetrahydrofuran at 20℃; for 2.5h; Inert atmosphere; Reflux; Stage #2: With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere; Stage #3: fullerene-C60 In tetrahydrofuran; 1,2-dichloro-benzene at -78 - 20℃; Inert atmosphere;	91%

3-(2-nitrophenyl)-1H-indole (56366-31-5) + 3-bromobiphenyl (2113-57-7) → C26H18N2O2 (1373266-33-1)

Conditions	Yield
With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine In 1,4-dioxane at 120℃; for 18h;	90%

9,9-dimethyl-9H-fluoren-2-ylamine (108714-73-4) + 3-bromobiphenyl (2113-57-7) → N-((1,1'-biphenyl)-3-yl)-9,9-dimethyl-9H-fluorene-2-amine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene at 108℃; for 4h; Buchwald-Hartwig Coupling; Inert atmosphere;	90%
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene at 108℃; for 4h; Inert atmosphere;	74.94%

Upstream product

• 108-86-1 bromobenzene 
• 2829-31-4 phenyl(phenylazo)methyl hydroperoxide 
• 94-36-0 dibenzoyl peroxide 
• 60108-72-7 1,2-dibromo-4-biphenyl 
• 66107-31-1 3-bromophenyl trifluoromethanesulfonate 
• 100-58-3 phenylmagnesium bromide 
• 92-52-4 biphenyl 
• 71-43-2 benzene 
• 17420-03-0 N-sulphinylphenylhydrazine 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 89598-96-9 (3-bromophenyl)boronic acid 
• 108-36-1 1,3-dibromobenzene 
• 96080-52-3 dipropyl phenylboronate 

Downstream Products

• 98586-20-0 di(1,1'-biphenyl-3-yl)methanol 
• 63242-11-5 (3'-bromobiphenyl-4-yl)phenylmethanone 
• 263916-95-6 1-(m-biphenylyl)-2-phenylethyne 
• 5122-95-2 3-Biphenylboronic acid 
• 121168-49-8 (2-amino-phenyl)-biphenyl-3-yl-methanone 
• 23948-77-8 1,1'-biphenyl-3-ylacetic acid 
• 910330-27-7 5-phenyl-3,4-dihydronaphthalen-2(1H)-one 
• 65685-01-0 biphenyl-3-sulfonyl chloride 
• 1204-60-0 biphenyl-3-carbaldehyde 
• 208943-97-9 3-(3-phenylphenoxy)anisole 
• 1365692-99-4 C₄₅H₃₁Cl 
• 1448644-25-4 3-{2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}aminobiphenyl 

Relevant articles and documents

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Synthesis and catalytic activity of nickel(II) complexes containing NCN pincer ligands

In this study, nickel(II) complexes [LmeNi(II)Cl]+(BPh4)?, [LmeNi(II)Cl]+(PF6)? and [Let2Ni(II)]+(BPh4)?2 were synthesised and characterized in the solution and solid states. Ligands Lme (C11H12N6) and Let (C13H17N6) featured a central carbene donor linked to pendant pyrazoles via either methylene or ethylene linkers. The catalytic activity of all three complexes was tested in the Kumada cross coupling reaction between phenylmagnesium bromide and aromatic halogen substituted substrates. [LmeNi(II)Cl]+(BPh4)?was found to be the most active catalyst.

The photochemistry of polyhaloarenes XIII. The photohydrodehalogenation of 3,4-dibromobiphenyl

Irradiation of 3,4-dibromobiphenyl (BpBr2) in acetonitrile resulted in the formation of 4-bromobiphenyl (BpBr) and 3- bromobiphenyl (3-BpBr) in a ratio of 7.6 ± 0.1 up to 22% conversion of starting material. The dependence of the reciprocal of the quantum yield (1/Φ) upon 1/BpBr2 is linear. Reduction of BpBr2 with lithium di-tert-butylbiphenylide generates a 3.6:1.0 ratio of BpBr to 3-BpBr, while photohydrodebromination of BpBr2 in the presence of triethylamine produces a similar ratio of 1.8:1.0. Product determining radical stability was assessed by radical debromination of BpBr2 using Ph3SnH in THF, which resulted in a BpBr:3-BpBr ratio of 1.5:1.0 AMI calculations on the product determining radicals provide the basis for rationalization of products via excimer and radical anion intermediates.

Synthesis, Structure, and Chiroptical Properties of Indolo- and Pyridopyrrolo-Carbazole-Based C2-Symmetric Azahelicenes

Treatment of 11,12-bis(1,1’-biphenyl-3-yl or 6-phenylpyridin-2-yl)-substituted 11,12-dihydro-indolo[2,3-a]carbazole with an oxidizing system of Pd(II)/Ag(I) induced effective double dehydrogenative cyclization to afford the corresponding π-extended azahelicenes. The optical resolutions were readily achieved by a preparative chiral HPLC. It was found that the pyridopyrrolo-carbazole-based azahelicene that contains four nitrogen atoms exhibits ca. 6 times larger dissymmetry factors both in circularly dichroism (CD) and circularly polarized luminescence (CPL), |gCD| and |gCPL| values being 1.1×10?2 and 4.4×10?3, respectively, as compared with the parent indolocarbazole-based azahelicene. Theoretical calculations at the RI-CC2 level were employed to rationalize the observed enhanced chiroptical responses. The (chir)optical properties of the former helicene was further tuned by a protonation leading to remarkable red-shift with a considerable enhancement of the |gCPL| value.

METHOD OF PRODUCING HALOGEN COMPOUND

PROBLEM TO BE SOLVED: To provide a method of efficiently producing an aromatic compound including a halogen group of interest. SOLUTION: A method of producing a halogen compound represented by the specified general formula (1) comprises reacting a compound represented by the specified general formula (2) with a compound represented by the specified general formula (3) in the presence of a transition metal compound, a phosphine compound being 1,1'-bis(diphenylphosphino)ferrocene or 4,5'-bis(diphenylphosphino)-9,9'-dimethylxanthene, and a base. (In the formula, Ar1 and Ar2 represent organic groups; X represents a halogen group; Z represents a halogen group different than X; m represents an integer greater than or equal to 0; p represents an integer greater than or equal to 1; and each R represents a hydrogen atom, alkyl group or phenyl group, where the two R's may be linked together to form a ring.) SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

Arylation of aryllithiums with: S-arylphenothiazinium ions for biaryl synthesis

Aryllithiums are one of the most common and important aryl nucleophiles; nevertheless, methods for arylation of aryllithums to produce biaryls have been limited. Herein, we report arylation of aryllithiums with S-arylphenothiazinium ions through selective