583-53-9

Basic information

• Product Name: 1,2-Dibromobenzene
• Synonyms: 1,2-DIBROMOBENZENE;O-DIBROMOBENZENE;1,2-Dibrombenzol;1,2-dibromo-benzen;Benzene, o-dibromo-;Benzene,1,2-dibromo-;Benzene,o-dibromo-;ortho-Dibromobenzene
• CAS NO: 583-53-9
• Molecular Formula: C₆H₄Br₂
• Molecular Weight: 235.9
• EINECS: 209-507-3
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Organics;Benzene derivates;Miscellaneous;Bromine Compounds;Aryl;C6;Halogenated Hydrocarbons;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks;alkyl bromide
• Mol File: 583-53-9.mol
• Article Data: 30

Chemical Properties

• Melting Point: 4-6 °C(lit.)
• Boiling Point: 224 °C(lit.)
• Flash Point: 91 °C
• Appearance: brown-yellow/Liquid
• Density: 1.956 g/mL at 25 °C(lit.)
• Vapor Density: 8.2 (vs air)
• Vapor Pressure: 0.129mmHg at 25°C
• Refractive Index: n20/D 1.611(lit.)
• Storage Temp.: Store at
• Solubility: 0.075g/l
• Water Solubility: Insoluble
• BRN: 970241
• CAS DataBase Reference: 1,2-Dibromobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Dibromobenzene(583-53-9)
• EPA Substance Registry System: 1,2-Dibromobenzene(583-53-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: UN 2711
• WGK Germany: 3
• TSCA: T
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 583-53-9(Hazardous Substances Data)

Usage

Chemical Properties

Clear colourless to light yellow liquid

Uses

1,2-Dibromobenzene is used as a precursor in the preparation of 3-(2-bromophenylthio)-4H-[1]benzopyran-4-one using copper as a reagent. It is involved in the preparation of isoindoloquinazolinones by the carbonylation reaction with 2-aminobenzyl amine using palladium as the catalyst.

Synthetic route

2-bromobenzoic-acid (88-65-3) → 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With dibromoisocyanuric acid In dichloromethane at 20℃; for 24h; Reagent/catalyst; Solvent; Temperature; UV-irradiation;	100%

3,4-dibromoaniline (615-55-4) → 1,2-dibromobenzene (583-53-9)

Conditions	Yield
Stage #1: 3,4-dibromoaniline With hydrogenchloride In diethyl ether; water for 0.0833333h; Stage #2: With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #3: With hypophosphorous acid In water at 4 - 25℃; for 72h;	81%

bromobenzene (108-86-1) → 1.4-dibromobenzene (106-37-6) + 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With PyHBrCl2; iron(III) chloride In dichloromethane at 20℃; for 2h;	A 19% B 72%
With lead(IV) acetate; trifluoroacetic acid; potassium bromide at 25℃; for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With bromine; ZnBr2 on silica (100 Angstroem) In hexane at 25℃; for 0.116667h; Yields of byproduct given;

o-Bromobenzenediazonium o-benzenedisulfonimide → 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With tetrabutylammomium bromide In acetonitrile at 60℃; for 0.75h; Substitution;	53%
With tetrabutylammomium bromide; copper In acetonitrile at 20℃; for 0.75h; Substitution;	51%

1,2-dibromobenzene-4-sulfonic acid (107573-20-6) → 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With hydrogen bromide at 250℃;

1,2-Dinitrobenzene (528-29-0) → 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With hydrogen bromide at 250 - 260℃;

2-bromoaniline (615-36-1) → 1,2-dibromobenzene (583-53-9)

benzene (71-43-2) → 1.4-dibromobenzene (106-37-6) + 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With bromine; Nitrogen dioxide In water; trifluoroacetic acid at 20℃; for 0.16h; Product distribution;
With bromine
With ferrocenium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; bromine; zinc(II) oxide In dichloromethane for 3h; Heating;
Multi-step reaction with 2 steps 1: bromine / 1.5 h / 40 °C / Darkness; Inert atmosphere; Green chemistry 2: bromine / dichloromethane / 2 h / 40 °C / Darkness; Inert atmosphere; Green chemistry View Scheme

bromobenzene (108-86-1) → bromochlorobenzene (106-39-8) + para-dichlorobenzene (106-46-7) + 2-bromo-1-chlorobenzene (694-80-4) + 1.4-dibromobenzene (106-37-6) + chlorobenzene (108-90-7) + 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With potassium chloride; cobalt(III) acetate; trifluoroacetic acid at 20℃; for 15h; Product distribution; Mn(CH3COO)3, 600 - 216 h, various conc. of aq. CF3COOH;

bromobenzene (108-86-1) → 1,3-dibromobenzene (108-36-1) + 1.4-dibromobenzene (106-37-6) + 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With hypobromous acid In 1,4-dioxane; water at 25℃; Rate constant;	A 1 % Chromat. B 64.3 % Chromat. C 35.7 % Chromat.

benzene (71-43-2) → bromobenzene (108-86-1) + 1.4-dibromobenzene (106-37-6) + 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With oxygen; potassium bromide; sodium nitrite In water; trifluoroacetic acid at 20℃; for 24h; Product distribution;
With hydrogen bromide; oxygen; ruthenium trichloride at 145℃; under 750.075 Torr; for 17h;

1,2,4-tribromobenzene (615-54-3) → bromobenzene (108-86-1) + 1,3-dibromobenzene (108-36-1) + 1.4-dibromobenzene (106-37-6) + benzene (71-43-2) + 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With potassium hydroxide; hydrogen; palladium on activated charcoal In 2,2,4-trimethylpentane at 50℃; for 0.666667h; Product distribution; var. cat.: Raney-Ni, add. of Aliquat 336;	A 18 % Chromat. B 3 % Chromat. C 1 % Chromat. D 42 % Chromat. E 30 % Chromat.

2-bromo-benzene-sulfonic acid-(1) → 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With copper(ll) bromide

2-bromo-phenylmercury acetate → 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With bromine; acetic acid

bromobenzene (108-86-1) + bromine (7726-95-6) → 1,2-dibromobenzene (583-53-9)

Conditions	Yield
at 200 - 700℃; Quantum yield;

chlorosulfonic acid (7790-94-5) + hydrogen bromide (10035-10-6, 12258-64-9) + iodine (7553-56-2) + benzene (71-43-2) → 1,2-dibromobenzene (583-53-9)

diazotized o-bromo-aniline → 1,2-dibromobenzene (583-53-9)

Conditions	Yield
man fuehrt in das Perbromid ueber und zersetzt dieses mit Soda;

sulfate 3.4-dibromo-aniline → 1,2-dibromobenzene (583-53-9)

Conditions	Yield
With ethyl nitrite; ethanol

bromobenzene (108-86-1) → 1,2-dibromobenzene (583-53-9) + 1.3-dibromo-benzene; 1.4-dibromo-benzene

Conditions	Yield
With bromine at 480℃;

aluminium trichloride (7446-70-0) + bromobenzene (108-86-1) → 1.4-dibromobenzene (106-37-6) + 1,2-dibromobenzene (583-53-9)

Conditions	Yield
at 90℃;

carbon disulfide (75-15-0) + bromobenzene (108-86-1) + bromine (7726-95-6) + aluminium bromide (7727-15-3) → 1.4-dibromobenzene (106-37-6) + 1,2-dibromobenzene (583-53-9)

Conditions	Yield
at 55℃; Kinetics;

bromine (7726-95-6) + benzene (71-43-2) → 1.4-dibromobenzene (106-37-6) + 1,2-dibromobenzene (583-53-9)

bromobenzene (108-86-1) + bromine (7726-95-6) → 1,3-dibromobenzene (108-36-1) + 1.4-dibromobenzene (106-37-6) + 1,2-dibromobenzene (583-53-9)

Conditions	Yield
at 375 - 500℃;

bromobenzene (108-86-1) + bromine (7726-95-6) + aluminium → 1,3-dibromobenzene (108-36-1) + 1.4-dibromobenzene (106-37-6) + 1,2-dibromobenzene (583-53-9)

Conditions	Yield
at 55℃; Product distribution;

bromobenzene (108-86-1) + bromine (7726-95-6) + iron → 1,3-dibromobenzene (108-36-1) + 1.4-dibromobenzene (106-37-6) + 1,2-dibromobenzene (583-53-9)

Conditions	Yield
at 55℃; Product distribution;

benzene (71-43-2) → bromobenzene (108-86-1) + 1,3-dibromobenzene (108-36-1) + 1.4-dibromobenzene (106-37-6) + 1,2,3,4,5,6-hexabromocyclohexane (1837-91-8) + 1,2-dibromobenzene (583-53-9) + HBr

Conditions	Yield
With bromine at 55℃; for 16h; Product distribution; Irradiation; temperature;

bromobenzene (108-86-1) → 1,2-dibromobenzene (583-53-9) + m and p-dibromo-benzene

Conditions	Yield
With bromine; aluminium at 55℃;
With bromine; iron at 55℃;

biphenyl (92-52-4) + benzene (71-43-2) → bromobenzene (108-86-1) + 2-Bromobiphenyl (2052-07-5) + 1,3-dibromobenzene (108-36-1) + 4-bromo-1,1'-biphenyl (92-66-0) + 3-bromobiphenyl (2113-57-7) + 1,2-dibromobenzene (583-53-9) + HBr

Conditions	Yield
With bromine at 50℃; for 20h; Product distribution; Irradiation; other time, reagents ratio;

...Expand

Methyl phenyl sulfone (3112-85-4) + bromine (7726-95-6) → methyl bromide (74-83-9) + bromobenzene (108-86-1) + 1,2-dibromobenzene (583-53-9)

Conditions	Yield
at 250℃;

2,4,6-trimethylaniline (88-05-1) + 1,2-dibromobenzene (583-53-9) → N1,N2-bis(2,4,6-trimethylphenyl)-1,2-benzenediamine (852414-57-4)

Conditions	Yield
With ammonium chloride; sodium t-butanolate; palladium diacetate In water; argon; toluene	100%
With tri-tert-butylphosphonium tetrafluoroborate; palladium diacetate; sodium t-butanolate In toluene at 60 - 135℃; Inert atmosphere;	87%
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; palladium diacetate In toluene for 12h; Heating;	86%

5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone (130222-84-3) + 1,2-dibromobenzene (583-53-9) → 1-(2-bromophenyl)-5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose (881423-76-3)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; diethyl ether; hexane at -110℃; for 3.5h;	100%

1,2-dibromobenzene (583-53-9) → N,N'-diphenyl-o-phenylenediamine (28394-83-4)

Conditions	Yield
With ammonium chloride; aniline; sodium t-butanolate; palladium diacetate In water; argon; toluene	100%

2,5-Dimethylaniline (95-78-3) + 1,2-dibromobenzene (583-53-9) → N,N'-bis(2,5-dimethylphenyl)-o-phenylenediamine (1068437-88-6)

Conditions	Yield
With ammonium chloride; sodium t-butanolate; palladium diacetate In water; argon; toluene	100%
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 14h; Inert atmosphere;	100 %Chromat.

3,5-dimethylaminoaniline (108-69-0) + 1,2-dibromobenzene (583-53-9) → N,N'-di(3,5-dimethylphenyl)benzene-1,2-diamine (1068437-89-7)

Conditions	Yield
With ammonium chloride; sodium t-butanolate; palladium diacetate In water; argon; toluene	100%
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In toluene at 110℃; for 14h; Inert atmosphere;	100 %Chromat.

2,5-di-tert-butylaniline (21860-03-7) + 1,2-dibromobenzene (583-53-9) → N,N'-bis(2,5-di-1-butylphenyl)-o-phenylenediamine + N,N'-bis(2,5-di-t-butylphenyl)-o-phenylenediamine (1068437-90-0)

Conditions	Yield
With ammonium chloride; sodium t-butanolate; palladium diacetate In water; argon; toluene	A n/a B 100%

3,4,5-trimethoxyphenylboronic Acid (182163-96-8) + 1,2-dibromobenzene (583-53-9) → 2-bromo-3′,4′,5′-trimethoxybiphenyl

Conditions	Yield
With palladium diacetate; potassium carbonate In ethanol; N,N-dimethyl acetamide at 20℃; for 3h; Suzuki Coupling;	100%

1,2-dibromobenzene (583-53-9) → 1,2-diamino-benzene (95-54-5)

Conditions	Yield
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 140℃; for 16h;	99%
With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 130℃; for 18h; Reagent/catalyst; Time; Sealed tube; Inert atmosphere;	92%
With ammonium hydroxide In water at 20℃; for 12h; Green chemistry;	92%
With ammonia; water; copper(II) sulfate at 180 - 190℃;
With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 120℃; for 16h; Sealed tube;	100 %Spectr.

ethyl trifluoroacetate, (383-63-1) + 1,2-dibromobenzene (583-53-9) → 1-(2-bromophenyl)-2,2,2-trifluoroethan-1-one (244229-34-3)

Conditions	Yield
Stage #1: 2,3-dibromobenzene With n-butyllithium Stage #2: ethyl trifluoroacetate,	99%
Stage #1: 2,3-dibromobenzene With n-butyllithium at -110℃; Metallation; Stage #2: ethyl trifluoroacetate, Acylation;

acrylic acid n-butyl ester (141-32-2) + 1,2-dibromobenzene (583-53-9) → 2E,2′E-3,3′-(1,2-phenylene) bis[2-propenoic acid] dibutyl ester

Conditions	Yield
With potassium carbonate; bis(dibenzylideneacetone)-palladium(0); 3-(2,6-diisopropylphenyl)-1-(2-diphenylphosphanylbenzyl)-3H-imidazol-1-ium chloride In N,N-dimethyl acetamide at 120℃; for 16h; Heck reaction;	99%
With palladium diacetate; tri-tert-butyl phosphine; sodium acetate In N,N-dimethyl acetamide at 130℃; for 24h; Heck reaction;	60%

(2,6-dimethylphenyl)magnesium bromide (21450-64-6) + 1,2-dibromobenzene (583-53-9) → 4-methylfluorene (1556-99-6)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 20h;	99%
palladium diacetate In tetrahydrofuran at 20℃; for 20h;	99%

2-Methoxyphenylboronic acid (5720-06-9) + 1,2-dibromobenzene (583-53-9) → 2’-bromo-2-methoxybiphenyl (20837-12-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; toluene for 24h; Suzuki reaction; Reflux; Inert atmosphere;	99%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 50℃; for 4h; Suzuki coupling;	71%

1,2-dibromobenzene (583-53-9) + 2-mesitylmagnesium bromide (2633-66-1) → 2,4-dimethyl-9H-fluorene (2928-44-1)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 20h;	99%
palladium diacetate In tetrahydrofuran at 20℃; for 20h;	99%

tert-butylamine (75-64-9) + 1,2-dibromobenzene (583-53-9) → N1,N2-di-tert-butylbenzene-1,2-diamine

Conditions	Yield
	99%
With palladium diacetate; sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride
With palladium diacetate; sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride

1,2-dibromobenzene (583-53-9) → 2-bromoaniline (615-36-1)

Conditions	Yield
With 2-((dicyclohexylphosphino)methyl)-1,3-bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium iodide; ammonia; palladium diacetate; sodium t-butanolate In 1,4-dioxane at 120℃; under 7500.75 Torr; for 24h; Autoclave; Inert atmosphere;	99%
With 2-(di-tert-butylphosphino)-1-mesityl-4,5-diphenyl-1H-imidazole; ammonia; palladium diacetate; sodium t-butanolate In 1,4-dioxane at 120℃; under 7500.75 Torr; for 24h; Autoclave; Inert atmosphere;	> 99 %Chromat.

9,9-dimethyl-3,6-dimethoxy-9-stannafluorene (5565-83-3) + 1,2-dibromobenzene (583-53-9) → 2,11-dimethoxytriphenylene (1115023-89-6)

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0) In tetrahydrofuran at 60℃; for 12h;	99%

thiophenol (108-98-5) + 1,2-dibromobenzene (583-53-9) → 1,2-bis(phenylthio)benzene (3379-36-0)

Conditions	Yield
With 1,2,3,4-tetrahydroquinolin-8-ol; caesium carbonate; copper(I) bromide In N,N-dimethyl-formamide at 130℃; for 48h; Inert atmosphere; chemoselective reaction;	99%

N-phenylacetamidine (14277-00-0) + 1,2-dibromobenzene (583-53-9) → 2-methyl-1-phenyl-1H-benzimidazole (1484-39-5)

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 140℃; for 24h; Molecular sieve; Inert atmosphere; regiospecific reaction;	99%

N-cyclohexylbenzimidamide (19673-06-4) + 1,2-dibromobenzene (583-53-9) → 1-cyclohexyl-2-phenyl-1H-benzo[d]imidazole (1350628-99-7)

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 140℃; for 24h; Molecular sieve; Inert atmosphere; regiospecific reaction;	99%

N-(naphthalen-1-yl)benzimidamide (607-54-5) + 1,2-dibromobenzene (583-53-9) → 1-(naphthalen-1-yl)-2-phenyl-1H-benzo[d]imidazole (1350628-96-4)

Conditions	Yield
With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 140℃; for 24h; Molecular sieve; Inert atmosphere; regiospecific reaction;	99%

N-phenylbenzamidine (1527-91-9) + 1,2-dibromobenzene (583-53-9) → 1,2-diphenyl-1H-benzoimidazole (2622-67-5)

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 140℃; for 24h; Molecular sieve; Inert atmosphere; regiospecific reaction;	99%
With potassium phosphate; 1,10-Phenanthroline; copper(II) oxide In diethylene glycol dimethyl ether at 140℃; for 24h; Inert atmosphere; regiospecific reaction;	51%

(R)-2-methoxy-1-phenylethylamine (64715-85-1, 91298-74-7, 127180-88-5) + 1,2-dibromobenzene (583-53-9) → (2-bromophenyl)-(R)-2-methoxy-1-phenylethylamine (361979-02-4)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 80℃; for 48h; Buchwald-Hartwig amination;	98%

1,2-dibromobenzene (583-53-9) + phenylboronic acid (98-80-6) → o-terphenyl (84-15-1)

Conditions	Yield
With {2,6-bis[(di-1-piperidinylphosphino)amino]phenyl}palladium(II) chloride; potassium carbonate In 1,4-dioxane; water; butan-1-ol at 100℃; for 0.5h; Suzuki-Miyaura reaction;	98%
With potassium phosphate; dichloro{bis[1-(dicyclohexylphosphanyl)piperidine]}palladium(II) In toluene at 80℃; for 0.166667h; Suzuki-Miyaura cross-coupling reaction; Air;	98%
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 6h; Suzuki coupling;	96%

4-methylphenylboronic acid (5720-05-8) + 1,2-dibromobenzene (583-53-9) → 4,4′′-dimethyl-o-terphenyl (64586-14-7)

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In tetrahydrofuran at 20℃; for 6h; Suzuki coupling;	98%
With bis(1,5-cyclooctadiene)nickel (0); potassium phosphate; tricyclohexylphosphine In tetrahydrofuran for 20h; Suzuki Coupling; Inert atmosphere;	97%
With potassium carbonate In ethanol; water at 20℃; for 8h; Suzuki-Miyaura coupling;	85%
With sodium tetrachloropalladate(II); C22H16O8S2(2-)*2Na(1+); sodium hydroxide In ethanol; water at 100℃; for 8h; Suzuki-Miyaura Coupling; Schlenk technique;	83%
With potassium carbonate In methanol at 80℃; for 0.5h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;

aminoferrocene (1273-82-1) + 1,2-dibromobenzene (583-53-9) → [C6H4(NH(C5H4)Fe(C5H5))2] (1198580-93-6)

Conditions	Yield
With t-BuONa; Pd(O2CCH3)2; 1,3-bis(2,6-diisopropylphenyl)imidazolim chloride In toluene mixt. of Fe complex, imidazolium salt, t-BuONa, Pd compd. and C6H4Br2 intoluene was heated at 110°C for 12 h;	98%

(3-(tert-butyl)-2-methoxyphenyl)boronic acid (1205536-16-8) + 1,2-dibromobenzene (583-53-9) → 2'-bromo-3-tert-butyl-2-methoxybiphenyl (1205536-18-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); water; potassium carbonate In 1,2-dimethoxyethane at 67℃; for 60h; Suzuki coupling; Inert atmosphere;	98%

4-(dimethylamino)-N-phenylbenzimidamide (52379-48-3) + 1,2-dibromobenzene (583-53-9) → 1-phenyl-2-(4-N,N-dimethylamino-phenyl)-1H-benzo[d]imidazole (2562-73-4)

Conditions	Yield
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 140℃; for 24h; Molecular sieve; Inert atmosphere; regiospecific reaction;	98%

bis(pinacol)diborane (73183-34-3) + 1,2-dibromobenzene (583-53-9) → 2-(3,4-dibromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1075719-78-6)

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; cyclopentyl methyl ether; 1,1'-di(pyridin-2-yl)-1,1',3,3'-tetrahydro-2,2'-bibenzo[d][1,3,2]diazaborole at 80℃; for 16h; Schlenk technique; Inert atmosphere;	98%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1-(4,4'-di-tert-butyl-[2,2'-bipyridin]-6-yl)-2-(dimethyl(phenyl)silyl)-2,3-dihydro-1H-benzo[d][1,3,2]diazaborole Inert atmosphere; Schlenk technique; Sealed tube;	97%
With (1,5-cyclooctadiene)(methoxy)iridium(l) dimer; 4,4'-ditert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 18h; Inert atmosphere; regioselective reaction;
Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran for 0.0333333h; Inert atmosphere; Sonication; Stage #2: 2,3-dibromobenzene In tetrahydrofuran at 80℃; for 24h; Inert atmosphere;
With (1,5-cyclooctadiene)(methoxy)iridium(l) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 24h; Inert atmosphere;

N'-(1-(2-aminophenyl)ethylidene)-4-methylbenzenesulfonohydrazide (1433772-22-5) + 1,2-dibromobenzene (583-53-9) → 9-methyl-acridine (611-64-3)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); lithium tert-butoxide; ruphos In 1,4-dioxane; water at 110℃; for 12h; Reagent/catalyst; Temperature; Microwave irradiation; Inert atmosphere;	98%

Upstream product

• 71-43-2 benzene 
• 108-86-1 bromobenzene 
• 7726-95-6 bromine 
• 7790-94-5 chlorosulfonic acid 
• 10035-10-6 hydrogen bromide 
• 7553-56-2 iodine 
• 7446-70-0 aluminium trichloride 
• 75-15-0 carbon disulfide 
• 7727-15-3 aluminium bromide 
• 3112-85-4 methylphenylsulfonate 
• 108-36-1 1,3-dibromobenzene 
• 67-66-3 chloroform 
• 49676-92-8 1,2-dibromocyclohex-1-ene 
• 106-37-6 1.4-dibromobenzene 

Downstream Products

• 19845-68-2 1,2-bis-(diethylphosphino)-benzene 
• 3379-36-0 1,2-bis(phenylthio)benzene 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 5411-50-7 3,4-dibromonitrobenzene 
• 26429-41-4 1,2-dibromo-3-nitrobenzene 
• 96558-80-4 1,2-dibromo-3,5-dinitrobenzene 
• 54558-18-8 1,2-dinitro-4,5-dibromobenzene 
• 13029-09-9 2,2'-dibromobiphenyl 
• 107573-20-6 1,2-dibromobenzene-4-sulfonic acid 
• 81903-80-2 3,4-dibromophenylsulfonic acid chloride 
• 108870-81-1 3,4-dibromo-benzenesulfonic acid-anhydride 
• 95-54-5 1,2-diamino-benzene 
• 71-43-2 benzene 
• 108-86-1 bromobenzene 

Relevant articles and documents

Oxidative bromination of non-activated aromatic compounds with AlBr3/KNO3 mixture

Bromination of non-activated aromatic compounds with reaction mixture containing KNO3 and AlBr3 was studied in liquid substrates and in solvent. Aluminium bromide has three different roles in this reaction mixture. First, it is a source of bromide ions, which are essential in oxidative bromination application. Second, it acts as a catalyst, and lastly, it forms acidic environment via its hydrolysis, which is necessary for enhancement of the oxidising properties of nitrate ions. It was shown that when changing the reaction conditions, different side reactions (like nitration or Friedel–Crafts type arylation) can occur. However, it is possible to guide the reaction path and receive the desired outcome by choosing the suitable reaction conditions. In addition, it was shown that there has to be water content in this reaction mixture as the bromine formation rate depends on it, while there exists an optimal volume of water, where bromine formation is the fastest.

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