608-30-0

Basic information

• Product Name: 2,6-Dibromoaniline
• Synonyms: Benzenamine,2,6-dibromo-;2,6-DIBROMO-PHENYLAMINE;2,6-DIBROMOANILINE;Dibromoaniline;2,6-Dibromoaniline,97+%;2,6-Dibromanilin;2,6-DibroMobenzanaMine;2,6-Dibromobenzenamine
• CAS NO: 608-30-0
• Molecular Formula: C₆H₅Br₂N
• Molecular Weight: 250.92
• EINECS: 210-158-4
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Amines;C2 to C6;Nitrogen Compounds;Building Blocks;C6;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 608-30-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 80-82 °C(lit.)
• Boiling Point: 262-264 °C(lit.)
• Flash Point: 262-264°C
• Appearance: White to pale yellow or gray/Crystalline Powder
• Density: 1.9318 (rough estimate)
• Vapor Pressure: 0.00896mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol
• PKA: 0.48±0.10(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 2207094
• CAS DataBase Reference: 2,6-Dibromoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dibromoaniline(608-30-0)
• EPA Substance Registry System: 2,6-Dibromoaniline(608-30-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 2811
• WGK Germany: 3
• F: 10
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 608-30-0(Hazardous Substances Data)

Usage

Chemical Properties

white to pale yellow or grey crystalline powder

Uses

2,5-Dibromoaniline was used in the synthesis of 2,4,5-tribromoaniline1. It was also used as starting reagent in the regioselective synthesis of 2-(3,4-dimethoxyphenyl)-5-bromobenzothiazole.

InChI:InChI=1/C6H5Br2N/c7-4-2-1-3-5(8)6(4)9/h1-3H,9H2

Synthetic route

2,6-dibromobenzamide (96237-91-1) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
With bromine; potassium hydroxide In water at 5℃; Reflux;	83%
With sodium hypobromide

2,6-dibromobenzoic acid (601-84-3) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
Stage #1: 2,6-dibromobenzoic acid With sulfuric acid at 60℃; for 1.5h; Stage #2: With sodium azide at 20℃; for 42h; Schmidt rearrangement; Stage #3: With ammonium hydroxide at 0℃;	78%

2-bromoaniline (615-36-1) → 2,4-dibromo-aniline (615-57-6) + 2,6-dibromoaniline (608-30-0)

Conditions	Yield
With dihydrogen peroxide; potassium bromide; HZSM-5 In acetic acid at 20℃; for 4h; Bromination;	A 67% B 29%
With sodium perborate; ammonium heptamolybdate; potassium bromide In acetic acid at 20℃; for 2h; Bromination;

C86H70Br2N2O5Si4W → 2,6-dibromoaniline (608-30-0) + 4-methoxybenzonitrile (874-90-8)

Conditions	Yield
With water Inert atmosphere;	A 60% B 56%

1,3-dibromo-2-nitrobenzene (13402-32-9) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride
bei der Reduktion;

3,5-dibromosulfanilamide (39150-45-3) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
With sulfuric acid at 175 - 180℃; Darst. Beim Einleiten von Wasserdampf;
With sulfuric acid

2,6-dibromo-benzoic acid hydrazide → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
With hydrogenchloride; acetic acid; sodium nitrite

3,5-dibromosulfanilic acid (78824-10-9) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
With sulfuric acid und leitet ueberhitzten Wasserdampf ein;
With sulfuric acid

4-amino-3,5-dibromobenzoic acid (4123-72-2) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
With sulfuric acid for 8h; Heating; Yield given;

sulfuric acid (7664-93-9) + 3,5-dibromosulfanilamide (39150-45-3) → 2,6-dibromoaniline (608-30-0)

2,6-dibromobenzamide (96237-91-1) + sodium hypobromite → 2,6-dibromoaniline (608-30-0)

sulfuric acid (7664-93-9) + 3,5-dibromosulfanilamide (39150-45-3) → 2,6-dibromoaniline (608-30-0) + 2,4,6-tribromoaniline (147-82-0)

sulfuric acid (7664-93-9) + (4-amino-3,5-dibromo-phenyl)-arsonic acid (171002-36-1) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
at 180℃;

sulfuric acid (7664-93-9) + 3,5-dibromosulfanilic acid (78824-10-9) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
Einleiten von ueberhitztem Wasserdampf;

hydrogenchloride (7647-01-0) + 2,6-dibromo-benzoic acid hydrazide + acetic acid (64-19-7) + sodium nitrite → 2,6-dibromoaniline (608-30-0)

2-bromoaniline (615-36-1) → 2,4-dibromo-aniline (615-57-6) + 2,6-dibromoaniline (608-30-0) + 2,4,6-tribromoaniline (147-82-0)

Conditions	Yield
With sodium perborate; potassium bromide In acetic acid at 20℃; for 14.5h; Bromination;

methyl 3,5-dibromo-4-aminobenzoate (3282-10-8) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / methanol 2: 70percent sulfuric acid / 8 h / Heating View Scheme

4-methoxycarbonyl aniline (619-45-4) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: Br2 2: KOH / methanol 3: 70percent sulfuric acid / 8 h / Heating View Scheme

2,6-dibromobenzoyl chloride (59870-37-0) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether; aqueous hydrazine hydrate 2: hydrochloric acid; glacial acetic acid; sodium nitrite View Scheme

4-aminobenzene sulfonic acid (121-57-3) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; hydrochloric acid; NaOH; bromine 2: sulfuric acid / und leitet ueberhitzten Wasserdampf ein View Scheme
Multi-step reaction with 2 steps 1: water; hydrochloric acid; NaOH; bromine / 0 °C 2: sulfuric acid / und leitet ueberhitzten Wasserdampf ein View Scheme

4-bromo-3-nitroaniline (53324-38-2) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: glacial acetic acid; NaOBr / 0 °C / man kocht das Reaktionsprodukt mit Essigsaeureanhydrid, trennt die beiden Acetylderivate durch fraktionierte Krystallisation aus Alkohol und verseift sie durch Erhitzen mit konz.Schwefelsaeure auf 120grad 3: bei der Reduktion View Scheme

2,4-dibromo-3-nitro-aniline → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
Multi-step reaction with 2 steps 2: bei der Reduktion View Scheme

3-nitro-aniline (99-09-2) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: concentrated acetic acid; NaOBr 2: glacial acetic acid; NaOBr / 0 °C / man kocht das Reaktionsprodukt mit Essigsaeureanhydrid, trennt die beiden Acetylderivate durch fraktionierte Krystallisation aus Alkohol und verseift sie durch Erhitzen mit konz.Schwefelsaeure auf 120grad 4: bei der Reduktion View Scheme
Multi-step reaction with 4 steps 1: chloroform; bromine 2: glacial acetic acid; NaOBr / 0 °C / man kocht das Reaktionsprodukt mit Essigsaeureanhydrid, trennt die beiden Acetylderivate durch fraktionierte Krystallisation aus Alkohol und verseift sie durch Erhitzen mit konz.Schwefelsaeure auf 120grad 4: bei der Reduktion View Scheme

2,6-dibromo-N-(trimethylsilyl)aniline (1159339-39-5) → 2,6-dibromo-N,N'-bis(trimethylsilyl)aniline (217662-69-6) + 2,6-dibromoaniline (608-30-0)

Conditions	Yield
at 50 - 60℃; for 19h;

aniline (62-53-3) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 3h;

2,6 difluorobenzonitrile (1897-52-5) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: ammonia / dimethyl sulfoxide / 80 - 120 °C 2.1: sulfuric acid; sodium nitrite / water / 10 °C 2.2: 45 °C 3.1: ammonia / dimethyl sulfoxide / 80 - 120 °C 4.1: sulfuric acid; sodium nitrite / water / 10 °C 4.2: 45 °C 5.1: sulfuric acid / 55 °C 6.1: potassium hydroxide; bromine / water / 5 °C / Reflux View Scheme

2-amino-6-fluorobenzonitrile (77326-36-4) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sulfuric acid; sodium nitrite / water / 10 °C 1.2: 45 °C 2.1: ammonia / dimethyl sulfoxide / 80 - 120 °C 3.1: sulfuric acid; sodium nitrite / water / 10 °C 3.2: 45 °C 4.1: sulfuric acid / 55 °C 5.1: potassium hydroxide; bromine / water / 5 °C / Reflux View Scheme

2-bromo-6-fluorobenzonitrile (79544-27-7) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: ammonia / dimethyl sulfoxide / 80 - 120 °C 2.1: sulfuric acid; sodium nitrite / water / 10 °C 2.2: 45 °C 3.1: sulfuric acid / 55 °C 4.1: potassium hydroxide; bromine / water / 5 °C / Reflux View Scheme

2-amino-6-bromobenzonitrile (77326-62-6) → 2,6-dibromoaniline (608-30-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuric acid; sodium nitrite / water / 10 °C 1.2: 45 °C 2.1: sulfuric acid / 55 °C 3.1: potassium hydroxide; bromine / water / 5 °C / Reflux View Scheme

2,6-dibromoaniline (608-30-0) + salicylaldehyde (90-02-8) → 2-((E)-(2,6-dibromophenyl)iminomethyl)phenol

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 2h; Heating / reflux;	100%

2,4,6-tris[4-(tert-butyldimethylsilanyloxy)phenyl]cyclotriboroxane (1192062-29-5) + 2,6-dibromoaniline (608-30-0) → 3-bromo-4’-(tert-butyldimethylsilyloxy)biphenyl-2-amine (1415755-46-2)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); ethanol; sodium carbonate In water; benzene for 3h; Inert atmosphere; Reflux;	100%

o-benzenedisulfonimide (4482-01-3) + 2,6-dibromoaniline (608-30-0) → 2,6-dibromobenzenediazonium o-benzenedisulfonimide

Conditions	Yield
With acetic acid; isopentyl nitrite at 0 - 5℃; Diazotization;	99%

2,6-dibromoaniline (608-30-0) + 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane (143825-84-7) → 2,6-bis(1-phenylvinyl)aniline

Conditions	Yield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium hydroxide In tetrahydrofuran at 70℃; for 24h;	99%

2,6-dibromoaniline (608-30-0) + phenylboronic acid (98-80-6) → 2,6-diphenylaniline (87666-57-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 95℃; for 48h; Inert atmosphere; Sealed tube;	98%
With potassium phosphate tribasic heptahydrate; palladium diacetate In water; N,N-dimethyl-formamide at 80℃; for 1.33333h; Suzuki Coupling;	96%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; benzene for 24h; Heating;	95%

2,6-dibromoaniline (608-30-0) + phenylacetylene (536-74-3) → 2,6-bis(phenylethynyl)aniline

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In neat (no solvent) at 90℃; Inert atmosphere; Schlenk technique;	98%
With copper(l) iodide; triethylamine; triphenylphosphine; palladium dichloride at 80℃; for 96h; Inert atmosphere; Schlenk technique;	55%

2,6-dibromoaniline (608-30-0) + 1-benzoyl-2-imidazolidinone (27034-77-1) → 1-benzoyl-2-(2,6-dibromo-anilino)-4,5-dihydro-1H-imidazole (57647-86-6)

Conditions	Yield
With trichlorophosphate	97.6%

2,6-dibromoaniline (608-30-0) + (4-((tert-butyldimethylsilyl)oxy)phenyl)boronic acid (159191-56-7) → 2,6-bis[4-(tert-butyldimethylsilyloxy)phenyl]aniline

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; benzene for 48h; Heating;	97%

2,6-dibromoaniline (608-30-0) + 4-tert-butylphenylboronic acid (123324-71-0) → 4,4''-di-tert-butyl-1,1':3',1''-terphenyl-2'-ylamine (340187-67-9)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; triphenylphosphine In ethanol; water; toluene at 95℃; for 96h; Inert atmosphere;	96%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; benzene for 48h; Suzuki reaction; Heating;	84%
With cesium fluoride; tris-(dibenzylideneacetone)dipalladium(0); benzyl(di-tert-butyl)phosphane In 1,4-dioxane at 20℃; for 12h;	67%

2,6-dibromoaniline (608-30-0) + 4-methylphenylboronic acid (5720-05-8) → 2,6-bis(4-methylphenyl)aniline (17798-71-9)

Conditions	Yield
With potassium phosphate tribasic heptahydrate; palladium diacetate In water; N,N-dimethyl-formamide at 80℃; for 0.75h; Suzuki Coupling;	96%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 72h; Suzuki Coupling;	70%

2,6-dibromoaniline (608-30-0) + 4-fluoroboronic acid (1765-93-1) → 2,6-bis(4-fluorophenyl)aniline (1097192-02-3)

Conditions	Yield
With potassium phosphate tribasic heptahydrate; palladium diacetate In water; N,N-dimethyl-formamide at 80℃; for 1h; Suzuki Coupling;	96%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 72h; Suzuki Coupling;	44%

2,6-dibromoaniline (608-30-0) + (3,4-difluorophenyl)boronic acid (168267-41-2) → 2,6-bis(3,4-difluorophenyl)aniline (1426332-55-9)

Conditions	Yield
With potassium phosphate tribasic heptahydrate; palladium diacetate In water; N,N-dimethyl-formamide at 80℃; for 1.08333h; Suzuki Coupling;	96%

2,4,6-tris[4-(tert-butyldimethylsilanyloxy)phenyl]cyclotriboroxane (1192062-29-5) + 2,6-dibromoaniline (608-30-0) → 2,6-bis[4-(tert-butyldimethylsilyloxy)phenyl]aniline

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); ethanol; sodium carbonate In water; benzene Reflux; Inert atmosphere;	96%

2,6-dibromoaniline (608-30-0) + 3-pentylzinc bromide lithium chloride → 2,6-bis(1-ethylpropyl)aniline

Conditions	Yield
Stage #1: 2,6-dibromoaniline With [1,3-bis(2,6-diisoheptylphenyl)-4,5-dichloroimidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride In toluene for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: 3-pentylzinc bromide lithium chloride In tetrahydrofuran; toluene at 40℃; Inert atmosphere; Schlenk technique;	96%

2,6-dibromoaniline (608-30-0) → 1,3-dibromo-2-nitrosobenzene (45739-16-0)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 4h;	95%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 2h; Heating;	83%
With dihydrogen peroxide; trifluoroacetic acid In water at 20℃; for 16h;	62%

2,6-dibromoaniline (608-30-0) + 4-methoxyphenylboronic acid (5720-07-0) → 4,4''-di(methoxy)-m-terphenyl-2-amine (340187-66-8)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; benzene for 50h; Suzuki cross-coupling reaction; Heating;	95%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; triphenylphosphine In ethanol; water; toluene for 12h; Balz-Schiemann Reaction; Inert atmosphere; Reflux;	92%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 80℃; for 72h; Suzuki Coupling;	69%

2,6-dibromoaniline (608-30-0) + 3,5-bis-trifluromethylphenylboronic acid (73852-19-4) → 3,3″,5,5″-tetrakis(trifluoromethyl)[1,1′:3′,1″-terphenyl]-2′-amine (667938-69-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; triphenylphosphine In ethanol; water; toluene for 12h; Balz-Schiemann Reaction; Inert atmosphere; Reflux;	95%
With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; triphenylphosphine In ethanol; water; toluene at 90℃; for 16h; Inert atmosphere; Autoclave;	65%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene Suzuki cross-coupling reaction;
Suzuki Coupling;

pyrrolidine (123-75-1) + 2,6-dibromoaniline (608-30-0) → 1-(2,6-dibromophenylazo)pyrrolidine

Conditions	Yield
Stage #1: 2,6-dibromoaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: pyrrolidine With potassium carbonate In water; acetonitrile at 0℃; for 0.5h;	95%

thiophene boronic acid (6165-68-0) + 2,6-dibromoaniline (608-30-0) → 2,6-di(thiophen-2-yl)aniline (1415512-67-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane for 72h; Suzuki-Miyaura Coupling; Reflux;	95%
Stage #1: thiophene boronic acid; 2,6-dibromoaniline With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 20℃; for 0.5h; Suzuki Coupling; Inert atmosphere; Stage #2: With water; potassium carbonate In 1,4-dioxane at 90℃; for 72h; Inert atmosphere;	87.3%

2,6-dibromoaniline (608-30-0) + 3,5-diperfluorohexylphenylboronic acid pinacol ester → 3,3’,5,5’-tetra(perfluorohexyl)terphenyl amine

Conditions	Yield
With triphenylphosphine; cesium fluoride; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100 - 130℃; for 20h; Suzuki Coupling;	95%

2,6-dibromoaniline (608-30-0) → 2,6-dibromophenylhexafluorophosphodiazonium salt

Conditions	Yield
With hydrogenchloride; sodium nitrite at -10 - -5℃; for 3h;	94%

2,6-dibromoaniline (608-30-0) + 2-Methoxybenzoyl chloride (21615-34-9) → N-(2,6-dibromophenyl)-2-methoxybenzamide (1381869-40-4)

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h;	93.5%
In tetrahydrofuran at 20℃; for 3h;	93.5%
In tetrahydrofuran at 20℃;	73%
In tetrahydrofuran at 20℃;	51%

pyrrolidine (123-75-1) + 2,6-dibromoaniline (608-30-0) → 1-(2,6-dibromophenylazo)pyrrolidine (338730-94-2)

Conditions	Yield
With sodium nitrite Inert atmosphere;	93%
Stage #1: 2,6-dibromoaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: pyrrolidine With potassium carbonate In acetonitrile at 0 - 20℃; for 2h;	85%

2,6-dibromoaniline (608-30-0) + allyl bromide (106-95-6) → 2,6-dibromo-N-(prop-2-enyl)aniline

Conditions	Yield
Stage #1: 2,6-dibromoaniline With methyllithium In tetrahydrofuran; diethyl ether at -78℃; for 0.5h; Stage #2: allyl bromide In tetrahydrofuran; diethyl ether at -78 - 20℃;	92%

2,6-dibromoaniline (608-30-0) + cyclopentylzinc bromide lithium chloride → 2,6-dicyclopentylaniline (67330-67-0)

Conditions	Yield
With 1-methyl-1H-imidazole; Pd-PEPPSI-IPrAn In tetrahydrofuran; 1,4-dioxane at 0 - 80℃; for 24h; Negishi Coupling; Schlenk technique; Inert atmosphere;	92%

2,6-dibromoaniline (608-30-0) + (3,5-diisopropylphenyl)boronic acid (263397-82-6) → 2,6-bis[3,5-diisopropylphenyl]aniline (1538589-65-9)

Conditions	Yield
Stage #1: 2,6-dibromoaniline; (3,5-diisopropylphenyl)boronic acid With triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In toluene at 20℃; for 0.166667h; Suzuki Coupling; Stage #2: With sodium carbonate In ethanol; water; toluene at 20℃; for 21h; Heating; Stage #3: In ethanol; water; toluene for 1h;	91%

2,6-dibromoaniline (608-30-0) → 1,3-dibromo-2-iodo-benzene (19821-80-8)

Conditions	Yield
Stage #1: 2,6-dibromoaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 1h; Sealed tube; Inert atmosphere; Stage #2: With potassium iodide In dichloromethane; water at 0 - 23℃; for 4.5h; Inert atmosphere;	90%
Stage #1: 2,6-dibromoaniline With hydrogenchloride In water at 0 - 5℃; Sandmeyer reaction; Inert atmosphere; Stage #2: With potassium iodide In dichloromethane; water at 25℃; Sandmeyer reaction; Inert atmosphere; Cooling with ice;	86%
Stage #1: 2,6-dibromoaniline With sulfuric acid; sodium nitrite at 0℃; for 3h; Stage #2: With potassium iodide In water at 0 - 20℃;	85%

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 2,6-dibromoaniline (608-30-0) → 1-(2,6-dibromo-phenyl)-1H-pyrrole (1372804-17-5)

Conditions	Yield
With acetic acid In cis-1,2-Dichloroethylene at 105℃; for 10h; Inert atmosphere;	90%
With acetic acid In 1,2-dichloro-ethane for 2h; Reflux;	84%
With acetic acid In water; 1,2-dichloro-ethane at 80℃; Paal-Knorr Pyrrole Synthesis;	84%

2,6-dibromoaniline (608-30-0) + di-2-pyridyl thionocarbonate (96989-50-3) → 2,6-dibromophenyl isothiocyanate (344326-23-4)

Conditions	Yield
In chlorobenzene at 140℃; for 3h;	90%

2,6-dibromoaniline (608-30-0) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 2,6-bis(3,4,5-trifluorophenyl)aniline (1426332-56-0)

Conditions	Yield
With potassium phosphate tribasic heptahydrate; palladium diacetate In water; N,N-dimethyl-formamide at 80℃; for 0.333333h; Suzuki Coupling;	88%

Upstream product

• 7664-93-9 sulfuric acid 
• 171002-36-1 (4-amino-3,5-dibromo-phenyl)-arsonic acid 
• 78824-10-9 3,5-dibromosulfanilic acid 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 1159339-39-5 2,6-dibromo-N-(trimethylsilyl)aniline 
• 77326-62-6 2-amino-6-bromobenzonitrile 
• 79544-27-7 2-bromo-6-fluorobenzonitrile 
• 77326-36-4 2-amino-6-fluorobenzonitrile 
• 1897-52-5 2,6 difluorobenzonitrile 
• 62-53-3 aniline 
• 601-84-3 2,6-dibromobenzoic acid 
• 99-09-2 3-nitro-aniline 
• 53324-38-2 4-bromo-3-nitroaniline 

Downstream Products

• 21155-37-3 4,4'-diamino-3,5,3',5'-tetrabromo-diphenylmethane 
• 56428-53-6 3-(benzoyl)-2'.6'-dibromoacrylanilide 
• 147-82-0 2,4,6-tribromoaniline 
• 681144-81-0 3-[(2,6-dibromophenyl)amino]cyclopent-2-en-1-one 
• 16807-11-7 1-bromo-9H-carbazole 
• 184170-43-2 2,6-dibromo-benzenesulfonyl chloride 
• 65295-79-6 1-(2,6-dibromophenyl)thiourea 
• 1159339-39-5 2,6-dibromo-N-(trimethylsilyl)aniline 
• 217662-69-6 2,6-dibromo-N,N'-bis(trimethylsilyl)aniline 

Relevant articles and documents

Preparation method of 2,6-dibromoaniline

The invention discloses a preparation method of 2,6-dibromoaniline. According to the method, 2,6-difluorobenzonitrile is used as an initial raw material, and the 2,6-dibromoaniline is synthesized through six steps of reactions including ammonolysis, diazotization bromination, re-ammonolysis, re-diazotization bromination, amidation and Hofmann degradation. The 2,6-dibromoaniline obtained in the process is a brown solid, and the purity of the 2,6-dibromoaniline is 98% or above.

The triple-bond metathesis of aryldiazonium salts: A prospect for dinitrogen cleavage

The {N2} unit of aryldiazonium salts undergoes unusually facile triple-bond metathesis on treatment with molybdenum or tungsten alkylidyne ate complexes endowed with triphenylsilanolate ligands. The reaction transforms the alkylidyne unit into a nitrile and the aryldiazonium entity into an imido ligand on the metal center, as unambiguously confirmed by X-ray structure analysis of two representative examples. A tungsten nitride ate complex is shown to react analogously. Since the bonding situation of an aryldiazonium salt is similar to that of metal complexes with end-on-bound dinitrogen, in which {N2}→M σ donation is dominant and electron back donation minimal, the metathesis described herein is thought to be a conceptually novel strategy toward dinitrogen cleavage devoid of any redox steps and, therefore, orthogonal to the established methods. Who knows? Although the extrusion of molecular nitrogen from aryldiazonium salts is extremely facile, the metathetic cleavage of the N-N triple bond on treatment with alkylidyne ate complexes of molybdenum or tungsten is shown to be even faster. The analogy between [Ar-N2]+ and known [M-N2] complexes makes this process a potential model for dinitrogen cleavage devoid of any redox steps.

Synthesis of pyrrolnitrin and related halogenated phenylpyrroles

A general approach to halogenated arylpyrroles, including the antifungal natural product pyrrolnitrin, is described using newly synthesized halogenated pyrroles and 2,6-disubstituted nitrobenzenes or 2,6-disubstituted anilines.