626-39-1

Basic information

• Product Name: Tribromobenzene
• Synonyms: 1,3,5-tribromo-benzen;Benzene,1,3,5-tribromo-;I,3,5-TribrombenzolC&W%16;Tribromobenzene;1,3,5-TRIBROMOBENZENE;Tribromobenzene,98%;1,3,5-TRIBROMOBENZENE OEKANAL, 250 MG;1,3,5-Tribromobenzene,98+%
• CAS NO: 626-39-1
• Molecular Formula: C₆H₃Br₃
• Molecular Weight: 314.8
• EINECS: 210-947-3
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Organics;Benzene derivates;Aryl;C6;Halogenated Hydrocarbons
• Mol File: 626-39-1.mol

Chemical Properties

• Melting Point: 117-121 °C(lit.)
• Boiling Point: 271 °C(lit.)
• Flash Point: 271°C
• Appearance: Almost white to orange-brown/Powder
• Density: 2.3515 (estimate)
• Vapor Pressure: 0.012mmHg at 25°C
• Refractive Index: 1.6340 (estimate)
• Storage Temp.: Room temperature.
• Solubility: Soluble in benzene, chloroform, and ether (Weast, 1986)
• Water Solubility: Soluble in hot ethanol and acetic acid. Insoluble in water.
• BRN: 1858917
• CAS DataBase Reference: Tribromobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: Tribromobenzene(626-39-1)
• EPA Substance Registry System: Tribromobenzene(626-39-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-53
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• RTECS: DC1957200
• TSCA: Yes
• Hazardous Substances Data: 626-39-1(Hazardous Substances Data)

Usage

Uses

1. Used in Drug Manufacturing:
Tribromobenzene is utilized as an intermediate in the drug manufacturing process. Its unique chemical structure allows it to be a valuable component in the synthesis of various pharmaceutical compounds.
2. Used in Organic Synthesis:
As a substituted bromobenzene, tribromobenzene serves as a general reagent in organic synthesis. Its bromine atoms can be replaced with other functional groups, making it a versatile building block for creating a wide range of organic molecules.
3. Used as an Internal Standard in Analysis:
Tribromobenzene is employed as an internal standard during the derivatization step in the determination of cyanide in human plasma and urine by gas chromatography-mass spectrometry. This application ensures accurate and reliable measurements by accounting for any variations in the analytical process.
4. Used in the Preparation of Inhibitors:
Tribromobenzene is a reagent that can be used in the preparation of different inhibitors. Its chemical properties make it suitable for the development of compounds that can inhibit specific biological or chemical processes.
5. Used in Palladium-Catalyzed Reactions:
Tribromobenzene is a general reagent in palladium-catalyzed reactions, which are widely used in organic chemistry for the formation of carbon-carbon and carbon-heteroatom bonds. Its presence can enhance the efficiency and selectivity of these reactions.
6. Used in the Synthesis of Grignard Reagents:
Tribromobenzene is also used in the synthesis of Grignard reagents, which are important in organic chemistry for their ability to add to carbonyl groups and participate in various carbon-carbon bond-forming reactions.
7. Used in the Formation of Molecular Complexes:
Tribromobenzene forms molecular complexes of 1:2 stoichiometry with [60]and [70] fullerenes. These complexes have potential applications in materials science and nanotechnology.
8. Used in the Synthesis of Novel Monomers:
Tribromobenzene reacts with perfluoroalkenylzinc reagent in the presence of Pd(Ph3)4 catalyst to yield a novel trifunctional monomer, 1,3,5-tris(α, β, β-trifluorovinyl)benzene. This monomer can be used in the development of new polymers and materials with unique properties.

Environmental fate

Photolytic. Peijnenburg et al. (1992) investigated the photodegradation of a variety of substituted aromatic halides using a Rayonet RPR-208 photoreactor equipped with 8 RUL 3,000- ? lamps (250–350 nm). The reaction of 1,3,5-tribromobenzene (initial concentration 10-5 M) was conducted in distilled water and maintained at 20 °C. Though no products were identified, the investigators reported photohydrolysis was the dominant transformation process. The measured pseudo-first-order reaction rate constant and corresponding half-life were 0.005/min and 140.5 min., respectively. Chemical/Physical. 1,3,5-Tribromobenzene will not hydrolyze to any reasonable extent.

Purification Methods

Crystallise it from glacial acetic acid/water (4:1), then wash with chilled EtOH and dry in air. [Beilstein 5 H 213, 5 IV 685.]

InChI:InChI=1/C6H3Br3/c7-4-1-5(8)3-6(9)2-4/h1-3H

Synthetic route

2,4,6-tribromobenzenediazonium o-benzenedisulfonimide → 1,3,5-trisbromobenzene (626-39-1)

Conditions	Yield
With dihydrogen peroxide In tetrahydrofuran for 0.166667h; Heating;	100%
Multi-step reaction with 2 steps 1: 92 percent / aq. NaOH / 0.5 h / 0 - 5 °C 2: 2 percent / aq. HI; HBF4 / acetonitrile / 24 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: 92 percent / aq. NaOH / 0.5 h / 0 - 5 °C 2: 13 percent / Et3PhCH2N(+)Cl(-); MeSO3H; Cu / acetonitrile / 1 h / 40 °C View Scheme

2,4,6-tribromoaniline (147-82-0) → 1,3,5-trisbromobenzene (626-39-1)

Conditions	Yield
Stage #1: 2,4,6-tribromoaniline With hydrogenchloride; sodium nitrite In water Stage #2: With ethanol In water	92%
With sulfuric acid; sodium nitrite In ethanol at 20℃; Reflux;	90%
With ethanol; sulfuric acid; benzene Reagens 4: Natriumnitrit;

(2,4,6-tribromophenyl)triethylsilane (722540-83-2) → 1,3,5-trisbromobenzene (626-39-1)

Conditions	Yield
With potassium fluoride In tetrahydrofuran; water for 12h; Heating;	91%

C10H12Br3N3 (401631-91-2) → 1,3,5-trisbromobenzene (626-39-1) + 2,4,6-tribromoiodobenzene (21521-51-7)

Conditions	Yield
With tetrafluoroboric acid; hydrogen iodide In acetonitrile at 60℃; for 24h;	A 2% B 84%

C10H12Br3N3 (401631-91-2) → 1,3,5-trisbromobenzene (626-39-1) + 1,3,5-tribromo-2-chloro-benzene (78904-10-6)

Conditions	Yield
With methanesulfonic acid; N-benzyl-N,N,N-triethylammonium chloride; copper In acetonitrile at 40℃; for 1h;	A 13% B 78%

2-methoxycarbonyl-3',5'-dibromobiphenyl + 2-methoxycarbonylphenylboronic acid (374538-03-1) → 1,3,5-trisbromobenzene (626-39-1)

Conditions	Yield
	54%

tribromo-benzenediazonium tetrafluoroborate → 1,3,5-trisbromobenzene (626-39-1) + 2,4,6-tribromobenzenediazohydroxide (134253-67-1)

Conditions	Yield
With 2,2,2-trifluoroethanol at 34℃; for 24h; Irradiation; Further byproducts given;	A 47% B 8.8%
With 2,2,2-trifluoroethanol at 34℃; for 24h; Irradiation; Further byproducts given;	A 47% B 8.8%
With 2,2,2-trifluoroethanol at 34℃; for 24h; Further byproducts given;	A 35.5% B 4.1%

tribromo-benzenediazonium tetrafluoroborate → 1,3,5-trisbromobenzene (626-39-1) + 2,4,6-tribromobenzenediazohydroxide (134253-67-1) + dibromo-hydroxybenzene

Conditions	Yield
With 2,2,2-trifluoroethanol at 34℃; for 24h; Product distribution; influence of magnetic field;	A 47% B 8.8% C n/a

2,4,6-tribromoaniline (147-82-0) + copper(I) cyanide (544-92-3) → 1,3,5-trisbromobenzene (626-39-1) + 1,2,3,5-tetrabromobenzene (634-89-9) + 2,4,6-tribromonitrobenzene (3463-40-9) + 2,4,6-tribromobenzonitrile (35851-93-5) + 2,4,6-tribromophenol (118-79-6)

Conditions	Yield
With tert.-butylnitrite In dimethyl sulfoxide at 60℃; for 1.5h; Product distribution; Mechanism; other anilines;	A 37% B 7% C 4% D 20% E 4%

2,4,6-tribromoaniline (147-82-0) + copper(I) cyanide (544-92-3) → 1,3,5-trisbromobenzene (626-39-1) + 2,4,6-tribromonitrobenzene (3463-40-9) + 2,4,6-tribromobenzonitrile (35851-93-5) + 2,4,6-tribromophenol (118-79-6)

Conditions	Yield
With tert.-butylnitrite In dimethyl sulfoxide at 60℃; for 1.5h; Further byproducts given;	A 37% B 4% C 20% D 4%

2,4,6-tribromoaniline (147-82-0) → 1,3,5-trisbromobenzene (626-39-1) + 1,2,3,5-tetrabromobenzene (634-89-9) + 2,4,6-tribromonitrobenzene (3463-40-9) + 2,4,6-tribromobenzonitrile (35851-93-5)

Conditions	Yield
With tert.-butylnitrite In dimethyl sulfoxide at 60℃; for 1.5h; Further byproducts given;	A 37% B 7% C 4% D 20%

2,4,6-tribromoaniline (147-82-0) → 1,3,5-trisbromobenzene (626-39-1) + 2,4,6-tribromonitrobenzene (3463-40-9) + 2,4,6-tribromobenzonitrile (35851-93-5) + 2,4,6-tribromophenol (118-79-6)

Conditions	Yield
With tert.-butylnitrite In dimethyl sulfoxide at 60℃; for 1.5h; Further byproducts given;	A 37% B 4% C 20% D 4%

C6H2Br3ClN2 → 1,3,5-trisbromobenzene (626-39-1)

Conditions	Yield
With trifluorormethanesulfonic acid at 25℃; for 24h; Irradiation;	34.3%

tribromo-benzenediazonium tetrafluoroborate → 1,3,5-trisbromobenzene (626-39-1)

Conditions	Yield
With trifluorormethanesulfonic acid at 34℃; for 24h; Further byproducts given. Yields of byproduct given;	25%

C8H2Br3F3N2O2 → 1,3,5-trisbromobenzene (626-39-1)

Conditions	Yield
With trifluorormethanesulfonic acid at 25℃; for 24h; Irradiation;	20%

2,4,6-tribromophenyl diazonium salt → 1,3,5-trisbromobenzene (626-39-1)

Conditions	Yield
With nitroxide	13%

C7H2Br3F3N2O3S → 1,3,5-trisbromobenzene (626-39-1)

Conditions	Yield
With trifluorormethanesulfonic acid at 25℃; for 24h; Irradiation;	4.4%

methanol (67-56-1) + 2,4,6-tribromo-benzenediazonium; hydrogen sulfate → 1,3,5-trisbromobenzene (626-39-1)

methanol (67-56-1) + 2,4,6-tribromo-benzenediazonium; hydrogen sulfate → 1,3,5-trisbromobenzene (626-39-1) + 2,4,6-tribromoanisole (607-99-8) + 3,5-dibromo-ortho quinone diazide (20648-40-2) + 2,4,6-tribromophenol (118-79-6)

Conditions	Yield
bei der Belichtung.Irradiation;

formic acid (64-18-6) + 2,4,6-tribromo-benzenediazonium; hydrogen sulfate → 1,3,5-trisbromobenzene (626-39-1) + 2,4,6-tribromophenol (118-79-6)

Conditions	Yield
bei der Belichtung.Irradiation;

ethanol (64-17-5) + 2,4,6-tribromo-benzenediazonium; hexachloro plumbate(IV) → 1,3,5-trisbromobenzene (626-39-1) + 1,3,5-tribromo-2-chloro-benzene (78904-10-6)

ethanol (64-17-5) + 2,4,6-tribromo-benzenediazonium; hydrogen sulfate → 1,3,5-trisbromobenzene (626-39-1)

Conditions	Yield
zersetzt sich in Dunkel;

ethanol (64-17-5) + 2,4,6-tribromo-benzenediazonium; hydrogen sulfate → 1,3,5-trisbromobenzene (626-39-1) + 1,3,5-tribromo-2-ethoxybenzene (98437-52-6)

Conditions	Yield
zersetzt sich in Sonnenlicht.Irradiation;

1.4-dibromobenzene (106-37-6) → 1,3,5-trisbromobenzene (626-39-1)

Conditions	Yield
With aluminium trichloride

1.4-dibromobenzene (106-37-6) → 1,3,5-trisbromobenzene (626-39-1) + 1,2,4-tribromobenzene (615-54-3)

Conditions	Yield
With aluminium trichloride

3,5-dibromoaniline (626-40-4) → 1,3,5-trisbromobenzene (626-39-1)

Conditions	Yield
durch Ueberfuehrung in das Diazoniumperbromid und dessen Zersetzung mit Alkohol;

1,2,3,5-tetrabromobenzene (634-89-9) + sodium ethanolate (141-52-6) → 1,3,5-trisbromobenzene (626-39-1)

2,4,6-tribromoacetophenone (2537-67-9) → 1,3,5-trisbromobenzene (626-39-1)

Conditions	Yield
With potassium hydroxide at 150℃;

2,4,6-tribromobenzaldehyde (45859-98-1) → 1,3,5-trisbromobenzene (626-39-1)

Conditions	Yield
With potassium hydroxide

2,4,6-tribromo-benzenesulfonic acid (101870-36-4) → 1,3,5-trisbromobenzene (626-39-1)

1,3,5-trisbromobenzene (626-39-1) + methyl 5-propyloxy-2-aminobenzoate → 1,3,5-tris(2-carbomethoxy-4-propyloxyphenylamino)benzene

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene for 72h; Inert atmosphere; Reflux;	100%

methanol (67-56-1) + 1,3,5-trisbromobenzene (626-39-1) → 1,2,3-trimethoxybenzene (621-23-8)

Conditions	Yield
Stage #1: methanol; 1,3,5-trisbromobenzene In toluene at 135℃; under 5320.36 Torr; for 0.75h; Stage #2: With triethylamine In toluene at 165℃; under 8360.56 Torr; for 11h; Temperature;	99.5%
With sodium methylate; copper(l) chloride In N,N-dimethyl-formamide at 100 - 110℃; for 6h;	90%
Stage #1: methanol; 1,3,5-trisbromobenzene In N,N-dimethyl-formamide Stage #2: With copper(l) iodide; sodium methylate

1,3,5-trisbromobenzene (626-39-1) + trimethylsilylacetylene (1066-54-2) → 1,3,5-tris-(1-trimethylsilylethynyl)benzene (18772-58-2)

Conditions	Yield
Stage #1: 1,3,5-trisbromobenzene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 50℃; for 0.25h; Sonogashira Cross-Coupling; Stage #2: trimethylsilylacetylene at 90℃; for 48h; Sonogashira Cross-Coupling;	99%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 65℃; for 16h; Sonogashira coupling;	96.4%
With pyridine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 90℃; for 12h; Inert atmosphere;	96.6%

1,3,5-trisbromobenzene (626-39-1) + tris((2-phenyl)ethynyl)indium (250643-76-6) → 1,3,5-tris(2-phenylethynyl)benzene (118688-56-5)

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran Heating;	99%

chloro-trimethyl-silane (75-77-4) + 1,3,5-trisbromobenzene (626-39-1) → 3,5-Bis-trimethylsilyl-bromobenzene (81500-92-7)

Conditions	Yield
Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether at -78℃; for 1h; Stage #2: chloro-trimethyl-silane In diethyl ether at -78 - 20℃; Further stages.;	99%
Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether; hexane at -80℃; for 0.25h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In diethyl ether; hexane at -80 - 20℃; for 1h; Inert atmosphere;	98%
Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether; hexane at -78℃; Stage #2: chloro-trimethyl-silane In diethyl ether; hexane at -78 - 20℃;	85%
With hydrogenchloride In diethyl ether; magnesium	56%

1,3,5-trisbromobenzene (626-39-1) + tert-butyl 1-(4-cyanophenyl)hydrazine-1-carboxylate (226065-32-3) → N'-{3,5-bis-[N'-tert-butoxycarbonyl-N'-(4-cyano-phenyl)-hydrazino]-phenyl}-N-(4-cyano-phenyl)-hydrazinecarboxylic acid tert-butyl ester

Conditions	Yield
With caesium carbonate; palladium diacetate; tri-tert-butyl phosphine In hexane; toluene at 20 - 110℃; for 2.5h;	99%

1,3,5-trisbromobenzene (626-39-1) + N-(4-benzoyl-phenyl)-hydrazinecarboxylic acid tert-butyl ester (226065-39-0) → N-(4-benzoyl-phenyl)-N'-{3,5-bis-[N'-(4-benzoyl-phenyl)-N'-tert-butoxycarbonyl-hydrazino]-phenyl}-hydrazinecarboxylic acid tert-butyl ester

Conditions	Yield
With caesium carbonate; palladium diacetate; tri-tert-butyl phosphine In hexane; toluene at 20 - 110℃; for 3.5h;	99%

1,3,5-trisbromobenzene (626-39-1) + N-(2-methoxy-phenyl)-hydrazinecarboxylic acid tert-butyl ester (380383-87-9) → N'-[3,5-bis-(N'-tert-butoxycarbonyl-N'-(2-methoxy-phenyl)-hydrazino)-phenyl]-N-(2-methoxy-phenyl)-hydrazinecarboxylic acid tert-butyl ester (681815-56-5)

Conditions	Yield
With caesium carbonate; palladium diacetate; tri-tert-butyl phosphine In hexane; toluene at 20 - 110℃; for 2.5h;	99%
With palladium diacetate; caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate In toluene for 2h; Heating;	99%

1,3,5-trisbromobenzene (626-39-1) + 1-tert-butoxycarbonyl-1-(4-phenylphenyl)hydrazine (360045-13-2) → N-(biphenyl-4-yl)-N'-[3,5-bis(N'-(biphenyl-4-yl)-N'-tert-butoxycarbonylhydrazino)phenyl]hydrazinecarboxylic acid tert-butyl ester

Conditions	Yield
With caesium carbonate; palladium diacetate; tri-tert-butyl phosphine In hexane; toluene at 20 - 110℃; for 3.5h;	99%

1,3,5-trisbromobenzene (626-39-1) + N-(4-hexyl-phenyl)-hydrazinecarboxylic acid tert-butyl ester → N'-{3,5-bis-[N'-tert-butoxycarbonyl-N'-(4-hexyl-phenyl)-hydrazino]-phenyl}-N-(4-hexyl-phenyl)-hydrazinecarboxylic acid tert-butyl ester

Conditions	Yield
With caesium carbonate; palladium diacetate; tri-tert-butyl phosphine In hexane; toluene at 20 - 110℃; for 2.5h;	99%

1,3,5-trisbromobenzene (626-39-1) + 3-methoxyphenylboronic acid (10365-98-7) → 3,3''-dimethoxy-5'-(3-methoxyphenyl)-1,1':3',1''-terphenyl (132361-34-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 80℃; for 48h;	99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 48h; Suzuki coupling; Inert atmosphere; Reflux;

1,3,5-trisbromobenzene (626-39-1) + 2-amino-5-methylbenzoic acid methyl ester (18595-16-9) → 1,3,5-tris(2-carbomethoxy-4-methylphenylamino)benzene (1305155-04-7)

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene for 72h; Inert atmosphere; Reflux;	99%

1,3,5-trisbromobenzene (626-39-1) + methyl 5-dodecyloxy-2-amino-benzoate → 1,3,5-tris(2-carbomethoxy-4-dodecyloxyphenylamino)benzene

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene for 72h; Inert atmosphere; Reflux;	99%

1,3,5-trisbromobenzene (626-39-1) + sodium methylate (124-41-4) → 3,5-dibromoanisole (74137-36-3)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 12h;	98%
In N,N-dimethyl-formamide at 80℃; for 8h;	70%
In N,N-dimethyl-formamide at 80℃; for 28h; Inert atmosphere;	48.9%
In pyridine; methanol at 115℃; Rate constant; Product distribution;
In N,N-dimethyl-formamide at 90℃; for 0.25h;

morpholine (110-91-8) + 1,3,5-trisbromobenzene (626-39-1) → 1,3,5-trimorpholinobenzene (16857-97-9)

Conditions	Yield
With sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 24h;	98%
With potassium tert-butylate In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 7h; Buchwald-Hartwig coupling reaction;	86%
With potassium tert-butylate In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 7h; Reagent/catalyst; Buchwald-Hartwig Coupling; Glovebox;	86%

4-phenyl-1-piperazine (92-54-6) + 1,3,5-trisbromobenzene (626-39-1) → C36H42N6

Conditions	Yield
With sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 24h;	98%

1,3,5-trisbromobenzene (626-39-1) + C9H15ClMg (245507-96-4) → 1,3,5-tris(3-tert-butylbicyclo[1.1.1]pent-1-yl)benzene

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 20℃; for 48h; Grignard reaction;	98%

1,3,5-trisbromobenzene (626-39-1) + sodium methylate (124-41-4) → 1,2,3-trimethoxybenzene (621-23-8)

Conditions	Yield
With methanol; Methyl formate; copper(l) chloride at 115℃; for 2h; Autoclave; Green chemistry;	98%
With copper(I) chloride In N,N-dimethyl-formamide at 130℃; for 6h;	91%

1,3,5-trisbromobenzene (626-39-1) + phenylboronic acid (98-80-6) → 1,3,5-triphenylbenzene (612-71-5)

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 1h; Suzuki-Miyaura reaction;	98%
With sodium carbonate; palladium diacetate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki;	97%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine In 1,1,1,2,3,3,3-Heptafluoropropane; ethanol; 1,1,1,3,3-pentafluorobutane at 20℃; for 24h; Inert atmosphere;	96%

1,3,5-trisbromobenzene (626-39-1) + N-phenyl-hydrazine carboxylic acid tert-butyl ester (226065-37-8) → N'-[3,5-bis-(N'-tert-butoxycarbonyl-N'-phenyl-hydrazino)-phenyl]-N-phenylhydrazinecarboxylic acid tert-butyl ester (681815-36-1)

Conditions	Yield
With caesium carbonate; palladium diacetate; tri-tert-butyl phosphine In hexane; toluene at 20 - 110℃; for 2.5h;	98%
With palladium diacetate; caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate In toluene for 2h; Heating;	98%

1,3,5-trisbromobenzene (626-39-1) + tert-butyl 1-p-tolylhydrazinecarboxylate (497064-60-5) → N'-[3,5-bis(N'-tert-butoxycarbonyl-N'-p-tolylhydrazino)phenyl]-N-p-tolylhydrazinecarboxylic acid tert-butyl ester

Conditions	Yield
With caesium carbonate; palladium diacetate; tri-tert-butyl phosphine In hexane; toluene at 20 - 110℃; for 2.5h;	98%

1,3,5-trisbromobenzene (626-39-1) + 1,1-dimethyl-1,3-dihydrobenzo[c][1,2]oxasilole (321903-29-1) → (3,5-dibromophenyl)[2-(hydroxymethyl)phenyl]dimethylsilane (1239354-49-4)

Conditions	Yield
Stage #1: 1,3,5-trisbromobenzene With n-butyllithium In diethyl ether; hexane at -78℃; for 2.5h; Stage #2: 1,1-dimethyl-1,3-dihydrobenzo[c][1,2]oxasilole In diethyl ether; hexane at -78 - 20℃;	98%

1,3,5-trisbromobenzene (626-39-1) + bis(pinacol)diborane (73183-34-3) → 1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (365564-05-2)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere;	98%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere;	98%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere;	96%

1,3,5-trisbromobenzene (626-39-1) + di-p-tolylamine (620-93-9) → N1,N1,N3,N3,N5,N5-hexakis(4-methylphenyl)-1,3,5-benzenetriamine (134257-64-0)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 60℃; for 7h; Inert atmosphere; Schlenk technique;	98%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 60℃; for 7h; Inert atmosphere;	98%

1,3,5-trisbromobenzene (626-39-1) + N-methylaniline (100-61-8) → N1,N3,N5-trimethyl-N1,N3,N5-triphenylbenzene-1,3,5-triamine

Conditions	Yield
With (6-Dipp)PdCl2-SPhos; sodium t-butanolate In neat (no solvent) at 110℃; for 24h; Buchwald-Hartwig Coupling;	98%

1,3,5-trisbromobenzene (626-39-1) → deuterated 1,3,5-tribromobenzene (52921-77-4)

Conditions	Yield
With water-d2; silver(l) oxide; 2-(dicyclohexylphosphino)-2'-methylbiphenyl In toluene at 60 - 80℃; Reagent/catalyst;	97.1%
With water-d2; potassium carbonate; silver carbonate; cyclohexyldiphenylphosphine In toluene at 120℃; for 12h;	90%

1,3,5-trisbromobenzene (626-39-1) + triphenylindium (3958-47-2) → 1,3,5-triphenylbenzene (612-71-5)

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran Heating;	97%
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran for 6h; Heating;	97%

1,3,5-trisbromobenzene (626-39-1) + 4-methoxyphenylboronic acid (5720-07-0) → 1,3,5-tris(4-methoxyphenyl)benzene (7509-20-8)

Conditions	Yield
With sodium carbonate; palladium diacetate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki;	97%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane for 48h; Suzuki Coupling; Inert atmosphere; Reflux;	95%
With potassium carbonate In ethanol; water at 20℃; for 0.333333h; Suzuki-Miyaura Coupling; Green chemistry;	95%

1,3,5-trisbromobenzene (626-39-1) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 3,5-dibromobenzoate (422569-46-8)

Conditions	Yield
Stage #1: 1,3,5-trisbromobenzene With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -10℃; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; hexane; toluene at -10℃; Stage #3: With citric acid In tetrahydrofuran; hexane; toluene Further stages.;	97%
Stage #1: 1,3,5-trisbromobenzene With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -5℃; for 1h; Inert atmosphere; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; hexane; toluene at -5℃; for 2h; Temperature; Inert atmosphere;	97%

Upstream product

• 67-56-1 methanol 
• 64-18-6 formic acid 
• 64-17-5 ethanol 
• 634-89-9 1,2,3,5-tetrabromobenzene 
• 141-52-6 sodium ethanolate 
• 64-19-7 acetic acid 
• 21521-51-7 2,4,6-tribromoiodobenzene 
• 71-43-2 benzene 
• 147-82-0 2,4,6-tribromoaniline 
• 544-92-3 copper(I) cyanide 
• 52722-79-9 2,4,6-tribromophenylhydrazine 
• 7697-37-2 nitric acid 
• 7664-93-9 sulfuric acid 
• 7446-70-0 aluminium trichloride 

Downstream Products

• 18141-34-9 me(ph-3.5-Br₂)SiCl₂ 
• 75307-79-8 1,3,5-tri(1H-pyrazol-1-yl)benzene 
• 126717-23-5 N¹,N¹,N³,N³,N⁵,N⁵-hexaphenyl-1,3,5-benzenetriamine 
• 118688-56-5 1,3,5-tris(2-phenylethynyl)benzene 
• 18772-58-2 1,3,5-tris-(1-trimethylsilylethynyl)benzene 
• 160976-68-1 Bis(3,5-dibromophenyl)methanol 
• 167013-92-5 Bis-(4-tert-butyl-phenyl)-(3,5-dibromo-phenyl)-methanol 
• 16372-96-6 3,5-dibromo-1,1′-biphenyl 
• 103068-20-8 1-bromo-3,5-diphenylbenzene 
• 170165-84-1 1,3,5-tri(pyridin-4-yl)benzene 
• 188774-41-6 N-(3,5-dehydrophenyl)-3-fluoropyridinium cation 
• 633-12-5 2,4,6-tribromobenzoic acid 
• 626-44-8 1,3,5-Triiodobenzene 
• 14862-52-3 1,3-dibromo-5-chlorobenzene 

Relevant articles and documents

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Drawbacks associated with the classic Balz-Schiemann reaction are eliminated in a series of examples by conducting fluorodediazoniation in ionic liquid solvents, thus opening up a new horizon for a much in demand process.