97511-05-2

Basic information

• Product Name: 4-BROMODIBENZOTHIOPHENE
• Synonyms: 4-BROMODIBENZOTHIOPHENE;Dibenzothiophene,4-broMo-;4-Bromodibenzo[b,d]thiophene
• CAS NO: 97511-05-2
• Molecular Formula: C₁₂H₇BrS
• Molecular Weight: 263.15
• EINECS: 1312995-182-4
• Product Categories: OLED
• Mol File: 97511-05-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 85.0 to 89.0 °C
• Boiling Point: 386.6 °C at 760 mmHg
• Flash Point: 187.6 °C
• Appearance: /
• Density: 1.611
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-BROMODIBENZOTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMODIBENZOTHIOPHENE(97511-05-2)
• EPA Substance Registry System: 4-BROMODIBENZOTHIOPHENE(97511-05-2)

Safety Data

• Hazardous Substances Data: 97511-05-2(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow powder

Synthetic route

dibenzothiophene (132-65-0) → 4-bromodibenzothiophene (97511-05-2)

Conditions	Yield
Stage #1: dibenzothiophene With n-butyllithium In tetrahydrofuran at -40 - 0℃; for 7h; Stage #2: With ethylene dibromide In tetrahydrofuran at -78 - 20℃; for 12h;	95%
Stage #1: dibenzothiophene With n-butyllithium In tetrahydrofuran at -40 - 0℃; for 6h; Stage #2: With ethylene dibromide In tetrahydrofuran at -78 - 20℃; for 14h;	71%
Stage #1: dibenzothiophene With n-butyllithium In tetrahydrofuran at -78 - 0℃; Stage #2: With ethylene dibromide In tetrahydrofuran at -78 - 20℃; for 12h;	60%

3-bromo-2-(methylsulfinyl)-1,1‘-biphenyl → 4-bromodibenzothiophene (97511-05-2)

Conditions	Yield
Stage #1: 3-bromo-2-(methylsulfinyl)-1,1‘-biphenyl With trifluoroacetic acid at 20℃; for 24h; Stage #2: With pyridine In water for 0.5h; Reflux;	88%
Stage #1: 3-bromo-2-(methylsulfinyl)-1,1‘-biphenyl With trifluorormethanesulfonic acid at 20℃; for 24h; Stage #2: With pyridine In water for 0.5h; Reflux;	81%
Stage #1: 3-bromo-2-(methylsulfinyl)-1,1‘-biphenyl With trifluorormethanesulfonic acid In water at 20℃; for 24h; Stage #2: With pyridine In water for 0.5h; Reflux;	81%

4-bromo-dibenzo[b,d]thiophene S-oxide → dibenzothiophene (132-65-0) + Dibenzothiophene sulfoxide (1013-23-6) + 4-bromodibenzothiophene (97511-05-2)

Conditions	Yield
In acetonitrile Quantum yield; Photolysis;

biphenyl (92-52-4) → 4-bromodibenzothiophene (97511-05-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminium chloride; sulfur 2: butyl lithium; diethyl ether / Behandeln der Reaktionsloesung mit Brom-Dampf in Stickstoff-Strom View Scheme

4-bromodibenzothiophene (97511-05-2) → 4-bromo-dibenzo[b,d]thiophene S-oxide

Conditions	Yield
With boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid In hexane; dichloromethane at -30℃; Inert atmosphere;	99%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -30℃; for 1.5h;	50%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 2h; Inert atmosphere;

4-bromodibenzothiophene (97511-05-2) + (2-methylsulfanylphenyl)boronic acid (168618-42-6) → 4-[2-(methylthio)phenyl]dibenzothiophene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 120℃; for 3h; Suzuki Coupling;	99%

4-bromodibenzothiophene (97511-05-2) + (2’-fluoro-[1,1’-biphenyl]2-yl)boronic acid → 4-(2'-fluoro-[1,1'-biphenyl]-2-yl)dibenzo[b,d]thiophene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; water; toluene for 18h; Suzuki Coupling; Inert atmosphere; Reflux;	99%

4-bromodibenzothiophene (97511-05-2) + phenylboronic acid (98-80-6) → 4-phenyldibenzo[b,d]thiophene (98251-31-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 80℃; for 24h; Inert atmosphere;	97%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 18h; Inert atmosphere;	84%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Reflux;	82%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Reflux;	82%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; for 3.5h;

4-bromodibenzothiophene (97511-05-2) + bis(pinacol)diborane (73183-34-3) → 2-(dibenzo[b,d]thiophen-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (912824-84-1)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane Reflux;	95%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃;	90%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 120℃;	80%

4-bromodibenzothiophene (97511-05-2) + C39H33BN4O2 → C45H28N4S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere;	95%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere;	92%

tetrahydrofuran (109-99-9) + 4-bromodibenzothiophene (97511-05-2) → 2-(dibenzo[b,d]thiophen-4-yl)tetrahydrofuran

Conditions	Yield
With bis(acetylacetonate)nickel(II); 5,5'-dimethyl-2,2'-bipyridine; (4-methoxyphenyl)(4-(trifluoromethyl)phenyl)methanone; sodium carbonate at 20℃; for 60h; Schlenk technique; Inert atmosphere; Irradiation; chemoselective reaction;	93%

4-bromodibenzothiophene (97511-05-2) → C12H7BrO2S

Conditions	Yield
With dihydrogen peroxide; acetic acid In tetrahydrofuran at 80℃; for 2h;	93%

4-bromodibenzothiophene (97511-05-2) + aniline (62-53-3) → N-(dibenzothiophene-4-yl)-N-phenyl-amine (1252914-52-5)

Conditions	Yield
Stage #1: 4-bromodibenzothiophene; aniline With sodium t-butanolate In toluene for 1h; Inert atmosphere; Stage #2: With tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate In toluene for 2h; Inert atmosphere; Reflux;	91%
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate In toluene at 100℃; for 10h; Inert atmosphere; Schlenk technique; Sealed tube;	86%
With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate In toluene at 100℃; for 7h; Schlenk technique; Inert atmosphere;	77.8%

4-bromodibenzothiophene (97511-05-2) + 2-carbomethoxyaniline (134-20-3) → methyl 2-(dibenzo[b,d]thiophen-4-ylamino)benzoate

Conditions	Yield
With palladium diacetate; caesium carbonate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 110℃; Inert atmosphere;	90%
Stage #1: 4-bromodibenzothiophene With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene for 3h; Stage #2: 2-carbomethoxyaniline In toluene Reflux;	86.8%
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene for 24h; Buchwald-Hartwig Coupling; Reflux; Inert atmosphere;

4-bromodibenzothiophene (97511-05-2) + (6-phenyldibenzo[b,d]furan-4-yl)boronic acid (1010068-85-5) → C30H18OS

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Reflux;	89%

4-bromodibenzothiophene (97511-05-2) + 2-methoxycarbonylphenylboronic acid (374538-03-1) → C20H14O2S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 95 - 100℃; Inert atmosphere;	87.4%

4-bromodibenzothiophene (97511-05-2) → 4-hydroxydibenzothiophene (24444-75-5)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium hydroxide; tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 16h;	87%
With sodium hydroxide; copper In water at 240 - 260℃; for 24h; autoclave;	72%

4-bromodibenzothiophene (97511-05-2) + C32H21NS → C44H27NS2

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene Inert atmosphere; Reflux;	87%

4-bromodibenzothiophene (97511-05-2) + (6-phenyldibenzo[b,d]thiophen-4-yl)boronic acid (1115640-18-0) → C30H18S2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Reflux;	86%

4-bromodibenzothiophene (97511-05-2) + C36H21NS4 → C48H27NS5

Conditions	Yield
With copper; potassium carbonate In nitrobenzene for 16h; Inert atmosphere; Reflux;	85%

4-bromodibenzothiophene (97511-05-2) + para-thiocresol (106-45-6) → 4-(p-tolylthio)dibenzo[b,d]thiophene (113525-43-2)

Conditions	Yield
With nickel(II) bromide dimethoxyethane; 4,4'-di-tert-butyl-2,2'-bipyridine; lithium bromide In N,N-dimethyl-formamide at 20℃; for 6h; Electrochemical reaction;	85%

4-bromodibenzothiophene (97511-05-2) + 3-chloro-6-(dibenzo[b,d]furan-4-yl)-9H-carbazole → 3-chloro-6-(dibenzo[b,d]furan-4-yl)-9-(dibenzo[b,d]thiophen-4-yl)-9H-carbazole

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 4h;	85%

4-bromodibenzothiophene (97511-05-2) + zinc(II) chloride (7646-85-7) → C12H7BrSZn

Conditions	Yield
With magnesium; fullerene-C60; lithium chloride In tetrahydrofuran; 1,2-dimethoxyethane at 25℃; for 1h; Schlenk technique; Inert atmosphere;	84%

4-bromodibenzothiophene (97511-05-2) + C36H23NOS → C48H29NOS2

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene Reflux; Inert atmosphere;	84%

4-bromodibenzothiophene (97511-05-2) + 2-(carbazol-9-yl)-9H-carbazole (1226810-15-6) → 9-(dibenzo[b,d]thiophen-4-yl)-9H-2,9'-bicarbazole

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 24h; Reflux; Inert atmosphere;	83%

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + 4-bromodibenzothiophene (97511-05-2) → dibenzo[b,d]thiophene-4-carboxamide (197571-97-4)

Conditions	Yield
With 1H-imidazole; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; ammonium chloride; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 90℃; for 3h; Sealed tube;	82%

4-bromodibenzothiophene (97511-05-2) + Trimethyl borate (121-43-7) → 4-dibenzothiophene boronic acid (108847-20-7)

Conditions	Yield
Stage #1: 4-bromodibenzothiophene With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 1h; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 12h;	82%
Stage #1: 4-bromodibenzothiophene With n-butyllithium In tetrahydrofuran for 2h; Cooling with acetone-dry ice; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 0℃; for 1h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0 - 20℃; for 8h;
Stage #1: 4-bromodibenzothiophene With n-butyllithium at -78 - 0℃; Stage #2: Trimethyl borate at -78 - 20℃; Stage #3: With hydrogenchloride In water at 0 - 20℃;

4-bromodibenzothiophene (97511-05-2) + C18H13NS2 → C30H19NS3

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene for 6h; Inert atmosphere; Reflux;	81%

4-bromodibenzothiophene (97511-05-2) + 4-(phenanthren-9-yl)aniline → C32H21NS

Conditions	Yield
With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene Reflux; Inert atmosphere;	81%

4-bromodibenzothiophene (97511-05-2) + 9-(9H-carbazol-3-yl)-9H-carbazole (18628-07-4) → 9-(dibenzo[b,d]thiophen-4-yl)-9H-3,9'-bicarbazole

Conditions	Yield
With copper(l) iodide; XPhos In 5,5-dimethyl-1,3-cyclohexadiene for 216h; Inert atmosphere; Reflux;	81%
With potassium phosphate; copper(l) iodide; rac-diaminocyclohexane In 5,5-dimethyl-1,3-cyclohexadiene for 576h; Inert atmosphere; Reflux;	81%

4-bromodibenzothiophene (97511-05-2) + C45H36BN3O2 → C51H31N3S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Reflux;	80%

4-bromodibenzothiophene (97511-05-2) + 3-chloro-6-(dibenzo[b,d]furan-3-yl)-9H-carbazole → 3-chloro-6-(dibenzo[b,d]furan-3-yl)-9-(dibenzo[b,d]thiophen-4-yl)-9H-carbazole

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 4h;	80%

Upstream product

• 132-65-0 dibenzothiophene 
• 92-52-4 biphenyl 

Downstream Products

• 72433-66-0 dibenzo[b,d]thiophene-4-amine 
• 1345970-20-8 3-bromo-9-(dibenzo[b,d]thiophen-4-yl)-9H-carbazole 
• 1345143-20-5 9-(dibenzo[b,d]thiophen-4-yl)-9?-phenyl-9H,9'H-3,3?-bicarbazole 
• 1345143-35-2 9-(dibenzo thiophen-4-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 
• 1353720-54-3 N-(3-(1,3-dioxolan-2-yl)phenyl)dibenzo[b,d]thiophen-4-amine 
• 108847-20-7 4-dibenzothiophene boronic acid 
• 912824-84-1 2-(dibenzo[b,d]thiophen-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 222-21-9 12H-benzo[4,5]thieno[2,3-a]carbazole 

Relevant articles and documents

S,S-dioxo-dibenzothiophene and phenanthroimidazole based small molecule and application thereof in electroluminescent devices

The invention discloses an S,S-dioxo-dibenzothiophene and phenanthroimidazole based small molecule and application thereof in electroluminescent devices. Phenanthroimidazole is used as a donor unit, S,S-dioxo-dibenzothiophene is used as an acceptor unit, and a novel donor-acceptor type blue fluorescent molecule is constructed. The molecule has the characteristics of S,S-dioxo-dibenzothiophene suchas wide band gap, high fluorescence quantum yield, strong electron affinity, high electron mobility, and also has the characteristics of phenanthroimidazole such as large conjugate rigid structure, bipolar transmission, and the like. The molecule has an asymmetric structure, and can inhibit molecular aggregation and reduce exciton quenching. In addition, the emission spectrum can be adjusted by changing the connection sites of the two units. The small molecule can be used for preparing high-efficiency blue light organic electroluminescent devices with different emission wavelengths.

COMPOUND FOR ORGANIC ELECTRIC ELEMENT, ORGANIC ELECTRIC ELEMENT COMPRISING THE SAME AND ELECTRONIC DEVICE THEREOF

Provided is a compound which is represented by chemical formula 1. Also, provided is an organic electrical device which comprises: a first electrode; a second electrode; and an organic material layer between the first electrode and the second electrode. The organic material layer includes the compound represented by chemical formula 1. When the compound represented by chemical formula 1 is contained in the organic material layer of the organic electrical device, driving voltage decreases, while luminous efficiency, color purity, and lifespan increase.COPYRIGHT KIPO 2017

COMPOUND FOR ORGANIC ELECTRIC ELEMENT, ORGANIC ELECTRIC ELEMENT COMPRISING THE SAME AND ELECTRONIC DEVICE THEREOF

The present invention refers to formula 1 compounds represented by number under public affairs substrate. In addition, electrode number 1, number 2 electrode and said number 1 electrode including said number 2 electrode and electrode under public affairs number organic solvent, said organic compound layer is formed comprises a formula 1 compound. Organic compound represented by formula 1 organic layer of the electrical component are included, a predetermined driving voltage, luminous efficiency, can be fixed to the color purity and their service life. (by machine translation)