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Bromobenzene Manufacturer/High quality/Best price/In stock
Cas No: 108-86-1
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High quality Bromobenzene supplier in China
Cas No: 108-86-1
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Bromobenzene
Cas No: 108-86-1
USD $ 1.0-2.0 / Metric Ton 1 Metric Ton 100 Metric Ton/Week Hebei yanxi chemical co.,LTD. Contact Supplier
bromobenzene
Cas No: 108-86-1
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Bromobenzene
Cas No: 108-86-1
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Amadis Chemical offer CAS#108-86-1;CAT#A801934
Cas No: 108-86-1
No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier
Bromobenzene
Cas No: 108-86-1
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Phenylbromide
Cas No: 108-86-1
USD $ 1.0-1.0 / Kilogram 1 Kilogram 1000 Metric Ton/Year Henan Sinotech Import&Export Corporation Contact Supplier
108-86-1 Bromobenzene
Cas No: 108-86-1
USD $ 1000.0-1000.0 / Kilogram 1 Kilogram 1 Metric Ton/Day Henan Tianfu Chemical Co., Ltd. Contact Supplier
Bromobenzene
Cas No: 108-86-1
USD $ 12.0-12.0 / Metric Ton 1 Metric Ton 100 Metric Ton/Year Jinan Finer Chemical Co., Ltd Contact Supplier

108-86-1 Usage

Air & Water Reactions

Flammable. Insoluble in water.

General Description

Mobile clear colorless liquid with a pungent odor. Flash point 124°F. Denser than water and insoluble in water. Hence sinks in water. Vapors are heavier than air. A skin irritant.

Reactivity Profile

Bromobenzene may be sensitive to light. May react with oxidizing agents .

Uses

In organic synthesis, especially to make phenyl magnesium bromide; as solvent, especially for crystallizations on a large scale and where a heavy liquid is desirable; as additive to motor oils.

Fire Hazard

Special Hazards of Combustion Products: Irritating hydrogen bromide and other gases may be produced in fire.

Chemical Properties

colourless liquid

Purification Methods

Wash bromobenzene vigorously with conc H2SO4, then 10% NaOH or NaHCO3 solutions, and H2O. Dry it with CaCl2 or Na2SO4, or pass it through activated alumina, before refluxing with, and distilling from, CaH2, using a glass helix-packed column. [Beilstein 5 IV 670.]

Health Hazard

Contact with liquid causes irritation of eyes and mild irritation of skin. Ingestion causes mild irritation of mouth and stomach.
InChI:InChI=1/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H

108-86-1 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A11407)  Bromobenzene, 99%    108-86-1 10000g 3312.0CNY Detail
Alfa Aesar (A11407)  Bromobenzene, 99%    108-86-1 2500g 861.0CNY Detail
Alfa Aesar (A11407)  Bromobenzene, 99%    108-86-1 500g 284.0CNY Detail
TCI America (B0439)  Bromobenzene  >99.0%(GC) 108-86-1 500g 280.00CNY Detail
TCI America (B0439)  Bromobenzene  >99.0%(GC) 108-86-1 25g 125.00CNY Detail

108-86-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name bromobenzene

1.2 Other means of identification

Product number -
Other names phenyl benzyl thioether

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:108-86-1 SDS

108-86-1Synthetic route

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
With potassium carbonate; iron pentacarbonyl In methanol at 60℃; under 760 Torr; for 48h;98%
With butyl magnesium bromide; zirconocene dichloride In tetrahydrofuran for 1h; Ambient temperature;98%
With tris-(trimethylsilyl)silane In acetonitrile for 24h; Schlenk technique; Inert atmosphere; Irradiation;93%
benzene
71-43-2

benzene

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
With carbon dioxide; bromine at 40℃; under 187519 Torr; for 2h; Supercritical conditions; Green chemistry;100%
With lead(II,IV) oxide; trifluoroacetic acid; potassium bromide at 20℃; Product distribution; reagents ratio;96%
With gold(III) chloride; N-Bromosuccinimide In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; regioselective reaction;94%
carbon monoxide
201230-82-2

carbon monoxide

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

A

bromobenzene
108-86-1

bromobenzene

B

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

C

benzene
71-43-2

benzene

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 50℃; under 2280 Torr;A 9 % Chromat.
B 70%
C 4 % Chromat.
With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 50℃; under 2280 Torr;A 4%
B 70%
C 10%
carbon monoxide
201230-82-2

carbon monoxide

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

A

bromobenzene
108-86-1

bromobenzene

B

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

Conditions
ConditionsYield
With hydrogen; potassium carbonate In 1,4-dioxane at 120 - 140℃; under 30003 Torr; for 20h; Autoclave;A 17%
B 39%
Diphenyliodonium triflate
66003-76-7

Diphenyliodonium triflate

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
With copper(I) bromide In acetonitrile at 80℃; for 2h; Reagent/catalyst; Solvent; Temperature;91%
benzoic acid
65-85-0

benzoic acid

A

bromobenzene
108-86-1

bromobenzene

B

chlorobenzene
108-90-7

chlorobenzene

Conditions
ConditionsYield
With trichloroisocyanuric acid; bromine In tetrachloromethane at -10 - 100℃; for 4h; Photolysis;A 7%
B 87%
diphenyliodonium p-toluenesulfonate
6293-66-9

diphenyliodonium p-toluenesulfonate

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
With copper(I) bromide In acetonitrile at 80℃; for 2h;71%
diphenyliodonium hexafluorophosphate
58109-40-3

diphenyliodonium hexafluorophosphate

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
With copper(I) bromide In acetonitrile at 80℃; for 2h;65%
diphenyliodonium tetrafluoroborate

diphenyliodonium tetrafluoroborate

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
With copper(I) bromide In acetonitrile at 80℃; for 2h;63%
diphenyliodonium chloride
1483-72-3

diphenyliodonium chloride

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
With copper(I) bromide In acetonitrile at 80℃; for 2h;45%
diphenyliodonium bromide
1483-73-4

diphenyliodonium bromide

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
With copper(I) bromide In acetonitrile at 80℃; for 2h;40%
4-bromo-aniline
106-40-1

4-bromo-aniline

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
Stage #1: 4-bromo-aniline With tetrafluoroboric acid; acetic acid; isopentyl nitrite In water at 18℃; for 0.0833333h;
Stage #2: With eosin Y disodium salt In N,N-dimethyl-formamide at 18℃; for 6h; Concentration; Reagent/catalyst; Solvent; Inert atmosphere; UV-irradiation; Schlenk technique;
81%
With formamide; triethylamine; trifluoroacetic acid; sodium nitrite 1.) formamide/water, r.t.; 2.) water, r.t.; Yield given. Multistep reaction;
Stage #1: 4-bromo-aniline With Nitrogen dioxide In acetonitrile at -20℃; Diazotization;
Stage #2: With calcium bis(hypophosphite); Fe2SO4*7H2O In methanol; acetonitrile at 20℃; Dediazonation;
16 % Chromat.
1-(2-bromophenyl)-2-(methylsulfonyl)diazene

1-(2-bromophenyl)-2-(methylsulfonyl)diazene

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
In water; isopropyl alcohol for 14h; Irradiation;97%
1-(4-bromophenyl)-2-(methylsulfonyl)diazene
56075-37-7

1-(4-bromophenyl)-2-(methylsulfonyl)diazene

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
In water; isopropyl alcohol for 14h; Irradiation;97%
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
With Triethoxysilane; C20H24N4Ni; sodium t-butanolate In toluene at 80℃; for 8h; Kumada Cross-Coupling; Inert atmosphere; Schlenk technique;93%
With hydrogen cation; copper 1) THF, -78 deg C, 10 min; Yield given. Multistep reaction;
With hydrogenchloride; CuI*P(Et)3; naphthalen-1-yl-lithium 1.) THF, -78 deg C, 10 min; Yield given. Multistep reaction;
With tetrabutylammomium bromide; palladium diacetate; potassium hydroxide; 2′-(diphenylphosphino)-N,N′-dimethyl-(1,1′-biphenyl)-2-amine In methanol; water at 120℃; Microwave irradiation;43 %Chromat.
para-bromobenzenethiol
106-53-6

para-bromobenzenethiol

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
dicobalt octacarbonyl In water; benzene at 185 - 190℃; under 46543.3 Torr;77%
1,4-benzenebisdiazonium tetrafluoroborate

1,4-benzenebisdiazonium tetrafluoroborate

A

bromobenzene
108-86-1

bromobenzene

B

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With dibenzo-18-crown-6; potassium bromide; copper(ll) bromide; 1,10-Phenanthroline; copper(I) bromide In acetonitrile at 20℃; for 0.333333h; Sandmeyer bromination;A 6%
B 91%
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

1-amino-2-propene
107-11-9

1-amino-2-propene

A

bromobenzene
108-86-1

bromobenzene

B

2-bromo-N-(prop-2-enyl)aniline
73396-91-5

2-bromo-N-(prop-2-enyl)aniline

Conditions
ConditionsYield
With dodecane; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; for 15h;A 6.6%
B 17.5%
phenylboronic acid
98-80-6

phenylboronic acid

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
With N-Bromosuccinimide In acetonitrile at 81℃; for 14h;57%
With water; copper(ll) bromide
With gold(III) chloride; N-Bromosuccinimide In 1,2-dichloro-ethane at 60℃; for 24h;
With potassium bromide In water at 80℃;
Triethoxysilane
998-30-1

Triethoxysilane

1,4-bromoiodobenzene
589-87-7

1,4-bromoiodobenzene

A

bromobenzene
108-86-1

bromobenzene

B

(4-bromophenyl)triethoxysilane
18954-74-0

(4-bromophenyl)triethoxysilane

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; johnphos; bis(dibenzylideneacetone)-palladium(0) In 1-methyl-pyrrolidin-2-one at 20℃; for 2h;A n/a
B 68%
phenylhydrazine hydrochloride
59-88-1

phenylhydrazine hydrochloride

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
With boron tribromide; dimethyl sulfoxide at 80℃; for 1h;42%
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

1-amino-2-propene
107-11-9

1-amino-2-propene

A

N-allyl-N-phenylamine
589-09-3

N-allyl-N-phenylamine

B

3-Methylindole
83-34-1

3-Methylindole

C

bromobenzene
108-86-1

bromobenzene

D

2-bromo-N-(prop-2-enyl)aniline
73396-91-5

2-bromo-N-(prop-2-enyl)aniline

Conditions
ConditionsYield
With dodecane; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; for 15h;A 4.3%
B 3.7%
C 11.4%
D 20.3%
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

1-amino-2-propene
107-11-9

1-amino-2-propene

A

N-allyl-N-phenylamine
589-09-3

N-allyl-N-phenylamine

B

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
With dodecane; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; for 15h;A 3.5%
B 20.9%
1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

phenylboronic acid
98-80-6

phenylboronic acid

A

bromobenzene
108-86-1

bromobenzene

B

4-bromo-1,1'-biphenyl
92-66-0

4-bromo-1,1'-biphenyl

C

[1,1';4',1'']terphenyl
92-94-4

[1,1';4',1'']terphenyl

Conditions
ConditionsYield
With (2,4-dibenzyl-2,4-dihydro-3H-1,2,4-triazol-3-ylidene)(dibromo)(pyridine)palladium; tetrabutylammomium bromide In N,N-dimethyl-formamide; isopropyl alcohol at 80℃; for 2h; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere;A 10%
B n/a
C n/a
Tetramethylammonium Bis<α,α-bis(trifluoromethyl)-benzenemethanolato(2-)-C2,O>phenylsilicate
70083-69-1

Tetramethylammonium Bis<α,α-bis(trifluoromethyl)-benzenemethanolato(2-)-C2,O>phenylsilicate

A

bromobenzene
108-86-1

bromobenzene

B

C18H8F12O2Si
70091-69-9

C18H8F12O2Si

Conditions
ConditionsYield
With bromine at 25℃; for 24h;A n/a
B 75%
1,3-dibromobenzene
108-36-1

1,3-dibromobenzene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

A

bromobenzene
108-86-1

bromobenzene

B

(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bromobenzene)
594823-67-3

(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bromobenzene)

Conditions
ConditionsYield
With copper(l) iodide; iron(III)-acetylacetonate; N,N,N,N,-tetramethylethylenediamine; sodium hydride In tetrahydrofuran; mineral oil at -10℃; Inert atmosphere;A n/a
B 79%
iodobenzene
591-50-4

iodobenzene

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
With copper(I) bromide at 135℃; for 24h;91%
With bromobenzene; tetrabutylammomium bromide; o-CH3C6H4NiBr(PEt3)2 In benzene at 80℃; for 20h; sealed tube; Yield given;
With aluminum oxide; copper(I) bromide In various solvent(s) at 150℃; for 9h;87 % Chromat.
With copper(I) bromide In N,N-dimethyl acetamide at 137℃; Equilibrium constant; Rate constant; equilibrium order; aalso at 53 deg C; also with CuBr2;
With n-hexylzirconocene chloride; [nickel(II) (4,4'-di-tert-butyl-2,2'-bipyridine)(bromide)2]; tetrabutylammonium p-toluenesulfonate In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Irradiation; Sealed tube;
tetraethylammonium bis<α,α-bis(trifluorometyl)benzenemethanolato(2-)-C2,O>-n-butylsilicate(1-)
97878-04-1

tetraethylammonium bis<α,α-bis(trifluorometyl)benzenemethanolato(2-)-C2,O>-n-butylsilicate(1-)

A

bromobenzene
108-86-1

bromobenzene

B

C18H8F12O2Si
70091-69-9

C18H8F12O2Si

Conditions
ConditionsYield
With bromine at 25℃; for 24h;A n/a
B 74.6%
1-Bromo-3-iodobenzene
591-18-4

1-Bromo-3-iodobenzene

bromobenzene
108-86-1

bromobenzene

Conditions
ConditionsYield
With hydrogenchloride; CuI*P(Et)3; naphthalen-1-yl-lithium 1.) THF, 25 deg C, 60 min; Yield given. Multistep reaction;
With tetrahydrofuran; 1,10-Phenanthroline; potassium tert-butylate at 70℃; for 24h; Schlenk technique; Inert atmosphere; chemoselective reaction;83 %Chromat.
1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

A

bromobenzene
108-86-1

bromobenzene

B

benzene
71-43-2

benzene

Conditions
ConditionsYield
With hydrogen bromide; bromine; iron(III) chloride at 60 - 62℃; for 2.66667h; Product distribution / selectivity;
With bromine; iron(III) chloride at 75 - 80℃; for 5.2h; Product distribution / selectivity;
With hydrogen bromide; bromine; ferric(III) bromide In water at 52 - 64℃; for 4.66667h; Product distribution / selectivity;
With hydrogen bromide; bromine; iron In water at 62 - 66℃; for 4.28333h; Product distribution / selectivity;
morpholine
110-91-8

morpholine

bromobenzene
108-86-1

bromobenzene

4-Phenylmorpholine
92-53-5

4-Phenylmorpholine

Conditions
ConditionsYield
With sodium t-butanolate; palladium diacetate; [(μ-PPh2CH2PPh2)Co2(CO)4][μ,η-PhCCP(tBu)2] In toluene at 60℃; for 20h; Product distribution; Further Variations:; Catalysts; Reagents; Solvents; Temperatures;100%
With C20H45N2OP; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 105℃; for 20h; Reagent/catalyst;100%
With bis(η3-allyl-μ-chloropalladium(II)); [(μ-Ph2PCH2PPh2)Co2(CO)4(μ,η-Me2NCH2CCP(C6H11)2)]; sodium t-butanolate In toluene at 80℃; for 2h; Inert atmosphere;99%
bromobenzene
108-86-1

bromobenzene

biphenyl
92-52-4

biphenyl

Conditions
ConditionsYield
With palladium diacetate; triethylamine; 2-diphenylphosphino-2'-methylbiphenyl In N,N-dimethyl-formamide at 100℃; for 5h; Ullmann reaction; Inert atmosphere;100%
With potassium carbonate In ethanol; water at 20℃; for 12h; Ullmann Condensation;100%
dibromobis(triphenylphosphine)nickel(II); tetraethylammonium iodide; zinc In tetrahydrofuran at 50℃; for 1.5h;99%
bromobenzene
108-86-1

bromobenzene

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

Conditions
ConditionsYield
With bromine fluoride In ethanol; chloroform at -78℃; for 0.5h;100%
With sulfuric acid; bromine; mercury(II) oxide In tetrachloromethane for 2.5h; Heating;76%
With bromine; silver perchlorate; magnesium oxide
bromobenzene
108-86-1

bromobenzene

aniline
62-53-3

aniline

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h;100%
With ammonia; copper In water at 100℃; for 24h; Ullmann reaction;99.1%
With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 80℃; for 23h; Inert atmosphere;98%
bromobenzene
108-86-1

bromobenzene

benzene
71-43-2

benzene

Conditions
ConditionsYield
With sodium hydroxide; ethanol; hydrogen; PdCl2-poly(N-vinyl-2-pyrrolidone); palladium dichloride at 65℃; under 760 Torr; for 2h;100%
With 9-borabicyclo[3.3.1]nonane dimer; triphenylstannane In toluene at 0℃;100%
With TiCpCl2; diisobutylaluminium hydride In 1,4-dioxane at 80℃; for 4h; Product distribution; further reagents(Zr, Hf complexes), solvents, and temperatures; further halobenzenes, alkyl, alkenyl and cyclopropyl halides;100%
bromobenzene
108-86-1

bromobenzene

aniline
62-53-3

aniline

diphenylamine
122-39-4

diphenylamine

Conditions
ConditionsYield
With sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; Pd{dba(OMe)}2 In toluene at 25℃; for 0.166667h; Buchwald-Hartwig cross coupling reaction;100%
With potassium ethoxide In 1,4-dioxane at 200℃; Catalytic behavior; Buchwald-Hartwig Coupling;100%
With C31H26N4PPdS(1+)*Cl(1-); sodium t-butanolate In toluene at 95℃; for 14h; Catalytic behavior;100%
2-pyrrolidinon
616-45-5

2-pyrrolidinon

bromobenzene
108-86-1

bromobenzene

1-phenylpyrrolidin-2-one
4641-57-0

1-phenylpyrrolidin-2-one

Conditions
ConditionsYield
With copper at 240℃; for 12h; Product distribution; further reagents, reaction temperature;100%
With copper at 180℃; for 12h;100%
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 16h; Arylation;98%
styrene
292638-84-7

styrene

bromobenzene
108-86-1

bromobenzene

stilbene
588-59-0

stilbene

Conditions
ConditionsYield
With cis-(N,N'-bis(2,2-diethoxyethyl)imidazolin-2-ylidene)dichlorotriphenylphosphinepalladium(II); tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 12h; Heck reaction;100%
With 1-naphthalenomethyl-3-(2,3,4,5,6-pentamethylbenzyl)imidazolidinium chloride; palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; for 2h; Reagent/catalyst; Green chemistry;100%
With tris-(dibenzylideneacetone)dipalladium(0); 2,5-di(2,4,6-trimethylphenyl)-1,2,5-thiadiazolidine-1-oxide; sodium acetate In 1-methyl-pyrrolidin-2-one at 200℃; for 0.5h; Heck reaction; Microwave irradiation;99%
Succinimide
123-56-8

Succinimide

bromobenzene
108-86-1

bromobenzene

N-phenylmaleimide
83-25-0

N-phenylmaleimide

Conditions
ConditionsYield
With copper at 210℃; for 12h;100%
cyclohexanedione monoethylene ketal
4746-97-8

cyclohexanedione monoethylene ketal

bromobenzene
108-86-1

bromobenzene

4-hydroxy-4-phenyl-cyclohexanone ethylene ketal
94112-58-0

4-hydroxy-4-phenyl-cyclohexanone ethylene ketal

Conditions
ConditionsYield
Stage #1: bromobenzene With magnesium In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Reflux;
Stage #2: cyclohexanedione monoethylene ketal In tetrahydrofuran for 0.5h; Inert atmosphere; Reflux;
100%
Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
Stage #2: cyclohexanedione monoethylene ketal In tetrahydrofuran at 0 - 55℃; Inert atmosphere;
41%
With tert.-butyl lithium 1.) THF, -60 deg C, 3 h, 2.) THF, RT, overnight; Yield given. Multistep reaction;
Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 0.5h; Inert atmosphere;
Stage #2: cyclohexanedione monoethylene ketal In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
phthalimide
136918-14-4

phthalimide

bromobenzene
108-86-1

bromobenzene

N-phenylphthalimide
520-03-6

N-phenylphthalimide

Conditions
ConditionsYield
With copper at 240℃; for 12h;100%
With copper at 240℃; for 12h; Product distribution; further reagents, reaction temperature;100%
With copper(I) oxide In various solvent(s) at 172℃; for 48h;80%
bromobenzene
108-86-1

bromobenzene

sodium thiophenolate
930-69-8

sodium thiophenolate

diphenyl sulfide
139-66-2

diphenyl sulfide

Conditions
ConditionsYield
o-phenylene-bis-nickel(II) bromide In ethylene glycol at 200℃; for 24h;100%
With 1,5-(2,9-dimethyl-1,10-phenanthroyl)-p-tert-butylcalix[8]arene; copper(l) chloride In toluene at 110℃; for 15h; Schlenk technique; Glovebox; Inert atmosphere;95%
With tetra(n-butyl)ammonium hydroxide In ammonia at -45℃; for 1.5h; Irradiation; further catalyst (Et3N);70%
With 2C21H11N3O6(4-)*H(1+)*2Ni(2+)*14H2O*Co(3+) In N,N-dimethyl-formamide at 80℃; for 6h; Reagent/catalyst; Inert atmosphere;65 %Chromat.
bromobenzene
108-86-1

bromobenzene

iodobenzene
591-50-4

iodobenzene

Conditions
ConditionsYield
With copper(l) iodide; potassium iodide at 200℃; for 5h; Finkelstein reaction; Inert atmosphere;100%
With aluminum oxide; copper(l) iodide In neat (no solvent) at 150℃; for 27h; Product distribution; different substrates, reagents, solvents and reaction times and temperature;94%
With aluminum oxide; copper(l) iodide In neat (no solvent) at 150℃; for 27h;94%
bromobenzene
108-86-1

bromobenzene

diphenyl sulfide
139-66-2

diphenyl sulfide

Conditions
ConditionsYield
With potassium carbonate; thiourea In ethanol for 0.583333h; Reflux;100%
With potassium phosphate; copper(l) iodide; sodiumsulfide nonahydrate at 150℃; for 24h;98%
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; bis(dibenzylideneacetone)-palladium(0); potassium thioacetate In acetone; toluene at 110℃; for 6h; Inert atmosphere;97%
bromobenzene
108-86-1

bromobenzene

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
ConditionsYield
With magnesium In tetrahydrofuran at 40℃; for 0.25h; Inert atmosphere; Flow reactor;100%
With magnesium In tetrahydrofuran
With magnesium In diethyl ether at 19.9℃; Rate constant; various concentrations of aryl halide;
bromobenzene
108-86-1

bromobenzene

thiophenol
108-98-5

thiophenol

diphenyl sulfide
139-66-2

diphenyl sulfide

Conditions
ConditionsYield
Stage #1: thiophenol With potassium carbonate In xylene at 0 - 20℃;
Stage #2: bromobenzene With tris(dibenzylideneacetone)dipalladium (0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In xylene at 140℃; for 0.4h;
100%
With potassium tert-butylate; bis(1,3-dibenzylimidazol-2-ylidene)nickel In N,N-dimethyl-formamide at 110℃; for 16h;99%
With potassium tert-butylate; nickel 1,3-dibenzylimidazolidene In N,N-dimethyl-formamide at 110℃; for 16h; Product distribution / selectivity;99%
bromobenzene
108-86-1

bromobenzene

phenylacetylene
536-74-3

phenylacetylene

diphenyl acetylene
501-65-5

diphenyl acetylene

Conditions
ConditionsYield
With triethylamine; bis(tert-butylaminophosphine)palladium(II) at 80℃; for 0.333333h; Sonogashira cross-coupling reaction;100%
With triethylamine; [Pd{t-Bu2PCH2N(CH2Ph)CH2Pt-Bu2}(OAc)2] at 80℃; for 0.333333h; Sonogashira coupling;100%
With tetrabutylammomium bromide; triethylamine In water; N,N-dimethyl-formamide at 70℃; for 12h; Sonogashira coupling;100%
bromobenzene
108-86-1

bromobenzene

acetophenone
98-86-2

acetophenone

1,1-diphenylethanol
599-67-7

1,1-diphenylethanol

Conditions
ConditionsYield
With iodine; magnesium In tetrahydrofuran 1.) reflux; 2.) 20 deg C then 22 deg C;100%
With lithium In diethyl ether for 0.5h; ultrasonic agitation;83%
Stage #1: bromobenzene With magnesium; ethylene dibromide In 2-methyltetrahydrofuran at 20℃; Inert atmosphere;
Stage #2: acetophenone In 2-methyltetrahydrofuran at 0 - 20℃; for 2.25h; Grignard reaction; Inert atmosphere; chemoselective reaction;
78%
bromobenzene
108-86-1

bromobenzene

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

2-Methyl-4-phenyl-3-butyn-2-ol
1719-19-3

2-Methyl-4-phenyl-3-butyn-2-ol

Conditions
ConditionsYield
With copper(l) iodide; C80H65BrN2O2P4Pd; triethylamine In water for 7h; Reagent/catalyst; Sonogashira Cross-Coupling; Inert atmosphere; Reflux;100%
With copper(l) iodide; diethylamine; triphenylphosphine; palladium diacetate for 36h; Heating;98%
With copper(l) iodide; palladium diacetate; triphenylphosphine; 3-aminopentane for 36h; Inert atmosphere; Reflux;98%
bromobenzene
108-86-1

bromobenzene

ethyl acrylate
140-88-5

ethyl acrylate

ethyl cinnamate
4192-77-2

ethyl cinnamate

Conditions
ConditionsYield
With potassium phosphate; tetrabutylammomium bromide; [PdCl{[η5-C5H5)]Fe[(η5-C5H3)C(CH3)=NC12H25]}]2 In N,N-dimethyl-formamide at 140℃; for 12h; Heck coupling;100%
With {4-[di(2-hydroxyethyl)amino]butyl}tri(n-butyl)ammonium bromide; palladium diacetate at 100℃; for 6h; Heck reaction; Inert atmosphere; stereoselective reaction;99%
With C37H38BrClFeN3Pd; potassium acetate In N,N-dimethyl acetamide at 150℃; for 12h; Heck reaction; Inert atmosphere; regioselective reaction;97%
bromobenzene
108-86-1

bromobenzene

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

1-Phenyl-2-(trimethylsilyl)acetylene
2170-06-1

1-Phenyl-2-(trimethylsilyl)acetylene

Conditions
ConditionsYield
With copper(l) iodide; diisopropylamine; polymer-supp. 11-(2-[Pd(OAc)2]-1-Mes-3-imidazolyl)undecanol In tetrahydrofuran at 20℃; for 2.5h; Sonogashira coupling;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine for 24h; Sonogashira coupling; Inert atmosphere; Reflux;99%
With potassium carbonate In water at 60℃; for 2h;95%
bromobenzene
108-86-1

bromobenzene

phenylboronic acid
98-80-6

phenylboronic acid

biphenyl
92-52-4

biphenyl

Conditions
ConditionsYield
With potassium carbonate; {1,3-di[(R)-1-PhEt]imidazolin-2-ylidene}(PPh3)PdI2 In xylene at 130℃; for 13h; Suzuki-Miyaura cross-coupling reaction;100%
With potassium phosphate; triphenylphosphine; Ni(II) complexes of bidentate carbene; phosphine ligand In toluene at 80℃; Suzuki cross-coupling;100%
With [PdCl2(2-ethyl-2-oxazoline)2]; potassium carbonate In toluene at 110℃; for 3h; Suzuki reaction;100%
bromobenzene
108-86-1

bromobenzene

acrylic acid n-butyl ester
141-32-2

acrylic acid n-butyl ester

(E)-3-(phenyl)acrylic acid butyl ester
52392-64-0

(E)-3-(phenyl)acrylic acid butyl ester

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; sodium carbonate; [PdClMe(MeSC6H4CH2PPh2)] at 130℃; for 72h; Heck arylation;100%
With tetrabutylammonium acetate; resin-PPh2-Pd(OAc)2 In carbon dioxide at 120℃; under 155149 Torr; for 16h; Heck reaction;100%
With tetrabutylammonium acetate; polyurea-encapsulated Pd(OAc)2 In various solvent(s) at 100℃; Heck reaction;99%
styrene
292638-84-7

styrene

bromobenzene
108-86-1

bromobenzene

(E)-1,2-diphenyl-ethene
103-30-0

(E)-1,2-diphenyl-ethene

Conditions
ConditionsYield
In neat (no solvent) at 150℃; for 0.366667h; Product distribution; Irradiation; varying method of heating;100%
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In neat (no solvent) at 150 - 160℃; for 0.366667h; Irradiation;100%
With sodium acetate; {1,1'-(3-MeOBn)2-3,3'-CH2-diimidazolin-2,2'-diylidene}PdBr2 In N,N-dimethyl acetamide at 165 - 175℃; for 1h; Product distribution; Further Variations:; Catalysts; Reaction partners; time; Heck coupling reaction;100%
indole
120-72-9

indole

bromobenzene
108-86-1

bromobenzene

1-phenyl-1H-indole
16096-33-6

1-phenyl-1H-indole

Conditions
ConditionsYield
With palladium diacetate; sodium hydroxide; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In 1,4-dioxane at 100℃; for 1h;100%
With rubidium carbonate; tri-tert-butyl phosphine; palladium diacetate In xylene at 120℃; for 4h; Condensation;96%
With copper(II) oxide; potassium carbonate In N,N-dimethyl-formamide at 40℃; for 1.5h; Ullmann Condensation;96%
bromobenzene
108-86-1

bromobenzene

(3-dimethylaminopropyl)dimethylgallium

(3-dimethylaminopropyl)dimethylgallium

toluene
108-88-3

toluene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine)palladium dichloride In benzene at 80℃; for 7h;100%
bromobenzene
108-86-1

bromobenzene

S-methyl-S-phenylsulfoximine
4381-25-3

S-methyl-S-phenylsulfoximine

(±)-methyl(phenyl)(phenylimino)-λ6-sulfanone
83706-39-2

(±)-methyl(phenyl)(phenylimino)-λ6-sulfanone

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; ruphos In toluene at 110℃; for 12h; Buchward-Hartwig coupling; Inert atmosphere;100%
Stage #1: bromobenzene With copper(l) iodide; N,N-dimethylethylenediamine; sodium iodide In 1,4-dioxane at 110℃; for 20h; Inert atmosphere; Schlenk technique;
Stage #2: S-methyl-S-phenylsulfoximine With caesium carbonate In 1,4-dioxane at 110℃; for 20h; Temperature; Reagent/catalyst; Inert atmosphere; Schlenk technique;
93%
With caesium carbonate; copper(I) oxide In N,N-dimethyl-formamide at 110℃; for 18h;89%
bromobenzene
108-86-1

bromobenzene

2-(tributylstannyl)furan
118486-94-5

2-(tributylstannyl)furan

2-phenylfuran
17113-33-6

2-phenylfuran

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In toluene for 24h; Heating;100%
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride; palladium diacetate In 1,4-dioxane at 100℃; for 16h; Stille reaction;98%
With 1,4-diaza-bicyclo[2.2.2]octane; potassium hydroxide; poly(ethylene glycol)-400; palladium diacetate In water at 80℃; for 15h; Stille coupling;87%
With potassium fluoride; 1,4-dicyclohexyl-diazabutadiene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 20h; Stille cross-coupling reaction;52%
With tetrakis(triphenylphosphine) palladium(0) In toluene Inert atmosphere; Reflux;45%
bromobenzene
108-86-1

bromobenzene

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

4-Methylbiphenyl
644-08-6

4-Methylbiphenyl

Conditions
ConditionsYield
With potassium carbonate; palladium dichloride In pyridine for 3h; Suzuki cross-coupling; Heating;100%
With potassium carbonate; carbapalladacycle complex*periodic mesoporous organosilica for 24h; Suzuki coupling; Heating;100%
With tetra-butylammonium acetate; Pd EnCat-30TM In ethanol at 120℃; for 0.166667h; Suzuki cross-coupling; microwave irradiation;100%

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