Bromobenzene supplier | CasNO.108-86-1

Name
Bromobenzene
EINECS 203-623-8
CAS No. 108-86-1
Article Data542
CAS DataBase
Density 1.486 g/cm³
Solubility insoluble in water
Melting Point -31 °C
Formula C₆H₅Br
Boiling Point 154.219 °C at 760 mmHg
Molecular Weight 157.01
Flash Point 51.111 °C
Transport Information UN 2514 3/PG 3
Appearance colourless liquid
Safety 61-45-36/37
Risk Codes 10-38-51/53-39/23/24/25-23/24/25
Molecular Structure
Hazard Symbols Xi,N
Synonyms Benzene, bromo-;Monobromobenzene;Benzene,bromo-;10005-81-9;NCI-C55492;Bromobenzene [UN2514] [Flammable liquid];
PSA 0.00000
LogP 2.44910

Synthetic route

: 589-87-7
1,4-bromoiodobenzene

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
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%

: 71-43-2
benzene

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
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%

: 201230-82-2
carbon monoxide

: 589-87-7
1,4-bromoiodobenzene

A: 108-86-1
bromobenzene

B: 1122-91-4
4-bromo-benzaldehyde

C: 71-43-2
benzene

Conditions

Conditions	Yield
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%

...Expand

: 201230-82-2
carbon monoxide

: 589-87-7
1,4-bromoiodobenzene

A: 108-86-1
bromobenzene

B: 1122-91-4
4-bromo-benzaldehyde

Conditions

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

...Expand

: 66003-76-7
Diphenyliodonium triflate

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
With copper(I) bromide In acetonitrile at 80℃; for 2h; Reagent/catalyst; Solvent; Temperature;	91%

: 65-85-0
benzoic acid

A: 108-86-1
bromobenzene

B: 108-90-7
chlorobenzene

Conditions

Conditions	Yield
With trichloroisocyanuric acid; bromine In tetrachloromethane at -10 - 100℃; for 4h; Photolysis;	A 7% B 87%

: 6293-66-9
diphenyliodonium p-toluenesulfonate

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
With copper(I) bromide In acetonitrile at 80℃; for 2h;	71%

: 58109-40-3
diphenyliodonium hexafluorophosphate

: 108-86-1
bromobenzene

Conditions

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

: diphenyliodonium tetrafluoroborate

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
With copper(I) bromide In acetonitrile at 80℃; for 2h;	63%

: 1483-72-3
diphenyliodonium chloride

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
With copper(I) bromide In acetonitrile at 80℃; for 2h;	45%

: 1483-73-4
diphenyliodonium bromide

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
With copper(I) bromide In acetonitrile at 80℃; for 2h;	40%

: 106-40-1
4-bromo-aniline

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
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

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
In water; isopropyl alcohol for 14h; Irradiation;	97%

: 56075-37-7
1-(4-bromophenyl)-2-(methylsulfonyl)diazene

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
In water; isopropyl alcohol for 14h; Irradiation;	97%

: 583-55-1
1-Bromo-2-iodobenzene

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
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.

: 106-53-6
para-bromobenzenethiol

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
dicobalt octacarbonyl In water; benzene at 185 - 190℃; under 46543.3 Torr;	77%

: 1,4-benzenebisdiazonium tetrafluoroborate

A: 108-86-1
bromobenzene

B: 106-37-6
1.4-dibromobenzene

Conditions

Conditions	Yield
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%

: 583-55-1
1-Bromo-2-iodobenzene

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

A: 108-86-1
bromobenzene

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

Conditions

Conditions	Yield
With dodecane; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; for 15h;	A 6.6% B 17.5%

...Expand

: 98-80-6
phenylboronic acid

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
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℃;

: 998-30-1
Triethoxysilane

: 589-87-7
1,4-bromoiodobenzene

A: 108-86-1
bromobenzene

B: 18954-74-0
(4-bromophenyl)triethoxysilane

Conditions

Conditions	Yield
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%

...Expand

: 59-88-1
phenylhydrazine hydrochloride

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
With boron tribromide; dimethyl sulfoxide at 80℃; for 1h;	42%

: 583-55-1
1-Bromo-2-iodobenzene

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

A: 589-09-3
N-allyl-N-phenylamine

B: 83-34-1
3-Methylindole

C: 108-86-1
bromobenzene

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

Conditions

Conditions	Yield
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%

...Expand

: 583-55-1
1-Bromo-2-iodobenzene

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

A: 589-09-3
N-allyl-N-phenylamine

B: 108-86-1
bromobenzene

Conditions

Conditions	Yield
With dodecane; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; for 15h;	A 3.5% B 20.9%

...Expand

: 106-37-6
1.4-dibromobenzene

: 98-80-6
phenylboronic acid

A: 108-86-1
bromobenzene

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

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

Conditions

Conditions	Yield
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

...Expand

: 70083-69-1
Tetramethylammonium Bis<α,α-bis(trifluoromethyl)-benzenemethanolato(2-)-C2,O>phenylsilicate

A: 108-86-1
bromobenzene

B: 70091-69-9
C18H8F12O2Si

Conditions

Conditions	Yield
With bromine at 25℃; for 24h;	A n/a B 75%

: 108-36-1
1,3-dibromobenzene

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

A: 108-86-1
bromobenzene

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

Conditions

Conditions	Yield
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%

...Expand

: 591-50-4
iodobenzene

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
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;

: 97878-04-1
tetraethylammonium bis<α,α-bis(trifluorometyl)benzenemethanolato(2-)-C2,O>-n-butylsilicate(1-)

A: 108-86-1
bromobenzene

B: 70091-69-9
C18H8F12O2Si

Conditions

Conditions	Yield
With bromine at 25℃; for 24h;	A n/a B 74.6%

: 591-18-4
1-Bromo-3-iodobenzene

: 108-86-1
bromobenzene

Conditions

Conditions	Yield
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.

: 103-29-7
1,1'-(1,2-ethanediyl)bisbenzene

A: 108-86-1
bromobenzene

B: 71-43-2
benzene

Conditions

Conditions	Yield
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;

: 110-91-8
morpholine

: 108-86-1
bromobenzene

: 92-53-5
4-Phenylmorpholine

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: 92-52-4
biphenyl

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: 106-37-6
1.4-dibromobenzene

Conditions

Conditions	Yield
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

: 108-86-1
bromobenzene

: 62-53-3
aniline

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: 71-43-2
benzene

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: 62-53-3
aniline

: 122-39-4
diphenylamine

Conditions

Conditions	Yield
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%

: 616-45-5
2-pyrrolidinon

: 108-86-1
bromobenzene

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

Conditions

Conditions	Yield
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%

: 292638-84-7
styrene

: 108-86-1
bromobenzene

: 588-59-0
stilbene

Conditions

Conditions	Yield
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%

: 123-56-8
Succinimide

: 108-86-1
bromobenzene

: 83-25-0
N-phenylmaleimide

Conditions

Conditions	Yield
With copper at 210℃; for 12h;	100%

: 4746-97-8
cyclohexanedione monoethylene ketal

: 108-86-1
bromobenzene

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

Conditions

Conditions	Yield
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;

: 136918-14-4
phthalimide

: 108-86-1
bromobenzene

: 520-03-6
N-phenylphthalimide

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: 930-69-8
sodium thiophenolate

: 139-66-2
diphenyl sulfide

Conditions

Conditions	Yield
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+)14H2OCo(3+) In N,N-dimethyl-formamide at 80℃; for 6h; Reagent/catalyst; Inert atmosphere;	65 %Chromat.

: 108-86-1
bromobenzene

: 591-50-4
iodobenzene

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: 139-66-2
diphenyl sulfide

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: 100-58-3
phenylmagnesium bromide

Conditions

Conditions	Yield
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;

: 108-86-1
bromobenzene

: 108-98-5
thiophenol

: 139-66-2
diphenyl sulfide

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: 536-74-3
phenylacetylene

: 501-65-5
diphenyl acetylene

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: 98-86-2
acetophenone

: 599-67-7
1,1-diphenylethanol

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

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

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

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: 140-88-5
ethyl acrylate

: 4192-77-2
ethyl cinnamate

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: 1066-54-2
trimethylsilylacetylene

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

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: 98-80-6
phenylboronic acid

: 92-52-4
biphenyl

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: 141-32-2
acrylic acid n-butyl ester

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

Conditions

Conditions	Yield
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%

: 292638-84-7
styrene

: 108-86-1
bromobenzene

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

Conditions

Conditions	Yield
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%

: 120-72-9
indole

: 108-86-1
bromobenzene

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

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: (3-dimethylaminopropyl)dimethylgallium

: 108-88-3
toluene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine)palladium dichloride In benzene at 80℃; for 7h;	100%

: 108-86-1
bromobenzene

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

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

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: 118486-94-5
2-(tributylstannyl)furan

: 17113-33-6
2-phenylfuran

Conditions

Conditions	Yield
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%

: 108-86-1
bromobenzene

: 5720-05-8
4-methylphenylboronic acid

: 644-08-6
4-Methylbiphenyl

Conditions

Conditions	Yield
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%

Bromobenzene Chemical Properties

Molecule structure of Bromobenzene (CAS NO.108-86-1):

IUPAC Name: Bromobenzene
Molecular Weight: 157.0079 g/mol
Molecular Formula: C₆H₅Br
Density: 1.486 g/cm³
Melting Point: -31 °C
Boiling Point: 154.2 °C at 760 mmHg
Flash Point: 51.1 °C
Index of Refraction: 1.555
Molar Refractivity: 33.94 cm³
Molar Volume: 105.6 cm³
Surface Tension: 35.4 dyne/cm
Enthalpy of Vaporization: 37.49 kJ/mol
Vapour Pressure: 4.12 mmHg at 25 °C
Storage Temp.: 2-8 °C
Water Solubility: insoluble. <0.1 g/100 mL at 20.5 °C
Stability: stable. incompatible with strong oxidizing agents.
XLogP3: 3
Exact Mass: 155.957463
MonoIsotopic Mass: 155.957463
Canonical SMILES: C1=CC=C(C=C1)Br
InChI: InChI=1S/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H
InChIKey: QARVLSVVCXYDNA-UHFFFAOYSA-N
EINECS: 203-623-8
Product Categories: Pharmaceutical Intermediates;Organics;BENZENE BASED BROMO;Analytical Chemistry;Standard Solution of Volatile Organic Compounds for Water & Soil Analysis;Standard Solutions (VOC);Chemical Class;C6Essential Chemicals;Aryl;Halogenated Hydrocarbons;Reagent Plus;Routine Reagents;A-BAlphabetic;Alpha Sort;B;BI - BZChemical Class;Bromo;Halogenated;Volatiles/ Semivolatiles

Bromobenzene Uses

Bromobenzene can be used to prepare the corresponding Grignard reagent, phenylmagnesium bromide which can be used in a number of fashions, e.g. the reaction with carbon dioxide to prepare benzoic acid. It is also used in the production of drugs.

Bromobenzene Toxicity Data With Reference

1.	mnt-mus-ipr:125 mg/kg/24H	MUTAEX Mutagenesis. 2 (1987),111.
2.	ipr-mus LD50:817 mg/kg	MUTAEX Mutagenesis. 2 (1987),111.
3.	orl-gpg LD50:1700 mg/kg	85GMAT Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,28.
4.	orl-rbt LD50:3300 mg/kg	85GMAT Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,28.
5.	orl-rat LD50:2699 mg/kg	GTPZAB Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 19 (9)(1975),36.
6.	orl-uns LD50:2700 mg/kg	GTPZAB Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 32 (10)(1988),25.
7.	ipr-rat LD50:3882 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 83 (1986),108.
8.	ihl-rat LC50:20,411 mg/m³	GTPZAB Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 19 (9)(1975),36.
9.	ipr-rat LD50:3882 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 83 (1986),108.

Bromobenzene Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Bromobenzene Safety Profile

Hazard Codes: Irritant Xi, Dangerous N, F, Toxic T
Risk Statements: 10-38-51/53-39/23/24/25-23/24/25
R10:Flammable.
R38:Irritating to skin.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R39:Danger of very serious irreversible effects.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 61-45-36/37
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37:Wear suitable protective clothing and gloves.
RIDADR: UN 2514 3/PG 3
WGK Germany: 2
RTECS: CY9000000
HazardClass: 3
PackingGroup: III
Moderately toxic by ingestion, subcutaneous, and intraperitoneal routes. Mildly toxic by inhalation. An eye and mucous membrane irritant. Mutation data reported. Flammable liquid when exposed to heat, sparks, or flame. Can react with oxidizing materials. To fight fire, use water to blanket fire, foam, CO₂, water spray or mist, dry chemical. Violent reaction with bromobutane + sodium when heated above 30°C. When heated to decomposition it emits toxic fumes of Br⁻. See also BROMIDES.

Bromobenzene Standards and Recommendations

DOT Classification: 3; Label: Flammable Liquid

Bromobenzene Specification

Bromobenzene (CAS NO.108-86-1) is also named as AI3-09059 ; Benzene, bromo- ; CCRIS 5887 ; HSDB 47 ; Monobromobenzene ; NCI-C55492 ; NSC 6529 ; Phenyl bromide . Bromobenzene (CAS NO.108-86-1) is colourless liquid with a pungent odor. It is insoluble in water, soluble in benzene, alcohol, ether, chlorobenzene and other organic solvents. Vapors are heavier than air. It is flammable. Bromobenzene may be sensitive to light. It may react with oxidizing agents. Contact with liquid causes irritation of eyes and mild irritation of skin. Ingestion causes mild irritation of mouth and stomach. It may produce irritating hydrogen bromide and other gases in fire.

Product Name

Bromobenzene

Synthetic route

Bromobenzene Chemical Properties

Bromobenzene Uses

Bromobenzene Toxicity Data With Reference

Bromobenzene Consensus Reports

Bromobenzene Safety Profile

Bromobenzene Standards and Recommendations

Bromobenzene Specification

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