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Iodobenzene

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Name

Iodobenzene

EINECS 209-719-6
CAS No. 591-50-4 Density 1.83 g/cm3
PSA 0.00000 LogP 2.29120
Solubility insoluble in water Melting Point -29 °C(lit.)
Formula C6H5I Boiling Point 188.329 °C at 760 mmHg
Molecular Weight 204.01 Flash Point 74.444 °C
Transport Information Appearance Clear yellow liquid
Safety 26-36 Risk Codes 22-36
Molecular Structure Molecular Structure of 591-50-4 (Iodobenzene) Hazard Symbols HarmfulXn, IrritantXi
Synonyms

Phenyl iodide;Benzene, iodo-;Iodinebenzol;Benzene,iodo-;Benzene iodide;

 

Iodobenzene Synthetic route

71-43-2

benzene

591-50-4

iodobenzene

Conditions
ConditionsYield
With cobalt(III) acetate; trifluoroacetic acid; potassium iodide In water at 25℃; for 0.00333333h; Mn(OAc)3 or (NH4)2Ce(SO4)3 instead Co(OAc)3; object of study: oxidative iodination promoted by Co(III), Ni(III) or Ce(IV);100%
With cobalt(III) acetate; trifluoroacetic acid In water at 25℃; for 0.00333333h;100%
With iodine; silver trifluoromethanesulfonate In dichloromethane at 20℃;100%
108-86-1

bromobenzene

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%
2217-79-0

diphenyliodonium iodide

591-50-4

iodobenzene

Conditions
ConditionsYield
In water Product distribution; Mechanism; Irradiation; laser flash photolyses, λ: 355 nm;100%

phenyl-1,1,7-trihydroperfluoroheptyliodonium fluoroborate

62-53-3

aniline

A

591-50-4

iodobenzene

B

anilinium tetrafluoroborate

C

85459-31-0

N-1,1,7-trihydroperfluoroheptylaniline

Conditions
ConditionsYield
In dichloromethane 1) 0 deg C, 2 h, 2) 20 deg C, 1 h;A n/a
B 100%
C 87%
691-38-3

(Z)-4-methyl-2-pentene

536-80-1

iodosylbenzene

A

591-50-4

iodobenzene

Conditions
ConditionsYield
iron 5(pentafluorophenyl)-10,15,20-tris(2,6-dichloropheny.. In dichloromethane Oxidation; iron 5-(pentafluorophenyl)-10,15,20-tris(2,6-dichlorophenyl)porphyrin was used as catalyst;A n/a
B 100%
5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin iron(II) In dichloromethane Oxidation;A n/a
B 100%
iron 5,10,15,20-tetrakis-(2',6'-dichlorophenyl)porphyrinate In dichloromethane Oxidation;A n/a
B 54%
iron 5(pentafluorophenyl)-10,15,20-tris(2,6-dichloropheny.. In dichloromethane Oxidation; iron 5-(pentafluorophenyl)-10,15,20-tris(2,6-dichlorophenyl)porphyrin fixed on silica was used as catalyst;A n/a
B 33%
674-76-0

(E)-4-methylpent-2-ene

536-80-1

iodosylbenzene

A

149117-14-6

2.3-Epoxy-4-methylpentan

B

591-50-4

iodobenzene

Conditions
ConditionsYield
5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin iron(II) In dichloromethane Oxidation;A 100%
B n/a
iron 5,10,15,20-tetrakis-(2',6'-dichlorophenyl)porphyrinate In dichloromethane Oxidation;A 96%
B n/a
iron 5(pentafluorophenyl)-10,15,20-tris(2,6-dichloropheny.. In dichloromethane Oxidation; iron 5-(pentafluorophenyl)-10,15,20-tris(2,6-dichlorophenyl)porphyrin fixed on silica was used as catalyst;A 60%
B n/a
iron 5(pentafluorophenyl)-10,15,20-tris(2,6-dichloropheny.. In dichloromethane Oxidation; iron 5-(pentafluorophenyl)-10,15,20-tris(2,6-dichlorophenyl)porphyrin was used as catalyst;A 60%
B n/a

(E)-1-decenyl(phenyl)(tetrafluoroborato)-λ3-iodane

A

764-93-2

1-decyne

B

591-50-4

iodobenzene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In dichloromethane at 20℃; for 10h; Elimination;A 94%
B 100%
34107-52-3

2,2-dimethyl-5-(phenyl-λ3-iodaneylidene)-1,3-dioxane-4,6-dione

A

2033-24-1

cycl-isopropylidene malonate

B

591-50-4

iodobenzene

C

67-64-1

acetone

Conditions
ConditionsYield
With dirhodium tetraacetate In dichloromethane at 20℃; Product distribution;A 33%
B 100%
C 5%
35895-70-6

tetrabutylammonium trifluoromethylsulfonate

(R)-4-methylcyclohexylidenemethyl(phenyl)iodonium tetrafluoroborate

A

591-50-4

iodobenzene

B

13609-59-1

(R)-4-methylcycloheptanone

C

(R)-4-methylcycloheptanone

Conditions
ConditionsYield
Stage #1: tetrabutylammonium trifluoromethylsulfonate; (R)-4-methylcyclohexylidenemethyl(phenyl)iodonium tetrafluoroborate In chloroform at 60℃;
Stage #2: With sulfuric acid In methanol; water at 60℃; for 9h;
A 100%
B n/a
C n/a

(R)-4-methylcyclohexylidenemethyl(phenyl)iodonium tetrafluoroborate

A

591-50-4

iodobenzene

B

(SR)-4-methylcyclohexylidenemethyl triflate

C

5-methylcyclohept-1-enyl triflate

Conditions
ConditionsYield
With tetrabutylammonium trifluoromethylsulfonate In chloroform at 60℃;A 100%
B 34%
C 63%
1483-73-4

diphenyliodonium bromide

mercury

A

591-50-4

iodobenzene

B

92-52-4

biphenyl

C

mercury(I) bromide

D

1192-89-8

bromo(phenyl)mercury

E

71-43-2

benzene

Conditions
ConditionsYield
In acetonitrile Kinetics; byproducts: C6H5Br; at different temp. between 20-70°C; UV; yields for 45°C;A 100%
B 6-7
C n/a
D n/a
E 1.4%
1483-72-3

diphenyliodonium chloride

mercury

A

591-50-4

iodobenzene

B

mercury(I) chloride

C

92-52-4

biphenyl

D

100-56-1

phenylmercury(II) chloride

E

71-43-2

benzene

Conditions
ConditionsYield
In acetonitrile Kinetics; at different temp. between 20-70°C; UV; yields for 45°C;A 100%
B 10-11
C 4-5
D 89-92
E 1.4%
81353-33-5

m-carboran-9-yl(phenyl)iodonium tetrafluoroborate

7647-14-5

sodium chloride

A

591-50-4

iodobenzene

B

17819-85-1

9-chloro-m-carborane

Conditions
ConditionsYield
In chloroform; water mixt. of aryl(m-carboran-9-yl)iodonium tetrafluoroborate, NaF, water and chloroform was vigorously stirred under reflux at 56°C, 1 h; internal standard (chlorobenzene) added and org. layer was analysed by GLC;A 100%
B 100%
97939-92-9

triphenylphosphinediiodogermylene

591-51-5

phenyllithium

A

591-50-4

iodobenzene

B

92-52-4

biphenyl

C

2816-43-5

triphenylgermane

D

1048-05-1

tetraphenylgermane

E

603-35-0

triphenylphosphine

Conditions
ConditionsYield
In diethyl ether under N2, to suspn. of Ph3PGeI2 in ether PhLi added dropwise (1:4 molarratio), stirred for 5 d under reflux, hydrolyzed; dried, analyzed by gas chromy.;A 10%
B 13%
C 39%
D 36%
E 100%
In diethyl ether under N2, to suspn. of Ph3PGeI2 in ether PhLi added dropwise (1:1 molarratio), stirred for 5 d under reflux, hydrolyzed; dried, analyzed by gas chromy.;A 2.9%
B 2.9%
C 1.9%
D 14%
E 82%
In diethyl ether under N2, to suspn. of Ph3PGeI2 in ether PhLi added dropwise (1:2 molarratio), stirred for 5 d under reflux, hydrolyzed; dried, analyzed by gas chromy.;A 7.7%
B 9.6%
C 1.3%
D 19%
E 79%

phenyl bis(trifluoroacetate)

7553-56-2

iodine

A

591-50-4

iodobenzene

B

Tl(1+)*Tl(3+)*4CF3COO(1-)=Tl2(CF3COO)4

Conditions
ConditionsYield
In acetonitrile soln. of iodine addn. to soln. of Tl-compd., mixing, standing (dark, 220h, room temperature), evacuation (under Ar, room temperature, then wate r bath, distillation of I-compd.), product remaining in solid residue;A 99%
B 100%
88242-78-8

phenyl(p-carboran-2-yl)iodonium tetrafluoroborate

sodium fluoride

A

591-50-4

iodobenzene

B

22784-33-4

2-iodo-closo-1,12-dodecaborane

C

22762-43-2

2-fluoro-p-caborane

D

71-43-2

benzene

Conditions
ConditionsYield
In dichloromethane; water 25°C, 0.6 h;A 99%
B 0%
C 99.5%
D <0.5
88242-78-8

phenyl(p-carboran-2-yl)iodonium tetrafluoroborate

sodium fluoride

A

591-50-4

iodobenzene

B

22762-43-2

2-fluoro-p-caborane

C

932-72-9

(Dichloroiodo)benzene

Conditions
ConditionsYield
With sodium fluoride In dichloromethane; water mixt. of iodonium salt, NaF, H2O and CH2Cl2 stirred at 25°C for 35 min; org. phase sepd. off, filtered through a short alumina plug and evapd., the residue is a mixt. of C6H5I and 2-fluoro-p-carborane; solid dissolved in dry CCl4; soln. satd. with Cl2 at 5°C, and then evapd., to give the mixt. of C6H3Cl2I and the fluorocarborane; the latter extd. with pentane, filtered through an alumina plug, evapd. to dryness, vac. sublimation; elem. anal.;A n/a
B 99.5%
C 70%
23586-54-1

phenylthalium(III) di(trifluoroacetate)

591-50-4

iodobenzene

Conditions
ConditionsYield
With iodine In acetonitrile for 220h; Ambient temperature;99.4%
75-18-3

dimethylsulfide

75067-08-2

benzene

A

591-50-4

iodobenzene

B

120188-75-2

methoxydimethylsulfonium tosylate

Conditions
ConditionsYield
In dichloromethane for 0.25h;A n/a
B 99%
13056-98-9

3,3-diethyl-1-phenyltriaz-1-ene

591-50-4

iodobenzene

Conditions
ConditionsYield
With cation exchange resin BioRad AG 50W-X12 (H+); sodium iodide In acetonitrile at 75℃; Product distribution; further solvent: THF, DMSO;99%
With chloro-trimethyl-silane; sodium iodide In acetonitrile at 60℃; for 0.0833333h;65%
With diiodomethane; isopentyl nitrite 1.) room temperature, 30 min, 2.) 80 deg C, 4 h;
104-95-0

(4-bromophenyl)thioanisole

75067-08-2

benzene

A

591-50-4

iodobenzene

B

120188-78-5

C8H10BrOS(1+)*C7H7O3S(1-)

Conditions
ConditionsYield
In dichloromethane for 0.25h;A n/a
B 99%
538-74-9

dibenzyl sulfide

75067-08-2

benzene

A

591-50-4

iodobenzene

B

120188-76-3

C15H17OS(1+)*C7H7O3S(1-)

Conditions
ConditionsYield
In dichloromethane for 0.25h;A n/a
B 99%

diphenyliodonium tetrafluoroborate

873-55-2

sodium benzenesulfonate

A

591-50-4

iodobenzene

B

127-63-9

diphenyl sulphone

Conditions
ConditionsYield
In chloroform; water at 20℃; for 64h;A n/a
B 99%
In chloroform; water at 56℃; for 2.5h; Product distribution; other temperatures, other reaction time;A 99 % Chromat.
B 97%

sodium hydrogenfluoride

88242-78-8

phenyl(p-carboran-2-yl)iodonium tetrafluoroborate

A

591-50-4

iodobenzene

B

22784-33-4

2-iodo-closo-1,12-dodecaborane

C

22762-43-2

2-fluoro-p-caborane

D

71-43-2

benzene

Conditions
ConditionsYield
In dichloromethane; water at 25°C, 0.5 h;A 95%
B <1
C 99%
D <0.5
77329-29-4

{3-(p-tolylthio)propyl}triphenyltin

A

591-50-4

iodobenzene

B

77329-37-4

(C6H5)2SnI(CH2)3SC6H4CH3

Conditions
ConditionsYield
With iodine In tetrachloromethane Kinetics; to soln. of Sn compd. I2 added dropwise, soln. left until become colourless;A 99%
B n/a
77329-30-7

(C6H5)3SnCH2CH2CH2CH2SC6H4CH3

A

591-50-4

iodobenzene

B

(C6H5)2SnI(CH2)4SC6H4CH3

Conditions
ConditionsYield
With iodine In tetrachloromethane Kinetics; to soln. of Sn compd. I2 added dropwise, soln. left until become colourless;A 99%
B n/a

1,1,16,16-tetraphenyl-3,3,14,14,18,18,29,29-octamethyl-3,14,18,29-tetrasila-1,16-distanna-[5,5]-ferrocenophane

7553-56-2

iodine

A

591-50-4

iodobenzene

B

260441-94-9, 260415-59-6

1,16-diiodo-1,16-diphenyl-3,3,14,14,18,18,29,29-octamethyl-3,14,18,29-tetrasila-1,16-distanna-[5,5]-ferrocenophane

Conditions
ConditionsYield
In dichloromethane under N2atm. i2 was added to soln. fc(SiMe2CH2SnPh2CH2SiMe2)2fc in CH2Cl2, react. mixt. was stirred overnight; solvent and iodobenzene were removed in vacuo, residue was recrystd. from hexane; elem. anal.;A n/a
B 99%
3240-34-4

[bis(acetoxy)iodo]benzene

591-50-4

iodobenzene

Conditions
ConditionsYield
With iodine In chloroform Ambient temperature;98%
With iodine In chloroform Product distribution; Ambient temperature; further regents, further products;98%
With hydrogen bromide at 0℃; for 0.333333h; Yield given;
3145-75-3

1-cyclohexyl-2-phenylcyclopropane

A

591-50-4

iodobenzene

B

94848-51-8

2-cyclohexyl-1-(4-iodophenyl)-cyclopropane

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; iodine In chloroform; trifluoroacetic acid at -30℃; for 8h;A n/a
B 98%
591-50-4

iodobenzene

92-52-4

biphenyl

Conditions
ConditionsYield
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; potassium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 2h; Microwave irradiation;100%
With sodium tetraphenyl borate; sodium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 4h; Suzuki coupling; Inert atmosphere;99%
With potassium carbonate In ethanol; water at 80℃; for 4h; Reagent/catalyst; Solvent; Ullmann Condensation; Green chemistry;99.2%
591-50-4

iodobenzene

932-72-9

(Dichloroiodo)benzene

Conditions
ConditionsYield
With hydrogenchloride; sodium hypochlorite In water at 20℃; for 0.0833333h;100%
With hydrogenchloride; sodium hypochlorite at 15℃; for 0.0833333h;99%
With chlorine In dichloromethane at 20℃;98%
591-50-4

iodobenzene

71-43-2

benzene

Conditions
ConditionsYield
With tetrabutoxytitanium; diisobutylaluminium hydride In diethyl ether for 6h; Heating;100%
With sodium hydroxide; ethanol; PdCl2-poly(N-vinyl-2-pyrrolidone); palladium dichloride at 65℃; under 760 Torr; for 1h;100%
With potassium tert-butylate; benzaldehyde In N,N-dimethyl-formamide at 90℃; for 1h; Schlenk technique; Inert atmosphere;99%
591-50-4

iodobenzene

107-19-7

propargyl alcohol

1504-58-1

3-Phenyl-2-propyn-1-ol

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 5h; Sonogashira coupling; Inert atmosphere;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 12h; Inert atmosphere;100%
Stage #1: iodobenzene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: propargyl alcohol Inert atmosphere;
99%
60-35-5

acetamide

591-50-4

iodobenzene

103-84-4

Acetanilid

Conditions
ConditionsYield
With acetamide; potassium phosphate; CuI In dodecane; ethyl acetate; toluene100%
With potassium phosphate; copper(l) iodide; L-arginine In 1,4-dioxane at 100℃; for 24h; Goldberg reaction;99%
With aluminum oxide; potassium fluoride; copper(l) iodide; 1,10-Phenanthroline In toluene at 110℃; for 5h;97%
591-50-4

iodobenzene

103-30-0

(E)-1,2-diphenyl-ethene

Conditions
ConditionsYield
With triethylamine In 1-butyl-3-methylimidazolium methyl phosphonate at 110℃; for 5h; Heck Reaction;100%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h; Heck reaction;100%
With triethylamine In dimethyl sulfoxide at 120℃; for 12h; Heck reaction;100%
67-56-1

methanol

591-50-4

iodobenzene

201230-82-2

carbon monoxide

93-58-3

benzoic acid methyl ester

Conditions
ConditionsYield
With tetrabutylammomium bromide; triethylamine; Pd-PVP at 90℃; for 3h;100%
With tetrabutyl-ammonium chloride; triethylamine; [Pd[P(O)(OPh)2]2]n at 90℃; under 3800 Torr; for 3h;100%
With 1-n-butyl-4-methylpyridinium chloride; triethylamine; PdCl2{P(OC6H5)3}2 at 90℃; under 3800 Torr; for 3h; Product distribution; Further Variations:; Catalysts; Reagents;100%
591-50-4

iodobenzene

5390-04-5

pent-1-yn-5-ol

24595-58-2

5-phenylpent-4-yn-1-ol

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; for 12h;100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; for 12h;99%
591-50-4

iodobenzene

3066-71-5

cyclohexyl acrylate

7779-17-1

(E)-cyclohexyl cinnamate

Conditions
ConditionsYield
With tributyl-amine; [bmim]PF6; palladium diacetate; silica gel at 100℃; for 4h; Mizoroki-Heck reaction;100%
With triethylamine; Pd(OAc)2 in [bmim]PF6 layer in silica pores In dodecane at 150℃; for 15.5h; Mizoroki-Heck reaction;99%
With tributyl-amine; montmorilloniteethylsilyldiphenylphosphine palladium(II) chloride at 100℃; for 6h;94%
591-50-4

iodobenzene

138535-23-6

2-propenethiotrimethylstannane

5296-64-0

allyl phenyl thioether

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In toluene Heating;100%
591-50-4

iodobenzene

C3F5IZn

41424-70-8

(Z)-1-phenyl-1,2,3,3,3-pentafluoro-1-propene

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) at 80℃; for 4h;100%
591-50-4

iodobenzene

139-66-2

diphenyl sulfide

Conditions
ConditionsYield
With sulfur; potassium fluoride; copper(II) ferrite; caesium carbonate at 120℃; for 20.5h; Catalytic behavior; Reagent/catalyst; Temperature;100%
With potassium carbonate; thiourea In ethanol for 0.25h; Catalytic behavior; Solvent; Reagent/catalyst; Temperature; Reflux;100%
With potassium phosphate; copper(l) iodide; potassium thioacyanate In PEG-400 at 150℃; for 20h; Inert atmosphere;98%
591-50-4

iodobenzene

78-94-4

methyl vinyl ketone

1896-62-4

(E)-benzalacetone

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 100℃; for 18h; Heck reaction;100%
With tetrabutyl-ammonium chloride; sodium hydrogencarbonate; palladium diacetate In N,N-dimethyl-formamide at 25℃; for 48h;98%
With triphenylphosphine on reverse phase silica; triethylamine; Pd(OAc)2 on reverse phase silica In methanol; water Addition; Heck reaction;97%
591-50-4

iodobenzene

107-13-1

acrylonitrile

4360-47-8

cinnamonitrile

Conditions
ConditionsYield
With C33H33N2(1+)*Cl(1-); palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide for 2h; Heck Reaction; Inert atmosphere; Sealed tube; Heating;100%
With sodium acetate; aluminum oxide; ruthenium In N,N-dimethyl-formamide at 115℃; for 12h; Heck-type olefination;99%
With triethylamine In d7-N,N-dimethylformamide at 120℃; for 1h; Heck Reaction;99%
591-50-4

iodobenzene

292638-85-8

acrylic acid methyl ester

103-26-4

Methyl cinnamate

Conditions
ConditionsYield
ς4,λ5-phosphinine palladium In 1-methyl-pyrrolidin-2-one at 100℃; for 120h; Heck reaction;100%
With palladium diacetate; 15-crown-15 tagged triarylphoshine; triethylamine In tetrahydrofuran for 8h; Heck reaction; Heating;100%
With triethylamine; polymer(fiber)-supported palladium In 1,4-dioxane at 100℃; for 1h; Heck reaction;100%
591-50-4

iodobenzene

292638-85-8

acrylic acid methyl ester

103-26-4

methyl cinnamate

Conditions
ConditionsYield
palladium/alumina for 0.166667h; Product distribution / selectivity;100%
With hollow carbonnanonets supported palladium nanoparticles; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.5h; Heck Reaction;100%
With triethylamine at 145℃; for 3h; Catalytic behavior; Heck Reaction;100%
591-50-4

iodobenzene

536-74-3

phenylacetylene

501-65-5

diphenyl acetylene

Conditions
ConditionsYield
With triethylamine; bis(tert-butylaminophosphine)palladium(II) at 80℃; for 0.25h; Sonogashira cross-coupling reaction;100%
With copper(l) iodide; diisopropylamine; triphenylphosphine; silica gel; palladium at 85℃; for 18h; Sonogashira coupling;100%
With triethylamine; [Pd{t-Bu2PCH2N(CH2Ph)CH2Pt-Bu2}(OAc)2] at 80℃; for 0.25h; Sonogashira coupling;100%
591-50-4

iodobenzene

201230-82-2

carbon monoxide

62-53-3

aniline

93-98-1

N-phenyl benzoyl amide

Conditions
ConditionsYield
With C11H14Cl2N6O2Pd; triethylamine In 1,4-dioxane at 100℃; under 2280.15 Torr; for 6h; Reagent/catalyst;100%
With triethylamine In N,N-dimethyl-formamide at 100℃; under 750.075 Torr; for 4h; Catalytic behavior; Pressure; Reagent/catalyst; Schlenk technique; Inert atmosphere;99%
With triethylamine In toluene at 100℃; under 3750.38 Torr; for 8h; Inert atmosphere;99%
591-50-4

iodobenzene

882-33-7

diphenyldisulfane

139-66-2

diphenyl sulfide

Conditions
ConditionsYield
at 230 - 270℃; for 8h; Mechanism; other aryl iodides;100%
at 230 - 270℃; for 8h;100%
With caesium carbonate In dimethyl sulfoxide at 100℃; for 24h; Inert atmosphere;97%
591-50-4

iodobenzene

1896-62-4

(E)-benzalacetone

5409-60-9

4,4-diphenylbutan-2-one

Conditions
ConditionsYield
With tributyl-amine; tetra-(n-butyl)ammonium iodide; trifluoroacetic acid; bis(triphenylphosphine) palladium (Il) acetate In N,N-dimethyl-formamide at 70℃;100%
With triethylamine; palladium diacetate In carbon dioxide at 80℃; under 75006 Torr; for 60h; Arylation; Hydroarylation;88%
591-50-4

iodobenzene

927-74-2

1-butyn-4-ol

10229-11-5

4-phenyl-but-3-yn-1-ol

Conditions
ConditionsYield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine for 16h; Sonogashira Cross-Coupling; Reflux; Inert atmosphere; Schlenk technique;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 10h; Inert atmosphere;99%
With copper(l) iodide; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)); Tedicyp In N,N-dimethyl-formamide at 100℃; Sonogashira reaction;97%
591-50-4

iodobenzene

140-88-5

ethyl acrylate

4192-77-2

ethyl cinnamate

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium acetate; Pd(0)-ferrocenyl In N,N-dimethyl-formamide at 60℃; for 2.5h;100%
With palladium nanoparticles on graphene; triethylamine In N,N-dimethyl-formamide at 120 - 125℃; for 2h; Heck Reaction;100%
With triethylamine; silica aerogel nanocomposite; palladium In acetonitrile for 8h; Mizoroki-Heck reaction; Heating;99%
591-50-4

iodobenzene

108-95-2

phenol

101-84-8

diphenylether

Conditions
ConditionsYield
With copper(I) oxide; caesium carbonate; hydroxybenzaldoxime; 3 A molecular sieve In acetonitrile at 82℃; for 24h; Ullmann-type coupling;100%
With caesium carbonate; copper(I) oxide; trans-N,N'-bis(pyridin-2-ylmethylene)cyclohexane-1,2-diamine In acetonitrile at 82℃; for 24h; Conversion of starting material; activated 3 A molecular sieve (KnNa12-n[(AlO2)12(SiO2)12]);100%
Stage #1: phenol With caesium carbonate; copper(I) oxide; trans-N,N'-bis(pyridin-2-ylmethylene)cyclohexane-1,2-diamine at 100℃; Molecular sieve 3 Å;
Stage #2: iodobenzene In acetonitrile at 82℃; for 24h;
100%
591-50-4

iodobenzene

98-80-6

phenylboronic acid

92-52-4

biphenyl

Conditions
ConditionsYield
With potassium carbonate; copper-palladium In N,N-dimethyl-formamide at 110℃; Kinetics; Product distribution; Further Variations:; Catalysts; Reaction partners; Suzuki cross-coupling;100%
With sodium hydroxide; Pd-dodecanethiolate nanoparticles In tetrahydrofuran at 20℃; for 24h; Suzuki-Miyaura cross-coupling;100%
With sodium carbonate; 1-butyl-3-methylimidazolium Tetrafluoroborate; 2C10H15N2(1+)*Cl4Pd(2-) In water at 110℃; for 12h; Conversion of starting material; Suzuki Coupling;100%
591-50-4

iodobenzene

79-10-7

acrylic acid

140-10-3

(E)-3-phenylacrylic acid

Conditions
ConditionsYield
With triethylamine; PdCl2(4,4'-bis(n-C10F21CH2OCH2)-2,2'-bpy) In N,N-dimethyl-formamide at 140℃; for 3h; Heck reaction;100%
With potassium carbonate; palladium dichloride In water at 20 - 100℃; Heck reaction; Inert atmosphere;99%
With potassium hydroxide In water at 90℃; for 5h; Mizoroki-Heck reaction;99%
591-50-4

iodobenzene

4187-87-5

1-Phenyl-2-propyn-1-ol

1817-49-8

1,3-diphenyl-1-propyn-3-ol

Conditions
ConditionsYield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In tetrahydrofuran Phenylation; Sonogashira coupling; Heating;100%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 2h;96%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 20℃; for 24h;94%

Iodobenzene Consensus Reports

Reported in EPA TSCA Inventory.

Iodobenzene Specification

The Iodobenzene is an organic compound with the formula C6H5I. The IUPAC name of this chemical is iodobenzene. With the CAS registry number 591-50-4, it is also named as phenyliodonium. The product's categories are Aromatic Halides (substituted); Organics; API Intermediates; Iodine Compounds; Pharmaceutical Intermediate; Aryl; C6; Halogenated Hydrocarbons. Besides, it is useful as a synthetic intermediate in organic chemistry.

Physical properties about Iodobenzene are: (1)ACD/LogP: 3.33; (2)ACD/LogD (pH 5.5): 3.325; (3)ACD/LogD (pH 7.4): 3.325; (4)ACD/BCF (pH 5.5): 198.31; (5)ACD/BCF (pH 7.4): 198.31; (6)ACD/KOC (pH 5.5): 1534.783; (7)ACD/KOC (pH 7.4): 1534.783; (8)Index of Refraction: 1.62; (9)Molar Refractivity: 39.16 cm3; (10)Molar Volume: 111.506 cm3; (11)Polarizability: 15.524×10-24cm3; (12)Surface Tension: 41.423 dyne/cm; (13)Density: 1.83 g/cm3; (14)Flash Point: 74.444 °C; (15)Enthalpy of Vaporization: 40.715 kJ/mol; (16)Boiling Point: 188.329 °C at 760 mmHg; (17)Vapour Pressure: 0.831 mmHg at 25°C.

Preparation: this chemical can be prepared in the laboratory from aniline via the Sandmeyer reaction. In the first step, the amine functional group is diazotized with hydrochloric acid and sodium nitrite. Potassium iodide is added to the resultant diazonium chloride, causing nitrogen gas to evolve. Any excess nitrite is hydrolyzed with a strong base; the mixture is acidified and the desired product is separated by steam distillation.



Uses of Iodobenzene: it can be used to produce biphenyl at temperature of 130 °C. It will need reagent triethylamine, t-butylmethylbenzyl sulfide, phenyl halide and solvent dimethylformamide with reaction time of 24 hours. The yield is about 96%.

 

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes. When you are using it, wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: c1ccc(cc1)I
(2)InChI: InChI=1/C6H5I/c7-6-4-2-1-3-5-6/h1-5H
(3)InChIKey: SNHMUERNLJLMHN-UHFFFAOYAQ
(4)Std. InChI: InChI=1S/C6H5I/c7-6-4-2-1-3-5-6/h1-5H
(5)Std. InChIKey: SNHMUERNLJLMHN-UHFFFAOYSA-N

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