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Iodobenzene 591-50-4 /manufacturer/low price/high quality/in stock
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591-50-4 Usage

Introduction

Iodobenzene is one Iodine substitution of benzene and its molecular formula is C6H5I. It Is a colorless liquid with special odor, insoluble in water, soluble in trichloromethane, ether and ethanol. It is Photosensitive and gradually turns yellow in case of light. Because the bond energy of C-I is lower than that of C-Cl and C-Br, its reactivity is much stronger. It can react with magnesium to generate grignard reagent Phenylmagnesium Iodide (PhMgI), which can be used as equivalent of phenyl anion in organic synthesis. Iodobenzene can be used as the raw material in Sonogashira coupling reaction, Heck reaction and Other metals catalyzed coupling reaction.

Preparation

Iodobenzene is obtained through the diazotization and replacement reaction of Aniline.
Hydrochloric acid( 30%) and aniline were added to Water, stirred and cooled to 2 ℃. Then,  sodium nitrite solution was added dropwise to the above solution and the temperature was controlled to be no more than 12℃. When the last part of sodium nitrite solution was added, potassium iodide starch paper was used to determine the blue reaction endpoint.
Then, diazotization liquid was obtained.  Potassium iodide solution was added to the diazotization solution in several batches until no nitrogen was released. After cooling, the upper aqueous solution was separated from the above system. Sodium hydroxide solution (10%) was added until the pH value was 14. A distillation process was carried out and aqueous layer was separated from the distillate. The atmospheric fractionation process was arried out after drying and the fraction at184-188 ℃ was collected, which is iodobenzene with a yield of 77%.

Uses

suzuki reaction

Chemical Properties

CLEAR YELLOW LIQUID

Purification Methods

Wash it with dilute aqueous Na2S2O3, then water. Dry it with CaCl2 or CaSO4, decolourise with charcoal and distil it under reduced pressure then store it with mercury or silver powder to stabilise it. [Beilstein 5 IV 688.]

Usage

A general reagent for organic synthesis and used as a standard liquid refractive index

Chemical Properties

Colorless liquid, melting point-31.27℃, boiling point 188.3℃, 63-64℃(1.07kPa), Flash point 74 ℃,density 1.8308(20/4℃), refractive index1.6200(18.5℃)
InChI:InChI=1/C6H6.HI/c1-2-4-6-5-3-1;/h1-6H;1H/p-1

591-50-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A12788)  Iodobenzene, 98%    591-50-4 1000g 2833.0CNY Detail
Alfa Aesar (A12788)  Iodobenzene, 98%    591-50-4 100g 329.0CNY Detail
Alfa Aesar (A12788)  Iodobenzene, 98%    591-50-4 50g 200.0CNY Detail

591-50-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name Iodobenzene

1.2 Other means of identification

Product number -
Other names IODOPHENYL

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:591-50-4 SDS

591-50-4Synthetic route

benzene
71-43-2

benzene

iodobenzene
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%
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%
diphenyliodonium iodide
2217-79-0

diphenyliodonium iodide

iodobenzene
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

phenyl-1,1,7-trihydroperfluoroheptyliodonium fluoroborate

aniline
62-53-3

aniline

A

iodobenzene
591-50-4

iodobenzene

B

anilinium tetrafluoroborate

anilinium tetrafluoroborate

C

N-1,1,7-trihydroperfluoroheptylaniline
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%
(Z)-4-methyl-2-pentene
691-38-3

(Z)-4-methyl-2-pentene

iodosylbenzene
536-80-1

iodosylbenzene

A

iodobenzene
591-50-4

iodobenzene

B

(2S,3S)-2-Isopropyl-3-methyl-oxirane
1192-31-0, 2390-95-6, 3204-02-2, 149117-09-9, 149117-14-6

(2S,3S)-2-Isopropyl-3-methyl-oxirane

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%
(E)-4-methylpent-2-ene
674-76-0

(E)-4-methylpent-2-ene

iodosylbenzene
536-80-1

iodosylbenzene

A

2.3-Epoxy-4-methylpentan
149117-14-6

2.3-Epoxy-4-methylpentan

B

iodobenzene
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

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

A

1-decyne
764-93-2

1-decyne

B

iodobenzene
591-50-4

iodobenzene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In dichloromethane at 20℃; for 10h; Elimination;A 94%
B 100%
2,2-dimethyl-5-(phenyl-λ3-iodaneylidene)-1,3-dioxane-4,6-dione
34107-52-3

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

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

iodobenzene
591-50-4

iodobenzene

C

acetone
67-64-1

acetone

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

tetrabutylammonium trifluoromethylsulfonate

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

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

A

iodobenzene
591-50-4

iodobenzene

B

(R)-4-methylcycloheptanone
13609-59-1

(R)-4-methylcycloheptanone

C

(R)-4-methylcycloheptanone

(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

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

A

iodobenzene
591-50-4

iodobenzene

B

(SR)-4-methylcyclohexylidenemethyl triflate

(SR)-4-methylcyclohexylidenemethyl triflate

C

5-methylcyclohept-1-enyl triflate

5-methylcyclohept-1-enyl triflate

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

diphenyliodonium bromide

mercury

mercury

A

iodobenzene
591-50-4

iodobenzene

B

biphenyl
92-52-4

biphenyl

C

mercury(I) bromide

mercury(I) bromide

D

bromo(phenyl)mercury
1192-89-8

bromo(phenyl)mercury

E

benzene
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%
diphenyliodonium chloride
1483-72-3

diphenyliodonium chloride

mercury

mercury

A

iodobenzene
591-50-4

iodobenzene

B

mercury(I) chloride

mercury(I) chloride

C

biphenyl
92-52-4

biphenyl

D

phenylmercury(II) chloride
100-56-1

phenylmercury(II) chloride

E

benzene
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%
m-carboran-9-yl(phenyl)iodonium tetrafluoroborate
81353-33-5

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

sodium chloride
7647-14-5

sodium chloride

A

iodobenzene
591-50-4

iodobenzene

B

9-chloro-m-carborane
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%
triphenylphosphinediiodogermylene
97939-92-9

triphenylphosphinediiodogermylene

phenyllithium
591-51-5

phenyllithium

A

iodobenzene
591-50-4

iodobenzene

B

biphenyl
92-52-4

biphenyl

C

triphenylgermane
2816-43-5

triphenylgermane

D

tetraphenylgermane
1048-05-1

tetraphenylgermane

E

triphenylphosphine
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)

phenyl bis(trifluoroacetate)

iodine
7553-56-2

iodine

A

iodobenzene
591-50-4

iodobenzene

B

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

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%
phenyl(p-carboran-2-yl)iodonium tetrafluoroborate
88242-78-8

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

sodium fluoride

sodium fluoride

A

iodobenzene
591-50-4

iodobenzene

B

2-iodo-closo-1,12-dodecaborane
22784-33-4

2-iodo-closo-1,12-dodecaborane

C

2-fluoro-p-caborane
22762-43-2

2-fluoro-p-caborane

D

benzene
71-43-2

benzene

Conditions
ConditionsYield
In dichloromethane; water 25°C, 0.6 h;A 99%
B 0%
C 99.5%
D <0.5
phenyl(p-carboran-2-yl)iodonium tetrafluoroborate
88242-78-8

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

sodium fluoride

sodium fluoride

A

iodobenzene
591-50-4

iodobenzene

B

2-fluoro-p-caborane
22762-43-2

2-fluoro-p-caborane

C

(Dichloroiodo)benzene
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%
phenylthalium(III) di(trifluoroacetate)
23586-54-1

phenylthalium(III) di(trifluoroacetate)

iodobenzene
591-50-4

iodobenzene

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

dimethylsulfide

benzene
75067-08-2

benzene

A

iodobenzene
591-50-4

iodobenzene

B

methoxydimethylsulfonium tosylate
120188-75-2

methoxydimethylsulfonium tosylate

Conditions
ConditionsYield
In dichloromethane for 0.25h;A n/a
B 99%
3,3-diethyl-1-phenyltriaz-1-ene
13056-98-9

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

iodobenzene
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;
(4-bromophenyl)thioanisole
104-95-0

(4-bromophenyl)thioanisole

benzene
75067-08-2

benzene

A

iodobenzene
591-50-4

iodobenzene

B

C8H10BrOS(1+)*C7H7O3S(1-)
120188-78-5

C8H10BrOS(1+)*C7H7O3S(1-)

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

dibenzyl sulfide

benzene
75067-08-2

benzene

A

iodobenzene
591-50-4

iodobenzene

B

C15H17OS(1+)*C7H7O3S(1-)
120188-76-3

C15H17OS(1+)*C7H7O3S(1-)

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

diphenyliodonium tetrafluoroborate

sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

A

iodobenzene
591-50-4

iodobenzene

B

diphenyl sulphone
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

sodium hydrogenfluoride

phenyl(p-carboran-2-yl)iodonium tetrafluoroborate
88242-78-8

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

A

iodobenzene
591-50-4

iodobenzene

B

2-iodo-closo-1,12-dodecaborane
22784-33-4

2-iodo-closo-1,12-dodecaborane

C

2-fluoro-p-caborane
22762-43-2

2-fluoro-p-caborane

D

benzene
71-43-2

benzene

Conditions
ConditionsYield
In dichloromethane; water at 25°C, 0.5 h;A 95%
B <1
C 99%
D <0.5
{3-(p-tolylthio)propyl}triphenyltin
77329-29-4

{3-(p-tolylthio)propyl}triphenyltin

A

iodobenzene
591-50-4

iodobenzene

B

(C6H5)2SnI(CH2)3SC6H4CH3
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
(C6H5)3SnCH2CH2CH2CH2SC6H4CH3
77329-30-7

(C6H5)3SnCH2CH2CH2CH2SC6H4CH3

A

iodobenzene
591-50-4

iodobenzene

B

(C6H5)2SnI(CH2)4SC6H4CH3

(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

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

iodine
7553-56-2

iodine

A

iodobenzene
591-50-4

iodobenzene

B

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
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%
[bis(acetoxy)iodo]benzene
3240-34-4

[bis(acetoxy)iodo]benzene

iodobenzene
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;
1-cyclohexyl-2-phenylcyclopropane
3145-75-3

1-cyclohexyl-2-phenylcyclopropane

A

iodobenzene
591-50-4

iodobenzene

B

2-cyclohexyl-1-(4-iodophenyl)-cyclopropane
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%
iodobenzene
591-50-4

iodobenzene

biphenyl
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%
iodobenzene
591-50-4

iodobenzene

(Dichloroiodo)benzene
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%
iodobenzene
591-50-4

iodobenzene

benzene
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%
iodobenzene
591-50-4

iodobenzene

propargyl alcohol
107-19-7

propargyl alcohol

3-Phenyl-2-propyn-1-ol
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%
acetamide
60-35-5

acetamide

iodobenzene
591-50-4

iodobenzene

Acetanilid
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%
styrene
292638-84-7

styrene

iodobenzene
591-50-4

iodobenzene

(E)-1,2-diphenyl-ethene
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%
methanol
67-56-1

methanol

iodobenzene
591-50-4

iodobenzene

carbon monoxide
201230-82-2

carbon monoxide

benzoic acid methyl ester
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%
iodobenzene
591-50-4

iodobenzene

pent-1-yn-5-ol
5390-04-5

pent-1-yn-5-ol

5-phenylpent-4-yn-1-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%
iodobenzene
591-50-4

iodobenzene

cyclohexyl acrylate
3066-71-5

cyclohexyl acrylate

(E)-cyclohexyl cinnamate
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%
iodobenzene
591-50-4

iodobenzene

2-propenethiotrimethylstannane
138535-23-6

2-propenethiotrimethylstannane

allyl phenyl thioether
5296-64-0

allyl phenyl thioether

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

iodobenzene

C3F5IZn

C3F5IZn

(Z)-1-phenyl-1,2,3,3,3-pentafluoro-1-propene
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%
iodobenzene
591-50-4

iodobenzene

diphenyl sulfide
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%
iodobenzene
591-50-4

iodobenzene

methyl vinyl ketone
78-94-4

methyl vinyl ketone

(E)-benzalacetone
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%
iodobenzene
591-50-4

iodobenzene

acrylonitrile
107-13-1

acrylonitrile

cinnamonitrile
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%
iodobenzene
591-50-4

iodobenzene

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

Methyl cinnamate
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%
iodobenzene
591-50-4

iodobenzene

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

methyl cinnamate
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%
iodobenzene
591-50-4

iodobenzene

phenylacetylene
536-74-3

phenylacetylene

diphenyl acetylene
501-65-5

diphenyl acetylene

Conditions
ConditionsYield
With triethylamine; bis(tert-butylaminophosphine)palladium(II) at 80℃; for 0.25h; 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%
iodobenzene
591-50-4

iodobenzene

carbon monoxide
201230-82-2

carbon monoxide

aniline
62-53-3

aniline

N-phenyl benzoyl amide
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%
iodobenzene
591-50-4

iodobenzene

diphenyldisulfane
882-33-7

diphenyldisulfane

diphenyl sulfide
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%
iodobenzene
591-50-4

iodobenzene

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

4,4-diphenylbutan-2-one
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%
iodobenzene
591-50-4

iodobenzene

1-butyn-4-ol
927-74-2

1-butyn-4-ol

4-phenyl-but-3-yn-1-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%
iodobenzene
591-50-4

iodobenzene

ethyl acrylate
140-88-5

ethyl acrylate

ethyl cinnamate
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%
iodobenzene
591-50-4

iodobenzene

phenol
108-95-2

phenol

diphenylether
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%
iodobenzene
591-50-4

iodobenzene

phenylboronic acid
98-80-6

phenylboronic acid

biphenyl
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%
iodobenzene
591-50-4

iodobenzene

acrylic acid
79-10-7

acrylic acid

(E)-3-phenylacrylic 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%
iodobenzene
591-50-4

iodobenzene

1-Phenyl-2-propyn-1-ol
4187-87-5

1-Phenyl-2-propyn-1-ol

1,3-diphenyl-1-propyn-3-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%

591-50-4Upstream product

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