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591-50-4

Basic Information
CAS No.: 591-50-4
Name: Iodobenzene
Article Data: 652
Cas Database
Molecular Structure:
Molecular Structure of 591-50-4 (Iodobenzene)
Formula: C6H5I
Molecular Weight: 204.01
Synonyms: Phenyl iodide;Benzene, iodo-;Iodinebenzol;Benzene,iodo-;Benzene iodide;
EINECS: 209-719-6
Density: 1.83 g/cm3
Melting Point: -29 °C(lit.)
Boiling Point: 188.329 °C at 760 mmHg
Flash Point: 74.444 °C
Solubility: insoluble in water
Appearance: Clear yellow liquid
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-36
Safety: 26-36
Transport Information: N/A
PSA: 0.00000
LogP: 2.29120
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%
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    Product Description Chemical Name Iodobenzene Synonyms IODOPHENYL;Benzene, iodo-;EINECS 209-719-6;Iodinebenzol;Iodo-benzene;Benzene iodide;Phenyl iodide;Benzene,iod CAS NO. 591-50-4 Purity 99% Appea

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    Iodobenzene CAS No.: 591-50-4 Molecular Formula:C6H5I Molecular Weight:204.01 Appearance: Colorless or light yellow transparent liquid Specification: GC>99.5%,Impurity max<0.2% Melting point: -29℃ Packaging:25kg/drum Capacity

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Consensus Reports

Reported in EPA TSCA Inventory.

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