What is the Iodobenzene?

Iodobenzene is Clear yellow liquid, while it's Molecular Formula is C6H5I. Clear yellow liquid

What is the CAS number for Iodobenzene?

The CAS number of Iodobenzene is 591-50-4.

What is Iodobenzene (591-50-4) used for?

Iodobenzene is a versatile aryl halide commonly used in organic synthesis, particularly in coupling reactions such as N-arylation of amides, Sonogashira coupling, and Pd-catalyzed a-arylation of thioamides. It serves as a key reactant in copper- or palladium-catalyzed transformations, enabling the formation of C–C or C–N bonds under mild to optimized conditions. Additionally, iodobenzene is involved in hypervalent iodine chemistry, where it can appear as a by-product in glycosidation reactions. Its reactivity with terminal alkynes, amides, and thioamides highlights its utility in constructing complex molecules, including pharmaceuticals and functional materials. Iodobenzene's compatibility with various catalysts (e.g., Cu2O, Pd, Ni) and ligands further underscores its broad applicability in synthetic chemistry.InChI:InChI=1/C6H6.HI/c1-2-4-6-5-3-1;/h1-6H;1H/p-1

What is the Iodobenzene?

Iodobenzene is Clear yellow liquid, while it's Molecular Formula is C6H5I. Clear yellow liquid

What is the CAS number for Iodobenzene?

The CAS number of Iodobenzene is 591-50-4.

What is Iodobenzene (591-50-4) used for?

Iodobenzene is a versatile aryl halide commonly used in organic synthesis, particularly in coupling reactions such as N-arylation of amides, Sonogashira coupling, and Pd-catalyzed α-arylation of thioamides. It serves as a key reactant in copper- or palladium-catalyzed transformations, enabling the formation of C–C or C–N bonds under mild to optimized conditions. Additionally, iodobenzene is involved in hypervalent iodine chemistry, where it can appear as a by-product in glycosidation reactions. Its reactivity with terminal alkynes, amides, and thioamides highlights its utility in constructing complex molecules, including pharmaceuticals and functional materials. Iodobenzene's compatibility with various catalysts (e.g., Cu2O, Pd, Ni) and ligands further underscores its broad applicability in synthetic chemistry.InChI:InChI=1/C6H6.HI/c1-2-4-6-5-3-1;/h1-6H;1H/p-1

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Buy Quality Iodobenzene 591-50-4 In Stock with Immediately Delivery

Molecular Formula: C6H5I
Molecular Weight: 204.01
Appearance/Colour: Clear yellow liquid
Melting Point: -29 °C(lit.)
Refractive Index: n20/D 1.62(lit.)
Boiling Point: 188.329 °C at 760 mmHg
Flash Point: 74.444 °C
PSA： 0.00000
Density: 1.83 g/cm³
LogP: 2.29120

Iodobenzene(Cas 591-50-4) Usage

Chemical Description

Iodobenzene is an organic compound with the formula C6H5I.

Use Description

Iodobenzene, a chemical compound, has various applications in different fields. In the pharmaceutical industry, it serves as a reagent in the synthesis of pharmaceutical compounds, particularly those related to radioimaging and radiopharmaceuticals. Its role is vital in introducing iodine isotopes into drug molecules for use in diagnostic imaging and cancer treatment. In the field of organic chemistry, iodobenzene is employed as a versatile building block for the creation of complex organic molecules, contributing to academic research and the development of new chemical reactions and methodologies. Additionally, it finds utility in the field of materials science, where it can be used as a dopant or precursor in the production of organic electronic materials and polymers, aiding in the creation of advanced electronic devices and materials. Its multifaceted applications underscore its importance in improving diagnostic imaging, advancing chemical research, and enhancing the performance of electronic materials across these diverse fields.

InChI:InChI=1/C6H6.HI/c1-2-4-6-5-3-1;/h1-6H;1H/p-1

591-50-4 Relevant articles

Mechanism of racemization in the reaction of 4-methylcyclohexylidenemethyliodonium salt with sulfonate ions: Formation of intermediate cycloheptyne [1]

Fujita,Sakanishi,Okuyama

, p. 9190 - 9191 (2001)

Microwave synthesis of charge-compensated dodecaborates bearing exohedral boron-phosphorus connectivities

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, p. 263 - 267 (2018)

Solution pyrolysis of arylphosphonium sa...

-

Whitmore,Thorpe

, p. 782,783 (1933)

GENERATION, TRAPPING AND FATE OF ALKYLIDENECARBENE-IODONIUM YLIDES FROM THE ADDITION OF NaN3 TO ALKYNYLPHENYLIODONIUM TOSYLATES

Kitamura, Tsugio,Stang, Peter J.

, p. 1887 - 1890 (1988)

Addition of NaN3 to RCCIPh(1+)*OTs(1-) r...

Gold-catalyzed synthesis of iodofulvenes

Noesel, Pascal,Lauterbach, Tobias,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.

, p. 8634 - 8641 (2013)

We report the gold-catalyzed synthesis o...

Stereoselective synthesis of (Z)-enethiols and their derivatives: Vinylic SN2 reaction of (E)-alkenyl(phenyl)-λ3-iodanes with thioamides

Ochiai, Masahito,Yamamoto, Shinji,Suefuji, Takashi,Chen, Da-Wei

, p. 2753 - 2756 (2001)

(Equation presented) Exposure of (E)-β-a...

(Diacetoxyiodo)benzene-Mediated Transition-Metal-Free Amination of C(sp3)-H Bonds Adjacent to Heteroatoms with Azoles: Synthesis of N-Alkylated Azoles

Sun, Bin,Yan, Zhiyang,Jin, Can,Su, Weike

, p. 2432 - 2436 (2018)

A novel PhI(OAc) 2 -mediated cross-dehyd...

KINETICS AND MECHANISM OF IODODESTANNYLATION OF STANNATRANES

Ravenscroft, M. D.,Roberts, R. M. G.

, p. 45 - 52 (1986)

A detailed kinetic study of iododestanny...

Functionalized Nitrogen Atom Transfer Catalyzed by Cytochrome P-450

Svastits, Edmund W.,Dawson, John H.,Breslow, Ronald,Gellman, Samuel H.

, p. 6427 - 6428 (1985)

Remote Para-C-H Acetoxylation of Electron-Deficient Arenes

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, p. 540 - 544 (2019)

One formidable challenge in sp2 C-H acti...

Preparation of Bis(arylthio)iodobenzene and Reaction with 1-Alkynes. A Novel Route to 1,2-Bis(arylthio)alkenes

Kita, Yasuyuki,Okuno, Takayuki,Tohma, Hirofumi,Akai, Shuji,Matsumoto, Keita

, p. 2717 - 2720 (1994)

The in situ reaction of a novel hyperval...

Reactions of Unsaturated Compounds with Iodine and Bromine on γ-Alumina

Pagni, Richard M.,Kabalka, George W.,Boothe, Richard,Gaetano, Kevan,Stewart, Lyman J.,et al.

, p. 4477 - 4482 (1988)

Iodine reacts with a diverse group of un...

On the mechanism of photoinduced addition of acetonitrile to phosphonium-iodonium ylides

Nekipelova, Tatiana D.,Kuzmin, Vladimir A.,Matveeva, Elena D.,Gleiter, Rolf,Zefirov, Nikolay S.

, p. 137 - 143 (2013)

Recently, a novel photochemical reaction...

Inversion of Configuration in Nucleophilic Vinylic Substitutions of (E)-β-Alkylvinyliodonium Tetrafluoroborates with Halides

Ochiai, Masahito,Oshima, Kunio,Masaki, Yukio

, p. 7059 - 7061 (1991)

Syntheses of (1,1-Dihydroperfluoroalkyl)aryliodonium Triflates and Their Analogues

Unemoto, Teruo,Gotoh, Yoshihiko

, p. 235 - 240 (1985)

(1,1-Dihydroperfluoroalkyl)phenyl- and -...

Reverse Halogenation Using Supported Copper(I) Iodide

Clark, James H.,Jones, Craig W.

, p. 1409 - 1410 (1987)

Alumina and charcoal supported copper(I)...

Radiolysis of Solutions of Diphenyliodonium and Triphenylsulfonium Hexafluorophosphates in Various Solvents

Ma, Xiao-Hua,Yamamoto, Yukio,Hayashi, Koichiro

, p. 5443 - 5445 (1988)

The radiolysis of solutions of Ph2IPF6 a...

Migratory insertion and reductive coupling of tetraarylruthenium(IV) complexes

So, Shiu-Chun,Cheung, Wai-Man,Wang, Guo-Cang,Kwan Huang, Enrique,Lau, Man-Kit,Zhang, Qian-Feng,Sung, Herman H.-Y.,Williams, Ian D.,Leung, Wa-Hung

, p. 4497 - 4502 (2014)

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The [closo-B12H11-1-IAr]- zwitterion as a precursor to monosubstituted derivatives of [closo-B12H12]2-

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, p. 70 - 79 (2015)

Reactions of [closo-B12H12]2- with ArI(O...

Iron-mediated desulphurization approach: synthesis of cyanamides and their conversions

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, (2022/01/12)

The iron-mediated efficient multi-compon...

A convenient synthetic approach to a novel class of aryldifluoromethyl pyrimidine derivatives containing strobilurin motif as insecticidal agents

Cai, Zengfei,Cao, Yangyang,Du, Xiaohua,Hao, Shulin,Zhang, Wenliang

supporting information, (2021/10/07)

A series of aryldifluoromethyl pyrimidin...

Efficient Pd(ii)-catalyzed regioselectiveortho-halogenation of arylcyanamides

Alam, M. Mujahid,Boddapati, S. N. M.,Bollikolla, Hari Babu,Gugulothu, Sailaja,Tamminana, Ramana,Varala, Ravi

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Regioselectiveortho-halogenation of aryl...

Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes

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supporting information, (2021/05/26)

Owing to both Lewis and Bronsted acid ac...

591-50-4 Process route

: 733-53-9
p-methoxyphenyl(phenyl)iodonium tetrafluoroborate

: 591-50-4
iodobenzene

: 100-17-4
para-methoxynitrobenzene

: 696-62-8
para-iodoanisole

: 98-95-3,26969-40-4
nitrobenzene

Conditions

Conditions	Yield
With sodium nitrite; In chloroform; water; at 56 ℃; for 3h; Title compound not separated from byproducts;	9% 90% 8 % Chromat. 90 % Chromat.
With sodium nitrite; In chloroform; water; at 56 ℃; for 3h;	90 % Chromat. 90% 8 % Chromat. 9%
With sodium nitrite; In chloroform; water; at 56 ℃; for 3h; Product distribution; other substituted arylphenyliodonium fluoroborates, diphenyliodonium fluoroborate, other reaction time;	90% 9% 90 % Chromat. 8 % Chromat.