Iodobenzene

Base Information

• Chemical Name: Iodobenzene
• CAS No.: 591-50-4
• Deprecated CAS: 172484-65-0,2222572-06-5
• Molecular Formula: C6H5I
• Molecular Weight: 204.01
• Hs Code.: 2827600000
• European Community (EC) Number: 209-719-6
• NSC Number: 9244
• UNII: 9HK5L7YBBR
• DSSTox Substance ID: DTXSID8060452
• Nikkaji Number: J3.012.523A,J2.690E
• Wikipedia: Iodobenzene
• Wikidata: Q420839
• Metabolomics Workbench ID: 146847
• ChEMBL ID: CHEMBL116296
• Mol file: 591-50-4.mol

Synonyms:iodobenzene;iodobenzene, 123I-labeled;iodobenzene, 125I-labeled;iodobenzene, 14C-labeled

Chemical Property of Iodobenzene

Chemical Property:

• 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
• Water Solubility.: insoluble
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 203.94360
• Heavy Atom Count: 7
• Complexity: 46.1

Purity/Quality:

99% ^*data from raw suppliers

Iodobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi:Irritant
• Statements: R22:; R36:
• Safety Statements: S26:; S36:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Monoaromatics
• Canonical SMILES: C1=CC=C(C=C1)I
• 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.

Technology Process of Iodobenzene

There total 1059 articles about Iodobenzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(4-nitrophenyl)(phenyl)iodonium tetrafluoroborate → p-nitrobenzene iodide (636-98-6) + para-dinitrobenzene (100-25-4) + iodobenzene (591-50-4) + nitrobenzene (98-95-3,26969-40-4)

Guidance literature:

With sodium nitrite; In chloroform; water; at 56 ℃; for 1h;

DOI:10.1007/BF00954097

Reference yield: 93.0%

3-butenyltriphenylplumbane (134879-52-0) → iodobenzene (591-50-4) + 4-iodobut-1-ene (7766-51-0) + lead(II) iodide (10101-63-0)

Guidance literature:

With I₂; In chloroform-d1; (N2), stirred, treated with 3 equiv I2 at 25°C; filtered; NMR, IR, mass. spectra;

DOI:10.1021/om00054a069

Reference yield: 90.0%

p-methoxyphenyl(phenyl)iodonium tetrafluoroborate (733-53-9) → iodobenzene (591-50-4) + para-methoxynitrobenzene (100-17-4) + para-iodoanisole (696-62-8) + nitrobenzene (98-95-3,26969-40-4)

Guidance literature:

With sodium nitrite; In chloroform; water; at 56 ℃; for 3h; Title compound not separated from byproducts;

DOI:10.1007/BF00954097

upstream raw materials:

pyridine

1-methyl-4-nitrosobenzene

diphenyliodonium chloride

methyl magnesium iodide

Downstream raw materials:

4-iodobenzophenone

(biphenyl-2-yl)(diphenyl)methanol

triphenylmethyl alcohol

Tetraphenyllead

Refernces

• 1、 Fujita,Sakanishi,Okuyama. "Mechanism of racemization in the reaction of 4-methylcyclohexylidenemethyliodonium salt with sulfonate ions: Formation of intermediate cycloheptyne [1]". . p. 9190 - 9191. Retrieved 2001.
• 2、 Dopke, Joel A.,Lincoln, Zachary S.,Blazejewski, Jacob,Staples, Richard J.,Lee, Mark E.. "Microwave synthesis of charge-compensated dodecaborates bearing exohedral boron-phosphorus connectivities". . p. 263 - 267. Retrieved 2018.
• 3、 Kitamura, Tsugio,Stang, Peter J.. "GENERATION, TRAPPING AND FATE OF ALKYLIDENECARBENE-IODONIUM YLIDES FROM THE ADDITION OF NaN3 TO ALKYNYLPHENYLIODONIUM TOSYLATES". . p. 1887 - 1890. Retrieved 1988.
• 4、 Ochiai, Masahito,Yamamoto, Shinji,Suefuji, Takashi,Chen, Da-Wei. "Stereoselective synthesis of (Z)-enethiols and their derivatives: Vinylic SN2 reaction of (E)-alkenyl(phenyl)-λ3-iodanes with thioamides". . p. 2753 - 2756. Retrieved 2001.
• 5、 Ravenscroft, M. D.,Roberts, R. M. G.. "KINETICS AND MECHANISM OF IODODESTANNYLATION OF STANNATRANES". . p. 45 - 52. Retrieved 1986.
• 6、 Li, Minghong,Shang, Ming,Xu, Hui,Wang, Xing,Dai, Hui-Xiong,Yu, Jin-Quan. "Remote Para-C-H Acetoxylation of Electron-Deficient Arenes". . p. 540 - 544. Retrieved 2019.
• 7、 Pagni, Richard M.,Kabalka, George W.,Boothe, Richard,Gaetano, Kevan,Stewart, Lyman J.,et al.. "Reactions of Unsaturated Compounds with Iodine and Bromine on γ-Alumina". . p. 4477 - 4482. Retrieved 1988.
• 8、 Nekipelova, Tatiana D.,Kuzmin, Vladimir A.,Matveeva, Elena D.,Gleiter, Rolf,Zefirov, Nikolay S.. "On the mechanism of photoinduced addition of acetonitrile to phosphonium-iodonium ylides". . p. 137 - 143. Retrieved 2013.
• 9、 Milas, N. A.,Surgenor, D. M.. "". . p. 643 - 644. Retrieved 1946.
• 10、 Hoizumi,Moriya. "". . p. 499,502. Retrieved 1974.