624-31-7 Usage
Description
4-Iodotoluene, also known as 4-methyliodobenzene, is an organic compound that belongs to the class of halogenated aromatic hydrocarbons. It is characterized by the presence of an iodine atom attached to a toluene molecule, which gives it unique chemical properties and reactivity. 4-Iodotoluene is a colorless to pale yellow liquid with a characteristic aromatic odor.
Uses
Used in Pharmaceutical Industry:
4-Iodotoluene is used as a pharmaceutical intermediate for the synthesis of various drugs and medications. Its unique chemical properties make it a valuable building block in the development of new pharmaceutical compounds.
Used in Chemical Industry:
4-Iodotoluene is used in the synthesis of various organic compounds, including dyes, agrochemicals, and other specialty chemicals. Its reactivity with other compounds makes it a versatile intermediate in the chemical industry.
Used in Suzuki Reaction:
4-Iodotoluene is used as a reactant in the Suzuki reaction, a widely used cross-coupling reaction in organic chemistry. This reaction allows for the formation of carbon-carbon bonds, which are essential in the synthesis of complex organic molecules.
Used in Liquid Crystal Display (LCD) Industry:
4-Iodotoluene is used in the production of polarizing films for liquid crystal displays (LCDs). Its unique optical properties make it an important component in the manufacturing of high-quality LCD screens.
Synthesis Reference(s)
The Journal of Organic Chemistry, 52, p. 691, 1987 DOI: 10.1021/jo00380a041Synthesis, p. 572, 1980 DOI: 10.1055/s-1980-29128
Purification Methods
Crystallise 4-iodotoluene from EtOH and.or distil it. [Beilstein 5 IV 840.]
Check Digit Verification of cas no
The CAS Registry Mumber 624-31-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 4 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 624-31:
(5*6)+(4*2)+(3*4)+(2*3)+(1*1)=57
57 % 10 = 7
So 624-31-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H7I/c1-6-2-4-7(8)5-3-6/h2-5H,1H3
624-31-7Relevant articles and documents
Friedman,Chlebowski
, p. 1636 (1968)
Synthesis of biaryl compounds via Suzuki homocoupling reactions catalyzed by metal organic frameworks encapsulated with palladium nanoparticles
Bao, Yan-Sai,Cui, Xin-Yu,Han, Zheng-Bo,Li, Xin,Tang, Hong,Yang, Ming,Zhang, Yu-Yang,Zhao, Kun,Zhou, Mei-Li
, (2020/12/17)
Heterogeneous homocoupling reactions of phenylboronic acids were greatly accelerated via Suzuki homocoupling reactions. In this work, a tandem route was designed which firstly one part of phenylboronic acids reacted with iodine to form iodobenzenes, then another part of phenylboronic acids coupled with iodobenzenes to produce biaryl compounds. The tandem reaction were catalyzed by a bifunctional heterogeneous catalyst of metal organic frameworks encapsulated with palladium nanoparticles (Pd?MOFs). This strategy for forming symmetric C-C bond between benzene rings has obvious advantages such as high efficiency, easy separation, good recyclability and no addition of toxic halogenated benzene.
Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange
Boehm, Philip,Cacherat, Bastien,Lee, Yong Ho,Martini, Tristano,Morandi, Bill
supporting information, p. 17211 - 17217 (2021/07/02)
We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C?P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.