53779-84-3

Basic information

• Product Name: 2,4-DIIODO-1,3,5-TRIMETHYL-BENZENE
• Synonyms: 2,4-DIIODO-1,3,5-TRIMETHYL-BENZENE;VITAS-BB TBB000524
• CAS NO: 53779-84-3
• Molecular Formula: C₉H₁₀I₂
• Molecular Weight: 371.98
• Mol File: 53779-84-3.mol

Chemical Properties

• Melting Point: 82-83 °C(Solv: ethanol (64-17-5))
• Boiling Point: 322.8±37.0 °C(Predicted)
• Appearance: /
• Density: 2.039±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2,4-DIIODO-1,3,5-TRIMETHYL-BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIIODO-1,3,5-TRIMETHYL-BENZENE(53779-84-3)
• EPA Substance Registry System: 2,4-DIIODO-1,3,5-TRIMETHYL-BENZENE(53779-84-3)

Safety Data

• Hazardous Substances Data: 53779-84-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,4-Diiodo-1,3,5-trimethylbenzene is utilized as a key intermediate in organic synthesis, contributing to the formation of complex organic molecules. Its unique structure with iodine and methyl groups allows for versatile chemical reactions, making it a valuable component in the synthesis of various organic compounds.
Used in Chemical Reactions as a Reagent:
As a reagent, 2,4-Diiodo-1,3,5-trimethylbenzene plays a crucial role in facilitating specific chemical transformations. Its presence can enhance the efficiency of certain reactions or enable the formation of desired products that may not be achievable with other reagents.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2,4-Diiodo-1,3,5-trimethylbenzene serves as a building block for the development of new drugs. Its unique chemical properties allow it to be incorporated into the molecular structures of potential therapeutic agents, contributing to the discovery and creation of novel medications.
Used in Agrochemical Production:
Similarly, in agrochemicals, 2,4-Diiodo-1,3,5-trimethylbenzene is employed as a fundamental component in the synthesis of various agricultural chemicals. Its integration into these products can enhance their effectiveness in crop protection and other agricultural applications.
Used in Specialty Chemicals Production:
2,4-Diiodo-1,3,5-trimethylbenzene is also used in the production of specialty chemicals, which are tailored for specific industries and applications. Its unique structure and reactivity make it suitable for creating customized chemical products that meet the needs of specialized markets.

Upstream product

• 108-67-8 1,3,5-trimethyl-benzene 
• 4028-63-1 iodomesitylene 
• 7446-11-9 sulfur trioxide 
• 3453-83-6 mesitylene sulfonic acid 

Downstream Products

• 1042414-02-7 2,4-bis(4-bromophenylthio)-1,3,5-trimethylbenzene 
• 38329-18-9 1,3-diiodo-2,4,6-trimethyl-5-nitro-benzene 
• 19025-36-6 2,4,6-triiodomesitylene 

Relevant articles and documents

R4NHal/NOHSO4: A Usable System for Halogenation of Isoxazoles, Pyrazoles, and beyond

A new convenient and versatile halogenating system (R4NHal/NOHSO4), giving straightforward and general access to halogenated 3,5-diaryl- and alkylarylisoxazoles, pyrazoles and electron-rich benzenes from the corresponding scaffolds, is suggested. The method provides excellent regioselectivity, scalability to the gram scale, and a broad scope for both aromatics and halogens. A three-step, one-pot reaction protocol was developed, and a series of 3,5-diaryl-4-haloisoxazoles has been efficiently synthesized from 1,2-diarylcyclopropanes under suggested nitrosating-halogenating conditions.

Polyiodine-Modified 1,3,5-Benzenetricarboxylic Acid Framework Zn(II)/Cd(II) Complexes as Highly Selective Fluorescence Sensors for Thiamine Hydrochloride, NACs, and Fe3+/Zn2+

Four new complexes, [Zn(TIBTC)(DMA)]·[NH2(CH3)2] (1), [Cd(TIBTC)(H2O)]·[NH2(CH3)2]·DMA (2), [Cd2(TIBTC)(2,2′-bipy)2(HCOO)] (3), and [Cd2(DIBTC)(2,2′-bipy)2(HCOO)] (4) (H3TIBTC = 2,4,6-triiodo-1,3,5-benzenetricarboxylic acid, H3DIBTC = 2,4-diiodo-1,3,5-benzenetricarboxylic acid, 2,2′-bipy = 2,2′-bipyridine, and DMA = dimethylacetamide), were successfully synthesized and characterized by elemental analysis, powder X-ray diffraction, infrared spectroscopy, ultraviolet-visible spectroscopy, and thermogravimetric analysis. Complexes 1 and 2 are three-dimensional supramolecular network structures, while complex 4 has a two-dimensional network structure. We preliminarily studied the fluorescence properties of the complexes and found that complexes 1-3 can detect thiamine hydrochloride, NACs, and Fe3+/Zn2+ with high sensitivity and selectivity.

Metal-Free, Oxidant-Free, and Controllable Graphene Oxide Catalyzed Direct Iodination of Arenes and Ketones

A direct, metal-free, and oxidant-free method for the graphene oxide (GO)-catalyzed iodination of arenes and ketones with iodine in a neutral medium was explored. This iodination protocol was performed by using a simple technique to avoid the use of external metal catalysts and oxidants and harsh acidic/basic reaction conditions. In addition, by this method the degree of iodination could be controlled, and the reaction was scalable and compatible with air. This strategy opens a new field for GO-catalyzed chemistry and provides an avenue for the convenient direct iodination of arenes and ketones.

Electrophilic aryl-halogenation using N-halosuccinimides under ball-milling

We report here a methodology of chemo- and regio-selective aryl bromination and iodination using respective N-halosuccinimides at room temperature in the absence of any solvents, catalyst/additives under ball-milling condition. However, for chlorination ceric ammonium nitrate was used as additive. The coupled product succinimide, produced from the reactions, was recycled via regeneration of NBS. This methodology works with the electron-donor substituted or unsubstituted arenes.

Electrophilic aryl-halogenation using N-halosuccinimides under ball-milling

We report here a methodology of chemo- and regio-selective aryl bromination and iodination using respective N-halosuccinimides at room temperature in the absence of any solvents, catalyst/additives under ball-milling condition. However, for chlorination ceric ammonium nitrate was used as additive. The coupled product succinimide, produced from the reactions, was recycled via regeneration of NBS. This methodology works with the electron-donor substituted or unsubstituted arenes.

Potassium 4-iodylbenzenesulfonate: Preparation, structure, and application as a reagent for oxidative iodination of arenes

A new hypervalent iodine(V) compound, potassium 4-iodylbenzenesulfonate, was prepared by the oxidation of 4-iodobenzensulfonic acid with Oxone in water. This potassium salt can be further converted into 4-iodylbenzenesulfonic acid by treatment with the acidic form of Amberlyst 15 in water. A single-crystal X-ray structure of potassium 4-iodylbenzenesulfonate revealed the presence of polymeric chains in the solid state due to a combination of numerous intra- and intermolecular interactions. Potassium 4-iodylbenzenesulfonate will likely find many practical applications as a thermally stable and water-soluble hypervalent iodine-based oxidant, particularly useful as a reagent for oxidative iodination of aromatic substrates. This reagent can be effectively recovered from the reaction mixture (92 % recovery) by treatment of the aqueous layer with Oxone at 60°C for 2 h, followed by filtration of the precipitate. A new hypervalent iodine(V) compound, potassium 4-iodylbenzenesulfonate, was prepared by oxidation of 4-iodobenzenesulfonic acid with Oxone in water. This new reagent promises many practical applications as a thermally stable, water-soluble and recyclable hypervalent iodine oxidant, particularly useful for oxidative iodination of aromatic substrates.

Desulfonyloxyiodination of arenesulfonic acids with mCPBA and molecular iodine

Treatment of p-alkylbenzenesulfonic acids with mCPBA and molecular iodine gave p-alkyliodobenzenes in good to moderate yields via electrophilic ipso-substitution by the iodonium species (I+) formed. This desulfonyloxyiodination was promoted by the addition of a catalytic amount of iodoarenes, such as o-iodobenzoic acid. The same treatment of dimethylbenzenesulfonic acids and trimethylbenzenesulfonic acids with mCPBA and molecular iodine proceeded smoothly both in the absence and in the presence of o-iodobenzoic acid to provide the corresponding monoiodo-dimethylbenzene and diiodo-dimethylbenzene, and diiodo-trimethylbenzene and triiodo- trimethylbenzene, in good to moderate yields, respectively. On the other hand, the same desulfonyloxyiodination of benzenesulfonic acid and p-chlorobenzenesulfonic acid with mCPBA and molecular iodine proceeded only in the presence of o-iodobenzoic acid to generate iodobenzene and p-chloroiodobenzene, respectively, in moderate yields.

1,3-Diiodo-5,5-dimethylhydantoin-An efficient reagent for iodination of aromatic compounds

1,3-Diiodo-5,5-dimethylhydantoin in organic solvents successfully iodinates alkylbenzenes, aromatic amines, and phenyl ethers. The reactivity of electrophilic iodine is controlled by acidity of the medium. Superelectrophilic iodine generated upon dissolution of 1,3-diiodo-5,5-dimethylhydantoin in sulfuric acid readily reacts with electron-deficient arenes at 0 to 20°C with formation of the corresponding iodo derivatives in good yields. The structure of electrophilic iodine species generated from 1,3-diiodo-5,5- dimethylhydantoin in sulfuric acid is discussed.

Selective and effective iodination of alkyl-substituted benzenes with elemental iodine activated by Selectfluor F-TEDA-BF4

Selective direct introduction of an iodine atom into alkyl-substituted benzene derivatives was effectively achieved by reaction of target molecules with elemental iodine in the presence of 1-chloromethyl-4-fluoro- 1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor F-TEDA-BF4). The number of iodine atoms introduced could be modulated by the molar ratio between substrate, iodine and F-TEDA-BF4.

2,4,6,8-tetraiodo-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione as a mild and convenient reagent for iodination of aromatic compounds

2,4,6,8-Tetraiodo-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione (tetraiodoglycoluril) is a convenient reagent for preparative iodination of benzene, alkylbenzenes, polycyclic hydrocarbons, aromatic amines, and phenol ethers in organic solvents under mild conditions.