1122-42-5

Usage

Uses

1. Used in Research Applications:
1,4-Dimethyl-2-iodobenzene is used as a fluorescence quencher for studying the solubilization sites provided by micelles. Its ability to quench fluorescence helps researchers understand the behavior of micelles in various environments and their interactions with other molecules.
2. Used in Chemical Synthesis:
As an organic compound, 1,4-Dimethyl-2-iodobenzene can be utilized as a starting material or intermediate in the synthesis of various other organic compounds, particularly those with similar structural features. Its unique combination of methyl and iodine substituents makes it a valuable building block for creating complex organic molecules.
3. Used in Analytical Chemistry:
The distinct chemical properties of 1,4-Dimethyl-2-iodobenzene, such as its clear yellow color and fluorescence quenching ability, make it a useful reference compound in analytical chemistry. It can be employed as a standard for calibrating instruments or for validating analytical methods that involve the detection and quantification of similar compounds.
4. Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 1,4-Dimethyl-2-iodobenzene may also find applications in the pharmaceutical industry as a precursor for the synthesis of various drugs or as a tool for studying drug-micelle interactions, which are crucial for understanding drug solubility, absorption, and distribution in the body.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 6, p. 709, 1988Tetrahedron Letters, 30, p. 3769, 1989 DOI: 10.1016/S0040-4039(01)80650-X

InChI:InChI=1/C8H9I/c1-6-3-4-7(2)8(9)5-6/h3-5H,1-2H3

Upstream product

• 95-78-3 2,5-Dimethylaniline 
• 106-42-3 para-xylene 
• 7697-37-2 nitric acid 
• 7664-93-9 sulfuric acid 
• 7553-56-2 iodine 
• 64-19-7 acetic acid 
• 420-87-1 sodium 2,2,2-trifluoroethanolate 
• 10534-59-5 tetrabutylammonium acetate 
• 4670-62-6 tetra-N-butylammonium benzenethiolate 
• 3674-54-2 tetrabutylammonium thiocyanate 
• 609-54-1 2,5-dimethylbenzenesulfonic acid 
• 127938-44-7 2-dichloroiodanyl-1,4-dimethyl-benzene 
• 75-03-6 ethyl iodide 
• 2712-78-9 bis-[(trifluoroacetoxy)iodo]benzene 

Downstream Products

• 127938-44-7 2-dichloroiodanyl-1,4-dimethyl-benzene 
• 57152-81-5 2'',3'',5'',6''-Tetrafluoro-2,5,2'''',5''''-tetramethyl-[1,4';1',1'';4'',1''';4''',1'''']quinquephenyl 
• 97053-04-8 N-(2,5-xylyl)pyrrolidine 
• 95-87-4 2,5-Dimethylphenol 
• 106-42-3 para-xylene 
• 72553-31-2 (4-Dimethylaminomethyl-2-iodo-benzyl)-dimethyl-amine 
• 13730-09-1 2,5-dimethylbenzonitrile 
• 30101-09-8 (2,5-dimethylphenyl)diiodoborane 
• 1416974-57-6 C₁₄H₁₃FS 
• 55312-97-5 2-(2,5-dimethylphenyl)acetyl chloride 
• 346691-76-7 (E,E)-2,5-bis(4’-hydroxy-3’-carbomethoxystyryl)-1-iodobenzene 
• 346691-75-6 (E,E)-2,5-bis(4’-methoxy-3’-carbomethoxystyryl)-1-iodobenzene 

Relevant academic research and scientific papers

Efficient and direct iodination of alkyl benzenes using polymer/HIO4 and I2 under mild condition

An efficient and rapid method has been found for the iodination of aromatic compounds using iodine and polymer-supported periodic acid (PSPIA) as an oxidant under mild aprotic conditions. The reagent after the completion of the reaction was easily removed by filtration and was regenerated for further use. This method has some advantages such as: mild reaction conditions, straight forward procedure, inexpensive method, high yields and one-pot conversion.

Iodination of (E)-2,2,5,5-tetramethyl-3,4-diphenylhex-3-ene: Catalytic effects of silver triflate and water in the I2/Ag2SO4 iodination

(E)-2,2,5,5-Tetramethyl-3 4-diphenylhex-3-ene does not iodinate under normal conditions. Silver trifluoromethanesulfonate catalysis of the silver sulfate/iodine promoted reaction is shown to add versatility to this reation and successfully produce (E)-3-(4'-iodophenyl)-2,2,5,5-tetramethyl-4-phenylhex-3-ene and (E)-2,2,5,5-tetramethyl-3,4-di(4'-iodophenyl)hex-3-ene in good yield under mild conditions. Success is shown to be dependent upon the presence of a trace of water in the dichloromethane solvent.

Mild and regioselective iodination of aromatic compounds with N,N′-diiodo-N,N′-1,2-ethanediylbis(p-toluenesulphonamide)

N,N′-Diiodo-N,N′-1,2-ethanediylbis(p-tolouenesulphonamide) [NIBTS] and catalytic trifluoroacetic acid can be used for the regioselective iodination of aromatic compounds in acetonitrile under mild conditions in excellent yields.

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.

A comparison of microwave-accelerated and conventionally heated iodination reactions of some arenes and heteroarenes, using ortho-periodic acid as the oxidant

A fast and simple method for the oxidative iodination of some activated arenes and heteroarenes, either under microwave irradiation or by conventional heating, is reported, using diiodine and ortho-periodic acid as the oxidant. The reactions were carried out in hot 95% ethanol under a reflux condenser. For the microwave assisted reactions, the reaction times were always notably shortened, but the yields were nearly the same as those afforded by the conventional method.

Aromatic iodination using N-iodosaccharin in room temperature ionic liquids

More reactive iodination conditions have been developed that combine the use of room temperature ionic liquids with N-iodosaccharin. Using these reaction conditions, even very modestly activated arenes such as toluene can be iodinated in good yield under very mild conditions.

Photochemically Activated Dimagnesium(I) Compounds: Reagents for the Reduction and Selective C?H Bond Activation of Inert Arenes

The photochemical activation of dimagnesium(I) compounds, and subsequent high yielding, regioselective reactions with inert arenes are reported. Irradiating benzene solutions of [{(ArNacnac)Mg}2] (ArNacnac=[HC(MeCNAr)2]?; Ar=2,6-diisopropylphenyl (Dip) or 2,4,6-tricyclohexylphenyl (TCHP)) with blue or UV light, leads to double reduction of benzene and formation of the “Birch-like” cyclohexadienediyl bridged compounds, [{(ArNacnac)Mg}2(μ-C6H6)]. Irradiation of [{(DipNacnac)Mg}2] in toluene, and each of the three isomers of xylene, promoted completely regio- and chemo-selective C?H bond activations, and formation of [(DipNacnac)Mg(Ar′)] (Ar′=meta-tolyl; 2,3-, 3,5- or 2,5-dimethylphenyl), and [{(DipNacnac)Mg(μ-H)}2]. Fluorobenzene was cleanly defluorinated by photoactivated [{(DipNacnac)Mg}2], leading to biphenyl and [{(DipNacnac)Mg(μ-F)}2]. Computational studies suggest all reactions proceed via photochemically generated magnesium(I) radicals, which reduce the arene substrate, before C?H or C?F bond activation processes occur.

Synthesis of polysubstituted iodobenzene derivatives from alkynylsilanes and 1,3-dienes via diels-alder/oxidation/iodination reaction sequence

The cobalt-catalyzed Diels-Alder reaction of trimethylsilyl-substituted alkynes with 1,3-dienes led to dihydroaromatic intermediates which were transformed into iodobenzene derivatives. For this transformation, the dihydroaromatic intermediates had to be oxidized and the trimethylsilyl-substituted arene had to undergo a silicon-iodine exchange reaction. For this purpose, a number of oxidizing agents and iodonium sources were tested in order to realize the desired two transformations in a single step. Eventually, the combination of tert-butyl hydroperoxide (TBHP), zinc iodide, and potassium carbonate led to the desired oxidation/iodination in good to excellent yields in a short reaction time at ambient temperatures.

Iodination of activated aromatic compounds using sodium peroxodisulfate and iodine: An efficient way to iodinate alkylated calix[4]arenes

A simple method for the iodination of activated arenes, using molecular iodine and sodium peroxodisulfate as the oxidant, is presented. The reaction is conducted in the presence of catalytic amounts of tetramethylammonium iodide as a phase-transfer catalyst in acetonitrile. For non-polar substances, which are not soluble in pure acetonitrile such as calix[4]arenes bearing long alkyl chains, a modified reaction is introduced. In this case the phase-transfer catalyst is changed to methyltriphenylphosphonium peroxodisulfate. Chloroform as a cosolvent mediates solubility. Furthermore, we show that the slightly basic conditions obtained upon the addition of sodium bicarbonate have a beneficial effect on the yield. Georg Thieme Verlag Stuttgart.

Effective and regioselective iodination of arenes using iron(III) nitrate in the presence of tungstophosphoric acid

An easy, cheap, and effective method for iodination of various aromatic compounds takes place with molecular iodine and iron nitrate nonahydrate as the oxidant in the presence of a catalytic amount of tungstophosphoric acid in dichloromethane, with good yield and high regioselectivity under very mild conditions.