1124-08-9

Usage

Uses

Used in Organometallic Chemistry:
1,4-Diiodo-2,5-dimethylbenzene is used as a synthetic intermediate for organometallic chemistry applications due to its ability to participate in various reactions involving the substitution of iodine atoms.
Used in Organic Syntheses:
1,4-Diiodo-2,5-dimethylbenzene is used as a building block in organic syntheses for the creation of more complex molecules, taking advantage of its reactivity and the ease with which the iodine atoms can be substituted.
Used in Pharmaceutical Industry:
1,4-Diiodo-2,5-dimethylbenzene is used as a starting material for the synthesis of pharmaceutical compounds, where its unique structure and reactivity can be exploited to develop new drugs with potential therapeutic applications.
Used in Material Science:
1,4-Diiodo-2,5-dimethylbenzene is used as a component in the development of new materials, such as polymers and composites, where its structural properties can contribute to the desired material characteristics.

InChI:InChI=1/C8H8I2/c1-5-3-8(10)6(2)4-7(5)9/h3-4H,1-2H3

Upstream product

• 106-42-3 para-xylene 
• 1122-42-5 2-iodo-p-xylene 
• 117832-13-0 2,5-dimethyl-4-iodoaniline 
• 609-54-1 2,5-dimethylbenzenesulfonic acid 

Downstream Products

• 20260-22-4 2',5'-dimethyl-[1,1':4',1'']terphenyl 
• 96802-47-0 Cyano-[4-(cyano-ethoxycarbonyl-methyl)-2,5-dimethyl-phenyl]-acetic acid ethyl ester 
• 96812-95-2 2-(4-Dicyanomethyl-2,5-dimethyl-phenyl)-malononitrile 
• 20856-79-5 2,5-diiodo-4-methylbenzoic acid 
• 203254-23-3 2',5',2''',5'''-Tetrakis-(4-butoxy-phenylethynyl)-2,5,2'',5'',2'''',5''''-hexamethyl-[1,4';1',1'';4'',1''';4''',1'''']quinquephenyl 
• 392240-20-9 2,5-dimethylbenzene-1,4-dipropynal 
• 869358-35-0 N,N'-dibutyl-N,N'-bis-[4-(4-iodo-2,5-dimethyl-phenylethynyl)-phenyl]-terephthalamide 
• 75867-43-5 1,4-bis((trimethylsilyl)ethynyl)-2,5-dimethylbenzene 
• 75867-45-7 1,4-diethynyl-2,5-dimethylbenzene 
• 53-70-3 dibenzo[a,h]anthracene 
• 144836-56-6 2',5'-bis(cyanomethyl)-1,1':4',1''-terphenyl 
• 144836-59-9 C₅₆H₄₆P₂⁽²⁺⁾*2Br^(1-) 
• 56403-45-3 1,4-Bis-(cyanomethyl)-2,5-diiodbenzol 
• 56403-60-2 Dicyano-[4-(dicyano-methoxycarbonyl-methyl)-2,5-diiodo-phenyl]-acetic acid methyl ester 

Relevant academic research and scientific papers

Staudinger ligation towards cyclodextrin dimers in aqueous/organic media. Synthesis, conformations and guest-encapsulation ability

β-Cyclodextrin (β-CD) dimers have been prepared using the bioorthogonal Staudinger ligation for the first time. In addition to a known linker, methyl 2-(diphenylphosphanyl)terephthalate, a doubly active linker was specifically developed that enabled conne

Reactivity and synthetic utility of 1-(arenesulfonyloxy) benziodoxolones

The reactivity and synthetic use of 1-(arenesulfonyloxy)benziodoxolones were studied. In the presence of iodine, 1-(arenesulfonyloxy)benziodoxolones iodinated various aromatics to give iodoarenes in moderate to good yields. In particular, 1-(p-chlorobenzenesulfonyloxy)benziodoxolone showed the best reactivity. Using a halide salt such as lithium bromide or lithium chloride instead of iodine, the corresponding aryl bromides and chlorides were also obtained in good yields. In the absence of aromatics, 1- (arenesulfonyloxy)benziodoxolones gave rise to desulfonyloxyiodination reactions to give the corresponding aryl iodides via electrophilic ipso substitution on the aromatic rings. Furthermore, the l-(p- toluenesulfonyloxy)benziodoxolone/iodine system iodotosyloxylated alkynes in good yields. These reactions proceeded via the formation of arenesulfonyl hypoiodites.

Triggering the dynamics of a carbazole-: P -[phenylene-diethynyl]-xylene rotor through a mechanically induced phase transition

A new rotor exhibits rich solvatomorphism behavior with eight X-ray structures obtained. A heterogeneous solid obtained by mechanical stress exhibited a dominant isotropic 2H line shape at high temperatures. The motion occurs only in the amorph

Synthetic use of 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one: Iodination of aromatic rings

Treatment of various aromatic compounds with 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one 1A and iodine gave the corresponding iodinated compounds in good yields. Similarly, chlorination and bromination proceeded effectively. As compared with other trivalent iodine compounds, the iodinane 1A showed the best reactivity as a halogenation reagent.

New cruciform structures: Toward coordination induced single molecule switches

(Chemical Equation Presented) New cruciform structures 1-4 were synthesized to investigate a new single molecule switching mechanism arising from the interplay between the molecule and the electrode surface. These molecular cruxes consist of two rod-type

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.

Exploring the nitro group reduction in low-solubility oligo-phenylenevinylene systems: Rapid synthesis of amino derivatives

A small series of amino oligo-phenylenevinylenes (OPVs) were successfully synthesized from their nitro-analogs in a rapid, simple, and highly efficient fashion employing a sodium sulfide/pyridine system as a reducing agent. In this research, classic and sustainable reduction methodologies including NH4HCO2/Zn and a choline chloride/tin (II) chloride deep eutectic solvent (DES) were also evaluated, showing degradation products, incomplete reactivity, and product isolation difficulties in all cases. The straightforward Na2S/pyridine synthetic protocol proved to maintain the E-E stereochemistry of the OPV backbone that has been previously assembled by the Mizoroki–Heck cross-coupling reaction. Also, the optoelectronic properties were determined and discussed, considering the amino group insertion in these conjugated systems as a contribution for future construction of novel materials with applications in supramolecular electronics, light harvesting, and photocatalysis.

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.

Substituent Effects That Control Conjugated Oligomer Conformation through Non-covalent Interactions

Although understanding the conformations and arrangements of conjugated materials as solids is key to their prospective applications, predictive power over these structural factors remains elusive. In this work, substituent effects tune non-covalent interactions between side-chain fluorinated benzyl esters and main-chain terminal arenes, in turn controlling the conformations and interchromophore aggregation of three-ring phenylene-ethynylenes (PEs). Cofacial fluoroarene-arene (ArF-ArH) interactions cause twisting in the PE backbone, interrupting intramolecular conjugation as well as blocking chromophore aggregation, both of which prevent the typically observed bathochromic shift observed upon transitioning PEs from solution to solid. This work highlights two structural factors that determine whether the ArF-ArH interactions, and the resulting twisted, unaggregated chromophores, occur in these solids: (i) the electron-releasing characteristic of substituents on ArH, with more electron-releasing character favoring ArF-ArH interactions, and (ii) the fluorination pattern of the ArF ring, with 2,3,4,5,6-pentafluorophenyl favoring ArF-ArH interactions over 2,4,6-trifluorophenyl. These trends indicate that considerations of electrostatic complementarity, whether through a polar-π or substituent-substituent mechanism, can serve as an effective design principle in controlling the interaction strengths, and therefore the optoelectronic properties, of these molecules as solids.

Oligo p-Phenylenevinylene Derivatives as Electron Transfer Matrices for UV-MALDI

Phenylenevinylene oligomers (PVs) have outstanding photophysical characteristics for applications in the growing field of organic electronics. Yet, PVs are also versatile molecules, the optical and physicochemical properties of which can be tuned by manipulation of their structure. We report the synthesis, photophysical, and MS characterization of eight PV derivatives with potential value as electron transfer (ET) matrices for UV-MALDI. UV-vis analysis show the presence of strong characteristic absorption bands in the UV region and molar absorptivities at 355 nm similar or higher than those of traditional proton (CHCA) and ET (DCTB) MALDI matrices. Most of the PVs exhibit non-radiative quantum yields (φ) above 0.5, indicating favorable thermal decay. Ionization potential values (IP) for PVs, calculated by the Electron Propagator Theory (EPT), range from 6.88 to 7.96 eV, making these oligomers good candidates as matrices for ET ionization. LDI analysis of PVs shows only the presence of radical cations (M+.) in positive ion mode and absence of clusters, adducts, or protonated species; in addition, M+. threshold energies for PVs are lower than for DCTB. We also tested the performance of four selected PVs as ET MALDI matrices for analytes ranging from porphyrins and phthalocyanines to polyaromatic compounds. Two of the four PVs show S/N enhancement of 1961% to 304% in comparison to LDI, and laser energy thresholds from 0.17 μJ to 0.47 μJ compared to 0.58 μJ for DCTB. The use of PV matrices also results in lower LODs (low fmol range) whereas LDI LODs range from pmol to nmol. [Figure not available: see fulltext.].