163704-47-0

Basic information

• Product Name: 2,6-Diisopropyliodobenzene
• Synonyms: 2-Iodo-1,3-diisopropylbenzene;2-iodo-1,3-di(propan-2-yl)benzene;2,6-Diisopropyliodobenzene
• CAS NO: 163704-47-0
• Molecular Formula: C₁₂H₁₇I
• Molecular Weight: 288.16785
• Mol File: 163704-47-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 2,6-Diisopropyliodobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Diisopropyliodobenzene(163704-47-0)
• EPA Substance Registry System: 2,6-Diisopropyliodobenzene(163704-47-0)

Safety Data

• Hazardous Substances Data: 163704-47-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Diisopropyliodobenzene is used as a synthetic intermediate for the production of various pharmaceuticals. Its ability to be incorporated into complex organic molecules makes it valuable in the development of new drugs and medicinal compounds.
Used in Pesticide Industry:
In the pesticide sector, 2,6-Diisopropyliodobenzene is utilized as a precursor in the synthesis of active ingredients for pest control agents. Its role in creating effective and targeted pesticides contributes to agricultural productivity and crop protection.
Used in Dye Industry:
2,6-Diisopropyliodobenzene is employed as a chemical intermediate in the manufacture of dyes. Its involvement in dye synthesis allows for the creation of a range of colorants used in various applications, including textiles, plastics, and printing inks.
Used in Organic Chemistry Research:
As a reagent in organic chemistry, 2,6-Diisopropyliodobenzene is used for the preparation of aryl iodides and other functionalized aromatic compounds. Its application in research settings aids in the exploration of new chemical reactions and the development of innovative synthetic pathways.

Upstream product

• 24544-04-5 2,6-diisopropylbenzenamine 
• 13922-41-3 1-Naphthylboronic acid 
• 82113-65-3 bis(trifluoromethanesulfonyl)amide 

Downstream Products

• 92035-95-5 2,6-bis-(1-methylethyl)benzoic acid 
• 25364-47-0 1-(2,6-diisopropylphenyl)-1H-imidazole 
• 85374-63-6 2,6-diisopropylbenzoyl chloride 
• 2078-54-8 2,6-diisopropylphenol 
• 854271-12-8 1,3-diisopropyl-2-(phenylethynyl)benzene 
• 156023-27-7 (2,6-diisopropylphenyl)acetylene 
• 1443747-04-3 1,4-di(2,6-diisopropylphenyl)-3-methyl-H-1,2,3-triazolium iodide 
• 1263862-50-5 1,4-bis(2,6-diisopropylphenyl)-1H-[1,2,3]-triazole 
• 1035347-44-4 2,6-diisopropylphenyl tert-butyldimethylsilyl ether 
• 863677-59-2 N-(2,6-diisopropyl)phenyl-N-(2-pyridyl)amine 

Relevant articles and documents

Arene diazonium saccharin intermediates: A greener and cost-effective alternative method for the preparation of aryl iodide

In the current protocol, the arene diazonium saccharin derivatives were initially produced from various substituted aromatic amines; subsequently, these intermediates were treated with a greener organic iodide for the preparation of the aryl iodide. We tried to choose low-cost, commercially available, biodegradable, recoverable, ecofriendly, and safe reagents and solvents. The arene diazonium saccharin intermediates could be stored in the liquid phase into a refrigerator for a long time with no significant loss activity. The outstanding merits of the current protocol (a) included the partial recovering of saccharin and tetraethylammonium salt, (b) reduce the use of solvents and the reaction steps due to eliminating separation and purification of intermediates, (c) good yield of the sterically hindered substrates, and (d) avoid the generation of heavy metal or corrosive waste.

Chromium(0) and Molydenum(0) Complexes with a Pyridyl-Mesoionic Carbene Ligand: Structural, (Spectro)electrochemical, Photochemical, and Theoretical Investigations

This work reports on the synthesis and in-depth electrochemical and photochemical characterization of two chromium(0) and molydenum(0) metal complexes with bidentate pyridyl-mesoionic carbene (MIC) ligands of the 1,2,3-triazol-5-ylidene type and carbonyl coligands. Metal complexes with MIC ligands have turned out to have very promising electrocatalytic and photochemical properties, but examples of MIC-containing complexes with early-transition-metal centers remain extremely rare. The electrochemistry of these new MIC complexes was studied by cyclic voltammetry and especially spectroelectrochemistry in the IR region consistent with a mainly metal-centered oxidation, which is fully reversible in the case of the chromium(0) complex. At the same time, the two reduction steps are predominantly ligand-centered according to the observed near-IR absorbance, with the first reduction step being reversible for both systems. The results of the electron paramagnetic resonance studies on the oxidized and reduced species confirm the IR spectroelectrochemistry experiments. The photochemical reactivity of the complexes with a series of organic ligands was investigated by time-resolved (step-scan) Fourier transform infrared (FTIR) spectroscopy. Interestingly, the photoreactions in pyridine and acetonitrile are fully reversible with a slow dark reverse reaction back to the educt species over minutes and even hours, depending on the metal center and reagent. This reversible behavior is in contrast to the expected loss of one or several CO ligands known from related homoleptic as well as heteroleptic M(CO)4L2 α-diimine transition-metal complexes.

A facile and sustainable protocol to the preparation of aryl iodides using stable arenediazonium bis(trifluoromethylsulfonyl)imide salts via the telescopic process

The preparation of aryl iodides in a telescopic reaction using tert-butyl nitrite as a diazotization reagent and a mixture of bis(trifluoromethane) sulfonamide and glacial acetic acid as a mild acidic agent in ethanol followed by iododediazoniation with tetraethylammonium iodide in water was investigated. The current method has other advantages such as minimized waste by avoiding solvent for the purification of products in diazotization step, simple experimental procedure, and good yield of the sterically hindered aryl amines, metal and strong acid-free waste and environmentally benign conditions. The noteworthy features of this study are the preparation of stable arenediazonium bis(trifluoromethylsulfonyl)imide salts that can be used with no significant loss activity after 1?week and bis(trifluoromethane)sulfonamide was recovered in high yields from reactions.

Two-photon absorbing compounds and methods of making same

A two-photon absorbing (TPA) compound is provided, along with a method of making same. The TPA compound has a general structural formula: where A is an acceptor moiety that is connected to m number of diarylaminofluorene arms (m=1-3); in each diarylaminofluorene arms, R is selected from linear or branched alkyl chains having a general formula CnH2n+1, where n is in a range from 2 to 25; where R1, R2, and R3 are independently selected from H or C1-C4 alkyls; where R4 is selected from C1-C5 alkyls; and wherein R5 through R10 are independently selected from H, alkoxyls, alkyls, or aryls. A may be benzothiazol-2-yl, benzo[1,2-d:4,5-d′]bisthiazole-2,6-diyl, thiazolo[5,4-d]thiazole-2,5-diyl-, 1,3,5-triazine-2,4,6-triyl, 1,3,5-triazine-2,4,6-triyl, benzo[1,2-d:3,4-d′:5,6-d″]tristhiazole-2,5,8-triyl-, or dithieno[3,2-b:2′,3′-d]thiophene-2,6-diyl-.

Cu-catalyzed fluorination of diaryliodonium salts with KF

A mild Cu-catalyzed nucleophilic fluorination of unsymmetrical diaryliodonium salts with KF is described. This protocol preferentially fluorinates the smaller aromatic ligand on iodine(III). The reaction exhibits a broad substrate scope and proceeds with high chemoselectivity and functional group tolerance. DFT calculations implicate a CuI/CuIII catalytic cycle.

Suzuki-Miyaura cross-coupling reaction catalyzed by PEPPSI-type 1,4-di(2,6-diisopropylphenyl)-1,2,3-triazol-5-ylidene (tzIPr) palladium complex

A 1,4-di(2,6-diisopropylphenyl)-1,2,3-triazol-5-ylidene (tzIPr)-based PEPPSI-type palladium complex was developed as an excellent precatalyst for the Suzuki-Miyaura cross-coupling reaction. The complex showed high activity under mild conditions for the cross-coupling reactions between various types of aryl chlorides and aryl boronic acids regardless of the steric and electronic nature of the substrates.

Tampering with molecular cohesion in crystals of hexaphenylbenzenes

(Chemical Equation Presented) Hexaphenylbenzene (HPB) and analogous compounds have properties of broad utility in science and technology, including conformationally well-defined molecular structures, high thermal stability, high HOMO-LUMO gaps, little self-association, inefficient packing, and high solubilities. Previous structural studies of HPB and its analogues have revealed persistent involvement of the central aromatic ring in strong C-H...π interactions. These interactions can be blocked by adding simple ortho alkyl substituents to the peripheral phenyl groups. Comparison of the structures of HPB and a series of ortho-substituted derivatives has shown systematic changes in molecular cohesion and packing, as measured by packing indices, densities, solubilities, temperatures of sublimation, melting points, and ratios of H...H, C...H, and C...C contacts. These results illustrate how crystal engineering can guide the search for improved materials by identifying small but telling molecular alterations that thwart established patterns of association.

Synthesis of rotationally restricted and modular biphenyl building blocks

A series of modular biphenyl building blocks with stepwise adjusted torsion angles and terminally functionalized with leaving groups have been synthesized. The two phenyl rings of the biphenyl synthon are clamped by alkyl chains of various lengths. The desired building blocks 3 and 4 were obtained by copper-mediated C-C biaryl coupling reactions followed by the construction of interlinking alkyl bridges. The key intermediates 14 and 15 were transformed into the corresponding cycloheptadienones 16 and 17, which were reduced to the desired propyl-bridged biphenyls 3b and 3c. The butyl-bridged derivatives 4b and 4c were obtained from 14 and 15 by an allylation reaction followed by ring-closing metathesis (RCM) and hydrogenation. The pentyl chain in precursor 24 was obtained by two aldol C-C bond-forming reactions followed by a sequence of reduction steps. It was subsequently cyclized in an aryl-aryl coupling reaction to the pentyl-bridged biphenyl 26 along with the macrocyclic dimer 25. The UV absorption spectra of the acetylsulfanyl-functionalized series 1a-8a were recorded and analyzed: A linear correlation between the conjugation band in the UV absorption spectra and the cos2Φ values (Φ is the interplanar torsion angle) is observed.

Structure-based approach to the development of potent and selective inhibitors of dihydrofolate reductase from Cryptosporidium

Cryptosporidiosis is an emerging infectious disease that can be life-threatening in an immune-compromised individual and causes gastrointestinal distress lasting up to 2 weeks in an immune-competent individual. There are few therapeutics available for eff

New building blocks for the assembly of sequence selective molecular zippers.

Synthetic H-bonded molecular zippers contain no sequence information that can be used to engineer the selective binding interactions characteristic of biopolymers; reversing the sense of the amide bonds in the two binding partners generates a new orthogonal recognition motif and the mutually complementary binding partners form complexes an order of magnitude more stable than the corresponding mismatch complexes.