25245-35-6

Usage

InChI:InChI=1/C8H9IO2/c1-10-6-3-4-8(11-2)7(9)5-6/h3-5H,1-2H3

Upstream product

• 150-78-7 1,4-dimethoxybezene 
• 102-56-7 2,5-dimethoxyaniline 
• 2785-98-0 2,5-dimethoxybenzoic acid 
• 186134-37-2 3-iodo-4-methoxyphenyl 4-methylbenzenesulfonate 
• 3899-91-0 4-methoxyphenyl p-toluenesulfonate 
• 98279-45-9 3-iodo-4-methoxyphenol 
• 74-88-4 methyl iodide 

Downstream Products

• 860190-93-8 2,5,2',5',2'',5'',2''',5'''-octamethoxy-[1,1';4',1'';4'',1''']quaterphenyl 
• 2785-98-0 2,5-dimethoxybenzoic acid 
• 54771-88-9 bis-(2,5-dimethoxyphenyl)methanone 
• 51560-21-5 1,4-diiodo-2,5-dimethoxybenzene 
• 90064-46-3 1-chloro-4-iodo-2,5-dimethoxybenzene 
• 103204-10-0 1-(4-iodo-2,5-dimethoxy-phenyl)-ethanone 
• 90584-83-1 4-methoxy-2-(1-pentynyl)anisole 
• 5312-97-0 2,5-dimethoxybenzonitrile 
• 141957-85-9 4-(2,5-Dimethoxy-phenyl)-2,7,10-trimethoxy-6H-benzo[c]chromene 
• 19718-50-4 6,2',5'-Trimethoxybiphenyl-3-carbonsaeure 
• 37104-56-6 bis(2,5-dimethoxyphenyl)acetylene 
• 247039-88-9 (CH₃O)2C₆H₃C₂C₆H₄C₆H₄C₂(C₁₈H₃₇O)2C₆H₂C₂C₅NH₃C₅NH₃C₂C₆H₂(OC₁₈H₃₇)2C₂C₆H₄C₆H₄C₂C₆H₃(OCH₃)2 
• 261617-76-9 bis(2,5-dimethoxyphenyl)phenylmethanol 
• 524047-42-5 2-[3-(2,5-dimethoxy-phenyl)-propyl]-2-methylsulfanyl-naphtho[1,8-de][1,3]dioxine 

Relevant academic research and scientific papers

Heck- And Suzuki-coupling approaches to novel hydroquinone inhibitors of calcium ATPase

In this study, we explored Heck- and Suzuki-coupling methodology to modify the template 2,5-di-tert-butylhydroquinone (BHQ, 2), an inhibitor of the enzyme sarco/endoplasmic reticulum calcium ATPase (SERCA). We found that by utilizing Suzuki coupling, we c

Photocatalytic Oxidative Iodination of Electron-Rich Arenes

A visible-light-mediated oxidative iodination of electron-rich arenes has been developed. 2.5 mol% of unsubstituted anthraquinone as photocatalyst were used in combination with elementary iodine, trifluoroacetic acid and oxygen as the terminal oxidant. The iodination proceeds upon irradiation in non- or weakly-electron donating solvents (DCM, DCE and benzene) wherein a spectral window in strongly coloured iodine solutions can be observed at around 400 nm. The method provides good to excellent yields (up to 98%) and shows excellent regioselectivity and good functional group tolerance (triple bonds, ketone, ester, amide). Moreover, the photo-iodination was also upscaled to a 5 mmol scale (1.1 g). Mechanistic investigations by intermediate trapping and competition experiments indicate a photocatalytic arene oxidation and the subsequent reaction with iodine as a likely mechanistic pathway. (Figure presented.).

One-pot ortho-amination of aryl C-H bonds using consecutive iron and copper catalysis

A one-pot approach for ortho-coupling of arenes with non-actived N-nucleophiles has been developed using sequential iron and copper catalysis. Regioselective ortho-activation of anisoles, anilines and phenols was achieved through iron(iii) triflimide catalysed iodination, followed by a copper(i)-catalysed, ligand-assisted coupling reaction with N-heterocycle, amide and sulfonamide-based nucleophiles. The synthetic utility of this one-pot, two-step method for the direct amination of ortho-aryl C-H bonds was demonstrated with the late-stage functionalisation of 3,4-dihydroquinolin-2-ones. This allowed the preparation of a TRIM24 bromodomain inhibitor and a series of novel analogues.

Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings

Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.

Rapid aerobic iodination of arenes mediated by hypervalent iodine in fluorinated solvents

Arenes are rapidly converted to the corresponding iodides by aerobic oxidative iodination at room temperature by treatment with iodine and catalytic quantities of nitrous acid in a fluorinated solvent. Dichloroiodic acid is proposed as the actual iodination reagent.

N-Iodosuccinimide (NIS) in Direct Aromatic Iodination

N-Iodosuccinimide (NIS) in pure trifluoroacetic acid (TFA) offers a time-efficient and general method for the iodination of a wide range of mono- and disubstituted benzenes at room temperature, as demonstrated in this paper. The starting materials were generally converted into mono-iodinated products in less than 16 hours at room temperature, without byproducts. A few deactivated substrates needed addition of sulfuric acid to increase the reaction rate. Another exception was methoxybenzenes that preferentially were iodinated by NIS in acetonitrile with only catalytic amounts of TFA.

High-capacity organic cathode active materials of 2,2′-bis-p-benzoquinone derivatives for rechargeable batteries

Rechargeable batteries using organic cathode materials are expected to afford high mass energy densities since these materials can undergo multiple electron redox reactions per molecule. Although the batteries using benzoquinone (BQ) derivatives as organic cathode active materials exhibited high theoretical capacity, their practical capacities and cycle retention were far from satisfactory. To overcome these problems, dimeric BQ derivatives based on the 2,2′-bis-p-benzoquinone (BBQ) framework were synthesized, and the charge-discharge behaviour of the prepared cells using BBQs as the cathode active materials was investigated. BBQ-based cells exhibited excellent performance compared to those based on BQ monomers. For example, the BBQ cell afforded a high initial capacity of 358 A h kg-1 (more than twice that of current lithium-ion batteries that use LiCoO2 as the cathode active material) and a high cycle retention of 198 A h kg-1 at 50 cycles. Electrochemical measurements and density functional theory (DFT) calculations indicated that three electron-redox reactions generally occur in BBQ derivatives, although (OMe)2-BBQ appeared to undergo a four-electron redox reaction.

C-substituted, 1H-azoles for amphoteric, solvent-less proton conductivity

Disclosed herein are the compounds shown below. Also disclosed are methods of making the compounds. R1=—O—; R2=any alkyl chain; R3=—CH3, —CN, —COOCH3, -tetrazole, -imidazole, or -triazole; R4=—H or —R5; R5=—H, -halogen, —C≡CH, or —C≡C—; n is a positive integer; and m is a positive integer.

Triflic acid mediated cascade cyclization of aryldiynes for the synthesis of indeno[1,2-c]chromenes: Application to dye-sensitized solar cells

A new triflic acid (TfOH)-mediated cascade cyclization of ortho-anisole-substituted aryldiynes is described for the construction of indeno[1,2-c]chromenes. The cascade cyclization proceeds through an unusual TfOH-induced alkyne-alkyne cyclization followed by nucleophilic attack of the methoxy group on the benzylidene cation, which is completely different to the cyclization of ortho-aniline- or ortho-thioanisole-substituted aryldiynes. A new class of organic dyes with the indeno[1,2-c]chromene framework as both donor and π-linker were synthesized. These compounds exhibit high photovoltaic performances in dyesensitized solar cells (DSCs).

C-SUBSTITUTED, 1H-AZOLES FOR AMPHOTERIC, SOLVENT-LESS PROTON CONDUCTIVITY

Disclosed herein are the compounds shown below. Also disclosed are methods of making the compounds. R1=—O—; R2=any alkyl chain; R3=—CH3, —CN, —COOCH3, -tetrazole, -imidazole, or -triazole; R4=—H or —R5; R5=—H, -halogen, —C≡CH, or —C≡C—; n is a positive integer; and m is a positive integer.