62615-24-1

Basic information

• Product Name: 2-Iodo-4-acetylphenol
• Synonyms: 2-Iodo-4-acetylphenol;3'-Iodo-4'-hydroxyacetophenone;4'-Hydroxy-3'-iodoacetophenone;4-Acetyl-2-iodophenol;4'-Hydroxy-3'-iodoacetophenone 97%;1-(4-Hydroxy-3-iodo-phenyl)-ethanone
• CAS NO: 62615-24-1
• Molecular Formula: C₈H₇IO₂
• Molecular Weight: 262.04445
• Mol File: 62615-24-1.mol

Chemical Properties

• Melting Point: 155-160°C
• Appearance: /
• CAS DataBase Reference: 2-Iodo-4-acetylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodo-4-acetylphenol(62615-24-1)
• EPA Substance Registry System: 2-Iodo-4-acetylphenol(62615-24-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 1
• Hazardous Substances Data: 62615-24-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Iodo-4-acetylphenol is used as a reactant for the preparation of cyclopentene fused benzofurans and indoles via Pd-catalyzed tandem ring opening-ring closing reaction with diazabicyclic alkenes. This application is crucial for the synthesis of novel drug candidates with potential therapeutic properties.
Used in Chemical Research:
In the field of chemical research, 2-Iodo-4-acetylphenol is utilized for the highly regioselective synthesis of spirocyclic compounds through a palladium-catalyzed intermolecular tandem reaction. This method allows for the creation of complex molecular structures with high precision.
Used in Organic Synthesis:
2-Iodo-4-acetylphenol is employed in the regioselective synthesis of indene derivatives via Pd/C-catalyzed cyclization reaction in air. This process is advantageous for the production of valuable intermediates in organic synthesis.
Used in Material Science:
In material science, 2-Iodo-4-acetylphenol is used in the preparation of carbazoles via cross-coupling with silylaryl triflates followed by palladium-catalyzed cyclization. This contributes to the development of new materials with unique properties.
Used in Heteropolycyclic Compounds Synthesis:
2-Iodo-4-acetylphenol is used as a reactant for the stereoselective preparation of heteropolycyclic compounds via palladium-catalyzed stereoselective heteroannulation with cyclic alkenes. This application is significant for the synthesis of complex heterocyclic structures with potential applications in various fields.
Used in Coumarins Production:
In the production of disubstituted coumarins, 2-Iodo-4-acetylphenol is used via palladium-catalyzed carbonylative annulation of internal alkynes. Coumarins are important due to their diverse applications, including as fragrances, flavorings, and pharmaceutical agents.
Used in Alkynes and Heterocycles Synthesis:
2-Iodo-4-acetylphenol is employed in the preparation of arylalkynes, benzofurans, and indoles via Sonogashira coupling and cyclization on alumina. This versatile application allows for the synthesis of a wide range of organic compounds with potential uses in various industries.

Preparation

Preparation by reaction of iodine and potassium iodide on 4-hydroxyacetophenone in aqueous ammonium hydroxide at r.t. (54–57%).

Upstream product

• 99-93-4 4-Hydroxyacetophenone 
• 32865-61-5 2-iodophenyl acetate 

Downstream Products

• 3015-20-1 dehydrotremetone 
• 173992-07-9 3'-iodo-4'-tosyloxyacetophenone 
• 190775-71-4 1-(benzofuran-5-yl)ethan-1-one 
• 73618-92-5 1-[4-(1,1-Dimethyl-prop-2-ynyloxy)-3-iodo-phenyl]-ethanone 
• 120608-34-6 1-(3-iodo-4-((3-methylbut-2-en-1-yl)oxy)phenyl)ethan-1-one 
• 861524-84-7 1-(4-ethoxy-3-iodophenyl)ethanone 
• 1198617-49-0 1-(4-isobutyloxy-3-iodophenyl)ethanone 

Relevant articles and documents

Fluorescence analysis of iodinated acetophenone derivatives

In the present paper the synthesis and optical characterization of iodinated acetophenone, 4-hydroxy-3-iodoacetophenone and 4-hydroxy-3,5-diiodoacetophenone obtained from 4-hydroxyacetophenone, were carried out. The optical features of iodinated molecules

Synthesis and bioevaluation of 1-phenylimidazole-4-carboxylic acid derivatives as novel xanthine oxidoreductase inhibitors

As part of a continuing study, we designed and synthesized four series of 1-phenylimidazole-4-carboxylic acid derivatives as xanthine oxidoreductase (XOR) inhibitors, evaluated their in vitro inhibitory potencies against XOR and hypouricemic effects in mi

Oxygen-substituted phenylimidazole XOR/URAT1 dual inhibitor, preparation and applications thereof

The invention belongs to the technical field of medicinal chemical industry, and discloses an oxygen-substituted phenylimidazole XOR/URAT1 dual inhibitor, preparation and applications thereof, whereinthe oxygen-substituted phenylimidazole XOR/URAT1 dual i

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.

Total synthesis of hibispeptin A via Pd-catalyzed C(sp3)-H arylation with sterically hindered aryl iodides

To access the key Ile-Hpa pseudodipeptide motif in hibispeptins, a series of bidentate carboxamide-based auxiliary groups have been explored to facilitate the palladium-catalyzed arylation of unactivated γ-C(sp3)-H bonds of Ile precursor with a

Regioselective iodination of aromatic compounds with potassium iodide in the presence of benzyltriphenylphosphonium perchlorate

A simple and efficient method for the selective iodination of various aromatic compounds by using potassium iodide in the presence of benzyltriphenylphosphonium perchlorate, is reported. This method provides several advantages such as good selectivity between ortho and para positions of aromatic compounds and high yields of the products.

Efficient and selective iodination of phenols promoted by iodine and hydrogen peroxide in water

A simple and selective reaction for the preparation of iodinated phenols was developed and phenol derivatives containing electron withdrawing groups were iodinated in very good yields under relatively mild conditions.

A mild and simple iodination of phenols with trichloroisocyanuric acid/I2/wet SiO2 system

Molecular iodine in the presence of trichloroisocyanuric acid and wet sio2 has been utilized efficiently for iodination of phenols under mild reaction conditions.

A practical iodination of aromatic compounds by using iodine and iodic acid

This article describes simple and efficient method for the iodination of different aromatic amines, hydroxy aromatic aldehydes, hydroxy acetophenones and phenols using iodine and iodic acid in ethanol as a solvent. Notable advantages include mild reaction condition, no need of catalyst, short reaction time, simple practical procedure, giving excellent yield of the product. Copyright Taylor & Francis Group, LLC.

Synthesis of some 5-phenylisoxazole-3-carboxylic acid derivatives as potent xanthine oxidase inhibitors

A number of 5-phenylisoxazole-3-carboxylic acid derivatives (5a-e, 11a-e) were synthesized and analyzed for their ability to inhibit xanthine oxidase. Most of the compounds exhibited potency levels in the micromolar/submicromolar range. The presence of a cyano group at the 3-position of phenyl moiety turned out to be the preferred substitution pattern, as its transformation into the nitro group determined a general reduction of the inhibitory potency. A molecular modeling study on compound 11a was performed to gain an insight into its binding mode with xanthine oxidase, and to provide the basis for further structure-guided design of new non-purine xanthine oxidase inhibitors related with 5-phenylisoxazole-3-carboxylic acid scaffold.