696-62-8

Usage

Uses

Used in Medical and Industrial Applications:
4-Iodoanisole is used as a versatile compound for a range of medical and industrial applications. Its iodine derivatives serve as organic building blocks and analytical reagents, contributing to the development and enhancement of various products and processes.
Used in Human and Animal Nutrition Products:
In the field of nutrition, 4-Iodoanisole is utilized as an additive in both human and animal nutrition products, playing a role in maintaining and improving overall health and well-being.
Used as Antiseptics and Disinfectants:
4-Iodoanisole is employed as an antiseptic and disinfectant, leveraging its properties to inhibit the growth of microorganisms and promote a cleaner, safer environment.
Used in Pharmaceutical Intermediates:
4-Iodoanisole is also used as a pharmaceutical intermediate, playing a crucial role in the synthesis of various drugs and medications.
Used in Polarizing Films for Liquid Crystal Display (LCD) Chemicals:
4-Iodoanisole finds application in the production of polarizing films for LCD chemicals, contributing to the advancement of display technology and enhancing the performance of LCD devices.

References

https://www.fishersci.pt/shop/products/4-iodoanisole-98-7/11480113

Preparation

4-Iodoanisole is synthesized by the reaction of anisole with iodine chloride. Add anisole to glacial acetic acid, stir and slowly add iodine chloride. After the addition was completed, the temperature was refluxed for 3.5h. Cool, pour into ice water, and precipitate p-iodoanisole. After it was separated, the free iodine was washed with 5% sodium sulfite, then washed with water, distilled under reduced pressure, and the fractions with a boiling point of 140-160 °C (5.33 kPa) were collected and cooled to 0 °C for filtration. Wash with methanol and recrystallize to obtain the finished product.

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 2058, 1993 DOI: 10.1021/jo00060a020Tetrahedron Letters, 27, p. 3497, 1986 DOI: 10.1016/S0040-4039(00)84832-7

Purification Methods

Crystallise 4-iodoanisole from aqueous EtOH and/or distil it under vacuum. [Beilstein 6 H 208, 6 I 109, 6 II 199, 6 III 744, 6 IV 1075.]

InChI:InChI=1/C7H7IO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H3

Upstream product

• 104-94-9 4-methoxy-aniline 
• 20469-63-0 1-iodo-2,4-dimethoxybenzene 
• 100-66-3 methoxybenzene 
• 76-03-9 trichloroacetic acid 
• 53904-18-0 (4-methoxy-phenyl)-phenyl-iodonium ; iodide 
• 68-12-2 N,N-dimethyl-formamide 
• 19231-06-2 4,4'-dimethoxy-diphenyliodonium bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 36719-69-4 1-(4-Methoxyphenyl)-3,3-diethyl-1-triazene 
• 33604-68-1 (4-methoxyphenyl)azo 4-methylphenyl sulfone 
• 3899-91-0 4-methoxyphenyl p-toluenesulfonate 
• 36309-68-9 p-methoxyphenyltellurium trichloride 
• 1950-78-3 p-toluenesulfonyl iodide 
• 201230-82-2 carbon monoxide 

Downstream Products

• 1825-21-4 Pentachloroanisole 
• 2786-00-7 2-methoxy-5-iodobenzoic acid 
• 100-09-4 4-methoxybenzoic acid 
• 613-37-6 4-methoxylbiphenyl 
• 875838-68-9 2-(4-methoxyphenoxy)-1,3-dimethylbenzene 
• 3393-77-9 bis(4-methoxyphenyl)sulfide 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 104-93-8 p-methylanizole 
• 14065-23-7 1-methoxy-2-[(4-methoxyphenyl)thio]benzene 
• 54480-44-3 N,N-dimethyl-N'-(4-methoxyphenyl)-1,4-phenylendiamine 
• 13050-56-1 tris(4-anisyl)amine 
• 20440-91-9 4,4’-dimethoxy-4’’-nitrotriphenylamine 
• 108478-59-7 4'-methoxy-2-methyl-biphenyl-4-carboxylic acid 
• 5633-57-8 1-methoxy-4-(phenylsulfanyl)benzene 

Relevant academic research and scientific papers

Preparation method of nitrogen-alkyl (deuterated alkyl) aromatic heterocycle and alkyl (deuterated alkyl) aryl ether compound

The invention provides a method for preparing nitrogen-alkyl(deuterated alkyl)aromatic heterocycle and alkyl(deuterated alkyl)aryl ether compounds. The method adopted in the invention specifically comprises the following steps: firstly, adding an alkoxy base (MOR') or a combination reagent Q (comprising a base M'X, an alcohol C and a molecular sieve E) into a solvent B to be stirred; then, addingan aromatic compound D of nitrogen sulfonyl or oxygen sulfonyl into a mixture; separating and purifying after reaction to obtain nitrogen-alkyl(deuterated alkyl)aromatic heterocycle or alkyl(deuterated alkyl)aryl ether. The method can realize one-step conversion from an electron withdrawing benzenesulfonyl protecting group on a nitrogen or oxygen atom to an electron donating alkyl protecting group, avoids using highly toxic alkyl halide, and has advantages of being efficient, economical, environmentally friendly, mild in condition, good in substrate universality and high in yield; the prepareddeuterated compounds can be widely applied to the fields of pharmaceutical chemistry and organic chemistry synthesis.

The graphite-catalyzed: ipso -functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes

An efficient, metal-free, and sustainable strategy has been described for the ipso-functionalization of phenylboronic acids using air as an oxidant in an aqueous medium. A range of carbon materials has been tested as carbocatalysts. To our surprise, graphite was found to be the best catalyst in terms of the turnover frequency. A broad range of valuable substituted aromatic compounds, i.e., phenols, anilines, nitroarenes, and haloarenes, has been prepared via the functionalization of the C-B bond into C-N, C-O, and many other C-X bonds. The vital role of the aromatic π-conjugation system of graphite in this protocol has been established and was observed via numerous analytic techniques. The heterogeneous nature of graphite facilitates the high recyclability of the carbocatalyst. This effective and easy system provides a multipurpose approach for the production of valuable substituted aromatic compounds without using any metals, ligands, bases, or harsh oxidants.

NCBSI/KI: A Reagent System for Iodination of Aromatics through in Situ Generation of I-Cl

In situ iodine monochloride (I-Cl) generation followed by iodination of aromatics using NCBSI/KI system has been developed. The NCBSI reagent requires no activation due to longer bond length, lower bond dissociation energy, and higher absolute charge density on nitrogen. The system is adequate for mono- and diiodination of a wide range of moderate to highly activated arenes with good yield and purity. Moreover, the precursor N-(benzenesulfonyl)benzenesulfonamide can be recovered and transformed to NCBSI, making the protocol eco-friendly and cost-effective.

Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes

Owing to both Lewis and Bronsted acid active sites on sulfated polyborate under homogenous conditions, we were keen on developing iodination protocol of arenes that can meet the requirement of regioselectivity and higher yield. The sulfated polyborate activates N-iodosuccinimide for mono iodination of highly activated substrates viz. phenols, anilines under anhydrous condition. Water tunes sulfated polyborate to generate more Bronsted acid sites resulting in rapid activation of NIS for diiodination. The protocol was equally applicable to diiodination of 4-hydroxyphenylacetic acid to synthesize 4-hydroxy-3,5-diiodophenylacetic acid, an intermediate of tiratricol, a thyroid treatment drug. This protocol was further integrated via one-pot sequential iodination and Sonogashira coupling to synthesize aryl acetylenes, building blocks for the synthesis of a variety of specialty chemicals, API, and natural products.

Selective C-H Iodination of (Hetero)arenes

Iodoarenes are versatile intermediates and common synthetic targets in organic synthesis. Here, we present a strategy for selective C-H iodination of (hetero)arenes with a broad functional group tolerance. We demonstrate the utility and differentiation to other iodination methods of supposed sulfonyl hypoiodites for a set of carboarenes and heteroarenes.

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.

One-Pot Synthesis of N-Iodo Sulfoximines from Sulfides

This is the first report on the synthesis and characterization of N-iodo sulfoximines. The synthesis was designed as a room temperature one-pot cascade reaction from readily available sulfides as starting compounds, converted into sulfoximines by reaction with ammonium carbonate and (diacetoxyiodo)benzene, followed by iodination with N-iodosuccinimide or iodine in situ, in up to 90% isolated yields, also at a multigram scale. Iodination of aryls with N-iodo sulfoximines, oxidation, and conversion to N-SCF3 congeners have been demonstrated.

A convenient synthetic approach to a novel class of aryldifluoromethyl pyrimidine derivatives containing strobilurin motif as insecticidal agents

A series of aryldifluoromethyl pyrimidine compounds containing strobilurin were synthesized through bioelectronic isometric design with azoxystrobin as the lead compound and a convenient approach to aryldifluoromethylpyrimidine intermediates was developed, which features mild reaction conditions and simple operation. The title compounds and aryldifluoromethylpyrimidine intermediates were characterized by NMR and HRMS. Both 7c and 7l of the preliminary screening tests showed 100% inhibition against Mythimna separata at 100 mg/L. At 20 mg/L, the lethal rate of 7l against Mythimna separata can be up to 80%.

Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions

A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.

Aryl Diazonium Salts: Powerful Arylating Agents for Catellani-Typeortho-Arylation

The Catellani reaction provides an efficient synthetic approach to polyfunctionalized arenes. However, the selectiveortho-arylating reagents employed in these reactions have been strictly limited to activated bromoarenes. As demonstrated in this work, aryl diazonium salts bearing both electron-donating and electron-withdrawing substituents, after in situ transformations with KI into the corresponding iodoarenes, were efficient arylating reagents for Catellani typeortho-arylation approaches.