696-62-8 Usage
Description
4-Iodoanisole, with the chemical formula C7H7IO, is an organic compound characterized by its off-white to brown crystalline appearance. It is soluble in ethanol, ether, and chloroform, and has a melting point of 51-52°C and a boiling point of 237°C (96.8kPa). 4-Iodoanisole is insoluble in water and features easily separable and analyzable iodine content. It is widely utilized across various industries due to its diverse applications and properties.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 696-62-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,9 and 6 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 696-62:
(5*6)+(4*9)+(3*6)+(2*6)+(1*2)=98
98 % 10 = 8
So 696-62-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H7IO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H3
696-62-8Relevant articles and documents
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Brenans
, p. 819 (1901)
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Preparation method of nitrogen-alkyl (deuterated alkyl) aromatic heterocycle and alkyl (deuterated alkyl) aryl ether compound
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Paragraph 0093-0098, (2021/04/03)
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.
NCBSI/KI: A Reagent System for Iodination of Aromatics through in Situ Generation of I-Cl
Palav, Amey,Misal, Balu,Chaturbhuj, Ganesh
, p. 12467 - 12474 (2021/08/24)
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.
Selective C-H Iodination of (Hetero)arenes
Tanwar, Lalita,B?rgel, Jonas,Lehmann, Johannes,Ritter, Tobias
supporting information, p. 5024 - 5027 (2021/06/30)
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.
