696-62-8 Usage
Description
4-Iodoanisole (chemical formula: C7H7IO) is an organic compound being soluble in ethanol, ether and chloroform. It has a wide range of medicals industrial applications. For example, it can be used as human and animal nutrition products, antiseptics, disinfectants, pharmaceutical intermediates, polarizing films for liquid crystal display (LCD) chemicals. Its iodine derivatives can also be used as organic building blocks and analytic reagents.
References
https://www.fishersci.pt/shop/products/4-iodoanisole-98-7/11480113
Chemical Properties
off-white to brown crystalline powder and chunks. Melting point 51-52 ℃, boiling point 237 ℃ (96.8kPa). Soluble in organic solvents such as alcohol and ether, but insoluble in water. Iodine can be easily separated and analyzed by light.
Uses
4-Iodoanisole is used in wide range of medicals industrial applications as well as in human and animal nutrition products, pharmaceutical intermediates, polarizing films for Liquid Crystal Display (LCD) chemicals. Iodine derivatives are also used as organic building blocks, analytical reagents.
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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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.
One-Pot Synthesis of N-Iodo Sulfoximines from Sulfides
Zupanc, An?e,Jereb, Marjan
, p. 5991 - 6000 (2021/05/05)
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.
