533-58-4 Usage
Description
2-Iodophenol is a halophenol characterized by its colorless needle-like crystals or pale yellow low melting solid appearance. It exhibits slight solubility in water and is easily soluble in organic solvents such as ethanol and ether. 2-Iodophenol is known for its antifungal activity and is utilized in various chemical reactions and applications.
Uses
Used in Chemical Synthesis:
2-Iodophenol is used as a key intermediate in the synthesis of various organic compounds, including aryl 2-benzofuranyl and aryl 2-indolyl carbinols with high enantiomeric purity. It also plays a role in the synthesis of 3,3-disubstituted-2,3-dihydrobenzofurans and 1,3,5-substituted benzenes. 2-Iodophenol is effective in carbonylative cyclization reactions with various alkyne under microwave irradiation, using Mo(CO)6 as the CO source.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Iodophenol is used as an additive tracer for resist plasm etching and Suzuki reaction, which are crucial processes in the development of new drugs and pharmaceutical compounds.
Used in Material Science:
2-Iodophenol is also utilized as an additive in material science, specifically for its application in resist plasm etching, which is an essential process in the manufacturing of semiconductors and other electronic components.
Preparation
synthesis of 2-iodophenol: phenol (1a) to react with 0.5 equivalent of iodine and 1 equivalent of hydrogen peroxide in water at room temperature for 24 h, 2,6-diiodophenol (2a) and 2-iodophenol (3) were isolated in yields of 21 and 49%, respectively.
Synthesis Reference(s)
The Journal of Organic Chemistry, 53, p. 5281, 1988 DOI: 10.1021/jo00257a014
Purification Methods
Crystallise 2-iodophenol from CHCl3 or diethyl ether. The acetate has m 65-66o (from MeOH). [Beilstein 6 H 208, 6 II 198, 6 III 774, 6 IV 1074.]
Check Digit Verification of cas no
The CAS Registry Mumber 533-58-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 3 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 533-58:
(5*5)+(4*3)+(3*3)+(2*5)+(1*8)=64
64 % 10 = 4
So 533-58-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H5IO/c7-5-3-1-2-4-6(5)8/h1-4,8H
533-58-4Relevant articles and documents
Whitmore,Hanson
, p. 319; deutsche Ausgabe, S. 323 (1932)
Biomimetic carbene cascades enabled imine derivative migration from carbene -bearing thiocarbamates
Li, Xue,Chen, Haohua,Xuan, Qingqing,Mai, Shaoyu,Lan, Yu,Song, Qiuling
supporting information, p. 3518 - 3523 (2021/05/29)
Inspired by the body circulation of Omeprazole (irreversible proton pump inhibitor), we disclose the carbene-triggered cascades for the synthesis of 2-aminobenzofuran derivatives from N-sulfonyl-1,2,3-triazoles or benzothioazole-bearing thiocarbamates, which represents an unprecedented imine derivative migration process. Furthermore, the desulfurizing reagent-free Barton-Kellogg-type reactions starting from N-sulfonyl-1,2,3-triazoles have also been achieved for the first time, and elemental sulfur is confirmed as a byproduct during this transformation. Both experimental data and DFT calculations further thoroughly explained the unique reactivity.
Transition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor
Heredia, Micaela D.,Guerra, Walter D.,Barolo, Silvia M.,Fornasier, Santiago J.,Rossi, Roberto A.,Budén, Mariá E.
supporting information, p. 13481 - 13494 (2020/12/15)
Novel approaches for N- and O-desulfonylation under room temperature (rt) and transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety of N-sulfonyl heterocycles and phenyl benzenesulfonates to the corresponding desulfonylated products in good to excellent yields using only KOtBu in dimethyl sulfoxide (DMSO) at rt. Alternately, a visible light method has been used for deprotection of N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction. The HE anion can be easily prepared in situ by reaction of the corresponding HE with KOtBu in DMSO at rt. Both protocols were further explored in terms of synthetic scope as well as mechanistic aspects to rationalize key features of desulfonylation processes. Furthermore, the HE anion induces reductive dehalogenation reaction of aryl halides under visible light irradiation.