533-58-4 Usage
Chemical Properties
colorless needle-like crystals or Pale Yellow Low Melting Solid. Slightly soluble in water, easily soluble in organic solvents such as ethanol and ether.
Uses
2-Iodophenol is used in the synthesis of aryl 2-benzofuranyl and aryl 2-indolyl carbinols of high enantiomeric purity and 3,3-disubstituted-2,3-dihydrobenzofurans. Coupling with phenylacetylene in the presence of a Pd complex and CuI gives 2-phenylbenzofuran in good yield.
Application
2-Iodophenol is a halophenol with antifungal activity. 2-Iodophenol was used in the synthesis of:aryl 2-benzofuranyl and aryl 2-indolyl carbinols of high enantiomeric purity3,3-disubstituted-2,3-dihydrobenzofurans1,3,5-substituted benzenes.2-Iodophenol is also used as additive tracers for resist plasm a etching and suzuki reaction.
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
General Description
Rapid palladium-catalyzed carbonylative cyclization reactions of 2-iodophenol with various alkyne under microwave irradiation using Mo(CO)6 as the CO source has been investigated.
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)
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.
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.