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281409

Sigma-Aldrich

2-Iodophenol

98%

Sinónimos:

1-Iodo-2-hydroxybenzene, 2-Hydroxyiodobenzene, o-Iodophenol

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About This Item

Fórmula lineal:
IC6H4OH
Número de CAS:
533-58-4
Peso molecular:
220.01
EC Number:
208-569-9
MDL number:
MFCD00013963
UNSPSC Code:
12352100
PubChem Substance ID:
24856973
NACRES:
NA.22

assay

98%

form

solid

bp

186-187 °C/160 mmHg (lit.)

mp

37-40 °C (lit.)

density

1.947 g/mL at 25 °C (lit.)

SMILES string

Oc1ccccc1I

InChI

1S/C6H5IO/c7-5-3-1-2-4-6(5)8/h1-4,8H

InChI key

KQDJTBPASNJQFQ-UHFFFAOYSA-N

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.

Application

2-Iodophenol was used in the synthesis of:
  • aryl 2-benzofuranyl and aryl 2-indolyl carbinols of high enantiomeric purity
  • 3,3-disubstituted-2,3-dihydrobenzofurans

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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J Philipp Wagner
Chemistry (Weinheim an der Bergstrasse, Germany), 26(53), 12119-12124 (2020-05-20)
Peroxy radical hydrogen-shifts are pivotal elementary reaction steps in the oxidation of small hydrocarbons in autoignition and the lower atmosphere. Although these reactions are typically associated with a substantial barrier, we demonstrate that the [1,5]H-shift in the peroxy species derived
Chao Fang et al.
Water research, 145, 103-112 (2018-08-20)
Haloacetamides (HAMs), an emerging class of disinfection by-products, have received increasing attention due to their elevated cyto- and genotoxicity. However, only limited information is available regarding the iodinated analogues. This study investigated the formation and speciation of iodinated haloacetamides (I-HAMs)
Microwave-accelerated, palladium-catalyzed carbonylative cyclization reactions of 2-iodophenol with alkynes Rapid and efficient synthesis of chromen-2-one derivatives.
Cao H and Xiao W-J.
Canadian Journal of Chemistry, 83(6-7), 826-831 (2005)
D M Otterness et al.
Molecular pharmacology, 36(6), 856-865 (1989-12-01)
Phenol sulfotransferase (PST) catalyzes the sulfate conjugation of phenolic drugs, neurotransmitters, and xenobiotic compounds. Human tissues contain at least two forms of PST, which differ in their substrate specificities, inhibitor sensitivities, physical properties, and regulation. One form of the enzyme
K Suzuki et al.
Journal of biochemistry, 109(5), 791-797 (1991-05-01)
Salicylate hydroxylase [EC 1.14.13.1] from Pseudomonas putida catalyzes the hydroxylation of salicylate, and also o-aminophenol, o-nitrophenol, and o-halogenophenols, to catechol. The reactions with these o-substituted phenols comprise oxygenative deamination, denitration, and dehalogenation, respectively. The reaction stoichiometry, as to NADH oxidized
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