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281409

Sigma-Aldrich

2-Iodophenol

98%

Synonym(s):

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

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About This Item

Linear Formula:
IC6H4OH
CAS Number:
533-58-4
Molecular Weight:
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

Signal Word

Warning

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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R Koteshwar Rao et al.
Organic letters, 11(9), 1923-1926 (2009-04-04)
trans-3,4-Dihydro-2H-1,4-benzoxazine moieties can be synthesized by domino aziridine ring opening with o-iodophenols followed by the copper-catalyzed Goldberg coupling cyclization (intramolecular C(aryl)-N(amide) bond formation) with good to excellent yields.
Andrea Strube et al.
Water research, 43(20), 5216-5224 (2009-09-29)
The aim of the present study was to identify the compounds responsible for a characteristic medicinal off-odour in mineral water. 2-Dimensional high resolution gas chromatography-mass spectrometry analysis, in combination with olfactometry (HRGC-MS/O), led to the identification of 2-iodophenol and 2-iodo-4-methylphenol
Synthesis of aryl 2-benzofuranyl and aryl 2-indolyl carbinols of high enantiomeric purity via palladium-catalyzed heteroannulation of chiral arylpropargylic alcohols.
Botta M, et al.
Tetrahedron Asymmetry, 7(5), 1263-1266 (1996)
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
Palladium-catalyzed cascade allylation/carbopalladation/cross coupling: a novel three-component reaction for the synthesis of 3, 3-disubstituted-2, 3-dihydrobenzofurans.
Szlosek-Pinaud, et al.
Tetrahedron Letters, 44(48), 8657-8659 (2003)
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