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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

Quality Level

100

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

Related Categories

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

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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.
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)
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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