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I10201

Sigma-Aldrich

4-Iodophenol

99%

Synonym(s):

1-Iodo-4-hydroxybenzene, 4-Hydroxyiodobenzene, 4-Hydroxyphenyl iodide, p-Hydroxyiodobenzene, p-Iodophenol

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10 G
$67.60
25 G
$106.00

About This Item

Linear Formula:
IC6H4OH
CAS Number:
Molecular Weight:
220.01
Beilstein/REAXYS Number:
1904544
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
assay:
99%

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Quality Level

assay

99%

bp

138 °C/5 mmHg (lit.)

mp

92-94 °C (lit.)

SMILES string

Oc1ccc(I)cc1

InChI

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

Inchi Key

VSMDINRNYYEDRN-UHFFFAOYSA-N

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Application

4-Iodophenol can be used as a building block for the synthesis of:
  • Hydroxybiaryls by reacting with aryl boronic acids via Pd-catalyzed Suzuki-Miyaura coupling reaction.[1][2]
  • Aryl substituted olefins by reacting with acrylates via Pd-catalyzed Heck reaction.[3]
  • Iodinated-4-aryloxymethylcoumarins [4]
  • Hydroxylated stilbenoids [5] and psammaplysenes A and B.[6]

pictograms

CorrosionExclamation mark

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Total synthesis of psammaplysenes A and B, naturally occurring inhibitors of FOXO1a nuclear export
Georgiades SN and Clardy J
Organic Letters, 7(19), 4091-4094 (2005)
Pd/C as a reusable catalyst for the coupling reaction of halophenols and arylboronic acids in aqueous media
Sakurai H, et al.
The Journal of Organic Chemistry, 67(8), 2721-2722 (2002)
Synthesis, structure-activity relationship of iodinated-4-aryloxymethyl-coumarins as potential anti-cancer and anti-mycobacterial agents
Basanagouda, M, et al.
European Journal of Medicinal Chemistry, 74(1), 225-233 (2014)
Carbon- carbon coupling reactions catalyzed by heterogeneous palladium catalysts
Yin L and Liebscher J
Chemical Reviews, 107(1), 133-173 (2007)
Jefferson D Revell et al.
Organic letters, 4(18), 3071-3073 (2002-08-31)
[reaction: see text] Room-temperature ionic liquids promote various transition metal-catalyzed reactions in the solution phase. Here, for the first time, we show that these effects are translatable to solid-phase reactions. The Suzuki-Miyaura cross-coupling of 4-iodophenol immobilized on polystyrene-Wang resin with

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