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Key Documents

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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About This Item

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

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.
  • Aryl substituted olefins by reacting with acrylates via Pd-catalyzed Heck reaction.
  • Iodinated-4-aryloxymethylcoumarins
  • Hydroxylated stilbenoids and psammaplysenes A and B.

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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)
Miriane da Costa et al.
The hematology journal : the official journal of the European Haematology Association, 5(6), 496-499 (2004-12-01)
In this report, we propose the application of the p-iodophenol-enhanced luminol chemiluminescent technique to the determination of peroxidase (myeloperoxidase and/or platelet peroxidase) activity in blasts of minimally differentiated acute myeloblastic leukemia (AML-M0) and acute megakaryoblastic leukemia (AML-M7). The frozen blast

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