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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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About This Item

Linear Formula:
IC6H4OH
CAS Number:
540-38-5
Molecular Weight:
220.01
Beilstein:
1904544
EC Number:
208-745-5
MDL number:
MFCD00002327
UNSPSC Code:
12352100
PubChem Substance ID:
24895917
NACRES:
NA.22

Quality Level

200

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
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302 + H312,H314

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

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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Carbon- carbon coupling reactions catalyzed by heterogeneous palladium catalysts
Yin L and Liebscher J
Chemical Reviews, 107(1), 133-173 (2007)
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)
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)
Zuxu Chen et al.
Acta crystallographica. Section D, Biological crystallography, 65(Pt 1), 34-40 (2009-01-21)
The enzyme dehaloperoxidase (DHP) from the terebellid polychaete Amphitrite ornata is a heme protein which has a globin fold but can function as both a hemoglobin and a peroxidase. As a peroxidase, DHP is capable of converting 2,4,6-trihalophenols to the
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