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HomeProduct name list4-Iodophenol

4-Iodophenol

  • CAS NO.:540-38-5
  • Empirical Formula: C6H5IO
  • Molecular Weight: 220.01
  • MDL number: MFCD00002327
  • EINECS: 208-745-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-12-24 16:54:11
4-Iodophenol Structural

What is 4-Iodophenol?

Chemical properties

Light brown powder. It dissolves slightly in water, but readily dissolves in ethanol, ether, and other organic solvents.

The Uses of 4-Iodophenol

4-Iodophenol is used in chemiluminescence imaging assays and experiments, as diagnostic agents in order to detect cancer cells in patients. Also it is used in the synthesis of agonists towards the est rogen β receptor.

What are the applications of Application

4-Iodophenol is 4-Iodophenol is a chemical used in chemiluminescence imaging assays and experiments, as diagnostic agents in order to detect cancer cells in patients.

Definition

ChEBI: 4-iodophenol is an iodophenol.

Preparation

It is obtained from 4-Aminophenol by diazotisation and substitution.

What are the applications of 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]

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 2, p. 355, 1943
The Journal of Organic Chemistry, 70, p. 8590, 2005 DOI: 10.1021/jo051191x
Tetrahedron Letters, 40, p. 6051, 1999 DOI: 10.1016/S0040-4039(99)01236-8

Metabolism

4-Iodophenol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(4-iodophenoxy)oxane-2-carboxylic acid.

Purification Methods

Crystallise 4-iodophenol from pet ether (b 80-100o) or distil it in vacuo. If the material has a brown or violet color, then dissolve it in CHCl3, shake it with 5% sodium thiosulfate solution until is colourless. Dry (Na2SO4), extract, evaporate and disil the residue in vacuo. [Dains & Eberly Org Synth Coll Vol II 355 1948, Beilstein 6 IV 1074.]

References

[1] HIDEHIRO SAKURAI Toshikazu H Tatsuya Tsukuda. Pd/C as a Reusable Catalyst for the Coupling Reaction of Halophenols and Arylboronic Acids in Aqueous Media[J]. The Journal of Organic Chemistry, 2002, 67 8: 2721-2722. DOI:10.1021/jo016342k.
[2] PIOTR WAWRZYNIAK Joachim H. Microwave-Promoted Suzuki—Miyaura Coupling of Arylboronic Acids with 1-Bromo-2-naphthol, o-Bromophenol, and o-Chlorophenol.[J]. ChemInform, 2007, 38 14. DOI:10.1002/chin.200714105.
[3] LUNXIANG YIN Juergen L. Carbon—Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts[J]. ChemInform, 2007, 38 22. DOI:10.1002/chin.200722237.
[4] MAHANTESHA BASANAGOUDA . Synthesis, structure–activity relationship of iodinated-4-aryloxymethyl-coumarins as potential anti-cancer and anti-mycobacterial agents[J]. European Journal of Medicinal Chemistry, 2014, 74: Pages 225-233. DOI:10.1016/j.ejmech.2013.12.061.
[5] AMIT SHARD. Tandem Heck/Decarboxylation/Heck Strategy: Protecting-Group-Free Synthesis of Symmetric and Unsymmetric Hydroxylated Stilbenoids?[J]. Angewandte Chemie International Edition, 2012, 51 49: 12250-12253. DOI:10.1002/anie.201206346.
[6] SAVVAS N. GEORGIADES Jon C. Total Synthesis of Psammaplysenes A and B, Naturally Occurring Inhibitors of FOXO1a Nuclear Export[J]. Organic Letters, 2005, 7 19: 4091-4094. DOI:10.1021/ol0513286.

Properties of 4-Iodophenol

Melting point: 92-94 °C(lit.)
Boiling point: 138 °C5 mm Hg(lit.)
Density  1.8573
Flash point: 138°C/5mm
storage temp.  Refrigerator
solubility  Chloroform (Slightly), Methanol (Slightly)
form  Crystals or Crystalline Powder
pka 9.33(at 25℃)
color  Pink or beige to brown
Water Solubility  slightly soluble
Sensitive  Light Sensitive
Merck  14,5036
BRN  1904544
Stability: Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference 540-38-5(CAS DataBase Reference)
NIST Chemistry Reference Phenol, 4-iodo-(540-38-5)
EPA Substance Registry System p-Iodophenol (540-38-5)

Safety information for 4-Iodophenol

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H314:Skin corrosion/irritation
Precautionary Statement Codes P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P270:Do not eat, drink or smoke when using this product.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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