4-Iodophenol Property

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

Hazard Codes 

C,Xi,Xn

Risk Statements 

21/22-34-36/37/38-20/21/22

Safety Statements 

26-36/37/39-45-22

RIDADR 

UN 3261 8/PG 3

WGK Germany 

3

RTECS 

SL5600000

Hazard Note 

Irritant

TSCA 

T

HazardClass 

IRRITANT, LACHRYMATOR

HS Code 

29081900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-Iodophenol Chemical Properties,Usage,Production

Chemical Properties

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

Uses

4-Iodophenol is used in chemiluminescence imaging assays and experiments, as diagnostic agents in order to detect cancer cells in patients. It is also utilized in synthesizing agonists for the estrogen β receptor. Additionally, The compound finds extensive applications in various medical industries as well as in human and animal nutrition products such as pharmaceutical intermediates, and polarizing films for Liquid Crystal Display (LCD) chemicals.

Preparation

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

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]

Definition

ChEBI: 4-iodophenol is an iodophenol.

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.