ChemicalBook > CAS DataBase List > 4-Iodophenol

4-Iodophenol

CAS No.540-38-5
Chemical Name:4-Iodophenol
CBNumber:CB8328252
Molecular Formula:C6H5IO
Formula Weight:220.01
MOL File:540-38-5.mol

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)
EWG's Food Scores 1
FDA UNII BH194BAK0B
NIST Chemistry Reference Phenol, 4-iodo-(540-38-5)
EPA Substance Registry System p-Iodophenol (540-38-5)
UNSPSC Code 12352100
NACRES NA.22

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

NFPA 704:

	1
3		1

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H302+H312-H314
Precautionary statements P260-P270-P280-P301+P312-P303+P361+P353-P305+P351+P338

4-Iodophenol Price More Price(11)

Brand: Sigma-Aldrich(India)
Product number: I10201
Product name : 4-Iodophenol
Purity: 99%
Packaging: 10G
Price: ₹5748.08
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: I10201
Product name : 4-Iodophenol
Purity: 99%
Packaging: 25G
Price: ₹7913.08
Updated: 2022/06/14
Buy: Buy

Brand: TCI Chemicals (India)
Product number: I0840
Product name : 4-Iodophenol [for Biochemical Research]
Purity: min. 98.0 %
Packaging: 1G
Price: ₹2700
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: I0840
Product name : 4-Iodophenol [for Biochemical Research]
Purity: min. 98.0 %
Packaging: 5G
Price: ₹4500
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: I0311
Product name : 4-Iodophenol
Purity: min. 98.0 %
Packaging: 10G
Price: ₹3100
Updated: 2022/05/26
Buy: Buy

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.