| Identification | More | [Name]
4-Iodophenol | [CAS]
540-38-5 | [Synonyms]
4-IODOPHENOL
PHENOL, 4-IODO-
P-IODOPHENOL
4-hydroxyiodobenzene
4-hydroxyphenyliodide
4-iodo-pheno
Phenol, p-iodo-
p-hydroxyiodobenzene
p-iodo-pheno
p-Iodophenol 4-Iodophenol
4-Iodophenol99%
4-Iodophenol, 98+%
PARA-IODOPHENOL
p-hydroxyiodobenzen
p-Jodphenol | [EINECS(EC#)]
208-745-5 | [Molecular Formula]
C6H5IO | [MDL Number]
MFCD00002327 | [Molecular Weight]
220.01 | [MOL File]
540-38-5.mol |
| Chemical Properties | Back Directory | [Appearance]
light brown powder | [Melting point ]
92-94 °C(lit.)
| [Boiling point ]
138 °C5 mm Hg(lit.)
| [density ]
1.8573 | [Fp ]
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 | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Water Solubility ]
slightly soluble | [Sensitive ]
Light Sensitive | [Merck ]
14,5036 | [BRN ]
1904544 | [CAS DataBase Reference]
540-38-5(CAS DataBase Reference) | [NIST Chemistry Reference]
Phenol, 4-iodo-(540-38-5) | [EPA Substance Registry System]
540-38-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C,Xi,Xn | [Risk Statements ]
R21/22:Harmful in contact with skin and if swallowed .
R34:Causes burns.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S22:Do not breathe dust . | [RIDADR ]
UN 3261 8/PG 3
| [WGK Germany ]
3
| [RTECS ]
SL5600000
| [Hazard Note ]
Irritant | [TSCA ]
T | [HazardClass ]
IRRITANT, LACHRYMATOR | [HS Code ]
29081900 |
| Hazard Information | Back Directory | [Chemical Properties]
Light brown powder. It dissolves slightly in water, but readily dissolves in ethanol, ether, and other organic solvents. | [Uses]
4-Iodophenol(540-38-5) is a chemical 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 estrogen β receptor. Also used in wide range of medicals industrial applications as well as in human and animal nutrition products such as pharmaceutical intermediates, and polarizing films for Liquid Crystal Display (LCD) chemicals.
| [Uses]
suzuki reaction | [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. | [Preparation]
It is obtained from 4-Aminophenol by diazotisation and substitution. | [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. |
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