2-Iodophenol

Base Information

• Chemical Name: 2-Iodophenol
• CAS No.: 533-58-4
• Molecular Formula: C6H5IO
• Molecular Weight: 220.01
• Hs Code.: 29081000
• European Community (EC) Number: 208-569-9
• NSC Number: 9245
• UNII: F27L34A8B9
• DSSTox Substance ID: DTXSID5052175
• Nikkaji Number: J53.758F
• Wikipedia: 2-Iodophenol
• Wikidata: Q27102035
• Metabolomics Workbench ID: 50606
• ChEMBL ID: CHEMBL225564
• Mol file: 533-58-4.mol

Synonyms:2-iodophenol;2-iodophenol, 123I-labeled;o-iodophenol;ortho-iodophenol

Chemical Property of 2-Iodophenol

Chemical Property:

• Appearance/Colour: Colorless needle-like crystals
• Vapor Pressure: 0.463mmHg at 25°C
• Melting Point: 37-40 °C(lit.)
• Refractive Index: 1.669
• Boiling Point: 187.2 °C at 760 mmHg
• PKA: 8.51(at 25℃)
• Flash Point: 67 °C
• PSA: 20.23000
• Density: 2.001 g/cm³
• LogP: 1.99680
• Storage Temp.: Store below +30°C.
• Sensitive.: Light Sensitive
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: slightly soluble
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 219.93851
• Heavy Atom Count: 8
• Complexity: 74.9

Purity/Quality:

99% ^*data from raw suppliers

2-Iodophenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Phenols
• Canonical SMILES: C1=CC=C(C(=C1)O)I
• Uses: 2-Iodophenol is used in the synthesis of aryl 2-benzofuranyl and aryl 2-indolyl carbinols of high enantiomeric purity and 3,3-disubstituted-2,3-dihydrobenzofurans. Coupling with phenylacetylene in the presence of a Pd complex and CuI gives 2-phenylbenzofuran in good yield.

Technology Process of 2-Iodophenol

There total 69 articles about 2-Iodophenol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2-iodo-1-(1-tetrahydro-2H-pyranyloxy)benzene (196106-22-6) → 2-Iodophenol (533-58-4)

Guidance literature:

With silica-supported NaHSO₄; In methanol; at 20 ℃; for 0.166667h;

DOI:10.1002/cjoc.201100358

Reference yield: 97.0%

1-allyloxy-2-iodobenzene (24892-63-5) → 2-Iodophenol (533-58-4)

Guidance literature:

With [2,2]bipyridinyl; (1,2-dimethoxyethane)dichloronickel(II); water; bis(pinacol)diborane; lithium tert-butoxide; In methanol; N,N-dimethyl acetamide; at 30 ℃; for 24h; Schlenk technique;

Reference yield: 95.0%

phenol (108-95-2,27073-41-2) → 2-Iodophenol (533-58-4) + p-Iodophenol (540-38-5)

Guidance literature:

With N-iodo-succinimide; toluene-4-sulfonic acid; In acetonitrile; at 20 ℃; for 14h; regioselective reaction;

DOI:10.1016/j.tetlet.2009.03.128

upstream raw materials:

2-iodophenylamine

sodium phenoxide

2-amino-phenol

phenol

Downstream raw materials:

1-(2-iodo-phenoxy)-3-piperidino-propan-2-ol

4-hydroxy-3-iodo-benzaldehyde

2-iodo(trimethylsilyloxy)benzene

2-(2-iodo-phenoxy)-butyric acid

Refernces

• 1、 Tanwar, Lalita,B?rgel, Jonas,Lehmann, Johannes,Ritter, Tobias. "Selective C-H Iodination of (Hetero)arenes". supporting information. p. 5024 - 5027. Retrieved 2021/06/30.
• 2、 Li, Xue,Chen, Haohua,Xuan, Qingqing,Mai, Shaoyu,Lan, Yu,Song, Qiuling. "Biomimetic carbene cascades enabled imine derivative migration from carbene -bearing thiocarbamates". supporting information. p. 3518 - 3523. Retrieved 2021/05/29.