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2-Iodophenol

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2-Iodophenol Basic information
Product Name:2-Iodophenol
Synonyms:Adjacent iodine phenol;2-IODOPHENOL;Phenol, o-iodo- (6CI,8CI);2-iodo-pheno;2-Jodfenol;o-iodo-pheno;o-Jodfenol;Phenol, o-iodo-
CAS:533-58-4
MF:C6H5IO
MW:220.01
EINECS:208-569-9
Product Categories:Building Blocks;C6 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Aromatic Phenols;Phenol&Thiophenol&Mercaptan;Iodine Compounds;Phenols;Phenyls & Phenyl-Het;Organic Building Blocks;Oxygen Compounds;alcohol| alkyl Iodine
Mol File:533-58-4.mol
2-Iodophenol Structure
2-Iodophenol Chemical Properties
Melting point 37-40 °C (lit.)
Boiling point 186-187 °C/160 mmHg (lit.)
density 1.947 g/mL at 25 °C (lit.)
Fp >230 °F
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Ethyl Acetate (Slightly)
form Crystalline Powder or Crystalline Low Melting Mass
pka8.51(at 25℃)
color White or cream to brown
Specific Gravity1.947
Water Solubility slightly soluble
Sensitive Light Sensitive
Merck 14,5035
BRN 1855300
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeyKQDJTBPASNJQFQ-UHFFFAOYSA-N
CAS DataBase Reference533-58-4(CAS DataBase Reference)
NIST Chemistry ReferencePhenol, 2-iodo-(533-58-4)
EPA Substance Registry SystemPhenol, 2-iodo- (533-58-4)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 20/21/22-36/37/38
Safety Statements 26-36-37/39
WGK Germany 3
RTECS SL5500000
TSCA T
HazardClass IRRITANT, LIGHT SENSITIVE
HS Code 29081000
MSDS Information
ProviderLanguage
2-Iodophenol English
SigmaAldrich English
ACROS English
ALFA English
2-Iodophenol Usage And Synthesis
Chemical Propertiescolorless needle-like crystals or Pale Yellow Low Melting Solid. Slightly soluble in water, easily soluble in organic solvents such as ethanol and ether.
Uses2-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.
DefinitionChEBI: 2-iodophenol is a 2-halophenol and an iodophenol.
Application2-Iodophenol is a halophenol with antifungal activity. 2-Iodophenol was used in the synthesis of:
aryl 2-benzofuranyl and aryl 2-indolyl carbinols of high enantiomeric purity
3,3-disubstituted-2,3-dihydrobenzofurans
1,3,5-substituted benzenes.
2-Iodophenol is also used as additive tracers for resist plasm a etching and suzuki reaction.
Preparationsynthesis of 2-iodophenol: phenol (1a) to react with 0.5 equivalent of iodine and 1 equivalent of hydrogen peroxide in water at room temperature for 24 h, 2,6-diiodophenol (2a) and 2-iodophenol (3) were isolated in yields of 21 and 49%, respectively.
synthesis of 2-iodophenol
Synthesis Reference(s)The Journal of Organic Chemistry, 53, p. 5281, 1988 DOI: 10.1021/jo00257a014
General DescriptionRapid palladium-catalyzed carbonylative cyclization reactions of 2-iodophenol with various alkyne under microwave irradiation using Mo(CO)6 as the CO source has been investigated.
Purification MethodsCrystallise 2-iodophenol from CHCl3 or diethyl ether. The acetate has m 65-66o (from MeOH). [Beilstein 6 H 208, 6 II 198, 6 III 774, 6 IV 1074.]
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