2-Iodophenol Property

Melting point:

37-40 °C (lit.)

Boiling point:

186-187 °C/160 mmHg (lit.)

Density 

1.947 g/mL at 25 °C (lit.)

Flash point:

>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

pka

8.51(at 25℃)

Specific Gravity

1.947

color 

White or cream to brown

Water Solubility 

slightly soluble

Sensitive 

Light Sensitive

Merck 

14,5035

BRN 

1855300

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

KQDJTBPASNJQFQ-UHFFFAOYSA-N

CAS DataBase Reference

533-58-4(CAS DataBase Reference)

NIST Chemistry Reference

Phenol, 2-iodo-(533-58-4)

EPA Substance Registry System

Phenol, 2-iodo- (533-58-4)

Safety

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

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

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

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

2-Iodophenol Chemical Properties,Usage,Production

Chemical Properties

colorless needle-like crystals or Pale Yellow Low Melting Solid. Slightly soluble in water, easily soluble in organic solvents such as ethanol and ether.

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.

Application

2-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.

Preparation

synthesis 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.

Definition

ChEBI: 2-iodophenol is a 2-halophenol and an iodophenol.

Synthesis Reference(s)

The Journal of Organic Chemistry, 53, p. 5281, 1988 DOI: 10.1021/jo00257a014

General Description

Rapid 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 Methods

Crystallise 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.]