4-Iodophenetole Chemical Properties

Melting point:

25-28 °C (lit.)

Boiling point:

133-134°C 19mm

Density 

1.6502 (estimate)

refractive index 

1.5970

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to lump to clear liquid

color 

White or Colorless to Yellow to Orange

Sensitive 

Light Sensitive

BRN 

2042067

InChIKey

WSWPHHNIHLTAHB-UHFFFAOYSA-N

CAS DataBase Reference

699-08-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29093090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Iodophenetole Usage And Synthesis

Chemical Properties

Off-white low melting solid

Uses

4-Iodophenetole may be used as one of the components in the synthesis of bis(4-ethoxyphenyl)amine.

Uses

Intermediates of Liquid Crystals

Uses

suzuki reaction

Synthesis

The general procedure for the synthesis of 4-iodophenylethyl ether from ethyl bromide and 4-iodophenol was as follows: 233.50 g (1.06 mol) of 4-iodophenol and 42.45 g (1.06 mol) of sodium hydroxide were ground to a powder in a dry mortar and pestle, and the mixture was subsequently transferred to a 1000 mL round-bottomed flask equipped with a magnetic stirrer. To the flask was added 300 mL of ethylene bromide, 15 mL of N,N-dimethylformamide and a catalytic amount of cesium hydroxide. The reaction mixture was stirred at room temperature for 1 hour and then gradually heated to 80 °C and refluxed for about 70 hours. Complete consumption of the reaction starting material was confirmed by thin layer chromatography (TLC). After the reaction solution was cooled to room temperature, the solvent ethyl bromide was removed by evaporation under reduced pressure. Subsequently, appropriate amounts of dichloromethane and water were added sequentially under stirring, the organic layer was separated, dried with anhydrous magnesium sulfate, filtered and concentrated to give 252.43 g of a red oily product in 96.2% yield. The structure of the product was characterized by 1H NMR, IR and HRMS: 1H NMR (400 MHz, (CD3)2SO) δ 7.57 (d, J = 8.8 Hz, 2H), 6.76 (d, J = 8.8 Hz, 2H), 3.98 (q, J = 6.9 Hz, 2H), 1.30 (t, J = 7.0 Hz, 3H); IR (KBr , cm-1) 2979, 2929, 1586, 1486, 1392, 1244, 1047, 820, 630, 507; HRMS (GCT-MS) calculated value C8H9IO [M+] 247.97, measured value 247.9692.

References

[1] Journal of Materials Chemistry B, 2014, vol. 2, # 33, p. 5430 - 5440
[2] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2015, vol. 150, p. 867 - 878
[3] Journal of Materials Chemistry C, 2014, vol. 2, # 19, p. 3686 - 3694
[4] Chemical Communications, 2009, # 19, p. 2756 - 2758
[5] Journal of Organometallic Chemistry, 1994, vol. 465, # 1-2, p. 97 - 100

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