2,6-Difluorophenol Chemical Properties

Melting point:

38-41 °C (lit.)

Boiling point:

59-61 °C/17 mmHg (lit.)

Density 

1,27 g/cm³

Flash point:

138 °F

storage temp. 

2-8°C

solubility 

ethanol: soluble50mg/mL, clear, colorless to light yellow

form 

Crystalline Low Melting Solid

pka

7.45±0.10(Predicted)

color 

Colorless

Water Solubility 

Slightly soluble in water. Soluble in ethanol.

BRN 

2043613

InChI

InChI=1S/C6H4F2O/c7-4-2-1-3-5(8)6(4)9/h1-3,9H

InChIKey

CKKOVFGIBXCEIJ-UHFFFAOYSA-N

SMILES

C1(O)=C(F)C=CC=C1F

CAS DataBase Reference

28177-48-2(CAS DataBase Reference)

NIST Chemistry Reference

2,6-Difluorophenol(28177-48-2)

Safety Information

Hazard Codes 

F,Xi,Xn

Risk Statements 

11-36/37/38-20/21/22

Safety Statements 

26-36/37/39

RIDADR 

UN 1325 4.1/PG 2

WGK Germany 

3

F 

10

Hazard Note 

Irritant

HazardClass 

4.1

PackingGroup 

II

HS Code 

29081000

MSDS

• Language:English Provider:2,6-Difluorophenol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,6-Difluorophenol Usage And Synthesis

Chemical Properties

colorless crystalline low melting solid

Uses

2,6-Difluorophenol undergoes oxidative polymerization in the presence of the Fe-N,N?-bis(salicylidene)ethylenediamine (salen) complex (catalyst) and hydrogen peroxide (oxidizing agent) to give poly(2,6-difluoro-1,4-phenylene oxide). It is also used as pharmaceutical intermediates.

Synthesis

General procedure for the synthesis of 2,6-difluorophenol from 2,6-difluoroanisole: 2,6-difluoroanisole (4.00 mL, 33.9 mmol) was dissolved in acetonitrile (50 mL), and trimethylchlorosilane (8.80 mL, 102 mmol) and sodium iodide (15.0 g, 100 mmol) were added sequentially. The reaction mixture was heated to 100 °C for 5 hours. After completion of the reaction, it was cooled to room temperature and the solvent was removed by evaporation under reduced pressure. Water (40 mL) was added to the residue and extracted with dichloromethane (30 mL x 3). The organic phases were combined and washed sequentially with water (40 mL) and saturated brine (40 mL), and then dried over anhydrous sodium sulfate. After filtration, the solvent was removed by evaporation under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (eluent: petroleum ether/ethyl acetate, v/v = 6/1) to afford the yellow oily product 2,6-difluorophenol (2.2 g, 50% yield).

References

[1] Patent: CN105384687, 2016, A. Location in patent: Paragraph 0479; 0480; 0481; 0482
[2] Journal of the American Chemical Society, 1959, vol. 81, p. 94,95, 97

2,6-Difluorophenol(28177-48-2)Related Product Information

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