2,3-DICHLOROANISOLE Chemical Properties

Melting point:

31-33 °C(lit.)

Boiling point:

115-116°C 12mm

Density 

1.2970 (rough estimate)

refractive index 

1.5430 (estimate)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform, Methanol

form 

Solid

color 

Off-White

Water Solubility 

Soluble in water (86.9 mg/L).

BRN 

1909166

InChI

InChI=1S/C7H6Cl2O/c1-10-6-4-2-3-5(8)7(6)9/h2-4H,1H3

InChIKey

HFEASCCDHUVYKU-UHFFFAOYSA-N

SMILES

C1(Cl)=CC=CC(OC)=C1Cl

CAS DataBase Reference

1984-59-4(CAS DataBase Reference)

EPA Substance Registry System

2,3-Dichloroanisole (1984-59-4)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-20/22

Safety Statements 

22-24/25-37/39-26

WGK Germany 

3

TSCA 

Yes

HS Code 

29093090

MSDS

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

2,3-DICHLOROANISOLE Usage And Synthesis

Chemical Properties

white to brownish crystalline low melting solid

Agricultural Uses

2,3-Dichloroanisole is a volatile organic compound that has been shown to be an attractant for termites. It is used as a pesticide and agrochemical. 2,3-Dichloroanisole is used as an insecticide against termites and other pests in agriculture. This chemical has been shown to inhibit the sodium channel of the nerve cell membrane, which leads to paralysis of insects. The mechanism of action for this compound is not well understood but it has been suggested that it may act by blocking the reorientation of the sodium ion channels. 2,3-Dichloroanisole can also be used as a metal salt in some thermodynamic reactions.

Synthesis

General procedure for the synthesis of 2,3-dichloroanisole from 2,3-dichlorophenol and dimethyl sulfate: 2,3-dichlorophenol (20.0 g, 122.7 mmol) was placed in a reaction flask, 120 mL of acetone was added to dissolve it, followed by the addition of potassium carbonate (18.7 g, 135.0 mmol), and magnetically stirred for 0.5 hours. Then dimethyl sulfate (17.0 g, 135.0 mmol) was slowly added dropwise through a dropping funnel and heated to 60°C and refluxed for 3 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) (unfolding agent: petroleum ether/ethyl acetate=5:1, Rf=0.8). After completion of the reaction, it was cooled to room temperature, potassium carbonate was removed by filtration with a pump and the filter cake was washed with acetone. After evaporation to remove acetone, ethyl acetate and saturated sodium bicarbonate solution were added sequentially, and the organic phase was washed twice each time with saturated aqueous sodium chloride solution, and then the organic phase was dried with anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to give 2,3-dichloroanisole. The product was a colorless oil with a yield of 21.5 g and 99.1%.

References

[1] Patent: CN106916116, 2017, A. Location in patent: Paragraph 0063; 0064; 0065
[2] Recueil des Travaux Chimiques des Pays-Bas, 1918, vol. 37, p. 105

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