2,6-DIMETHOXYBENZONITRILE Chemical Properties

Melting point:

119-123 °C

Boiling point:

310 °C

Density 

1.2021 (rough estimate)

refractive index 

1.5300 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

Crystalline Powder

color 

Light beige

CAS DataBase Reference

16932-49-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22

Safety Statements 

36/37-36-26

Hazard Note 

Irritant

HS Code 

29269095

Toxicity

rat,LD,oral,> 500mg/kg (500mg/kg),National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 17, 1953.

MSDS

• Language:English Provider:ACROS

2,6-DIMETHOXYBENZONITRILE Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 3, p. 293, 1955
Tetrahedron, 49, p. 10843, 1993 DOI: 10.1016/S0040-4020(01)80238-6

Synthesis

At 0 °C, n-butyllithium (1.67 M hexane solution, 2.9 mL, 4.8 mmol) was slowly added dropwise to a tetrahydrofuran (THF, 5 mL) solution of 1,3-dimethoxybenzene (0.55 g, 4.0 mmol). After the reaction mixture was stirred at 0 °C for 2 h, N,N-dimethylformamide (DMF, 0.34 mL, 4.4 mmol) was added and stirring was continued at 0 °C for 2 h. The reaction mixture was then mixed with N,N-dimethylformamide (DMF, 0.34 mL, 4.4 mmol). Subsequently, ammonia solution (8 mL, 120 mmol) and dihydroammonium iodide (DIH, 0.91 g, 2.4 mmol) were added to the reaction system and the mixture was transferred to room temperature and stirred for 2 hours. Upon completion of the reaction, the reaction was quenched with saturated aqueous sodium sulfite solution (15 mL) and then extracted with ether (3 x 20 mL). The organic layers were combined, washed with brine and dried over anhydrous sodium sulfate. The crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3:1) to afford pure 2,6-dimethoxybenzonitrile in 94% yield as a colorless solid.

References

[1] Tetrahedron, 2011, vol. 67, # 5, p. 958 - 964
[2] Synlett, 2010, # 10, p. 1562 - 1566

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