2,5-DIMETHOXYBENZONITRILE Chemical Properties

Melting point:

81-85 °C (lit.)

Boiling point:

288.8±25.0 °C(Predicted)

Density 

1.12±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Yellow to Orange

BRN 

2691937

CAS DataBase Reference

5312-97-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37

RIDADR 

3276

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

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

2,5-DIMETHOXYBENZONITRILE Usage And Synthesis

Synthesis

At 0 °C, n-butyllithium (1.67 M hexane solution, 2.9 mL, 4.8 mmol) was slowly added dropwise to a solution of 1,3-dimethoxybenzene (0.55 g, 4.0 mmol) in tetrahydrofuran (5 mL). The reaction mixture was stirred continuously at 0 °C for 2 hours. Subsequently, N,N-dimethylformamide (0.34 mL, 4.4 mmol) was added to the mixture and stirring was continued for 2 hours at 0 °C. Upon completion of the reaction, ammonia solution (8 mL, 120 mmol) and iodine (1.12 g, 4.4 mmol) were added and the mixture was transferred to room temperature and stirred for 2 hours. The reaction mixture was quenched with saturated aqueous sodium sulfite solution (15 mL) and extracted several times with ether (3 x 20 mL). The organic layers were combined, washed with saturated saline and dried over anhydrous sodium sulfate to give the crude product 2,6-dimethoxybenzonitrile with a purity of over 80%. The crude product was purified by silica gel short-column chromatography (eluent: hexane/ethyl acetate=3:1) to afford pure 2,6-dimethoxybenzonitrile as a colorless solid in 91% yield.

References

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

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