2,6-DIMETHYLANILINE HYDROCHLORIDE Chemical Properties

Melting point:

275°C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Sonicated)

form 

powder or crystals

color 

White to Pale Brown

Stability:

Hygroscopic

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

RTECS 

ZF0375000

HS Code 

2921490002

Toxicity

rat,LD50,oral,2042mg/kg (2042mg/kg),Journal of Pharmacology and Experimental Therapeutics. Vol. 167, Pg. 223, 1969.

2,6-DIMETHYLANILINE HYDROCHLORIDE Usage And Synthesis

Uses

2,6-Dimethylaniline hydrochloride may be used in the preparation of 2,6-dimethylphenyl isocyanate via phosgenation. This product was previously listed as CDS000447.

Synthesis

The general procedure for the synthesis of 2,6-dimethylaniline hydrochloride from 2,6-dimethylacetanilide and ethylmagnesium bromide was as follows: trifluoromethanesulfonic anhydride (Tf2O, 185 μL, 1.1 mmol) was added slowly and dropwise to a cooled-to-0°C dichloromethane ( 4 mL) solution. The reaction mixture was stirred at 0 °C for 30 min, then transferred to -78 °C and a solution of tetrahydrofuran (THF, 15 mL) of freshly prepared organocerium reagent/complex (3.0 mmol) was added, and stirring was continued for 2 hours. Upon completion of the reaction, the reaction was quenched by the addition of a 3 mol/L aqueous hydrochloric acid solution (5 mL) and the mixture was gradually warmed to room temperature with continued stirring for 2 hours. Subsequently, 25% ammonium hydroxide solution (5 mL) was added to the mixture. The organic layer was separated and the aqueous phase was extracted with ether (3 x 10 mL). The organic layers were combined, washed with saturated saline (3 x 3 mL) and concentrated under reduced pressure to about 1/3 of the original volume. the residual organic phase was extracted with 3 mol/L aqueous hydrochloric acid solution (3 x 5 mL). The separated organic phase was washed with saturated saline (5 mL), dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure, and the residue was purified by silica gel fast column chromatography to obtain the target ketone product. All aqueous phases were combined, washed with ether (5 mL) and alkalized with 25% ammonium hydroxide solution (5 mL), then back-extracted with ether (5×20 mL). The ether layers were combined, washed with saturated saline (5 mL), dried over anhydrous magnesium sulfate (MgSO4), filtered and acidified with 3 mol/L ethyl acetate hydrochloride solution (5 mL), and finally concentrated under reduced pressure to give 2,6-dimethylaniline hydrochloride.

References

[1] Chinese Chemical Letters, 2015, vol. 26, # 9, p. 1055 - 1058

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