| Identification | More | [Name]
2,6-DIMETHOXYBENZONITRILE | [CAS]
16932-49-3 | [Synonyms]
2,6-DIMETHOXYBENZONITRILE
AKOS 227-44
2,6-dimethoxy-benzonitril
Benzonitrile, 2,6-dimethoxy- | [EINECS(EC#)]
241-000-2 | [Molecular Formula]
C9H9NO2 | [MDL Number]
MFCD00001788 | [Molecular Weight]
163.17 | [MOL File]
16932-49-3.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [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 Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [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. |
| Hazard Information | Back Directory | [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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