| Identification | More | [Name]
2,5-DIMETHOXYBENZONITRILE | [CAS]
5312-97-0 | [Synonyms]
2,5-DIMETHOXYBENZONITRILE
2-cyanohydroquinone dimethyl ether | [EINECS(EC#)]
226-169-2 | [Molecular Formula]
C9H9NO2 | [MDL Number]
MFCD00016375 | [Molecular Weight]
163.17 | [MOL File]
5312-97-0.mol |
| Chemical Properties | Back Directory | [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 | [InChI]
1S/C9H9NO2/c1-11-8-3-4-9(12-2)7(5-8)6-10/h3-5H,1-2H3 | [InChIKey]
HWAMEJIMXIXLIH-UHFFFAOYSA-N | [SMILES]
COc1ccc(OC)c(c1)C#N | [CAS DataBase Reference]
5312-97-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
3276 | [WGK Germany ]
3
| [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29269090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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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