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1,4-Dimethoxybenzene is an endogenous metabolite.

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Product Details of 1,4-Dimethoxybenzene

CAS No. :150-78-7
Formula : C8H10O2
M.W : 138.16
SMILES Code : COC1=CC=C(OC)C=C1
MDL No. :MFCD00008401
InChI Key :OHBQPCCCRFSCAX-UHFFFAOYSA-N
Pubchem ID :9016

Safety of 1,4-Dimethoxybenzene

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 1,4-Dimethoxybenzene

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 150-78-7 ]
  • Downstream synthetic route of [ 150-78-7 ]

[ 150-78-7 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 150-78-7 ]
  • [ 53581-81-0 ]
References: [1] Journal of Medicinal Chemistry, 1975, vol. 18, # 12, p. 1201 - 1204.
  • 2
  • [ 68-12-2 ]
  • [ 150-78-7 ]
  • [ 5312-97-0 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2 h;
Stage #2: at 0℃; for 2 h;
Stage #3: With ammonia; iodine In tetrahydrofuran; hexane; water at 0 - 20℃; for 2 h;
General procedure: n-Butyllithium (1.67 M solution in hexane, 2.9 mL, 4.8 mmol) was added dropwise into a solution of 1,3-dimethoxybenzene (0.55 g, 4.0 mmol) in THF (5 mL) at 0 °C and the mixture was stirred for 2 h at the same temperature. Then, DMF (0.34 mL, 4.4 mmol) was added to the mixture and the obtained mixture was stirred at 0 °C. After 2 h at the same temperature, aq NH3 (8 mL, 120 mmol) and I2 (1.12 g, 4.4 mmol) were added and stirred for 2 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (15 mL) and was extracted with Et2O (3.x.20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide 2,6-dimethoxybenzonitrile in over 80percent purity. The product was purified by a short column chromatography on silica gel (Hexane/EtOAc=3:1) to give pure 2,6-dimethoxybenzonitrile in 91percent yield as a colorless solid.
References: [1] Synlett, 2010, # 10, p. 1562 - 1566.
[2] Tetrahedron, 2011, vol. 67, # 5, p. 958 - 964.
  • 3
  • [ 93-61-8 ]
  • [ 150-78-7 ]
  • [ 5312-97-0 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: at 0℃; for 0.5 h;
Stage #2: at 100℃; for 10 h;
Stage #3: With ammonia; iodine In tetrahydrofuran; water; N,N-dimethyl-formamide at 20℃; for 3 h;
General procedure: To an ice cooled solution of N-methylformanilide (2.2 mmol) was added dropwise diphosphoryl chloride (2.2 mmol). The solution was stirred for 30 min at 0 °C, and then 1,2-dimethoxybenzene (276.3 mg, 2 mmol) in DMF (1.0 mL) was added dropwise. After being stirred for 10 h at 100 °C, I2 (1015.2 mg, 4 mmol), aq NH3 (4 mL, 28-30percent) and THF (1 mL) were added to the reaction mixture. The obtained mixture was stirred for 3 h at rt. After the reaction, the mixture was poured into aq satd Na2SO3 solution and extracted with CHCl3 (3.x.20 mL). The organic layer was dried over Na2SO4, filtered, and evaporated. The product was purified by flash short column chromatography (Hexane:AcOEt=3:1) to afford 3,4-dimethoxybenzonitrile as a white solid in 92percent yield.
References: [1] Tetrahedron, 2012, vol. 68, # 24, p. 4588 - 4595.
  • 4
  • [ 150-78-7 ]
  • [ 5312-97-0 ]
References: [1] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 7, p. 866 - 872.
[2] Justus Liebigs Annalen der Chemie, 1906, vol. 344, p. 46[3] Chemische Berichte, 1905, vol. 38, p. 796.
  • 5
  • [ 506-68-3 ]
  • [ 150-78-7 ]
  • [ 5312-97-0 ]
References: [1] Helvetica Chimica Acta, 1920, vol. 3, p. 266.
  • 6
  • [ 143-33-9 ]
  • [ 150-78-7 ]
  • [ 5312-97-0 ]
  • [ 874-90-8 ]
References: [1] Bulletin de la Societe Chimique de France, 1989, # 2, p. 156 - 167.
 

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