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Chemical Structure| 5381-79-3 Chemical Structure| 5381-79-3

Structure of 1-Methyl-6-nitrobenzimidazole
CAS No.: 5381-79-3

Chemical Structure| 5381-79-3

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Product Details of [ 5381-79-3 ]

CAS No. :5381-79-3
Formula : C8H7N3O2
M.W : 177.16
SMILES Code : O=[N+](C1=CC=C2C(N(C)C=N2)=C1)[O-]
MDL No. :MFCD00962814

Safety of [ 5381-79-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 5381-79-3 ]

* 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.

  • Downstream synthetic route of [ 5381-79-3 ]

[ 5381-79-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 5381-79-3 ]
  • [ 26530-93-8 ]
YieldReaction ConditionsOperation in experiment
With palladium on activated charcoal; hydrogen; at 20℃; under 760.051 Torr; for 16h; Palladium on carbon (0.300 g, 2.82 mmol) was added to a solution of 1-methyl-6- nitro-1H-benzo[d]imidazole (1.00 g, 5.64 mmol) in methanol (10 mL). The mixture was sparged under an atmosphere of of hydrogen (1 atm) and stirred at ambient temperature for 16 hours. The mixture was sparged under nitrogen, filtered through a CELITE pad, and the solids were washed with methanol. The combined filtrates were concentrated in vacuo to provide the title compound.
  • 2
  • [ 5381-79-3 ]
  • [ 5381-78-2 ]
  • [ 10394-38-4 ]
  • [ 26530-93-8 ]
YieldReaction ConditionsOperation in experiment
45%; 40% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 2h; General procedure: Procedure B: The nitro-group containing compound was dissolved in MeOH (or a mixture of MeOH and tetrahydrofuran) and then 10percent Pd/C was added. The mixture was stirred at room temperature under hydrogen gas until the starting material had been consumed. The crude mixture was filtered through Celite, washed with methanol, and then concentrated. The product was carried on to the next step without further purification or was purified by column chromatography.
  • 3
  • [ 5381-79-3 ]
  • [ 5381-78-2 ]
  • [ 10394-38-4 ]
  • [ 26530-93-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;palladium 10% on activated carbon; In methanol; Powdered potassium hydroxide (5.1g, 92mmol) was added to a solution of 6-nitro-lH- benzoimidazole (3g, 18.4mmol) in acetone (30ml) in an ice bath and stirred for 30 min. Methyl iodide (1.7ml, 27.6mmol) was added and the reaction mixture was stirred for 3 hr at room temperature. The solvent was evaporated under reduced pressure to give a residue to which was added water and ethyl acetate. The organic layer was separated and washed with water, dried and concentrated to dryness to yield a mixture of 1- methyl-6-nitro-lH-benzoimidazole and l-methyl-5-nitro-lH-benzoimidazole (3.2g, 98percent) as oil. The mixture of isomers (3.2g, 18.07mmol) was dissolved in methanol (50ml) and hydrogenated at atmospheric pressure over 10percent Pd-C (300mg) until no further gas uptake was observed. The reaction mixture was then filtered over celite and concentrated to yield a mixture of l-methyl-lH-benzimidazol-5-yl amine and 3-methyl- 3H-benzimidazol-5-yl amine (2.53g, 95percent) as solid. The mixture was used in the next stage without purification.
 

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