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Chemical Structure| 139481-38-2 Chemical Structure| 139481-38-2

Structure of 139481-38-2

Chemical Structure| 139481-38-2

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Product Details of [ 139481-38-2 ]

CAS No. :139481-38-2
Formula : C27H25N3O6
M.W : 487.50
SMILES Code : O=C(OC)C1=CC=CC([N+]([O-])=O)=C1N(CC2=CC=C(C3=CC=CC=C3C#N)C=C2)C(OC(C)(C)C)=O

Safety of [ 139481-38-2 ]

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 [ 139481-38-2 ]

* 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 [ 139481-38-2 ]

[ 139481-38-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 57113-90-3 ]
  • [ 114772-54-2 ]
  • [ 139481-38-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetonitrile; at 80 - 85℃; for 5h;Heating / reflux; Industry scale; methyl 2-t-butoxycarbonylamino-3-nitrobenzoate [BAN] obtained in Reference Example 3 (354 kg), a solution of 4-(2-bromomethylphenyl)benzonitrile [BMB] in acetonitrile obtained in Reference Example 4 (1), and anhydrous potassium carbonate (475 kg) were added to acetonitrile (1600 kg), and the mixture was heated (80 to 85 C) under reflux for about 5 hours.. The reaction solution was cooled, and the insoluble were separated and washed with acetonitrile (320 kg).. The filtrated washing was concentrated under reduced pressure to give concentrate of methyl 2-[N-t-butoxycarbonyl-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [BBN].
  • 2
  • [ 139481-38-2 ]
  • [ 139481-44-0 ]
  • 3
  • [ 209911-63-7 ]
  • [ 57113-90-3 ]
  • [ 139481-38-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetonitrile; at 82℃; for 5h; 23 g of 2-(4-methylphenyl)benzonitrile [MPB], 22g of N-bromosuccinic acid imide [NBS] and 47 mg of 2,2'-azobis(2,4-dimethylvaleronitrile) were suspended in 44 ml of dichoromethane, and the reaction was allowed to proceed at 45 to 50C for 5 hours under stirring. 46 ml of water was added, and the layers were separated to obtain organic layer (The same procedure was carried out three times totally).. The organic layer was concentrated, and 50 ml of acetonitrile was added.. The solution was concentrated again, and 50 ml of acetonitrile was added thereto to obtain 116 g of a solution of 2-(4-bromomethylphenyl)benzonitrile [BMB] in acetonitrile (yield calculated from a quantitated value of 2-(4-bromomethylphenyl)benzonitrile: 84 %). 30.1 g of methyl 2-tert-butoxycarbonylamino-3-nitrobenzoate [BAN], 40.8 g of potassium carbonate and 160 ml of acetonitrile were added to the acetonitrile solution in which unreacted 2-(4-methylphenyl)benzonitrile [MPB] and <strong>[209911-63-7]2-(4,4-dibromomethylphenyl)benzonitrile</strong> as an analogue of BMB were contaminated, and the reaction was allowed to proceed at about 82 C for about 5 hours under stirring.. After cooling to room temperature, the precipitated crystals were filtered off, and the filtrate was concentrated to give methyl 2-[N-t-butoxycarbonyl-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [BBN].. The concentrated material was dissolved in 190 g of methanol, and 106 g of concentrated hydrochloric acid was added dropwise thereto.. The resulting solution was heated to a reflux temperature over 2 hours, and stirred for 2 hours under reflux, whereby, the reaction was allowed to proceed.. The reaction solution was cooled, and precipitated crystals were collected by filteration and dried to give 35.1 g of methyl 2-[N-(2'-cyanobiphenyl-4-yl)methylamino]-3-nitrobenzoate [MBN] (yield relative to 2-(4-methylphenyl)benzonitrile [MPB] was 76.1 %).
 

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