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Chemical Structure| 4769-96-4 Chemical Structure| 4769-96-4
Chemical Structure| 4769-96-4

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Product Citations

Product Citations

Shriver, James A. ; Kaller, Kaylie S. ; Kinsey, Ally L. ; Wang, Katelyn R. ; Sterrenberg, Summer R. ; Van Vors, Madison K. , et al.

Abstract: The spontaneous conversion of 3-indoxyl to indigo was a well-established process used to produce indigo dyes. It was recently shown that some indoles, when reacted with molybdenum hexacarbonyl and cumyl peroxide, proceed through an indoxyl intermediate to produce significant amounts of indirubin through a competing mechanism. Modulation of this system to lower temperatures allows for careful tuning, leading to selective production of indirubins in a general process. A systematic assay of indoles show that electron deficient indoles work well when substituted at the 5 and 7 positions. In contrast, 6-substituted electron rich indoles give the best results whereas halogeno indoles work well in all cases. This process shows broad functional group tolerance for generally reactive carbonyl-containing compounds such as aldehydes and carboxylic acids.

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Product Details of 6-Nitroindole

CAS No. :4769-96-4
Formula : C8H6N2O2
M.W : 162.15
SMILES Code : O=[N+](C1=CC2=C(C=C1)C=CN2)[O-]
MDL No. :MFCD00051497
InChI Key :PSWCIARYGITEOY-UHFFFAOYSA-N
Pubchem ID :78502

Safety of 6-Nitroindole

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H341
Precautionary Statements:P201-P202-P281-P308+P313-P403-P501

Application In Synthesis of 6-Nitroindole

* 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 [ 4769-96-4 ]

[ 4769-96-4 ] Synthesis Path-Downstream   1~2

  • 2
  • [ 4769-96-4 ]
  • [ 56612-14-7 ]
  • [ 873055-03-9 ]
YieldReaction ConditionsOperation in experiment
30% To a mixture of <strong>[56612-14-7][2-(tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetic acid</strong> (13.8 g, 53 mmol) and TFFH (21.0 g, 79.5 mmol) in anhydrous THF (125 mL) was added DIEA (27.7 mL, 159 mmol) at room temperature under nitrogen. The solution was stirred at room temperature for 20 min. A solution of 6-nitroindole (8.6 g, 53 mmol) in THF (75 mL) was added and the reaction mixture was heated at 60 C. for 18 h. The solvent was evaporated and the crude mixture was re-partitioned between EtOAc and water. The organic layer was separated, washed with water (×3), dried over Na2SO4 and concentrated. Diethyl ether followed by EtOAc was added. The resulting solid was collected via filtration, washed with diethyl ether and air dried to yield methyl-({methyl-[2-(6-nitro-indol-1-yl)-2-oxo-ethyl]-carbamoyl}-methyl)-carbamic acid tert-butyl ester (6.42 g, 30%). 1H NMR (400 MHz, DMSO-d6) δ 1.37 (m, 9H), 2.78 (m, 3H), 2.95 (d, J=1.5 Hz, 1H), 3.12 (d, J=2.1 Hz, 2H), 4.01 (d, J=13.8 Hz, 0.6H), 4.18 (d, J=12.0 Hz, 1.4H), 4.92 (d, J=3.4 Hz, 1.4H), 5.08 (d, J=11.4 Hz, 0.6H), 7.03 (m, 1H), 7.90 (m, 1H), 8.21 (m, 1H), 8.35 (d, J=3.8 Hz, 1H), 9.18 (m, 1H); HPLC ret. time 3.12 min, 10-99% CH3CN, 5 min run; ESI-MS 405.5 m/z (MH+).
 

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