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Chemical Structure| 10328-92-4 Chemical Structure| 10328-92-4
Chemical Structure| 10328-92-4

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N-Methylisatoic Anhydride is a selective 2'-OH acylating agent for RNA, commonly used to resolve secondary RNA structures using SHAPE technology.

Synonyms: NMIA

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Product Details of N-Methylisatoic Anhydride

CAS No. :10328-92-4
Formula : C9H7NO3
M.W : 177.16
SMILES Code : O=C(N(C)C1=CC=CC=C12)OC2=O
Synonyms :
NMIA
MDL No. :MFCD00006815
InChI Key :KJMRWDHBVCNLTQ-UHFFFAOYSA-N
Pubchem ID :25160

Safety of N-Methylisatoic Anhydride

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

Application In Synthesis of N-Methylisatoic Anhydride

* 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 [ 10328-92-4 ]

[ 10328-92-4 ] Synthesis Path-Downstream   1~10

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  • [ 6519-67-1 ]
  • [ 114262-67-8 ]
  • 4
  • [ 10328-92-4 ]
  • [ 200283-08-5 ]
  • N,N'-bis(tert-butoxycarbonyl)-2-[(2-aminoethyl)amino]ethyl-2-(methylamino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With potassium carbonate; In acetonitrile; at 20℃; for 48h; General procedure: The corresponding Boc-protected aminoalcohol was dissolved in dry acetonitrile.N-methylisatoic anhydride and K2CO3 were added to the solution. The mixture was stirredfor 48 h at room temperature. The solvent then was removed by evaporation and the crudeproduct was purified by centrifugally accelerated, radial, thin-layer chromatography. Theeluent was changed from n-hexane to n-hexane/acetone to acetone. The fractions whichcontained the product (TLC) were combined and the solvent was removed by evaporation. 3a: For the synthesis of 3a, the following was used: 2a (2.94 g, 9.7 mmol), CH3CN (100 mL),N-methylisatoic anhydride (2.60 g, 14.7 mmol), K2CO3 (6.9 g, 50 mmol). Yield: 1.26 g (31%).White powder. 1H NMR (200 MHz, CDCl3), delta (ppm): 1.40 (s, 18H, 6CH3), 2.88 (s, 3H, CH3), 3.27(br, 2H, CH2), 3.38 (br, 2H, CH2), 3.55 (br, 2H, CH2), 4.32 (t, 3J(H/H) = 5.43 Hz, 2H, CH2), 6.54 (ddd,J(H/H) = 8.1, 7.2, 1.0 Hz, 1H, CArH), 6.63 (d, 3J(H/H) = 8.5 Hz, 1H, CArH), 7.35 (ddd, J(H/H) = 8.6,7.1, 1.7 Hz, 1H, CArH), 7.85 (dd, J(H/H) = 8.0, 1.6 Hz, 1H, CArH). 13C NMR (200 MHz, CDCl3), delta(ppm): 28.51 (s, CH3), 28.57 (s, CH3), 29.7 (s, CH3), 39.7 (s, CH2), 46.7 (s, CH2), 62.4 (s, CH2), 80.5(s, OC(CH3)3), 109.8 (s, CipsoCOO), 111.0 (s, CAr), 114.6 (s, CAr), 131.8 (s, CAr), 135.0 (s, CAr), 152.3(s, CipsoN), 156.1 (s, N(CO)O), 168.5 (s, (CO)O).
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  • [ 604-50-2 ]
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  • [ 26260-02-6 ]
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  • 7
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  • [ 81290-20-2 ]
  • [ 202270-41-5 ]
  • [ 168704-83-4 ]
YieldReaction ConditionsOperation in experiment
87%; 2% With potassium fluoride; tetrabutylammomium bromide; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere; General procedure: To a solution of the corresponding 1-alkyl-2H-3,1-benzoxazine-2,4(1H)-dione (N-alkylisatoic anhydride) 1a-d (10 mmol), KF (174 mg, 3 mmol) and TBAB (967 mg, 3 mmol) in dry DMF (20 ml) was added trimethyl(trifluoromethyl)silane (1.85 g, 13 mmol) dropwise at 0 8C under argon. After completion of addition, the reaction mixture was allowed to warm to rt and stirred for 5 h. The reaction was quenched with 5% aq HCl solution (10 ml) at 0 8C, allowed to warm to rt, and stirred for 0.5 h. To the reaction mixture was added 10% aq Na2CO3 solution (50 ml) with vigorous stirring, and stirring was continued for 1 h at rt. The resulting emulsion was extracted with hexanes (60 ml 3). The organic layer was separated, washed with brine (30 ml 2), dried over anhydrous MgSO4, and concentrated under reduced pressure.
  • 8
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  • [ 81290-20-2 ]
  • [ 202270-41-5 ]
YieldReaction ConditionsOperation in experiment
61% With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20℃; for 20.0h;Inert atmosphere; To a solution of 1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione 1a (0.61 g, 3.45 mmol) and trimethyl(trifluoromethyl)silane (638 mg, 4.49 mmol) in dry THF (15 ml) was added TBAF (1M in THF; 0.52 ml, 0.52 mmol) dropwise at 0 8C under argon. After completion of addition, the reaction mixture was allowed to warm to rt and stirred for 24 h. The reaction was quenched with 5% aq HCl solution (10 ml) at 0 8C, allowed to warm to rt, and stirred 0.5 h.To the reaction mixture was added 10% aq Na2CO3 solution (50 ml) under vigorous stirring, and stirring was continued for 1 h at rt. The resulting solution was extracted with hexanes (60 ml 3). The organic layer was washed with brine (30 ml 2), dried over anhydrous MgSO4, and concentrated under reduced pressure
  • 9
  • [ 2899-28-7 ]
  • [ 10328-92-4 ]
  • (S)-3-(1H-indol-3-yl)-2-(2-(methylamino)benzoylamino)propionic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With pyridine; sodium hydrogencarbonate; at 20℃; for 12h; L-Tryptophan ethyl ester hydrochloride (1 g, 7 mmol) was dissolved in pyridine solution (30 mL). Add N-methyl isatoic anhydride (1.3 g, 7.3 mmol), the reaction was carried out at room temperature for 12 hours. After the reaction, the reaction solution was evaporated to dryness. The residue was purified by silica gel column chromatography ( petroleum ether: ethyl acetate = 4:1). A yellow solid 710 mg was obtained in a yield of 52%.
  • 10
  • [ 141871-02-5 ]
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YieldReaction ConditionsOperation in experiment
General procedure: To a solution of anthranilic acid (0.5g, 3.64mmol) in acetonitrile (10mL) were added TEA (0.73g, 7.28mmol), Boc anhydride (0.95g, 4.37mmol), and DMAP (0.044g, 0.36mmol). The mixture was stirred at rt for 2.0 h. CMPI (1.1g, 4.36mmol) was added in one lot to the reaction mixture. The reaction mixture was stirred at rt for 10 min. 1N HCl (20mL) was added to the reaction and the mixture was extracted two times with EtOAc. The combined organic layers were washed with brine, dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting solid was crystallized in DCM and MeOH to afford 0.56g (95%) of 1H-benzo[d][1,3]oxazine-2,4-dione as an off white solid. 1H NMR (400MHz, DMSO) δ 7.14-7.16 (d, J=8Hz, 1H), 7.23-7.27 (t, J=16Hz,1H), 7.72-7.74 (t, J=8Hz, 1H), 7.90-7.92 (d, J=8Hz,1H), 11.72 (s, 1H). 13C NMR (100MHz, DMSO-d6) δ 110.6, 115.7, 123.9, 129.3, 137.3, 141.8, 147.5, 160.3. IR (thin film) 3461, 3173, 2937, 1984, 1753, 1604, 1486, 1358, 1258, 1138, 1009, 765, 673, 492. ES-MS (m/z): 161.8 (M+-H). MP (C): 236.
 

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