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Chemical Structure| 3471-31-6 Chemical Structure| 3471-31-6
Chemical Structure| 3471-31-6

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5-Methoxyindole-3-acetic acid is a metabolite of melatonin.

Synonyms: 5-methoxy IAA; 5-MIAA; 5-Methoxyindoleacetic Acid

4.5 *For Research Use Only !

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Product Details of 5-Methoxyindole-3-acetic acid

CAS No. :3471-31-6
Formula : C11H11NO3
M.W : 205.21
SMILES Code : O=C(O)CC1=CNC2=C1C=C(OC)C=C2
Synonyms :
5-methoxy IAA; 5-MIAA; 5-Methoxyindoleacetic Acid
MDL No. :MFCD00005638
InChI Key :COCNDHOPIHDTHK-UHFFFAOYSA-N
Pubchem ID :18986

Safety of 5-Methoxyindole-3-acetic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of 5-Methoxyindole-3-acetic acid

* 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 [ 3471-31-6 ]

[ 3471-31-6 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 3471-31-6 ]
  • [ 54-16-0 ]
  • 3
  • [ 3471-31-6 ]
  • [ 57000-49-4 ]
  • 4
  • 3-ethoxycarbonylmethyl-5-methoxy-indole-2-carboxylic acid [ No CAS ]
  • [ 3471-31-6 ]
  • 5
  • [ 3471-31-6 ]
  • [ 24589-78-4 ]
  • [ 55887-55-3 ]
  • 6
  • [ 3471-31-6 ]
  • [ 1972-28-7 ]
  • [ 57000-49-4 ]
  • 7
  • [ 3471-31-6 ]
  • [ 3471-31-6 ]
  • 8
  • [ 75-89-8 ]
  • [ 356-42-3 ]
  • [ 3471-31-6 ]
  • [5-Methoxy-1-(2,2,3,3,3-pentafluoro-propionyl)-1H-indol-3-yl]-acetic acid 2,2,2-trifluoro-ethyl ester [ No CAS ]
  • 9
  • [ 422-05-9 ]
  • [ 356-42-3 ]
  • [ 3471-31-6 ]
  • [5-Methoxy-1-(2,2,3,3,3-pentafluoro-propionyl)-1H-indol-3-yl]-acetic acid 2,2,3,3,3-pentafluoro-propyl ester [ No CAS ]
  • 10
  • [ 375-01-9 ]
  • [ 356-42-3 ]
  • [ 3471-31-6 ]
  • [5-Methoxy-1-(2,2,3,3,3-pentafluoro-propionyl)-1H-indol-3-yl]-acetic acid 2,2,3,3,4,4,4-heptafluoro-butyl ester [ No CAS ]
  • 11
  • [ 356-42-3 ]
  • [ 3471-31-6 ]
  • [ 440-60-8 ]
  • [5-Methoxy-1-(2,2,3,3,3-pentafluoro-propionyl)-1H-indol-3-yl]-acetic acid pentafluorophenylmethyl ester [ No CAS ]
  • 12
  • [ 75-89-8 ]
  • [ 3471-31-6 ]
  • [ 407-25-0 ]
  • [5-Methoxy-1-(2,2,2-trifluoro-acetyl)-1H-indol-3-yl]-acetic acid 2,2,2-trifluoro-ethyl ester [ No CAS ]
  • 13
  • [ 422-05-9 ]
  • [ 3471-31-6 ]
  • [ 407-25-0 ]
  • [5-Methoxy-1-(2,2,2-trifluoro-acetyl)-1H-indol-3-yl]-acetic acid 2,2,3,3,3-pentafluoro-propyl ester [ No CAS ]
  • 14
  • [ 375-01-9 ]
  • [ 3471-31-6 ]
  • [ 407-25-0 ]
  • [5-Methoxy-1-(2,2,2-trifluoro-acetyl)-1H-indol-3-yl]-acetic acid 2,2,3,3,4,4,4-heptafluoro-butyl ester [ No CAS ]
  • 15
  • [ 3471-31-6 ]
  • [ 440-60-8 ]
  • [ 407-25-0 ]
  • [5-Methoxy-1-(2,2,2-trifluoro-acetyl)-1H-indol-3-yl]-acetic acid pentafluorophenylmethyl ester [ No CAS ]
  • 16
  • [ 3471-31-6 ]
  • [ 183591-62-0 ]
  • (5-Methoxy-1H-indol-3-yl)-acetic acid 4-(4-benzyl-piperazine-1-carbonyl)-phenyl ester [ No CAS ]
  • 17
  • [ 3471-31-6 ]
  • [ 183591-66-4 ]
  • 4-[2-(5-Methoxy-1H-indol-3-yl)-acetoxy]-benzoic acid 2-(4-isopropyl-piperazin-1-yl)-2-oxo-ethyl ester [ No CAS ]
  • 18
  • [ 3471-31-6 ]
  • [ 100-39-0 ]
  • [ 185064-27-1 ]
YieldReaction ConditionsOperation in experiment
96% In NaH; N,N-dimethyl-formamide; mineral oil; A. 5-Methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid phenylmethyl ester. A solution of 2.0 g (10 mmol) of <strong>[3471-31-6]5-methoxy-1H-indole-3-acetic acid</strong> in 100 mL of DMF was treated in portions with 1.0 g (25 mmol) of 60percent NaH/mineral oil and after 10 minutes, 3 mL of benzyl bromide added. After 22 hours, the mixture was diluted with water, extracted with EtOAc, the EtOAc solution washed with water, saturated NaCl solution and dried over Na2 SO4. After concentrating at reduced pressure, the residue was chromatographed over silica eluding with CH2 Cl2 to give 3.7 g (96percent yield) of 5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid phenylmethyl ester as an oil (structure confirmed by nmr).
  • 19
  • [ 67-56-1 ]
  • [ 3471-31-6 ]
  • [ 23304-48-5 ]
YieldReaction ConditionsOperation in experiment
85% General procedure: A reaction mixture containing the indoleacetic acid derivative (1 equivalent) and BOP-Cl (1 equivalent) in 3 mL/mmol of anhydrous CH2Cl2 is treated with triethylamine (2 equivalents) and aged at ambient temperature for 5 min. The mixture is combined with anhydrous methanol (0.14 mL/mmol) and then continuously stirred overnight at room temperature. Following dilution with dichloromethane (12 mL/mmol), the organic solution is washed with water (2x6 mL/mmol), dried over Na2SO4, and filtered. The organic filtrate is collected and concentrated in vacuo and the crude ester is purified by flash chromatography on silica gel (ethyl acetate/hexane gradient) to afford the title compound at first as viscous yellow oil, which stably crystallizes upon seeding and subsequent cold storage.#10;
85% A reaction mixture containing <strong>[3471-31-6]2-<strong>[3471-31-6](5-methoxy-1H-indol-3-yl)acetic acid</strong></strong> (0.5 g, 2.44 mmol) and BOP-CI (0.62 g, 2.44 mmol) in 7 mL of anhydrous CH2CI2 was treated with triethyl amine (0.49 g, 4.87 mmol) and allowed to stir at ambient temperature for 5 min. The mixture was then combined with anhydrous methanol (0.34 mL) and continuously stirred overnight at room temperature. Following dilution with dichloromethane (30 mL), the organic solution was washed with water (2x15 mL), dried over Na2S04, and filtered (using a commercial phase separator syringe with attached drying cartridge). The organic filtrate was collected and concentrated in vacuo and the crude ester was purified by flash chromatography on silica gel (ethyl acetate/hexane gradient) to afford the title compound as viscous yellow oil, which permanently crystallized upon storage at -20 "C (453 mg, 85percent). Ci2H 3N03, r = 219.24; 1H NMR (400 MHz, DMSO-d6) d: 3.60 (s, 3H), 3.70 (s, 2H), 3.74 (s, 3H), 6.72 (dd, J=2.4/8.8 Hz, 1 H), 6.96 (d, J=2.4 Hz, 1 H), 7.19 (d, J=2.4 Hz, 1 H), 7.23 (d, J=8.8 Hz, 1 H), 10.77 (s, 1 H); LCMS (ESI) fR: 1.95 min (>99percent, UV254), m/z: 220.1 [M+1]+.
60% With thionyl chloride; at 0 - 20℃; for 2h; A solution of 5-methoxy-3-indoleacetic acid (4) (205 mg, 1 mmol) in dry MeOH (500 mL) was cooled to 0 °C and SOCl2 (5 mmol) was added slowly. After stirring for 2 h at room temperature, the mixture was concentrated under reduced pressure, the residue taken up in EtOAc (10 mL) and subsequently washed with saturated aqueous NH4Cl (10 mL), saturated aqueous NaHCO3 (3 * 15 mL) and brine (3 * 10 mL). After drying over Na2SO4, the mixture was concentrated to dryness to give the pure methyl ester. Experimental data are in accordance with literature. 19 Yield 60percent; mp 73-75 °C.
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 2.5h;Inert atmosphere; To a suspension of 5-methoxy-3-indolylacetic acid (500 mg, 2.44 mmol) in CH2CI2 (7 mL) were added DCC (553 mg, 2.68 mmol), DMAP (30 mg, 0.244 mmol) and methanol (99 mu, 2.44 mmol). The resulting white suspension was stirred at RT under nitrogen for 2.5 h. The mixture was filtered and the filtrate concentrated to give a brown oil which was purified by flash column chromatography on silica gel (c-hexane to c-hexane/ EtOAc 8-2) to afford the desired material as a brown oil. TLC, Rf (EtOAc) = 0.82; MS (LC-MS): 220.0 [M+H]+, 242.1 [M+Na]+, 461.0 [2M+Na]+, 218.1 [M-H]-; tR (HPLC conditions f) 3.2 min.

  • 20
  • [ 3471-31-6 ]
  • [ 108-24-7 ]
  • 6-Methoxy-1-methyl-9H-pyrano[3,4-b]indol-3-one [ No CAS ]
  • 21
  • [ 3471-31-6 ]
  • [ 74-88-4 ]
  • methyl 2-(5-methoxy-1-methyl-1H-indol-3-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With potassium hydroxide; In acetone; at 0 - 20℃; for 20h; Synthesis of 2-(5-hydroxy-1-methyl-1H-indol-3-yl)acetic acid (Examples 9, 18)Step 1: To a well stirred and cooled suspension of <strong>[3471-31-6]2-<strong>[3471-31-6](5-methoxy-1H-indol-3-yl)acetic acid</strong></strong> (1.95 g, 9.51 mmol) and KOH (3.18 g, 57.07 mmol) in acetone (60 mL) at 0° C., methyl iodide (3.56 mL, 57.07 mmol) was slowly added. The reaction mixture was stirred at room temperature for 20 h and concentrated under reduced pressure. The residue obtained was diluted with ethyl acetate (60 mL), washed with water (20 mL), 1N HCl (20 mL) and brine (20 mL), dried over anhydrous Na2SO4, and concentrated. The crude compound was purified by column chromatography (100-200 mesh silica gel) using 10percent EtOAc in petroleum ether as eluent to get methyl 2-(5-methoxy-1-methyl-1H-indol-3-yl)acetate as white solid (2.10 g, 95percent yield).
95% With potassium hydroxide; In acetone; at 0 - 20℃; To a well stirred and cooled suspension of 2-(5-methoxy-1 H-indol-3-yl)acetic acid (1.95 g, 9.51 mmol) and KOH (3.18 g, 57.07 mmol) in acetone (60 mL) at 0°C, methyl iodide (3.56 mL, 57.07 mmol) was slowly added. The reaction mixture was stirred at room temperature for 20 h and concentrated under reduced pressure. The residue obtained was diluted with ethyl acetate (60 mL), washed with water (20 mL), 1 N HCI (20 mL) and brine (20 mL), dried over anhydrous Na2S04, and concentrated. The crude compound was purified by column chromatography (100-200 mesh silica gel) using 10percent EtOAc in petroleum ether as eluent to get methyl 2-(5-methoxy-1-methyl-1 H-indol-3-yl)acetate as white solid (2.10 g, 95percent yield).
With potassium hydroxide; In water; acetone; Stage 1 Methyl 2-(5-methoxy-1-methylindol-3-yl)acetate 8.2 g (0.1464 mol) of powdered potassium hydroxide and 13.8 g (0.0972 mol) of methyl iodide are added to a solution of 10 g (0.0487 mol) of (5-methoxyindol-3-yl)acetic acid in 120 ml of acetone. After stirring for 4 hours at room temperature, 13.8 g of methyl iodide are again added and then, 12 hours later, 13.8 g of methyl iodide and 8 g of potassium hydroxide are again added. The whole reaction mixture is then concentrated, the residue is taken up in water and extracted with dichloromethane, the organic phase is washed with a 1N sodium hydroxide solution and then with 1N hydrochloric acid and separated by settling, the organic solution is dried over magnesium sulfate and the solvent evaporated under vacuum.
  • 22
  • [ 504-24-5 ]
  • [ 3471-31-6 ]
  • 2-(5-methoxy-1<i>H</i>-indol-3-yl)-<i>N</i>-pyridin-4-yl-acetamide [ No CAS ]
  • 23
  • [ 57000-49-4 ]
  • [ 3471-31-6 ]
YieldReaction ConditionsOperation in experiment
80% General procedure: It will be apparent to those skilled in the art that various modifications that may be derived or recited directly from the disclosure and common sense of the present patent, as well as by the prior art, are well known in the art, Such as changing the substituents on the indole ring or changing the position of the substituents, the solvent of the reaction solvent not indicated in the specification, the change in the reaction temperature, the time, the change of the acid and the base, and the like Non-substantive changes, the same can be applied, can achieve the patent description of the function and effect, no longer one by one for example, are within the scope of this patent
  • 26
  • [ 3471-31-6 ]
  • [ 213008-46-9 ]
  • 2-(5-methoxy-1<i>H</i>-indol-3-yl)-<i>N</i>-[3-(4-{3-[2-(5-methoxy-1<i>H</i>-indol-3-yl)-acetylamino]-propylamino}-butylamino)-propyl]-acetamide [ No CAS ]
  • 27
  • [ 3471-31-6 ]
  • (S)-3-((Z)-3-Methoxy-allyl)-1,2,3,6-tetrahydro-pyridine [ No CAS ]
  • [ 329771-40-6 ]
  • 28
  • [ 3471-31-6 ]
  • [ 313983-96-9 ]
  • 2-(5-methoxy-1<i>H</i>-indol-3-yl)-<i>N</i>-(3-{3-[2-(5-methoxy-1<i>H</i>-indol-3-yl)-acetylamino]-propylamino}-propyl)-acetamide [ No CAS ]
  • 29
  • [ 3471-31-6 ]
  • [ 313983-98-1 ]
  • 2-(5-methoxy-1<i>H</i>-indol-3-yl)-<i>N</i>-(3-{4-[2-(5-methoxy-1<i>H</i>-indol-3-yl)-acetylamino]-butylamino}-propyl)-acetamide [ No CAS ]
  • 30
  • [ 3471-31-6 ]
  • [ 60-12-8 ]
  • (5-methoxy-1<i>H</i>-indol-3-yl)-acetic acid phenethyl ester [ No CAS ]
  • 31
  • [ 3471-31-6 ]
  • [ 64-04-0 ]
  • 2-(5-methoxy-1<i>H</i>-indol-3-yl)-<i>N</i>-phenethyl-acetamide [ No CAS ]
  • 32
  • [ 3471-31-6 ]
  • [ 104-83-6 ]
  • [ 3446-79-5 ]
  • 33
  • [ 3471-31-6 ]
  • [ 98930-01-9 ]
  • bis-Fmoc protected spermidine attached to an aminomethyl polystyrene resin via an acid cleavable Wang type urethane linker [ No CAS ]
  • N1,N8-bis([2-(5-methoxy-1H-indol-2-yl)-acetyl]arginyl(4-methoxy-2,3,6-trimethylbenzenesulfonyl))spermidine [ No CAS ]
  • 34
  • [ 3471-31-6 ]
  • [ 119831-72-0 ]
  • bis-Fmoc protected spermidine attached to an aminomethyl polystyrene resin via an acid cleavable Wang type urethane linker [ No CAS ]
  • C69H97N13O12S2 [ No CAS ]
  • 35
  • [ 3471-31-6 ]
  • [ 139090-50-9 ]
  • bis-Fmoc protected spermidine attached to an aminomethyl polystyrene resin via an acid cleavable Wang type urethane linker [ No CAS ]
  • C55H73N13O10S2 [ No CAS ]
 

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