5-Methoxy-3-methyl-1H-indole-2-carboxylic acid

Base Information

• Chemical Name: 5-Methoxy-3-methyl-1H-indole-2-carboxylic acid
• CAS No.: 16381-50-3
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.213
• Hs Code.: 2933990090
• European Community (EC) Number: 804-868-9
• DSSTox Substance ID: DTXSID80357246
• Wikidata: Q82137080
• Mol file: 16381-50-3.mol

Synonyms:5-Methoxy-3-methyl-1H-indole-2-carboxylic acid;16381-50-3;MFCD03848040;5-methoxy-3-methylindole-2-carboxylic acid;SCHEMBL2396662;DTXSID80357246;CPXMQDRGVOOXSQ-UHFFFAOYSA-N;BBL013293;STK504674;AKOS000558614;AS-42835;BB 0260627;CS-0447864;FT-0671270;EN300-113143;5-Methoxy-3-methyl-1H-indole-1-carboxylic acid;A882544;Z1203159535;BB_NC-0826;5-Methoxy-3-methyl-1H-indole-2-carboxylic acid, AldrichCPR

Chemical Property of 5-Methoxy-3-methyl-1H-indole-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.45E-08mmHg at 25°C
• Melting Point: 200-201 °C (decomp)
• Refractive Index: 1.657
• Boiling Point: 441.3°C at 760 mmHg
• PKA: 4.10±0.30(Predicted)
• Flash Point: 220.7°C
• PSA: 62.32000
• Density: 1.326g/cm³
• LogP: 2.18310
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 205.07389321
• Heavy Atom Count: 15
• Complexity: 256

Purity/Quality:

98%min ^*data from raw suppliers

5-Methoxy-3-methyl-1H-indole-2-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(NC2=C1C=C(C=C2)OC)C(=O)O
• Uses: 5-Methoxy-3-Methyl-1H-indole-2-carboxylic Acid is an indole derivative with antispasmodic activity. It is used in the preparation of oxazinones as potential bactericides and monoamine oxidase inhibitors.

Technology Process of 5-Methoxy-3-methyl-1H-indole-2-carboxylic acid

There total 5 articles about 5-Methoxy-3-methyl-1H-indole-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

ethyl 5-methoxy-3-methyl-1H-indole-2-carboxylate (16381-42-3) → 5-methoxy-3-methyl-1H-indole-2-carboxylic acid (16381-50-3)

Guidance literature:

With potassium hydroxide; In ethanol; for 1h; Heating;

DOI:10.1021/jo030055u

Reference yield:

4-methoxy-aniline (104-94-9) → 5-methoxy-3-methyl-1H-indole-2-carboxylic acid (16381-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aq. HCl; NaNO₂ / H₂O / 0.25 h / 0 °C

1.2: KOH / ethanol; H₂O / 15 h / 0 - 4 °C / pH 5 - 6

1.3: 74 percent / HCl / ethanol / 2 h / 78 °C

2.1: 100 percent / KOH / ethanol / 1 h / Heating

With hydrogenchloride; potassium hydroxide; sodium nitrite; In ethanol; water; 1.2: Japp-Klingmann reaction / 1.3: Fischer indole synthesis;

DOI:10.1021/jo030055u

Reference yield:

ethyl 5-methoxy-1H-indole-2-carboxylate (4792-58-9) → 5-methoxy-3-methyl-1H-indole-2-carboxylic acid (16381-50-3)

Guidance literature:

Multi-step reaction with 3 steps

1: trichlorophosphate / N,N-dimethyl-formamide / 2.5 h / 110 °C / Cooling with ice

2: triethylsilane; trifluoroacetic acid / 5 h / 20 °C

3: lithium hydroxide monohydrate / tetrahydrofuran; water / 3 h / 20 °C

With triethylsilane; lithium hydroxide monohydrate; trifluoroacetic acid; trichlorophosphate; In tetrahydrofuran; water; N,N-dimethyl-formamide; 1: |Vilsmeier-Haack Formylation;

DOI:10.1016/j.ejmech.2013.07.037

upstream raw materials:

ethyl 5-methoxy-3-methyl-1H-indole-2-carboxylate

4-methoxy-aniline

ethyl 5-methoxy-1H-indole-2-carboxylate

3-formyl-5-methoxy-indole-2-carboxylic acid ethyl ester

Downstream raw materials:

(6S,10S)-methyl 12-benzyl-9-hydroxy-2-methoxy-6,7,10,11-tetrahydro-5H-6,10-epimino-cycloocta[b]indole-8-carboxylate

2-ethoxycarbonyl-3-benzyl-9-methoxy-1,2,3,3a,4,5-hexahydrocanthin-6-one

N_b-benzyl-5-methoxy-1-methyl-D-tryptophan ethyl ester

tert-butyl 3-(Hydroxymethyl)-5-methoxy-1H-indole-1-carboxylate

Refernces

• 1、 -. "INDOLE DERIVATIVES AND THEIR USE AS THYROID RECEPTOR LIGANDS". Page/Page column 38. . Retrieved 2008/06/13.
• 2、 Zhang,Cook. "Enantiospecific synthesis of 5-methoxy-D(+)- or L(-) tryptophan". . p. 3883 - 3900. Retrieved 2007/10/03.