methyl 1H-indole-4-carboxylate

Base Information

• Chemical Name: methyl 1H-indole-4-carboxylate
• CAS No.: 39830-66-5
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 29339900
• European Community (EC) Number: 622-802-5
• DSSTox Substance ID: DTXSID80960395
• Nikkaji Number: J258.257K
• Wikidata: Q27454827
• ChEMBL ID: CHEMBL3416133
• Mol file: 39830-66-5.mol

Synonyms:Methyl indole-4-carboxylate;39830-66-5;methyl 1H-indole-4-carboxylate;Indole-4-carboxylic Acid Methyl Ester;MFCD00191222;1H-indole-4-carboxylic acid methyl ester;Methyl 4-indolecarboxylate;1H-Indole-4-carboxylic acid, methyl ester;4-METHOXYCARBONYLINDOLE;4-indolecarboxylic acid methyl ester;101277-72-9;4ME;Indole-4-carboxylate;methyl indole4-carboxylate;methylindole-4-carboxylate;methyl indol-4-carboxylate;methyl 4-indole carboxylate;4-methoxycarbonyl-1h-indole;SCHEMBL45030;methyl 1H-4-indolecarboxylate;Methyl 1H-indol-4-carboxylate;methyl 1H-indole 4-carboxylate;CHEMBL3416133;BDBM93017;WEAXQUBYRSEBJD-UHFFFAOYSA-;DTXSID80960395;4b35;WEAXQUBYRSEBJD-UHFFFAOYSA-N;Methyl indole-4-carboxylate, 99%;BCP26865;CS-D1452;indole-4-carboxylic-acid-methylester;BBL013278;STK503877;AKOS000266632;AC-2619;PB32168;SS-6025;SY002750;AM20040378;FT-0618756;FT-0654755;M1773;EN300-217411;I-2510;Q-102106;Q27454827;InChI=1/C10H9NO2/c1-13-10(12)8-3-2-4-9-7(8)5-6-11-9/h2-6,11H,1H3;4-Indole-carboxylic acid methyl ester;Indole-4-carboxylic acid methyl ester

Chemical Property of methyl 1H-indole-4-carboxylate

Chemical Property:

• Appearance/Colour: off-white to green crystalline powder
• Vapor Pressure: 0.000153mmHg at 25°C
• Melting Point: 68-71 °C(lit.)
• Refractive Index: 1.639
• Boiling Point: 331.7 °C at 760 mmHg
• PKA: 15.80±0.30(Predicted)
• Flash Point: 154.4 °C
• PSA: 42.09000
• Density: 1.253 g/cm³
• LogP: 1.95450
• Storage Temp.: 0-6°C
• Solubility.: soluble in Methanol
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

99% ^*data from raw suppliers

Methyl Indole-4-Carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1=C2C=CNC2=CC=C1
• Uses: ? ;Reactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators1? ;Reactant for preparation of cytotoxic agents against multidrug-resistant cancer cells2? ;Reactant for preparation of inhibitor for β-tryptase3? ;Reactant for preparation of histamine H3 antagonists4? ;Reactant for preparation of JNK3 MAP kinase inhibitors5? ;Reactant for preparation of nucleosides6 Reactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulatorsReactant for preparation of cytotoxic agents against multidrug-resistant cancer cellsReactant for preparation of inhibitor for β-tryptaseReactant for preparation of histamine H3 antagonistsReactant for preparation of JNK3 MAP kinase inhibitorsReactant for preparation of nucleosides

Technology Process of methyl 1H-indole-4-carboxylate

There total 2 articles about methyl 1H-indole-4-carboxylate 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:

N,N-dimethylformamide dimethyl acetal (52755-02-9) + 2-methyl-3-nitrobenzic acid (1975-50-4) → methyl 1H-indole-4-carboxylate (39830-66-5) + Methyl trans-2-<β-(dimethylamino)vinyl>-3-nitrobenzoate (73816-11-2)

Guidance literature:

In N-methyl-acetamide;

Reference yield:

C8H6NO4Pol + vinyl magnesium bromide (1826-67-1) + sodium methylate (124-41-4) → methyl 1H-indole-4-carboxylate (39830-66-5) + indole-6-carboxylic acid methyl ester (50820-65-0)

Guidance literature:

C₈H₆NO₄Pol; vinyl magnesium bromide; In tetrahydrofuran; at -40 - 0 ℃; Inert atmosphere; solid phase reaction;

With ammonium chloride; In tetrahydrofuran; water; solid phase reaction;

sodium methylate; In tetrahydrofuran; methanol; at 25 ℃; for 3h; solid phase reaction;

DOI:10.3762/bjoc.8.132

Reference yield: 99.0%

methyl 1H-indole-4-carboxylate (39830-66-5) + benzyl bromide (100-39-0) → 1-benzyl-1H-indole-4-carboxylic acid methyl ester

Guidance literature:

methyl 1H-indole-4-carboxylate; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

benzyl bromide; In N,N-dimethyl-formamide; at 80 ℃; for 5h;

DOI:10.1248/cpb.47.1538

upstream raw materials:

N,N-dimethylformamide dimethyl acetal

2-methyl-3-nitrobenzic acid

vinyl magnesium bromide

sodium methylate

Downstream raw materials:

(1H-indol-4-yl)methanol

4-methoxycarbonyl-1-<(4-methylphenyl)sulfonyl>-1H-indole

1-Benzenesulfonyl-1H-indole-4-carboxylic acid methyl ester

3-Benzylsulfanyl-1H-indole-4-carboxylic acid methyl ester