39830-66-5

Basic information

• Product Name: Methyl indole-4-carboxylate
• Synonyms: METHYL-1H-INDOLE-4-CARBOXYLATE;Methyl indole-4-carboxylate ,99%;methylindole-4-carboxylate , (4-indole-carboxylic acid methyl ester);Methyl indole-4-carboxylate ,98%;Methyl indole-4-carboxyla...;4-(Methoxycarbonyl)-1H-indole;4-Methoxycarbonylindole;RARECHEM AH BS 0113
• CAS NO: 39830-66-5
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• EINECS: -0
• Product Categories: Indoles and derivatives;pharmacetical;Indole;Indoles;Simple Indoles;Building Blocks;Heterocyclic Building Blocks;Building Blocks;C10;Chemical Synthesis;Heterocyclic Building Blocks;blocks;Carboxes;IndolesOxindoles;Acids and Derivatives;Heterocycles
• Mol File: 39830-66-5.mol

Chemical Properties

• Melting Point: 68-71 °C(lit.)
• Boiling Point: 306.47°C (rough estimate)
• Flash Point: 154.4 °C
• Appearance: Off-white to green/Crystalline Powder
• Density: 1.1999 (rough estimate)
• Vapor Pressure: 0.000153mmHg at 25°C
• Refractive Index: 1.5060 (estimate)
• Storage Temp.: 0-6°C
• Solubility: soluble in Methanol
• PKA: 15.80±0.30(Predicted)
• BRN: 141826
• CAS DataBase Reference: Methyl indole-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl indole-4-carboxylate(39830-66-5)
• EPA Substance Registry System: Methyl indole-4-carboxylate(39830-66-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 39830-66-5(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
Methyl indole-4-carboxylate is used as a reactant for the preparation of tryptophan dioxygenase inhibitors, specifically pyridyl-ethenyl-indoles, which serve as potential anticancer immunomodulators.
2. Used in Cancer Treatment:
Methyl indole-4-carboxylate is used as a reactant for the preparation of cytotoxic agents against multidrug-resistant cancer cells, aiding in the development of novel therapeutic strategies to combat drug resistance in cancer treatment.
3. Used in Enzyme Inhibition:
Methyl indole-4-carboxylate is used as a reactant for the preparation of inhibitors for β-tryptase, an enzyme involved in various physiological processes and diseases.
4. Used in Allergy and Inflammation Treatment:
Methyl indole-4-carboxylate is used as a reactant for the preparation of histamine H3 antagonists, which have potential applications in the treatment of allergies and inflammation.
5. Used in Neurodegenerative Disease Research:
Methyl indole-4-carboxylate is used as a reactant for the preparation of JNK3 MAP kinase inhibitors, which may have implications in the study and treatment of neurodegenerative diseases.
6. Used in Nucleoside Synthesis:
Methyl indole-4-carboxylate is used as a reactant for the preparation of nucleosides, which are essential components of nucleic acids and have applications in genetic research and the development of antiviral drugs.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 26, p. 1405, 1989 DOI: 10.1002/jhet.5570260533Chemical and Pharmaceutical Bulletin, 29, p. 249, 1981 DOI: 10.1248/cpb.29.249

InChI:InChI=1/C10H9NO2/c1-13-10(12)8-3-2-4-9-7(8)5-6-11-9/h2-6,11H,1H3

Upstream product

• 52755-02-9 N,N-dimethylformamide dimethyl acetal 
• 1975-50-4 2-methyl-3-nitrobenzic acid 
• 1826-67-1 vinyl magnesium bromide 
• 124-41-4 sodium methylate 

Downstream Products

• 1074-85-7 (1H-indol-4-yl)methanol 
• 31271-85-9 4-methoxycarbonyl-1-<(4-methylphenyl)sulfonyl>-1H-indole 
• 146073-02-1 1-Benzenesulfonyl-1H-indole-4-carboxylic acid methyl ester 
• 188656-65-7 3-Benzylsulfanyl-1H-indole-4-carboxylic acid methyl ester 
• 183283-78-5 3-[(trans-1-(N-carbobenzyloxy)aminomethylcyclohex-4-yl)carbonyl]indole-4-carboxylic acid methyl ester 
• 200418-12-8 3-(4-Chloromethyl-benzoyl)-1H-indole-4-carboxylic acid methyl ester 
• 175675-85-1 3-p-Tolylsulfanyl-1H-indole-4-carboxylic acid methyl ester 
• 206767-65-9 methyl 1-(4-fluorophenyl)-1H-indole-4-carboxylate 
• 220499-11-6 1-(tert-butyl) methyl 1H-1,4-indoledicarboxylate 
• 1444-12-8 1-methyl-1H-indole-4-carboxylic acid methyl ester 
• 53462-88-7 3-Formylindole-4-carboxylic acid methyl ester 
• 887922-92-1 indole-4-isocyanate 
• 90924-06-4 1-methyl-1H-indole-4-carboxylic acid 
• 1074-86-8 4-formyl indole 

Relevant articles and documents

Synthesis of diverse indole libraries on polystyrene resin - Scope and limitations of an organometallic reaction on solid supports

The synthesis of diverse substituted indole structures on solid supports is described. The immobilization of nitrobenzoic acid onto Merrifield resin and the subsequent treatment with alkenyl Grignard reagents delivered indole carboxylates bound to solid s

Processes for preparing 4-substituted indoles

A new chemical sequence for preparing indoles is disclosed whose key reactions are reaction of a o-nitrotoluene with tris(dimethylamino)methane to give a β-dimethylamino-o-nitrostyrene which is converted into a semicarbazone and cyclized.