| Identification | More | [Name]
Methyl indole-4-carboxylate | [CAS]
39830-66-5 | [Synonyms]
1H-INDOLE-4-CARBOXYLIC ACID METHYL ESTER
4-INDOLE-CARBOXYLIC ACID METHYL ESTER
INDOLE-4-CARBOXYLIC ACID METHYL ESTER
METHYL 4-INDOLECARBOXYLATE
METHYL-(INDOL-4-CARBOXYLATE)
METHYL INDOLE-4-CARBOXYLATE
RARECHEM AH BS 0113
INDOLE-4-CARBOXYLIC
METHYL-1H-INDOLE-4-CARBOXYLATE
Methyl indole-4-carboxylate ,99%
methylindole-4-carboxylate , (4-indole-carboxylic acid methyl ester) | [EINECS(EC#)]
622-802-5 | [Molecular Formula]
C10H9NO2 | [MDL Number]
MFCD00191222 | [Molecular Weight]
175.18 | [MOL File]
39830-66-5.mol |
| Questions And Answer | Back Directory | [Synthesis]
Under stirring at room temperature, concentrated sulfuric acid (0.5 mL) was slowly added to a methanol (10 mL) solution of indolecarboxylic acid. The resulting mixture was stirred at 80°C for 2-3 hours. The reaction progress was monitored by TLC. After the starting materials had completely reacted, a large amount of ice water was slowly added to quench the reaction. The mixture was neutralized with a saturated sodium carbonate solution and extracted three times with ethyl acetate. The combined ethyl acetate solutions were dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under vacuum and the residue was subjected to rapid chromatography (petroleum ether/AcOEt) to obtain the target product, Methyl indole-4-carboxylate. 
Figure: Synthetic route of Methyl indole-4-carboxylate |
| Chemical Properties | Back Directory | [Appearance]
off-white to green crystalline powder | [Melting point ]
68-71 °C(lit.)
| [Boiling point ]
306.47°C (rough estimate) | [density ]
1.1999 (rough estimate) | [refractive index ]
1.5060 (estimate) | [storage temp. ]
0-6°C | [solubility ]
soluble in Methanol | [form ]
Crystalline Powder | [pka]
15.80±0.30(Predicted) | [color ]
Off-white to green | [Detection Methods]
GC,NMR | [BRN ]
141826 | [InChI]
InChI=1S/C10H9NO2/c1-13-10(12)8-3-2-4-9-7(8)5-6-11-9/h2-6,11H,1H3 | [InChIKey]
WEAXQUBYRSEBJD-UHFFFAOYSA-N | [SMILES]
N1C2=C(C(C(OC)=O)=CC=C2)C=C1 | [CAS DataBase Reference]
39830-66-5(CAS DataBase Reference) | [Storage Precautions]
Light sensitive |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [REACH Registrations]
Active | [HazardClass ]
IRRITANT | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
off-white to green crystalline powder | [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 | [Synthesis Reference(s)]
Journal of Heterocyclic Chemistry, 26, p. 1405, 1989 DOI: 10.1002/jhet.5570260533
Chemical and Pharmaceutical Bulletin, 29, p. 249, 1981 DOI: 10.1248/cpb.29.249 | [General Description]
The IR and UV spectra of methyl indole-4-carboxylate was studied. |
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