| Identification | More | [Name]
Ethyl 5-chloro-2-indolecarboxylate | [CAS]
4792-67-0 | [Synonyms]
2-CARBETHOXY-5-CHLOROINDOLE
2-(ethoxycarbonyl)-5-chloro-indole
5-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER
5-CHLORO-2-INDOLECARBOXYLIC ACID ETHYL ESTER
5-CHLOROINDOLE-2-CARBOXYLIC ACID ETHYL ESTER
5-CHLORO-INDOLE-2-ETHYL FORMATE
ETHYL 5-CHLORO-1H-INDOLE-2-CARBOXYLATE
ETHYL 5-CHLORO-2-INDOLECARBOXYLATE
ETHYL 5-CHLOROINDOLE-2-CARBOXYLATE
TIMTEC-BB SBB003329
5-CHLORO-2-INDOLECARBOXYLIC
5-CHLOROINDOLE-2-CARBOXYLIC ACID ETHYL ESTE
5-Cl-ICA-OEt
ethyl 4-chloro-2-indolecarboxylate
1H-Indole-2-carboxylic acid, 5-chloro-, ethyl ester
Ethyl 5-chloro-2-indolecarboxylate ,97% | [EINECS(EC#)]
225-345-6 | [Molecular Formula]
C11H10ClNO2 | [MDL Number]
MFCD00005610 | [Molecular Weight]
223.66 | [MOL File]
4792-67-0.mol |
| Chemical Properties | Back Directory | [Appearance]
yellowish to light brown crystalline powder | [Melting point ]
166-168 °C (lit.) | [Boiling point ]
375.0±22.0 °C(Predicted) | [density ]
1.2405 (rough estimate) | [refractive index ]
1.5500 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
Powder or Crystals | [pka]
14.10±0.30(Predicted) | [color ]
Yellow to orange to tan or light brown | [Detection Methods]
HPLC,NMR | [BRN ]
170255 | [InChI]
InChI=1S/C11H10ClNO2/c1-2-15-11(14)10-6-7-5-8(12)3-4-9(7)13-10/h3-6,13H,2H2,1H3 | [InChIKey]
LWKIFKYHCJAIAB-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C(Cl)C=C2)C=C1C(OCC)=O | [CAS DataBase Reference]
4792-67-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
yellowish to light brown crystalline powder | [Uses]
Ethyl 5-chloro-2-indolecarboxylate was used in the synthesis of anti-allergic agents. | [Uses]
5-Chloroindole-2-carboxylic acid ethyl ester is a used in the synthetic preparation of a potent anticonvulsant Ethyl 4-methylamino-5,7-dichloro-2-quinolinecarboxylate. | [Synthesis]
General procedure for the synthesis of ethyl 5-chloroindole-2-carboxylate from ethyl 2-[(4-chlorophenyl)hydrazinylidene]propionate: 500 g of polyphosphoric acid was mixed with 250 g of phosphoric acid and heated to 70 °C under stirring. 70 g of raw material 4-chlorophenylhydrazine pyruvic acid phenylhydrazone was added in batches, and the reaction temperature was controlled in the range of 70-90 °C. After 1 hour of reaction, it was confirmed that the feedstock was completely consumed. The reaction temperature was continued to be maintained for 40 minutes to ensure complete reaction. After completion of the reaction, the reaction mixture was poured into 1500 g of ice-water mixture and cooled to room temperature. The precipitate was collected by filtration and dried to give a light yellow solid product. Upon further drying, 58 g of ethyl 5-chloroindole-2-carboxylate was obtained in 90% yield. | [References]
[1] Patent: CN104402795, 2017, B. Location in patent: Paragraph 0045; 0047
[2] Journal of the Chemical Society, 1955, p. 3499,3502
[3] Journal of Medicinal Chemistry, 1988, vol. 31, # 5, p. 944 - 948
[4] Archiv der Pharmazie, 2008, vol. 341, # 5, p. 294 - 300
[5] Tetrahedron, 2016, vol. 72, # 22, p. 3014 - 3021 |
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