ethyl 4,6-dichloro-3-formyl-1H-indole-2-carboxylate

Base Information

• Chemical Name: ethyl 4,6-dichloro-3-formyl-1H-indole-2-carboxylate
• CAS No.: 153435-96-2
• Molecular Formula: C12H9 Cl2 N O3
• Molecular Weight: 286.1108
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40383501
• Nikkaji Number: J1.492.061G
• Wikidata: Q72474216
• Mol file: 153435-96-2.mol

Synonyms:ethyl 4,6-dichloro-3-formyl-1H-indole-2-carboxylate;153435-96-2;4,6-dichloro-3-formyl-1H-indole-2-carboxylic acid ethyl ester;SCHEMBL5397544;DTXSID40383501;NFILHPVBZNKVNP-UHFFFAOYSA-N;1H-Indole-2-carboxylic acid, 4,6-dichloro-3-formyl-, ethyl ester;MFCD02090087;AKOS015911358;AB10686;AS-68806;3-formyl-2-carboethoxy-4,6-dichloroindole;BB 0249873;CS-0314257;FT-0626058;ethyl 3-formyl-4,6-dichloroindole-2-carboxylate;A809428;ethyl-3-formyl-4,6-dichloro-indole-2-carboxylate;3-Formyl-4,6-dichloro-1H-indole-2-carboxylic acid ethyl ester;4,6-DICHLORO-2-(ETHOXYCARBONYL)-3-FORMYL-1H-INDOLE;4,6-Dichloro-3-formyl-1H-indole-2-carboxylic acid ethyl ester

Chemical Property of ethyl 4,6-dichloro-3-formyl-1H-indole-2-carboxylate

Chemical Property:

• Vapor Pressure: 1.45E-09mmHg at 25°C
• Melting Point: 213 ºC
• Boiling Point: 485.1 ºC at 760 mmHg
• Flash Point: 247.2 ºC
• PSA: 59.16000
• Density: 1.491 g/cm³
• LogP: 3.46390
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 284.9959485
• Heavy Atom Count: 18
• Complexity: 339

Purity/Quality:

98%Min ^*data from raw suppliers

Ethyl4,6-Dichloro-3-formyl-2-indolecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: Xi:Irritant
• 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.; S37/39:Wear suitable g

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C2=C(N1)C=C(C=C2Cl)Cl)C=O
• Uses: Ethyl 4,6-Dichloro-3-formyl-2-indolecarboxylate has been used as a reactant for the preparation of 3-[2-(3-aminophenyl)-2-carboxyvinyl]-4,6-dichloro-1H-indole-2-carboxylic acid to be used as a selective glycine-site N-methyl-D-aspartate (NMDA) receptor antagonist.

Technology Process of ethyl 4,6-dichloro-3-formyl-1H-indole-2-carboxylate

There total 8 articles about ethyl 4,6-dichloro-3-formyl-1H-indole-2-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: 95.0%

4,6-dichloro-indole-2-carboxylic acid,ethyl ester (53995-82-7) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → ethyl-3-formyl-4,6-dichloro-indole-2-carboxylate (153435-96-2)

Guidance literature:

With trichlorophosphate; In dichloromethane; for 2.5h; Reflux;

DOI:10.1021/ml400399f

Reference yield: 76.0%

4,6-dichloro-indole-2-carboxylic acid,ethyl ester (53995-82-7) + N-methyl-N-phenylformamide (93-61-8) → ethyl-3-formyl-4,6-dichloro-indole-2-carboxylate (153435-96-2)

Guidance literature:

N-methyl-N-phenylformamide; With trichlorophosphate; at 20 ℃; Inert atmosphere;

4,6-dichloro-indole-2-carboxylic acid,ethyl ester; In 1,2-dichloro-ethane; for 8h; Inert atmosphere; Reflux;

DOI:10.1002/jlcr.1901

Reference yield:

4,6-dichloro-indole-2-carboxylic acid,ethyl ester (53995-82-7) → ethyl-3-formyl-4,6-dichloro-indole-2-carboxylate (153435-96-2)

Guidance literature:

With sodium acetate; trichlorophosphate; In N-methyl-acetamide; 1,1-dichloroethane;

upstream raw materials:

4,6-dichloro-indole-2-carboxylic acid,ethyl ester

N-methyl-N-phenylformamide

N,N-dimethyl-formamide

ethyl 2-[2-(3,5-dichlorophenyl)hydrazinylidene]propanoate

Downstream raw materials:

4,6-dichloro-3-[2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-1H-indole-2-carboxylic acid ethyl ester

4,6-dichloro-3-[2-cyano-2-(4-methoxy-phenyl)-vinyl]-1H-indole-2-carboxylic acid ethyl ester

4,6-dichloro-3-(1-hydroxy-2-methoxycarbonyl-3-phenyl-propyl)-1H-indole-2-carboxylic acid ethyl ester

(E)-2-(4-nitrophenyl)-3-(2-carboethoxy-4,6-dichloroindol-3-yl)-propenonitrile

Refernces

• 1、 Chen, Huayan,Yang, Hui,Wang, Zhilong,Xie, Xin,Nan, Fajun. "Discovery of 3-Substituted 1H-Indole-2-carboxylic Acid Derivatives as a Novel Class of CysLT1 Selective Antagonists". supporting information. p. 335 - 339. Retrieved 2016/03/25.
• 2、 Baron, Bruce M.,Cregge, Robert J.,Farr, Robert A.,Friedrich, Dirk,Gross, Raymond S.,Harrison, Boyd L.,Janowick, David A.,Matthews, Donald,McCloskey, Timothy C.,Meikrantz, Scott,Nyce, Philip L.,Vaz, Roy,Metz, William A.. "CoMFA, synthesis, and pharmacological evaluation of (E)-3-(2-carboxy-2- arylvinyl)-4,6-dichloro-1H-indole-2-carboxylic acids: 3-[2-(3-Aminophenyl)-2- carboxyvinyl]-4,6-dichloro-1H-indole-2-carboxylic acid, a potent selective glycine-site NMDA receptor antagonist". . p. 995 - 1018. Retrieved 2007/10/03.