Methyl 5-chloro-1H-indole-3-carboxylate

Base Information

• Chemical Name: Methyl 5-chloro-1H-indole-3-carboxylate
• CAS No.: 172595-67-4
• Molecular Formula: C10H8 Cl N O2
• Molecular Weight: 209.632
• Hs Code.: 2933990090
• ChEMBL ID: CHEMBL4860942
• DSSTox Substance ID: DTXSID40578935
• Nikkaji Number: J1.875.499A
• Wikidata: Q72489234
• Mol file: 172595-67-4.mol

Synonyms:172595-67-4;Methyl 5-chloro-1H-indole-3-carboxylate;5-Chloro-1H-indole-3-carboxylic acid methyl ester;CHEMBL4860942;MFCD06203871;1H-INDOLE-3-CARBOXYLIC ACID,5-CHLORO-,METHYL ESTER;Methyl 5-Chloroindole-3-carboxylate;1H-Indole-3-carboxylic acid, 5-chloro-, methyl ester;1H-Indole-3-carboxylicacid, 5-chloro-, methyl ester;SCHEMBL4242189;AMY2738;DTXSID40578935;QFNXAQPCYKEICY-UHFFFAOYSA-N;AB1517;BDBM50577595;5-chloro-3-methoxycarbonyl-1H-indole;AKOS015898557;SB34238;Methyl5-chloro-1H-indole-3-carboxylate;DS-15241;SY058816;CS-0148295;A811436;1H-Indole-3-carboxylicacid,5-chloro-,methyl ester

Chemical Property of Methyl 5-chloro-1H-indole-3-carboxylate

Chemical Property:

• Melting Point: 196-198℃
• PSA: 42.09000
• Density: 1.381
• LogP: 2.60790
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 209.0243562
• Heavy Atom Count: 14
• Complexity: 234

Purity/Quality:

97% ^*data from raw suppliers

Methyl5-chloro-1H-indole-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CNC2=C1C=C(C=C2)Cl

Technology Process of Methyl 5-chloro-1H-indole-3-carboxylate

There total 10 articles about Methyl 5-chloro-1H-indole-3-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: 83.0%

methanol (67-56-1) + 2,2,2-trichloro-1-(5-chloro-1H-indol-3-yl)ethan-1-one → methyl 5-chloro-1H-indole-3-carboxylate (172595-67-4)

Guidance literature:

With potassium hydroxide; In water; at 85 ℃; for 3h;

DOI:10.1016/j.tet.2016.03.048

Reference yield: 83.0%

methyl 2-(5-chloro-2-nitrophenyl)acrylate (1308803-45-3) → methyl 5-chloro-1H-indole-3-carboxylate (172595-67-4)

Guidance literature:

With carbon monoxide; [Rh(CO)2(Me₂NCH₂CH₂NMe₂)][RhCl₂(CO)2]; In tetrahydrofuran; at 100 ℃; for 20h; under 5171.62 Torr; Autoclave;

DOI:10.1021/jo200320k

Reference yield: 78.0%

propynoic acid methyl ester (922-67-8) + N-(4-chlorophenyl)hydroxylamine (823-86-9) → methyl 5-chloro-1H-indole-3-carboxylate (172595-67-4)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.3390/molecules25235595

upstream raw materials:

methyl 3-(5-chloro-2-nitrophenyl)-3-hydroxy-2-methylenepropanoate

methyl 2-(5-chloro-2-nitrophenyl)acrylate

(Z)-methyl 3-((4-chlorophenyl)amino)acrylate

4-chloro-aniline