5-Chloro-1H-indole-3-carboxylic acid

Base Information

• Chemical Name: 5-Chloro-1H-indole-3-carboxylic acid
• CAS No.: 10406-05-0
• Molecular Formula: C9H6ClNO2
• Molecular Weight: 195.605
• Hs Code.: 2933990090
• European Community (EC) Number: 676-025-1
• ChEMBL ID: CHEMBL3416135
• DSSTox Substance ID: DTXSID90591215
• Wikidata: Q72452280
• Mol file: 10406-05-0.mol

Synonyms:5-Chloro-1H-indole-3-carboxylic acid;10406-05-0;5-chloroindole-3-carboxylic acid;1H-Indole-3-carboxylic acid, 5-chloro-;MFCD03410308;5-Chloro-1H-indole-3-carboxylicacid;CHEMBL3416135;SCHEMBL1434913;DTXSID90591215;XUDITEOFEQOSAK-UHFFFAOYSA-N;BBL101490;BDBM50498201;STL555286;AKOS005259083;5-Chloro-1H-indole-3-carboxylic?acid;AC-6606;AM84315;CS-W019236;FS-2271;SB30339;SY040069;DB-007027;C-4525;EN300-179563;5-Chloro-1H-indole-3-carboxylic acid, AldrichCPR

Chemical Property of 5-Chloro-1H-indole-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 7.12E-09mmHg at 25°C
• Melting Point: 209-210℃
• Refractive Index: 1.728
• Boiling Point: 449.7 °C at 760 mmHg
• PKA: 3.69±0.30(Predicted)
• Flash Point: 225.8 °C
• PSA: 53.09000
• Density: 1.548 g/cm³
• LogP: 2.51950
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 195.0087061
• Heavy Atom Count: 13
• Complexity: 222

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Chloroindole-3-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R20/21/22:; R36/37/38:
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: S22:; S26:; S36/37/39:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Cl)C(=CN2)C(=O)O

Technology Process of 5-Chloro-1H-indole-3-carboxylic acid

There total 8 articles about 5-Chloro-1H-indole-3-carboxylic acid 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: 93.0%

5-chloro-1H-indole (17422-32-1) + trifluoroacetic anhydride (407-25-0) → 5-chloro-1H-indole-3-carboxylic acid (10406-05-0)

Guidance literature:

5-chloro-1H-indole; trifluoroacetic anhydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;

With sodium hydroxide; In water; Heating / reflux;

Reference yield: 92.0%

1-(5-chloro-1H-indol-3-yl)-2,2,2-trifluoroethanone (1419517-55-7) → 5-chloro-1H-indole-3-carboxylic acid (10406-05-0)

Guidance literature:

With water; potassium hydroxide; Reflux;

DOI:10.1021/jm500588w

Reference yield: 79.0%

5-bromo-1H-indole-3-carboxylic acid (10406-06-1) → 5-chloro-1H-indole-3-carboxylic acid (10406-05-0)

Guidance literature:

With copper(l) chloride; In 1-methyl-pyrrolidin-2-one; at 205 - 210 ℃; for 15h;

DOI:10.5012/jkcs.2011.55.2.240

upstream raw materials:

5-chloro-1H-indole

trifluoroacetic anhydride

5-bromo-1H-indole-3-carboxylic acid

1-(5-chloro-1H-indol-3-yl)-2,2,2-trifluoroethanone

Downstream raw materials:

5-chloro-1H-indole

5-chloro-1H-indole-3-carbonyl chloride

2R,4S,5S-6-cyclohexyl-5-(5'-chloroindol-3'-yl-carbonylamino)-2-(2'-methylpropyl)-gamma-hexanolactone

{3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-chloro-indol-1-yl}acetic acid methyl ester

Refernces

• 1、 Luo, Yang-Hui,Sun, Bai-Wang. "An investigation into the substituent effect of halogen atoms on the crystal structures of indole-3-carboxylic acid (ICA)". . p. 7490 - 7497. Retrieved 2013.
• 2、 Pratihar, Sanjay. "Electrophilicity and nucleophilicity of commonly used aldehydes". . p. 5781 - 5788. Retrieved 2014/07/22.
• 3、 -. "BIS-INDOLIC DERIVATIVES, A PROCESS FOR PREPARING THE SAME AND THEIR USES AS A DRUG". . . Retrieved 2013/03/26.