5-Chloroindole-2-carboxylic acid

Base Information

• Chemical Name: 5-Chloroindole-2-carboxylic acid
• CAS No.: 10517-21-2
• Molecular Formula: C9H6ClNO2
• Molecular Weight: 195.605
• Hs Code.: 29339990
• European Community (EC) Number: 234-050-1
• NSC Number: 75651
• DSSTox Substance ID: DTXSID60146993
• Nikkaji Number: J212.441F
• Wikidata: Q27185969
• ChEMBL ID: CHEMBL23906
• Mol file: 10517-21-2.mol

Synonyms:5-chloroindole-2-carboxylate

Chemical Property of 5-Chloroindole-2-carboxylic acid

Chemical Property:

• Appearance/Colour: light pink to beige or light brown powder
• Vapor Pressure: 7.12E-09mmHg at 25°C
• Melting Point: 283-287 °C
• Refractive Index: 1.5790 (estimate)
• Boiling Point: 449.7 °C at 760 mmHg
• PKA: 4.26±0.30(Predicted)
• Flash Point: 225.8 °C
• PSA: 53.09000
• Density: 1.548 g/cm³
• LogP: 2.51950
• Storage Temp.: 0-6°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.9
• 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:

99% ^*data from raw suppliers

5-Chloroindole-2-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Cl)C=C(N2)C(=O)O
• Uses: NMDA receptor antagonist (gly) 5-Chloroindole-2-carboxylic Acid is used in the synthesis of 4-(3-aminomethylphenyl)piperidine-1-carboxamides as potent, selective, and orally bioavailable inhibitors of βII tryptase. It is also a reagent used to prepare indole amides with possible antihistaminic activities.

Technology Process of 5-Chloroindole-2-carboxylic acid

There total 11 articles about 5-Chloroindole-2-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: 96.0%

5-chloro-indole-2-carboxylic acid ethyl ester (4792-67-0) → 5-chloro-1H-Indole-2-carboxylic acid (10517-21-2)

Guidance literature:

With water; sodium hydroxide; In ethanol; at 40 ℃;

DOI:10.1111/cbdd.12928

Reference yield: 95.0%

p-chloro-o-iodoaniline (63069-48-7) + 2-oxo-propionic acid (127-17-3) → 5-chloro-1H-Indole-2-carboxylic acid (10517-21-2)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; In N,N-dimethyl-formamide; Reflux; Inert atmosphere;

DOI:10.1002/cmdc.201800033

Reference yield: 76.0%

(Z)-4-(2,4-dichloro-benzylidene)-2-phenyloxazole-5(4H)-one → 5-chloro-1H-Indole-2-carboxylic acid (10517-21-2)

Guidance literature:

With ethanol; sodium hydrogencarbonate; copper(I) bromide; In N,N-dimethyl-formamide; at 20 - 140 ℃; Reagent/catalyst; Solvent; Temperature;

upstream raw materials:

5-chloro-indole-2-carboxylic acid ethyl ester

(5-chloro-2-nitro-phenyl)-pyruvic acid

4-chlorophenyldiazonium salt

2-[(4-chlorophenyl)-hydrazono]-propionic acid ethyl ester

Downstream raw materials:

1-(5-chloro-1H-indol-3-yl)ethan-1-one

5-chloro-1-methyl-1H-indole-2-carboxylic acid

(+/-)-5-Chloro-1H-indole-2-carboxylic acid [1-(3-chloro-benzyl)-2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-amide

(+/-)-5-Chloro-1H-indole-2-carboxylic acid [2-oxo-2-thiazolidin-3-yl-1-(3-trifluoromethyl-benzyl)-ethyl]-amide

Refernces

• 1、 -. "Preparation method of indole-2-formic acid derivative". Paragraph 0046-0048. . Retrieved 2020/07/14.
• 2、 Shen, Qing-Kun,Deng, Hao,Wang, Shi-Ben,Tian, Yu-Shun,Quan, Zhen-Shan. "Synthesis, and evaluation of in vitro and in vivo anticancer activity of 14-substituted oridonin analogs: A novel and potent cell cycle arrest and apoptosis inducer through the p53-MDM2 pathway". . p. 15 - 31. Retrieved 2019/04/10.