10517-21-2

Basic information

• Product Name: 5-Chloroindole-2-carboxylic acid
• Synonyms: 5-Cl-ICA;5-Chloroindole-2-carboxylic acid ,98%;5-CHLOROINDOLE-2-CARBOXYLIC ACID(5ClI2CA);5-chloro-1H-indole-2-carboxylic acid(SALTDATA: FREE);5-chloro-1H-indol-2-carboxylic acid;5-Chloroindole-2-carboxylic acid 98%;1H-Indole-2-carboxylic acid, 5-chloro-;5-chloro-1h-indole-2-carboxylicaci
• CAS NO: 10517-21-2
• Molecular Formula: C₉H₆ClNO₂
• Molecular Weight: 195.6
• EINECS: 234-050-1
• Product Categories: Indole/indoline/oxindole;Indole and Indoline;Indoles and derivatives;Organic acids;Indoles;Simple Indoles;Halogenated Heterocycles;Heterocyclic Building Blocks;IndolesBuilding Blocks;Pharmaceutical Intermediates;Building Blocks;C7 to C10;C7 to C9;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 10517-21-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 287 °C (dec.)(lit.)
• Boiling Point: 449.7 °C at 760 mmHg
• Flash Point: 225.8 °C
• Appearance: light pink to beige or light brown powder
• Density: 1.3228 (rough estimate)
• Vapor Pressure: 7.12E-09mmHg at 25°C
• Refractive Index: 1.5790 (estimate)
• Storage Temp.: 0-6°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.26±0.30(Predicted)
• BRN: 153229
• CAS DataBase Reference: 5-Chloroindole-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloroindole-2-carboxylic acid(10517-21-2)
• EPA Substance Registry System: 5-Chloroindole-2-carboxylic acid(10517-21-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: NL5998400
• HazardClass: IRRITANT
• Hazardous Substances Data: 10517-21-2(Hazardous Substances Data)

Usage

Chemical Properties

light pink to beige or light brown fine

Uses

Different sources of media describe the Uses of 10517-21-2 differently. You can refer to the following data:
1. NMDA receptor antagonist (gly)
2. 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.

InChI:InChI=1/C9H6ClNO2/c10-6-1-2-7-5(3-6)4-8(11-7)9(12)13/h1-4,11H,(H,12,13)/p-1

Upstream product

• 4792-67-0 5-chloro-indole-2-carboxylic acid ethyl ester 
• 127-17-3 2-oxo-propionic acid 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 63069-48-7 p-chloro-o-iodoaniline 
• 91473-66-4 (E)-ethyl 2-(2-(4-chlorophenyl)hydrazono)propanoate 
• 106-47-8 4-chloro-aniline 
• 1073-70-7 4-chlorophenylhydrazine hydrochloride 
• 5296-86-6 2-[(4-chlorophenyl)-hydrazono]-propionic acid ethyl ester 
• 17333-85-6 4-chlorophenyldiazonium salt 
• 36255-90-0 (5-chloro-2-nitro-phenyl)-pyruvic acid 

Downstream Products

• 827-01-0 5-chloro-1H-indole-3-carboxaldehyde 
• 3764-94-1 5-chlorotryptamine 
• 365997-38-2 ethyl (1S,3R,4S)-3-[(tert-butoxycarbonyl)amino]-4-{[(5-chloroindol-2-yl)carbonyl]amino}cyclohexanecarboxylate 
• 889140-50-5 5-chloro-1H-indole-2-carboxylic acid [2-hydroxy-2-(4-nitro-phenyl)ethyl]amide 
• 186430-31-9 5-Chloro-1H-indole-2-carboxylic acid ((1S)-methoxycarbamoyl-2-phenyl-ethyl)-amide 
• 186430-69-3 (+/-)-Methyl 2-[(5-chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-butyrate 
• 186430-71-7 (+/-)-5-Chloro-1H-indole-2-carboxylic acid [1-(2-chloro-benzyl)-2-oxo-2-thiazolidin-3-yl-ethyl]-amide 
• 186430-72-8 (+/-)-5-Chloro-1H-indole-2-carboxylic acid [2-(3-cyano-phenyl)-1-(thiazolidine-3-carbonyl)-ethyl]-amide 
• 186430-73-9 (+/-)-5-Chloro-1H-indole-2-carboxylic acid [1-(3-chloro-benzyl)-2-oxo-2-thiazolidin-3-yl-ethyl]-amide 
• 186430-74-0 (+/-)-5-Chloro-1H-indole-2-carboxylic acid [2-oxo-2-thiazolidin-3-yl-1-(3-trifluoromethyl-benzyl)-ethyl]-amide 
• 186430-76-2 (+/-)-5-Chloro-1H-indole-2-carboxylic acid [1-(3-chloro-benzyl)-2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-amide 
• 365996-91-4 4-Nitrophenyl 5-chloroindole-2-carboxylate 
• 51843-24-4 1-(5-chloro-1H-indol-3-yl)ethan-1-one 

Relevant articles and documents

Synthesis and Biological Evaluation of Indole-2-carbohydrazide Derivatives as Anticancer Agents with Anti-angiogenic and Antiproliferative Activities

A novel series of indole-2-carbohydrazide derivatives were synthesized, characterized, and evaluated for their antiproliferative activities against two cancer cell lines, HCT116 and SW480, and a normal human fetal lung fibroblast cell line, MRC-5. Among this series, compound 24 f displayed potent cytotoxic activities in vitro against HCT116 and SW480 cell lines with GI50 values of 8.1 and 7.9 μm, respectively, and was inactive against MRC-5 cells. The newly synthesized compounds were also evaluated for anti-angiogenesis capabilities by chick chorioallantoic membrane, human umbilical vein endothelial cell (HUVEC) migration, and endothelial microtubule formation assays. Moreover, the effects of 24 f on the vascular endothelial growth factor receptor-2 and the signaling pathway in HUVECs indicated that this compound inhibits VEGFR-2 and its downstream related proteins. These results indicate that compound 24 f, as well as the other derivatives, are promising inhibitors of angiogenesis.

Preparation method of indole-2-formic acid derivative

The invention discloses a preparation method of an indole-2-formic acid derivative, wherein the preparation method comprises the steps: by using an oxazolone compound as a raw material, carrying out areaction in an organic solvent at the temperature of 70-150 DEG C under the action of alcohol, alkali and a catalyst, tracking by TLC until the raw material is completely reacted, and separating andpurifying the obtained reaction solution to obtain the indole-2-formic acid derivative. The technology is adopted, the target product indole-2-formic acid derivative is prepared by taking an oxazolonecompound as a raw material through one-pot reaction under the action of alcohol, alkali and a catalyst, so that direct conversion from an oxazolone ring to an indole ring is realized, reaction stepsand an intermediate process are reduced, and the method has the characteristics of cheap raw materials, environmental friendliness and the like, and is suitable for industrial production.

ANTIBACTERIAL COMPOUNDS

The present application provides compounds of formula: Methods of using these compounds for killing bacterial growth and treating bacterial infections are also provided.