1670-82-2

Basic information

• Product Name: Indole-6-carboxylic acid
• Synonyms: 6-INDOLECARBOXYLIC ACID;6-CARBOXYINDOLE;4-CARBOXAMIDOBENZOIC ACID;1H-INDOLE-6-CARBOXYLIC ACID;LABOTEST-BB LT00441293;INDOLE-6-CARBOXYLIC ACID;RARECHEM AL BE 1265;RARECHEM AL BO 0290
• CAS NO: 1670-82-2
• Molecular Formula: C₉H₇NO₂
• Molecular Weight: 161.16
• EINECS: -0
• Product Categories: blocks;Carboxes;IndolesOxindoles;Indole/indoline/oxindole;Indole and Indoline;Indoles and derivatives;Carboxylic Acids;Pyrroles & Indoles;Organic acids;Indoles;Simple Indoles;Indole;Carboxylic Acids;Pyrroles & Indoles;Building Blocks;Heterocyclic Building Blocks;Building Blocks;C7 to C9;Chemical Synthesis;Heterocyclic Building Blocks;Heterocycle-Indole series
• Mol File: 1670-82-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: 249-253 °C(lit.)
• Boiling Point: 287.44°C (rough estimate)
• Flash Point: 207.6 °C
• Appearance: Yellow-beige to orange-brown/Powder
• Density: 1.2480 (rough estimate)
• Vapor Pressure: 8.6E-08mmHg at 25°C
• Refractive Index: 1.5050 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 4.44±0.30(Predicted)
• BRN: 123991
• CAS DataBase Reference: Indole-6-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Indole-6-carboxylic acid(1670-82-2)
• EPA Substance Registry System: Indole-6-carboxylic acid(1670-82-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-21/22-20/21/22-51-36-22
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 1670-82-2(Hazardous Substances Data)

Usage

Chemical Properties

yellow-beige to orange-brown powder

Uses

Different sources of media describe the Uses of 1670-82-2 differently. You can refer to the following data:
1. ? ;Reactant for preparation of D-glutamic acid-based inhibitors of E. coli MurD ligase1? ;Reactant for preparation of indolylindazoles and indolylpyrazolopyridines as interleukin-2 inducible T cell kinase inhibitors2? ;Reactant for preparation of amide conjugates with ketoprofen, as inhibitors of Gli1-mediated transcription in Hedgehog pathway3? ;Reactant for preparation of piperazine-bisamide analogs as human growth hormone secretagogue receptor antagonists for treatment of obesity4? ;Reactant for preparation of pyridinyl carboxylates via esterification with chlorohyd
2. Reactant for preparation of D-glutamic acid-based inhibitors of E. coli MurD ligase ? Reactant for preparation of indolylindazoles and indolylpyrazolopyridines as interleukin-2 inducible T cell kinase inhibitors ? Reactant for preparation of amide conju
3. Reactant for preparation of D-glutamic acid-based inhibitors of E. coli MurD ligaseReactant for preparation of indolylindazoles and indolylpyrazolopyridines as interleukin-2 inducible T cell kinase inhibitorsReactant for preparation of amide conjugates with ketoprofen, as inhibitors of Gli1-mediated transcription in Hedgehog pathwayReactant for preparation of piperazine-bisamide analogs as human growth hormone secretagogue receptor antagonists for treatment of obesityReactant for preparation of pyridinyl carboxylates via esterification with chlorohydroxypyridine as SARS-CoV 3CL proinhibitorsReactant for preparation of (indolecarbonyl)-D-phenylglycinamide amides as factor Xa inhibitors

Synthesis Reference(s)

Journal of Medicinal Chemistry, 35, p. 2419, 1992 DOI: 10.1021/jm00091a010

InChI:InChI=1/C9H7NO2/c11-9(12)7-2-1-6-3-4-10-8(6)5-7/h1-5,10H,(H,11,12)/p-1

Upstream product

• 15861-36-6 1H-Indole-6-carbonitrile 
• 106851-27-8 3-Amino-4-(2,2-dimethoxy-ethyl)-benzoic acid 
• 96-98-0 4-methyl-3-nitrobenzoic acid 
• 93247-78-0 methyl 1H-indole-7-carboxylate 
• 106867-41-8 methyl 4-(2-(trimethylsilyl)ethynyl)-3-nitrobenzoate 
• 106851-22-3 4-(2,2-Dimethoxy-ethyl)-3-nitro-benzoic acid 
• 14719-83-6 methyl 3-nitro-4-chlorobenzoate 
• 104447-80-5 (E)-1-(dimethylamino)-2-[4-(methoxycarbonyl)-2-nitrophenyl]ethene 
• 7356-11-8 4-methyl-3-nitro-benzoic acid methyl ester 
• 50820-65-0 indole-6-carboxylic acid methyl ester 

Downstream Products

• 104447-78-1 6-indole 
• 199589-62-3 tert-butyl indole-6-carboxylate 
• 338959-28-7 benzyl 1-benzyl-1H-indole-6-carboxylate 
• 223438-52-6 benzyl 1H-indole-6-carboxylate 
• 251106-49-7 4-benzylpiperidinyl-indole-6-carboxamide 
• 50820-65-0 indole-6-carboxylic acid methyl ester 
• 1075-26-9 6-(hydroxymethyl)indole 
• 219507-60-5 N₄-Acetyl-N₂-(4-t-butylbenzoyl)-N₁-(6-indolylcarbonyl)-1,2,4-benzenetriamine 
• 219508-17-5 3-chloro-1H-indole-6-carboxylic acid 
• 219507-09-2 N₂-(4-t-butylbenzoyl)-N₁-(6-indolylcarbonyl)-1,2-benzenediamine 
• 319474-35-6 3-formyl-1H-indazole-6-carboxylic acid 
• 1034776-13-0 {4-[(1H-indole-6-carbonyl)-amino]-phenyl}-acetic acid tert-butyl ester 
• 400653-16-9 1-Cbz-3-[(6-indolyl)carbonyl]aminopyrrolidine 
• 1181282-48-3 N-(2-(4-(dimethylamino)-4-phenylpiperidin-1-yl)ethyl)-N-methyl-1H-indole-6-carboxamide 

Relevant articles and documents

Nickel-Catalyzed Dearomative Arylboration of Indoles: Regioselective Synthesis of C2- And C3-Borylated Indolines

Indole dearomatization is an important strategy to access indolines: a motif present in a variety of natural products and biologically active molecules. Herein, a method for transition-metal catalyzed regioselective dearomative arylboration of indoles to

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Recently, we have demonstrated that N-((trans)-4-(2-(7-cyano-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)cyclohexyl)-1H-indole-2-carboxamide (SB269652) (1) adopts a bitopic pose at one protomer of a dopamine D2 receptor (D2R) dimer to negatively modulate the binding of dopamine at the other protomer. The 1H-indole-2-carboxamide moiety of 1 extends into a secondary pocket between the extracellular ends of TM2 and TM7 within the D2R protomer. To target this putative allosteric site, we generated and characterized fragments that include and extend from the 1H-indole-2-carboxamide moiety of 1. N-Isopropyl-1H-indole-2-carboxamide (3) displayed allosteric pharmacology and sensitivity to mutations of the same residues at the top of TM2 as was observed for 1. Using 3 as an "allosteric lead", we designed and synthesized an extensive fragment library to generate novel SAR and identify N-butyl-1H-indole-2-carboxamide (11d), which displayed both increased negative cooperativity and affinity for the D2R. These data illustrate that fragmentation of extended compounds can expose fragments with purely allosteric pharmacology.

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