Indole-6-carboxylic acid Chemical Properties

Melting point:

249-253 °C(lit.)

Boiling point:

287.44°C (rough estimate)

Density 

1.2480 (rough estimate)

refractive index 

1.5050 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

4.44±0.30(Predicted)

form 

Powder

color 

Yellow-beige to orange-brown

BRN 

123991

InChI

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

InChIKey

GHTDODSYDCPOCW-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC(C(O)=O)=C2)C=C1

CAS DataBase Reference

1670-82-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-21/22-20/21/22-51-36-22

Safety Statements 

22-24/25-37/39-26

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Indole-6-carboxylic acid Usage And Synthesis

Chemical Properties

yellow-beige to orange-brown powder

Uses

• ;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

Uses

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

Uses

• 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 conjugates with ketoprofen, as inhibitors of Gli1-mediated transcription in Hedgehog pathway
• Reactant for preparation of piperazine-bisamide analogs as human growth hormone secretagogue receptor antagonists for treatment of obesity
• Reactant for preparation of pyridinyl carboxylates via esterification with chlorohydroxypyridine as SARS-CoV 3CL proinhibitors
• Reactant 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

Synthesis

(c) Methyl indole-6-carboxylate (11.0 g) was dissolved in a solvent mixture of tetrahydrofuran (150 ml), methanol (150 ml) and water (63 ml) and lithium hydroxide monohydrate (15.8 g) was added. The reaction mixture was stirred at 60 °C for 6 h. After completion of the reaction, the organic solvent was removed by concentration under reduced pressure. The residue was dissolved in water and acidified with 50% (v/v) hydrochloric acid to pH < 3. The precipitate precipitated was collected by filtration and dried to give indole-6-carboxylic acid (9.6 g, 95% yield) as a tan powder with a melting point of 253°C-254°C. The NMR hydrogen spectroscopic (80 MHz, CDCl3) data were as follows: δ 6.51 (m, 1H, H-3) 8.04 (m, 1H, H-7), 11.43 (br s, 1H, NH), 12.42 (br s, 1H, OH).

References

[1] Journal of Medicinal Chemistry, 2015, vol. 58, # 17, p. 6819 - 6843
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439
[3] Patent: US4898863, 1990, A
[4] Patent: EP242167, 1991, B1
[5] Patent: US2007/60567, 2007, A1. Location in patent: Page/Page column 19

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