4-Methoxy-1H-indole-2-carboxylic acid Chemical Properties

Melting point:

234-235 °C

Boiling point:

447.6±25.0 °C(Predicted)

Density 

1.381±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

solid

pka

4.52±0.30(Predicted)

color 

Yellow

InChI

InChI=1S/C10H9NO3/c1-14-9-4-2-3-7-6(9)5-8(11-7)10(12)13/h2-5,11H,1H3,(H,12,13)

InChIKey

ZZAVIQXQBBOHBB-UHFFFAOYSA-N

SMILES

N1C2=C(C(OC)=CC=C2)C=C1C(O)=O

CAS DataBase Reference

103260-65-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2933998090

4-Methoxy-1H-indole-2-carboxylic acid Usage And Synthesis

Synthesis

Methyl 4-methoxy-2-indolecarboxylate (4 g, 19.49 mmol, 1 eq) was added to an aqueous solution of sodium hydroxide (2M, 98 mL, 0.20 mmol, 10 eq). The suspension was stirred and heated until the reaction mixture was uniform, and then the mixture was refluxed for 30 minutes with heating. The mixture solution was acidified, and the resulting precipitate was extracted three times with ethyl acetate (100 mL). The extracts were combined, washed with water, dried over magnesium sulfate, and concentrated to give a white solid of 4-methoxy-1H-indole-2-carboxylic acid (3.71 g, yield 99 per cent).

References

[1] Journal of Medicinal Chemistry, 2004, vol. 47, # 25, p. 6270 - 6282
[2] Patent: EP1533299, 2005, A1. Location in patent: Page/Page column 8
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 19, p. 3624 - 3634
[4] Patent: WO2008/60621, 2008, A2. Location in patent: Page/Page column 118
[5] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 5, p. 483 - 486

4-Methoxy-1H-indole-2-carboxylic acid(103260-65-7)Related Product Information

• 4-Chloropyridine-2-carboxylic acid
• 4-Methoxyphenylboronic acid
• 4-(METHOXYCARBONYL)PHENYLBORONIC ACID
• 4-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER
• 4-Methoxy-1H-indole-2-carboxylic acid
• 4-[3-[(1,1-DIMETHYLETHYL)AMINO]-2-HYDROXYPROPOXY]-1H-INDOLE-2-CARBOXYLIC ACID, 1-METHYLETHYL ESTER
• 6-METHOXY-1H-INDOLE-3-CARBOXYLIC ACID
• 7-METHOXY-1H-INDOLE-3-CARBOXYLIC ACID
• 5-METHOXY-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER
• 5-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID
• 5-METHOXY-1H-INDOLE-3-CARBOXYLIC ACID
• 5-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER
• 4-METHOXY-1H-INDOLE-3-CARBOXYLIC ACID
• 5-BENZYLOXYINDOLE-2-CARBOXYLIC ACID
• 6-METHOXY-1H-INDOLE-2-CARBOXYLIC ACID
• 4-Methoxyindole
• 4,7-DIMETHOXY-1H-INDOLE-2-CARBOXYLIC ACID
• 4-BENZYLOXYINDOLE-2-CARBOXYLIC ACID ETHYL ESTER