5-Methoxyindole-3-carboxaldehyde Chemical Properties

Melting point:

179-183 °C (lit.)

Boiling point:

306.47°C (rough estimate)

Density 

1.1999 (rough estimate)

refractive index 

1.5060 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Crystalline Powder or Needles

pka

15.21±0.30(Predicted)

color 

Yellow to beige

Water Solubility 

insoluble

Sensitive 

Air Sensitive

BRN 

132769

CAS DataBase Reference

10601-19-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-26

WGK Germany 

3

HazardClass 

IRRITANT, AIR SENSITIVE

HS Code 

29339900

MSDS

• Language:English Provider:5-Methoxyindole-3-carboxaldehyde
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Methoxyindole-3-carboxaldehyde Usage And Synthesis

Chemical Properties

yellowish to beige crystalline powder or needles

Uses

reactant in synthesis of tryptophan dioxygenase inhibitors as potential anticancer immunomodulators 1 reactant in preparation of inhibitor of the C-terminal domain of RNA polymerase II reactant in preparation of imidazopyridines and imidazobenzothiazoles 2 reactant in preparation of fluorescent neuroactive probes for brain imaging 3 reactant in preparation of antibacterial agents 4 reactant in synthesis of antiandrogens.

Uses

• reactant in synthesis of tryptophan dioxygenase inhibitors as potential anticancer immunomodulators
• reactant in preparation of inhibitor of the C-terminal domain of RNA polymerase II
• reactant in preparation of imidazopyridines and imidazobenzothiazoles
• reactant in preparation of fluorescent neuroactive probes for brain imaging
• reactant in preparation of antibacterial agents
• reactant in synthesis of antiandrogens

Definition

ChEBI: 5-methoxyindole-3-carbaldehyde is a member of indoles.

Synthesis

GENERAL STEPS: Oxalyl chloride (0.3 mL) was added dropwise to stirring N,N-dimethylformamide (DMF, 3 mL) under ice bath cooling. The reaction mixture was stirred continuously at 0 °C for 1 hour. Subsequently, a solution of 5-methoxyindole (4 mmol) dissolved in DMF (1.5 mL) was added dropwise to the above mixture. The resulting mixture was stirred at room temperature for 5 hours. Upon completion of the reaction, 2 N sodium hydroxide solution (2 mL) was added and the mixture was heated to 100°C maintained for 10 minutes. The reaction solution was cooled and extracted with ethyl acetate (3 x 50 mL). The organic phases were combined and washed sequentially with water and saturated saline. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by fast column chromatography with the eluent of ethyl acetate/petroleum ether (3:1, v/v) to finally obtain pure 5-methoxyindole-3-carboxaldehyde.

References

[1] Organic Letters, 2013, vol. 15, # 11, p. 2636 - 2639
[2] Chinese Chemical Letters, 2010, vol. 21, # 11, p. 1307 - 1309
[3] Synthetic Communications, 1988, vol. 18, # 7, p. 671 - 674
[4] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 158 - 167
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 21, p. 2561 - 2566

5-Methoxyindole-3-carboxaldehyde(10601-19-1)Related Product Information

• 3-Methoxybenzaldehyde
• 5-Methoxy-3-indolecarboxylic acid
• 5-Methoxyindole
• Anisole
• p-Anisaldehyde
• (Trifluoromethoxy)benzene
• 1H-INDOL-3-OL
• o-Anisaldehyde
• 5-Methoxyoxindole
• 5-Methoxyindole-3-acetonitrile
• 5-Methoxy-2,3-dihydroindoline
• 5-(Phenylmethoxy)-1H-indole-3-carbaldehyde
• Ethyl 5-acetyloxy-1,2-dimethylindole-3-carboxylate
• 4-Benzyloxyindole-3-carboxaldehyde
• 4-METHOXYINDOLE-3-CARBOXALDEHYDE
• BOC-5-METHOXYINDOLE-3-CARBOXALDEHYDE,5-Methoxyindole-3-carboxaldehyde, N-BOC protected 98%,5-METHOXYINDOLE-3-CARBOXALDEHYDE, N-BOC PROTECTED
• Indole-3-carboxaldehyde
• 7-METHOXYINDOLE-3-CARBOXALDEHYDE