Indole-6-carboxaldehyde Chemical Properties

Melting point:

127-131 °C(lit.)

Boiling point:

339.1±15.0 °C(Predicted)

Density 

1.278±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Dichloromethane

pka

15.84±0.30(Predicted)

form 

Crystalline Powder

color 

Yellow to orange to brown

CAS DataBase Reference

1196-70-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36-43

Safety Statements 

26-36/37/39-36/37

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

29339980

MSDS

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

Indole-6-carboxaldehyde Usage And Synthesis

Chemical Properties

Crystalline Solid

Uses

Reactant in preparation of analogs of botulinum neurotoxin serotype A protease inhibitors 1 Reactant in synthesis of stilbene-based antitumor agents 2 Reactant in acid-catalyzed preparation of aromatic gem-dihalides from aldehydes and acid halides.

Uses

Indole-6-carboxaldehyde (cas# 1196-70-9) is a compound useful in organic synthesis.

Synthesis

General procedure for the synthesis of indole-6-carbaldehyde from 6-cyanoindole: 1. Preparation of LIX N-[tert-butoxycarbonyl] 2-(1H-indol-6-yl)ethylamine indole-6-carboxaldehyde[6] - 6-Cyanoindole (15.0 g) and sodium hypophosphite (90 g) were dissolved in a solvent mixture of water (326 mL), acetic acid (326 mL) and pyridine (652 mL). - Raney nickel catalyst was added and the reaction mixture was stirred at 45°C for 45 minutes. - Upon completion of the reaction, the mixture was filtered through diatomaceous earth and the filtrate was extracted with ethyl acetate (3 x 500 mL). - The organic phases were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure. - The residue was crystallized by a solvent mixture of dichloromethane and hexane to give 13.6 g (89%) of the target product.MS(EI, m/z): C9H2NO(M+1) 145.9. 2. Preparation of 6-(2-nitrovinyl)-1H-indole [0168] - Indole-6-carboxaldehyde (2.8 g), nitromethane (30 mL) and ammonium acetate (0.560 g) were mixed and stirred at 100 °C for 30 minutes. - Excess nitromethane was removed under pressure reduction and the residue was washed with water and dissolved in ethyl acetate (500 mL). - The organic phase was dried with sodium sulfate, filtered and concentrated under reduced pressure to about 50 mL. - The suspension was diluted with petroleum ether, filtered and dried to give 3.3 g (91%) of the target product.MS (EI, m/z): C10H8N2O2 (M-1) 186.9. 3. Preparation of 2-(1H-indol-6-yl)ethylamine [689] - To a solution of 6-(2-nitrovinyl)-1H-indole (1.0 g) in tetrahydrofuran (100 mL) was added lithium aluminum hydride (0.95 g) in one portion and stirred at reflux for 1 hour. - The reaction was quenched by sequential addition of water (0.95 mL), 15% sodium hydroxide (0.95 mL) and water (2.85 mL). - The suspension was filtered and the filtrate was diluted with ethyl acetate (200 mL) and washed sequentially with saturated aqueous sodium bicarbonate (100 mL) and saturated aqueous sodium chloride. - The organic phase was dried with sodium sulfate, filtered and concentrated under reduced pressure. - The residue was purified by silica gel column chromatography, and the product-containing fractions were combined and concentrated under reduced pressure to give 0.525 g (62%) of the target product.MS (EI, m/z): C10H12N2(M+1) 160.9. 4. Nitrogen protection [0392] - 2-(1H-indol-6-yl)ethylamine (0.50 g) was dissolved in acetonitrile (25 mL), dimethylaminopyridine and di-tert-butyl dicarbonate (45 mg) were added. - After stirring at room temperature for 24 hours, the reaction mixture was diluted with ethyl acetate (500 mL). - The organic phase was washed sequentially with saturated aqueous sodium bicarbonate solution (200 mL), water (2 x 200 mL) and saturated aqueous sodium chloride solution. - The organic phase was dried with sodium sulfate, filtered and concentrated under reduced pressure. - The residue was purified by silica gel column chromatography, eluting with a hexane solution of 20-40% ethyl acetate. - The product-containing fractions were combined and concentrated under reduced pressure to give 0.42 g (52%) of the target product.MS (EI, m/z): C15H20N2O2 (M-1) 258.9.

References

[1] Patent: US2003/229026, 2003, A1. Location in patent: Page 26

Indole-6-carboxaldehyde(1196-70-9)Related Product Information

• Indole-3-butyric acid
• Formaldehyde
• Indole-3-acetic acid
• Indometacin
• cyclamen aldehyde
• 1-Nonanal
• Indole
• Paraldehyde
• Methyl indole-6-carboxylate
• Indole-6-carboxylic acid
• Ethyl 1H-indole-4-carboxylate
• Methyl indole-3-carboxylate
• INDOLIZINE
• INDOLIZINE-2-CARBOXYLIC ACID
• Indoline
• 11,12-Dihydroindolo[2,3-a]carbazole
• Ethyl indole-3-carboxylate
• 6-Cyanoindole