Indole-6-carboxaldehyde
- Product Name
- Indole-6-carboxaldehyde
- CAS No.
- 1196-70-9
- Chemical Name
- Indole-6-carboxaldehyde
- Synonyms
- 1H-INDOLE-5-CARBALDEHYDE;1H-INDOLE-6-CARBALDEHYDE;6-FORMYLINDOLE;6-indolealdehyde;INDOLE-5-ALDEHYDE;INDOLE-6-ALDEHYDE;6-Formyl-1H-indole;INDOLE-5-CARBALDEHYDE;INDOLE-6-CARBALDEHYDE;INDOLE-6-CARBOXALEHYDE
- CBNumber
- CB3155237
- Molecular Formula
- C9H7NO
- Formula Weight
- 145.16
- MOL File
- 1196-70-9.mol
Indole-6-carboxaldehyde Property
- 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
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H317May cause an allergic skin reaction
H319Causes serious eye irritation
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- I0743
- Product name
- Indole-6-carboxaldehyde
- Purity
- >98.0%(GC)
- Packaging
- 1g
- Price
- $102
- Updated
- 2025/07/31
- Product number
- I0743
- Product name
- Indole-6-carboxaldehyde
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $403
- Updated
- 2025/07/31
- Product number
- I615000
- Product name
- Indole-6-carboxaldehyde
- Packaging
- 2g
- Price
- $260
- Updated
- 2021/12/16
- Product number
- I615000
- Product name
- Indole-6-carboxaldehyde
- Packaging
- 5g
- Price
- $560
- Updated
- 2021/12/16
- Product number
- CHM0018035
- Product name
- 1H-INDOLE-6-CARBALDEHYDE
- Purity
- 95.00%
- Packaging
- 250MG
- Price
- $750.75
- Updated
- 2021/12/16
Indole-6-carboxaldehyde Chemical Properties,Usage,Production
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
15861-36-6
1196-70-9
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 Preparation Products And Raw materials
Raw materials
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View Lastest Price from Indole-6-carboxaldehyde manufacturers
- Product
- Indole-6-carboxaldehyde 1196-70-9
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98.0%
- Supply Ability
- 10000KGS
- Release date
- 2025-02-27
- Product
- Indole-6-carboxaldehyde 6-Formylindole in stock Factory 1196-70-9
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- TOP 3 Factory in China
- Supply Ability
- Top 3 largest production capacity Factory
- Release date
- 2019-04-03
- Product
- Indole-6-carboxaldehyde in stock Factory 1196-70-9
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- TOP 3 Factory in China
- Supply Ability
- Top 3 production capacity Factory
- Release date
- 2019-04-03