ChemicalBook > CAS DataBase List > Indole-6-carboxaldehyde

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
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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)
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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
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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.

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N-Bromosuccinimide Price

TCI Chemical
Product number
I0743
Product name
Indole-6-carboxaldehyde
Purity
>98.0%(GC)
Packaging
1g
Price
$102
Updated
2025/07/31
TCI Chemical
Product number
I0743
Product name
Indole-6-carboxaldehyde
Purity
>98.0%(GC)
Packaging
5g
Price
$403
Updated
2025/07/31
TRC
Product number
I615000
Product name
Indole-6-carboxaldehyde
Packaging
2g
Price
$260
Updated
2021/12/16
TRC
Product number
I615000
Product name
Indole-6-carboxaldehyde
Packaging
5g
Price
$560
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
CHM0018035
Product name
1H-INDOLE-6-CARBALDEHYDE
Purity
95.00%
Packaging
250MG
Price
$750.75
Updated
2021/12/16
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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

N,N-Dimethylformamide Manganese dioxide 4-Methyl-3-nitrobenzoic acid methyl ester Titanous chloride Palladium N,N-Dimethylformamide dimethyl acetal

Preparation Products

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View Lastest Price from Indole-6-carboxaldehyde manufacturers

Shaanxi Dideu New Materials Co. Ltd
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
Chemwill Asia Co.,Ltd.
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
Chemwill Asia Co.,Ltd.
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

1196-70-9, Indole-6-carboxaldehydeRelated Search:

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

  • 1H-INDOLE-5-CARBOXALDEHYDE
  • 1H-INDOLE-5-CARBALDEHYDE
  • 1H-INDOLE-6-CARBALDEHYDE
  • INDOLE-6-CARBALDEHYDE
  • INDOLE-6-CARBOXALDEHYDE
  • INDOLE-6-CARBOXALEHYDE
  • INDOLE-6-ALDEHYDE
  • INDOLE-5-ALDEHYDE
  • INDOLE-5-CARBALDEHYDE
  • 6-FORMYLINDOLE
  • Indole-6-Carboxaldehyde (6-Formylindole)
  • 1H-Indole-6-carboxaldehyde (9CI)
  • 6-Indole carboxaldehyde
  • 1H-INDOLE-6-CARBALDEHYDEINDOLE-6-CARBOXALDEHYDE6-FORMYLINDOLE
  • 1H-Indole-6-carboxaldehyde
  • 1H-indole-6-carbaldehyde(SALTDATA: FREE)
  • octahydro-1H-indole-6-carbaldehyde
  • ndole-6-carboxaldehyde
  • 6-Formyl-1H-indole
  • Indole-6-carboxaldehyde 6-Formylindole in stock Factory
  • Indole-6-carboxaldehyde in stock Factory
  • Indole-6-carboxaldehyde&gt
  • Indole-6-carboxaldehyde ISO 9001：2015 REACH
  • 1H-Indole-6-carboxaldehyde (9CI, ACI)
  • 6-indolealdehyde
  • 1H-Indol-6-carbaldehyde
  • 1196-70-9
  • Building Blocks
  • Indoles
  • Heterocyclic Building Blocks
  • Heterocycle-Indole series
  • Building Blocks
  • Indole Derivatives
  • Nitrogen cyclic compounds
  • Aldehydes
  • blocks
  • IndolesOxindoles
  • Indoles and derivatives
  • Indole
  • Indoles
  • ALDEHYDE