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1-Methyl-1H-indole-6-carbaldehyde

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1-Methyl-1H-indole-6-carbaldehyde Basic information
Product Name:1-Methyl-1H-indole-6-carbaldehyde
Synonyms:1-Methyl-1H-indole-6-carboxaldehyde 97%;1-Methyl-1H-indol-6-carbaldehyde;6-Formyl-1-methylindole;1-METHYL-1H-INDOLE-6-CARBALDEHYDE;1H-Indole-6-carboxaldehyde, 1-methyl- (9CI);1-Methyl-1H-Indole-6-carboxaldehyde;1-Methylindole-6-carbaldehyde;1-methyl-1H-indole-6-carbaldehyde(SALTDATA: FREE)
CAS:21005-45-8
MF:C10H9NO
MW:159.18
EINECS:
Product Categories:Carbonyl Compounds;Heterocycles;ALDEHYDE
Mol File:21005-45-8.mol
1-Methyl-1H-indole-6-carbaldehyde Structure
1-Methyl-1H-indole-6-carbaldehyde Chemical Properties
Melting point 81 °C
Boiling point 318.7±15.0 °C(Predicted)
density 1.10±0.1 g/cm3 (20 ºC 760 Torr)
storage temp. 2-8°C
form solid
AppearanceLight yellow to brown Solid
InChI1S/C10H9NO/c1-11-5-4-9-3-2-8(7-12)6-10(9)11/h2-7H,1H3
InChIKeyQGAKKGIWURKKHV-UHFFFAOYSA-N
Safety Information
Hazard Codes Xi
Risk Statements 41-52-36
Safety Statements 26-39
WGK Germany 3
HazardClass IRRITANT
HS Code 2933998090
Storage Class11 - Combustible Solids
Hazard ClassificationsAquatic Chronic 3
Eye Irrit. 2
MSDS Information
1-Methyl-1H-indole-6-carbaldehyde Usage And Synthesis
Uses1-methyl-1H-indole-6-carbaldehyde is used as a component of organic synthesis or pharmaceutical intermediates.
Synthesis
Indole-6-carboxaldehyde

1196-70-9

Iodomethane

74-88-4

1-Methyl-1H-indole-6-carbaldehyde

21005-45-8

GENERAL METHOD: Indole-6-carboxaldehyde (435 mg, 3 mmol) was dissolved in acetonitrile (30 mL), cesium carbonate (829 mg, 6 mmol) was added, and the reaction mixture was heated and refluxed for 2 hours. Subsequently, iodomethane (3.3 mmol) was added to the reaction system and heating and refluxing was continued for 1 hour. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. Water was added to the residue and extracted three times with ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure. Finally, the resulting residue was purified by fast column chromatography to give the target product 1-methylindole-6-carbaldehyde.

References[1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 7, p. 2060 - 2079
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5888 - 5891
[3] Patent: WO2004/52890, 2004, A1. Location in patent: Page 46-47
1-Methyl-1H-indole-6-carbaldehyde Preparation Products And Raw materials
Raw materials6-Hydroxymethylindole-->Indole-6-carboxaldehyde-->Iodomethane-->Cesium carbonate-->Acetonitrile
Tag:1-Methyl-1H-indole-6-carbaldehyde(21005-45-8) Related Product Information
1-(Cyanomethyl)-1H-indole-6-carboxylic acid 1-METHYL-1H-INDOLE-6-CARBOXYLIC ACID 97 AKOS B006681 1-Methyl-1H-indole-6-carbaldehyde Indole-6-carboxaldehyde KY 234 1-Carbamoylmethyl-6-indolecarboxylic acid 1-(2-Carbamoylethyl)-6-indolecarboxylic acid 1-(2-Cyanoethyl)-1H-indole-6-carboxylic acid 9-Methyl-9 H-carbazole-2-carbaldehyde 1-[3-[(tert-Butoxycarbonyl)amino]propyl]-1H-indole-6-carboxylic acid 6-CHLOROACETYL-1-(2,2-DIMETHYLPROPANOYL)INDOLE 1-(2-TERT-BUTOXYCARBONYLAMINO-ETHYL)-1H-INDOLE-6-CARBOXYLIC ACID 1-tert-Butyl 6-methyl 3-formyl-1H-indole-1,6-dicarboxylate 4-(tert-Butyldimethylsilanyloxy)-1-(2-cyanoethyl)-1H-indole-6-carboxylic acid 1-Acetyl-4-hydroxy-6-indole carboxylic acid ethyl ester 1-(tert-Butyl) 6-methyl 3-iodo-1H-indole-1,6-dicarboxylate N-Acetyl-4-acetoxyl-6-ethylindole carboxylate