5-(Phenylmethoxy)-1H-indole-3-carbaldehyde Chemical Properties

Melting point:

237-238°C

Boiling point:

474.2±30.0 °C(Predicted)

Density 

1.267±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Ethanol

pka

15.13±0.30(Predicted)

form 

powder

color 

yellow to brown

Sensitive 

Air Sensitive

BRN 

208873

CAS DataBase Reference

6953-22-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36-43

Safety Statements 

22-24/25-36/37-26

WGK Germany 

3

HazardClass 

IRRITANT, AIR SENSITIVE

HS Code 

29339990

MSDS

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

5-(Phenylmethoxy)-1H-indole-3-carbaldehyde Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

Reactant for preparation of:

• Rhodanine merocyanine dyes
• Potential topoisomerase II inhibitors
• Azithromycin derivatives
• Inhibitors of PI3 kinase-α and the mammalian target of rapamycin
• Cytotoxic agents
• Vascular endothelial growth factor (VEGF) inhibitor
• Derivatives of vancomycin and eremomycin
• Benzimidazoles as potential antibacterial agents
• Light-dependent tumor necrosis factor-α antagonists
• Serotonin 5-HT4 Receptor agonists

Uses

An antibacterial agent

Synthesis

a) Synthesis of 5-(benzyloxy)-1H-indole-3-carbaldehyde: Phosphoryl chloride (1.5 g, 9.9 mmol) was slowly added dropwise to 15 mL of N,N-dimethylformamide (DMF) cooled in an ice bath under stirring conditions. After removing the ice bath, the reaction was continued with stirring for 15 min. Subsequently, 5-benzyloxyindole (2.00 g, 8.96 mmol) was added and the reaction mixture was heated to 50-60 °C and maintained at this temperature for 1.5 hours. After completion of the reaction, the mixture was poured into ice water and adjusted to alkaline with 2 M sodium hydroxide solution. The mixture was refluxed for 2 minutes, cooled and filtered to collect the solid product. The solid was washed with water and dried to give the target compound 5-(benzyloxy)-1H-indole-3-carboxaldehyde in a yield of 1.88 g (84% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6) with the following chemical shifts: δ 5.88 (s, 1H), 8.20 (s, 1H), 7.68 (d, 1H), 7.50-7.25 (m, 6H), 6.96 (dd, 1H), 5.11 (s, 2H), 4.02 (s, 1H).

References

[1] Patent: WO2005/66132, 2005, A1. Location in patent: Page/Page column 90-91
[2] Patent: US2007/299061, 2007, A1. Location in patent: Page/Page column 17
[3] Synthesis (Germany), 2017, vol. 49, # 18, p. 4141 - 4150
[4] Journal of the Chemical Society, 1958, p. 3493,3494
[5] Journal of the Chemical Society, 1958, p. 3887,3892

5-(Phenylmethoxy)-1H-indole-3-carbaldehyde(6953-22-6)Related Product Information

• Formaldehyde
• 5-Benzyloxyindole
• Indole-3-carboxaldehyde
• 7-Benzyloxyindole-3-carbaldehyde
• 6-Benzyloxyindole-3-carboxaldehyde
• 4-Benzyloxyindole-3-carboxaldehyde
• 5-(Phenylmethoxy)-1H-indole-3-carbaldehyde
• 5-BENZYLOXYINDOLE-3-GLYOXYLIC ACID ETHYL ESTER
• 3,6A,11,14-TETRAHYDRO-9-METHOXY-2-METHYL-(12H)-ISOQUINO[1,2-B]PYRROLO[3,2-F][1,3]BENZOXAZINE-1-CARBOXYLIC ACID, ETHYL ESTER
• 5-BENZYLOXYINDOLE-3-GLYOXYLAMIDE
• 5-BENZYLOXY-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER
• 5-BENZYLOXY-1H-INDOLE-3-CARBOXYLIC ACID
• RARECHEM AL BI 1490
• ETHYL 5-(BENZOYLOXY)-1-ISOPROPYL-2-METHYL-1H-INDOLE-3-CARBOXYLATE
• SPECS AN-068/25067031
• 5-(BENZYLOXY)-1-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-1H-INDOLE-3-CARBALDEHYDE
• ETHYL 5-[(4-FLUOROBENZOYL)OXY]-1,2-DIMETHYL-1H-BENZO[G]INDOLE-3-CARBOXYLATE
• 5-BENZYLOXY-3-FORMYLINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER