6953-22-6

Basic information

• Product Name: 5-(Phenylmethoxy)-1H-indole-3-carbaldehyde
• Synonyms: 5-BENZYLOXYINDOLE-3-ALDEHYDE;5-BENZYLOXYINDOLE-3-CARBALDEHYDE;5-BENZYLOXYINDOLE-3-CARBOXALDEHYDE;5-BENZYLOXY INDOLE-3-CARBOXYALDEHYDE;5-BENZYLOXYINDOLE-3-FORMALDEHYDE;5-(BENZYLOXY)-3-INDOLECARBOXYALDEHYDE;5-BENZYLOXY-3-FORMYLINDOLE;5-(BENZYLOXY)-1H-INDOLE-3-CARBALDEHYDE
• CAS NO: 6953-22-6
• Molecular Formula: C₁₆H₁₃NO₂
• Molecular Weight: 251.28
• EINECS: 230-134-7
• Product Categories: blocks;Carboxes;IndolesOxindoles;Indoles and derivatives;Indoline & Oxindole;Indoles;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;Heterocyclic Building Blocks
• Mol File: 6953-22-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 237-238°C
• Boiling Point: 474.2 °C at 760 mmHg
• Flash Point: 240.6 °C
• Appearance: yellow to brown/powder
• Density: 1.267 g/cm³
• Storage Temp.: 2-8°C
• Solubility: Ethanol
• PKA: 15.13±0.30(Predicted)
• Sensitive: Air Sensitive
• BRN: 208873
• CAS DataBase Reference: 5-(Phenylmethoxy)-1H-indole-3-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(Phenylmethoxy)-1H-indole-3-carbaldehyde(6953-22-6)
• EPA Substance Registry System: 5-(Phenylmethoxy)-1H-indole-3-carbaldehyde(6953-22-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 22-24/25-36/37-26
• WGK Germany: 3
• HazardClass: IRRITANT, AIR SENSITIVE
• Hazardous Substances Data: 6953-22-6(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 6953-22-6 differently. You can refer to the following data:
1. Reactant for preparation of:Rhodanine merocyanine dyesPotential topoisomerase II inhibitorsAzithromycin derivativesInhibitors of PI3 kinase-α and the mammalian target of rapamycinCytotoxic agentsVascular endothelial growth factor (VEGF) inhibitorDerivatives of vancomycin and eremomycinBenzimidazoles as potential antibacterial agentsLight-dependent tumor necrosis factor-α antagonistsSerotonin 5-HT4 Receptor agonists
2. An antibacterial agent

InChI:InChI=1/C16H13NO2/c18-10-13-9-17-16-7-6-14(8-15(13)16)19-11-12-4-2-1-3-5-12/h1-10,17H,11H2

Synthetic route

1H-imidazole (288-32-4) + 5-benzyloxy-1H-indole (1215-59-4) → 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

Conditions	Yield
Stage #1: 1H-imidazole; 5-benzyloxy-1H-indole With acetic anhydride at 130℃; for 1h; Stage #2: With sodium hydroxide In ethanol; water for 1h; Heating; Further stages.;	91%

5-benzyloxy-1H-indole (1215-59-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.25h; Stage #2: 5-benzyloxy-1H-indole at 50 - 60℃; for 1.5h; Stage #3: With sodium hydroxide In water at 0℃; for 0.0333333h; Heating / reflux;	84%
Stage #1: 5-benzyloxy-1H-indole; N,N-dimethyl-formamide With trichlorophosphate at 20℃; for 0.5h; Stage #2: With sodium hydroxide In water at 0℃;	83%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at -30 - 20℃; for 0.5h; Vilsmeier-Haack Formylation; Stage #2: 5-benzyloxy-1H-indole at 20℃; for 1h; Vilsmeier-Haack Formylation;	81%

5-benzyloxy-1-tosyl-1H-indole-3-carboxaldehyde → 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

Conditions	Yield
With triethylamine; 2-amino-3-(5-hydroxy-1H-indol-3-yl)propionic acid methyl ester In methanol for 6h; Microwave irradiation; Reflux;	55%

5-benzyloxy-1H-indole (1215-59-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) → 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

Conditions	Yield
und Erwaermen des Reaktionsprodukts mit wss.Natronlauge oder mit wss.Natriumcarbonat-Loesung.;

3-methyl-4-nitrophenol (2581-34-2) + 2-nitro-m-cresol; 6-nitro-m-cresol → 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 5 h / Heating 2: 2.) hydrazine hydrate / 2.) Raney nickel / 1.) reflux, 3 h, 2.) THF, MeOH, RT, 30 min 3: 1.) phosphorus oxychloride, 2.) conc. HCl / 1.) 0 deg C, 1 h, 2.) MeOH, THF, RT, 45 min View Scheme

5-benzyloxy-2-nitrotoluene (22424-58-4) → 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2.) hydrazine hydrate / 2.) Raney nickel / 1.) reflux, 3 h, 2.) THF, MeOH, RT, 30 min 2: 1.) phosphorus oxychloride, 2.) conc. HCl / 1.) 0 deg C, 1 h, 2.) MeOH, THF, RT, 45 min View Scheme

benzyl bromide (100-39-0) + CO → 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 5 h / Heating 2: 2.) hydrazine hydrate / 2.) Raney nickel / 1.) reflux, 3 h, 2.) THF, MeOH, RT, 30 min 3: 1.) phosphorus oxychloride, 2.) conc. HCl / 1.) 0 deg C, 1 h, 2.) MeOH, THF, RT, 45 min View Scheme

5-benzyloxy-1H-indole-2-carboxylic acid (6640-09-1) → 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper oxide-chromium oxide; quinoline / 280 °C 2: phosphoryl chloride / und anschliessenden Hydrolysieren mit wss.Natronlauge bzw. wss.Natriumcarbonat-Loesung View Scheme

5-benzyloxy-1H-indole (1215-59-4) → 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

oxalyl dichloride (79-37-8) + 5-benzyloxy-1H-indole (1215-59-4) → 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

Conditions	Yield
With N,N-dimethyl-formamide at 20℃; for 5h;

indol-5-ol (1953-54-4) → 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / Reflux 2.1: trichlorophosphate / 0.5 h / -30 - 20 °C 2.2: 1 h / 20 °C View Scheme

benzyl bromide (100-39-0) → 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / Reflux 2.1: trichlorophosphate / 0.5 h / -30 - 20 °C 2.2: 1 h / 20 °C View Scheme

indol-5-ol (1953-54-4) + benzyl bromide (100-39-0) → 5-benzyloxyindole-3-carboxaldehyde (6953-22-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetone 2: trichlorophosphate View Scheme

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + methyl iodide (74-88-4) → 5-(benzyloxy)-1-methyl-1H-indole-3-carbaldehyde (58630-07-2)

Conditions	Yield
Stage #1: 5-benzyloxyindole-3-carboxaldehyde With sodium hydride In DMF (N,N-dimethyl-formamide) for 0.0833333h; Stage #2: methyl iodide In DMF (N,N-dimethyl-formamide) for 0.5h;	95%
Stage #1: 5-benzyloxyindole-3-carboxaldehyde With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 0.5h; Stage #2: methyl iodide In DMF (N,N-dimethyl-formamide) at 20℃; for 16h;

1-ethenyl-4-methylbenzene (622-97-9) + 5-benzyloxyindole-3-carboxaldehyde (6953-22-6) → 5-(benzyloxy)-1-(1-(p-tolyl)vinyl)-1H-indole-3-carbaldehyde

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); lithium acetate; oxygen; copper dichloride In 1,2-dimethoxyethane at 70℃; for 7h; Mechanism; regioselective reaction;	95%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + (S)-alaninamide hydrochloride (33208-99-0) → (S)-2-((5-(benzyloxy)-1H-indol-3-yl)methylamino)propanamide

Conditions	Yield
Stage #1: (S)-alaninamide hydrochloride With sodium cyanoborohydride In methanol at 20℃; for 0.25h; Molecular sieve; Inert atmosphere; Stage #2: 5-benzyloxyindole-3-carboxaldehyde In methanol at 20 - 35℃; for 4h; Inert atmosphere;	92.1%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) → 5-benzyloxy-1H-indole-3-carbonitrile (194490-25-0)

Conditions	Yield
With 1,3-dimethyl-2-imidazolidinone; sodium hexamethyldisilazane In tetrahydrofuran at 185℃; for 12h;	87%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) → 5-(benzyloxy)-3-methyl-1H-indole (21987-24-6)

Conditions	Yield
With sodium tetrahydroborate; palladium on activated charcoal In isopropyl alcohol for 3h; Heating;	84%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Schlenk technique;
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃;	578 mg

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + benzenesulfonyl chloride (98-09-9) → 5-benzyloxy-1-phenylsulfonyl-1H-indole-3-carboxaldehyde (1000056-62-1)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide at 0℃; for 2h; Reflux; Inert atmosphere;	81%
With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In water; benzene at 20℃; for 2.5h;	65%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran; dichloromethane; water at 0 - 20℃; for 1.5h;

piperidine (110-89-4) + 2-thioxo-4-thiazolidinone (141-84-4) + 5-benzyloxyindole-3-carboxaldehyde (6953-22-6) → 5-[(5-benzyloxy-1H-indol-3-yl)methylene]-2-(1-piperidinyl)rhodanine (1315457-00-1)

Conditions	Yield
for 0.05h; Microwave irradiation; neat (no solvent);	81%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + acetic anhydride (108-24-7) → 1-acetyl-5-(benzyloxy)-1H-indole-3-carbaldehyde

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; for 0.666667h;	81%
With dmap; triethylamine In dichloromethane at 20℃; for 0.666667h;	81%
With dmap; triethylamine In dichloromethane at 20℃; for 0.666667h;	81%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + p-toluenesulfonyl chloride (98-59-9) → 5-benzyloxy-1-tosyl-1H-indole-3-carboxaldehyde

Conditions	Yield
Stage #1: 5-benzyloxyindole-3-carboxaldehyde With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 0.166667h; Stage #2: p-toluenesulfonyl chloride In dichloromethane; water at 20℃; for 0.5h;	76%

2-furoic acid hydrazide (3326-71-4) + 5-benzyloxyindole-3-carboxaldehyde (6953-22-6) → N’-{(E)-[5-(benzyloxy)-1H-indol-3-yl]methylidene}furan-2-carbohydrazide

Conditions	Yield
In ethanol Reflux;	76%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + ethyl iodide (75-03-6) → 5-benzyloxy-1-ethyl-1H-indole-3-carboxaldehyde

Conditions	Yield
Stage #1: 5-benzyloxyindole-3-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.666667h; Inert atmosphere; Stage #2: ethyl iodide In N,N-dimethyl-formamide at 25℃; for 12h; Inert atmosphere;	76%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + 1,2,6-trimethylquinolin-1-ium iodide (31385-19-0) → 3-[2-(1,6-Dimethyl-quinolium-2-yl)-vinyl]-1H-5-benzyloxy-indole iodide

Conditions	Yield
With piperidine In ethanol at 30℃; for 0.133333h; Microwave irradiation;	75%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + benzoyl chloride (98-88-4) → 1-benzoyl-5-benzyloxy-1H-indole-3-carbaldehyde (380220-38-2)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	70%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + acetyl chloride (75-36-5) → 1-acetyl-5-(benzyloxy)-1H-indole-3-carbaldehyde

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	70%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + C14H17NO3S → 3-[2-(1-propanesulfonate-quinolium-2-yl)-vinyl]-1H-5-benzyloxy-indole

Conditions	Yield
With piperidine In ethanol at 50℃; for 0.133333h; Microwave irradiation;	70%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + aminoguanidine bicarbonate (2582-30-1) → 3-<<5-(benzyloxy)-1H-indol-3-yl>methylene>carbazimidamide hydrochloride

Conditions	Yield
With hydrogenchloride In methanol for 2h; Heating; pH 3-4;	69%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + N1-[3-(2-naphthyl)prop-2-ynyl]benzene-1,2-diamine → 2-(benzyloxy)-6-(2-naphthyl)-5,8-dihydroindolo[3',2':3,4]azepino[1,2-a]benzimidazole

Conditions	Yield
With silver hexafluoroantimonate; (triphenylphosphine)gold(I) chloride In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 30h; Inert atmosphere;	68%

2,4-thiazolidinedion (2295-31-0) + 5-benzyloxyindole-3-carboxaldehyde (6953-22-6) → (5Z)-5-(5-benzyloxy-3-indolylmethylene)-1,3-thiazolidine-2,4-dione

Conditions	Yield
With piperidine In ethanol at 70℃; for 24h; Knoevenagel Condensation;	62%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + ethyl acetoacetate (141-97-9) → 4-[(5-benzyloxy-1H-indole-3-yl)-methylene]-3-methyl-isoxazole-5-one (1353122-23-2)

Conditions	Yield
With pyridine; hydroxylamine hydrochloride In ethanol Reflux;	60%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + 2-[4-(benzyloxy)benzyl]acetic acid (6547-53-1) → (αE)-α-[[1-acetyl-5-(phenylmethoxy)-1H-indol-3-yl]methylene]-4-phenylmethoxybenzeneacetic acid (1450604-63-3)

Conditions	Yield
Stage #1: 5-benzyloxyindole-3-carboxaldehyde; 2-[4-(benzyloxy)benzyl]acetic acid With acetic anhydride; triethylamine at 130℃; for 6h; Stage #2: With water In tetrahydrofuran; ethanol at 22 - 90℃; for 16h;	60%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + diphenyl acetylene (501-65-5) → 2-(benzyloxy)-6,7,8,9-tetraphenylpyrido[1,2-a]indole-10-carbaldehyde

Conditions	Yield
With copper diacetate; palladium diacetate In toluene at 110℃; for 24h; Inert atmosphere;	60%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + 2-methylbenzoindolium perchlorate (78915-06-7) → 2-[2-(5-benzyloxyindole-3-yl)vinyl]benzo[c,d]indolium perchlorate

Conditions	Yield
In ethanol at 45℃; for 0.166667h;	58%

4-Methoxyphenylacetic acid (104-01-8) + 5-benzyloxyindole-3-carboxaldehyde (6953-22-6) → (αE)-α-[[1-acetyl-5-(phenylmethoxy)-1H-indol-3-yl]methylene]-4-methoxybenzeneacetic acid (1450604-55-3)

Conditions	Yield
Stage #1: 4-Methoxyphenylacetic acid; 5-benzyloxyindole-3-carboxaldehyde With acetic anhydride; triethylamine at 130℃; for 6h; Stage #2: With water In tetrahydrofuran; ethanol at 22 - 90℃; for 16h;	56%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + acetophenone O-acetyloxime (19433-17-1) → 5-(benzyloxy)-3-(2,6-diphenylpyridin-4-yl)-1H-indole

Conditions	Yield
With pyridine; iodine In 1,4-dioxane at 110℃; regioselective reaction;	56%
With pyridine; iodine In 1,4-dioxane at 110℃; for 12h; Sealed tube;	56%

5-benzyloxyindole-3-carboxaldehyde (6953-22-6) + C16H15FN2 → 2-(benzyloxy)-11-fluoro-6-(4-methylphenyl)-5,8-dihydroindolo[3',2':3,4]azepino[1,2-a]benzimidazole

Conditions	Yield
With silver hexafluoroantimonate; (triphenylphosphine)gold(I) chloride In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 30h; Inert atmosphere;	53%

2,4-imidazolidinedione (461-72-3) + 5-benzyloxyindole-3-carboxaldehyde (6953-22-6) → (5Z)-5-(5-benzyloxy-3-indolylmethylene)-1,3-imidazolidine-2,4-dione

Conditions	Yield
With piperidine In ethanol at 70℃; for 24h; Knoevenagel Condensation;	52%

Upstream product

• 1953-54-4 indol-5-ol 
• 100-39-0 benzyl bromide 
• 79-37-8 oxalyl dichloride 
• 1215-59-4 5-benzyloxy-1H-indole 
• 6640-09-1 5-benzyloxy-1H-indole-2-carboxylic acid 
• 22424-58-4 5-benzyloxy-2-nitrotoluene 
• 2581-34-2 3-methyl-4-nitrophenol 
• 288-32-4 1H-imidazole 
• 68-12-2 N,N-dimethyl-formamide 
• 10025-87-3 trichlorophosphate 

Downstream Products

• 15997-55-4 5-(5-benzyloxy-indol-3-ylmethylene)-2-thioxo-thiazolidin-4-one 
• 380220-38-2 1-benzoyl-5-benzyloxy-1H-indole-3-carbaldehyde 
• 21987-24-6 5-(benzyloxy)-3-methyl-1H-indole 
• 1304522-65-3 5-benzyloxy-3-ethenyl-1-phenylsulfonyl-1H-indole 
• 914348-98-4 tert-butyl 5-benzyloxy-3-formyl-1H-indole-1-carboxylate 
• 1953-54-4 indol-5-ol 

Relevant articles and documents

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