5-Benzyloxyindole-3-carboxaldehyde supplier

Name
5-(Phenylmethoxy)-1H-indole-3-carbaldehyde
EINECS 230-134-7
CAS No. 6953-22-6
Article Data18
CAS DataBase
Density 1.267 g/cm³
Solubility
Melting Point 237-238 °C
Formula C₁₆H₁₃NO₂
Boiling Point 474.2 °C at 760 mmHg
Molecular Weight 251.285
Flash Point 240.6 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 22-24/25-36/37-26
Risk Codes 36-43
Molecular Structure
Hazard Symbols Xi
Synonyms Indole-3-carboxaldehyde,5-(benzyloxy)- (7CI);5-Benzyloxy-1H-indole-3-carboxaldehyde;5-Benzyloxy-3-formylindole;5-Benzyloxy-3-indolecarboxaldehyde;NSC 71049;
PSA 42.09000
LogP 3.55940

Synthetic route

: 288-32-4
1H-imidazole

: 1215-59-4
5-benzyloxy-1H-indole

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

Conditions

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%

: 1215-59-4
5-benzyloxy-1H-indole

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

Conditions

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

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

Conditions

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%

: 1215-59-4
5-benzyloxy-1H-indole

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 10025-87-3, 12599-09-6, 63736-95-8
trichlorophosphate

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

Conditions

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

...Expand

: 2581-34-2
3-methyl-4-nitrophenol

2-nitro-m-cresol; 6-nitro-m-cresol: 2-nitro-m-cresol; 6-nitro-m-cresol

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

Conditions

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

: 22424-58-4
5-benzyloxy-2-nitrotoluene

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

Conditions

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

: 100-39-0
benzyl bromide

CO: CO

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

Conditions

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

: 6640-09-1
5-benzyloxy-1H-indole-2-carboxylic acid

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

Conditions

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

: 1215-59-4
5-benzyloxy-1H-indole

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 79-37-8
oxalyl dichloride

: 1215-59-4
5-benzyloxy-1H-indole

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

Conditions

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

: 1953-54-4
indol-5-ol

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

Conditions

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

: 100-39-0
benzyl bromide

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

Conditions

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

: 1953-54-4
indol-5-ol

: 100-39-0
benzyl bromide

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

Conditions

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

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 74-88-4
methyl iodide

: 58630-07-2
5-(benzyloxy)-1-methyl-1H-indole-3-carbaldehyde

Conditions

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;

: 622-97-9
1-ethenyl-4-methylbenzene

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 5-(benzyloxy)-1-(1-(p-tolyl)vinyl)-1H-indole-3-carbaldehyde

Conditions

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%

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 33208-99-0
(S)-alaninamide hydrochloride

: (S)-2-((5-(benzyloxy)-1H-indol-3-yl)methylamino)propanamide

Conditions

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%

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 194490-25-0
5-benzyloxy-1H-indole-3-carbonitrile

Conditions

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

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 21987-24-6
5-(benzyloxy)-3-methyl-1H-indole

Conditions

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

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 98-09-9
benzenesulfonyl chloride

: 1000056-62-1
5-benzyloxy-1-phenylsulfonyl-1H-indole-3-carboxaldehyde

Conditions

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;

: 110-89-4
piperidine

: 141-84-4
2-thioxo-4-thiazolidinone

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 1315457-00-1
5-[(5-benzyloxy-1H-indol-3-yl)methylene]-2-(1-piperidinyl)rhodanine

Conditions

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

...Expand

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 108-24-7
acetic anhydride

: 1-acetyl-5-(benzyloxy)-1H-indole-3-carbaldehyde

Conditions

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%

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 98-59-9
p-toluenesulfonyl chloride

: 5-benzyloxy-1-tosyl-1H-indole-3-carboxaldehyde

Conditions

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%

: 3326-71-4
2-furoic acid hydrazide

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: N’-{(E)-[5-(benzyloxy)-1H-indol-3-yl]methylidene}furan-2-carbohydrazide

Conditions

Conditions	Yield
In ethanol Reflux;	76%

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 75-03-6
ethyl iodide

: 5-benzyloxy-1-ethyl-1H-indole-3-carboxaldehyde

Conditions

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%

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 31385-19-0
1,2,6-trimethylquinolin-1-ium iodide

: 3-[2-(1,6-Dimethyl-quinolium-2-yl)-vinyl]-1H-5-benzyloxy-indole iodide

Conditions

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

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 98-88-4
benzoyl chloride

: 380220-38-2
1-benzoyl-5-benzyloxy-1H-indole-3-carbaldehyde

Conditions

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

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 75-36-5
acetyl chloride

: 1-acetyl-5-(benzyloxy)-1H-indole-3-carbaldehyde

Conditions

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

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: C14H17NO3S

: 3-[2-(1-propanesulfonate-quinolium-2-yl)-vinyl]-1H-5-benzyloxy-indole

Conditions

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

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 2582-30-1
aminoguanidine bicarbonate

: 3-<<5-(benzyloxy)-1H-indol-3-yl>methylene>carbazimidamide hydrochloride

Conditions

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

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 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

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

: 2295-31-0
2,4-thiazolidinedion

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: (5Z)-5-(5-benzyloxy-3-indolylmethylene)-1,3-thiazolidine-2,4-dione

Conditions

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

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 141-97-9
ethyl acetoacetate

: 1353122-23-2
4-[(5-benzyloxy-1H-indole-3-yl)-methylene]-3-methyl-isoxazole-5-one

Conditions

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

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 6547-53-1
2-[4-(benzyloxy)benzyl]acetic acid

: 1450604-63-3
(αE)-α-[[1-acetyl-5-(phenylmethoxy)-1H-indol-3-yl]methylene]-4-phenylmethoxybenzeneacetic acid

Conditions

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%

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 501-65-5
diphenyl acetylene

: 2-(benzyloxy)-6,7,8,9-tetraphenylpyrido[1,2-a]indole-10-carbaldehyde

Conditions

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

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 78915-06-7
2-methylbenzoindolium perchlorate

: 2-[2-(5-benzyloxyindole-3-yl)vinyl]benzo[c,d]indolium perchlorate

Conditions

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

: 104-01-8
4-Methoxyphenylacetic acid

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 1450604-55-3
(αE)-α-[[1-acetyl-5-(phenylmethoxy)-1H-indol-3-yl]methylene]-4-methoxybenzeneacetic acid

Conditions

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%

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: 19433-17-1
acetophenone O-acetyloxime

: 5-(benzyloxy)-3-(2,6-diphenylpyridin-4-yl)-1H-indole

Conditions

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%

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: C16H15FN2

: 2-(benzyloxy)-11-fluoro-6-(4-methylphenyl)-5,8-dihydroindolo[3',2':3,4]azepino[1,2-a]benzimidazole

Conditions

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

: 461-72-3
2,4-imidazolidinedione

: 6953-22-6
5-benzyloxyindole-3-carboxaldehyde

: (5Z)-5-(5-benzyloxy-3-indolylmethylene)-1,3-imidazolidine-2,4-dione

Conditions

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

5-Benzyloxyindole-3-carboxaldehyde Chemical Properties

Molecular Structure of 5-Benzyloxyindole-3-carboxaldehyde(6953-22-6):

IUPAC Name:5-phenylmethoxy-1H-indole-3-carbaldehyde
Molecular Formula:C₁₆H₁₃NO₂
Molecular Weight:251.279920 g/mol
Appearance:white to light yellow crystal powder
Melting Point:237-238 °C
Density:1.267 g/cm³
Flash Point:240.6 °C
Enthalpy of Vaporization:73.74 kJ/mol
Boiling Point:474.2 °C at 760 mmHg
Vapour Pressure:3.7E-09 mmHg at 25°C
Water Solubility:21.18 mg/L at 25 °C
Sensitive:Air
EINECS:230-134-7
Synonyms of 5-Benzyloxyindole-3-carboxaldehyde(6953-22-6):
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
Categories of 5-Benzyloxyindole-3-carboxaldehyde(6953-22-6):
blocks;Carboxes;IndolesOxindoles;Indoles and derivatives;Indoline & Oxindole;Indoles;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;Heterocyclic Building Blocks

5-Benzyloxyindole-3-carboxaldehyde Uses

5-Benzyloxyindole-3-carboxaldehyde(6953-22-6) is used as a pharmaceutical intermediate.

5-Benzyloxyindole-3-carboxaldehyde Safety Profile

Safety Information of 5-Benzyloxyindole-3-carboxaldehyde(6953-22-6):
Hazard Codes:Xi

Risk Statements:36-43
36:Irritating to the eyes
43:May cause sensitization by skin contac
Safety Statements:22-24/25-36/37-26
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
36/37:Wear suitable protective clothing and gloves
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany:3

Product Name

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

Synthetic route

5-Benzyloxyindole-3-carboxaldehyde Chemical Properties

5-Benzyloxyindole-3-carboxaldehyde Uses

5-Benzyloxyindole-3-carboxaldehyde Safety Profile

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