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5-Benzyloxyindole-3-carboxaldehyde

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Name

5-Benzyloxyindole-3-carboxaldehyde

EINECS 230-134-7
CAS No. 6953-22-6 Density 1.267 g/cm3
PSA 42.09000 LogP 3.55940
Solubility N/A 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 N/A Appearance white to light yellow crystal powder
Safety 22-24/25-36/37-26 Risk Codes 36-43
Molecular Structure Molecular Structure of 6953-22-6 (5-(Phenylmethoxy)-1H-indole-3-carbaldehyde) Hazard Symbols IrritantXi
Synonyms

Indole-3-carboxaldehyde,5-(benzyloxy)- (7CI);5-Benzyloxy-1H-indole-3-carboxaldehyde;5-Benzyloxy-3-formylindole;5-Benzyloxy-3-indolecarboxaldehyde;NSC 71049;

Article Data 18

5-Benzyloxyindole-3-carboxaldehyde Synthetic route

288-32-4

1H-imidazole

1215-59-4

5-benzyloxy-1H-indole

6953-22-6

5-benzyloxyindole-3-carboxaldehyde

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

6953-22-6

5-benzyloxyindole-3-carboxaldehyde

Conditions
ConditionsYield
und Erwaermen des Reaktionsprodukts mit wss.Natronlauge oder mit wss.Natriumcarbonat-Loesung.;
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With N,N-dimethyl-formamide at 20℃; for 5h;

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
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