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487-89-8

Basic Information
CAS No.: 487-89-8
Name: Indole-3-carboxaldehyde
Molecular Structure:
Molecular Structure of 487-89-8 (Indole-3-carboxaldehyde)
Formula: C9H7NO
Molecular Weight: 145.16
Synonyms: 3-Indolecarboxaldehyde;.beta.-Indolylaldehyde;5-21-08-00246 (Beilstein Handbook Reference);1H-Indole-3-carboxaldehyde;beta-Indolylaldehyde;3-Indolealdehyde;246045-99-8;3-Formylindole;1H-indole-3-carbaldehyde;3-Indolecarbaldehyde;
EINECS: 207-665-8
Density: 1.278 g/cm3
Melting Point: 193-198 °C(lit.)
Boiling Point: 339.1 °C at 760 mmHg
Flash Point: 166.8 °C
Solubility: Insoluble in water.
Appearance: off-white to beige-brown crystalline powder
Hazard Symbols: IrritantXi
Risk Codes:
Safety: 22-24/25
Transport Information:
PSA: 32.86000
LogP: 1.98040
Synthetic route
118481-30-4

1-(methanesulfonyl)-1H-indole-3-carboxaldehyde

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 1h; Heating;100%
57476-50-3

1-tert-butoxycarbonyl-3-formylindole

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With potassium phosphate In methanol at 120℃; under 5171.62 Torr; for 0.0333333h; Microwave irradiation;100%
With sodium carbonate In 1,2-dimethoxyethane; water for 1.5h; Heating;98%
In various solvent(s) at 150℃; for 0.0833333h; microwave irradiation;96%
22948-94-3

1-acetyl-3-indolylcarbaldehyde

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With polymer-supported potassium thiophenolate In tetrahydrofuran; methanol at 20℃; for 3h;99%

1-pivaloyl-1H-indole-3-carbaldehyde

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane at 40 - 45℃; for 2h;99%
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -78 - 45℃; for 2h; Inert atmosphere;99%
120-72-9

indole

68-12-2, 33513-42-7

N,N-dimethyl-formamide

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With trichlorophosphate at 0 - 35℃; for 2.08333h;98%
With trichlorophosphate at 0 - 55℃; for 2h;98%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 2℃; for 0.5h; Vilsmeier-Haack Formylation;
Stage #2: indole at 35℃; for 1h; Vilsmeier-Haack Formylation;
Stage #3: With water; sodium hydroxide for 0.5h; Reflux;
98%
700-06-1

indole-3-carbinol

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide for 8h; Ambient temperature;98%
With 1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide In acetonitrile for 0.0333333h; Irradiation;90%
With LACTIC ACID; dihydrogen peroxide at 30℃; for 7h;87%
120-72-9

indole

64-18-6

formic acid

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With chloro-trimethyl-silane; 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;88%
2592-05-4

1H-indole-3-carboxaldehyde oxime

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With copper(II) choride dihydrate; water In acetonitrile at 75℃; for 1h;88%
With iron(III) chloride In N,N-dimethyl-formamide at 25℃; for 0.666667h; sonication;76%
141692-10-6

(3-formylindol-4-yl)thallium (III) bistrifluoroacetate

78-94-4

methyl vinyl ketone

A

487-89-8

Indole-3-carboxaldehyde

B

4-(3-formylindol-4-yl)-3-buten-2-one

Conditions
ConditionsYield
palladium diacetate In N,N-dimethyl-formamide at 120℃;A n/a
B 86%
87-52-5

3-(Dimethylaminomethyl)indole

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With pyridinium chlorochromate In N,N-dimethyl-formamide at 100℃; for 0.5h; Reagent/catalyst;85%
Stage #1: 3-(Dimethylaminomethyl)indole With iodine; sodium carbonate In 1,4-dioxane at 20℃; for 12h;
Stage #2: With water In 1,4-dioxane for 3h; Reagent/catalyst; Solvent;
81%
With hexamethylenetetramine; water; propionic acid
Multi-step reaction with 2 steps
1: PhIO/TMSN3
2: water
View Scheme
171734-95-5

1-<2-(2-bromophenyl)-1-oxoethyl>-1H-indole-3-carboxaldehyde

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II); N-benzyl-N,N,N-triethylammonium chloride In N,N-dimethyl-formamide85%
51597-80-9

N-((1H-indol-3-yl)methyl)aniline

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With tert.-butylhydroperoxide; ruthenium(III)chloride hydrate; trimethylpyruvic acid In N-methyl-acetamide at 25℃; for 24h; Inert atmosphere;85%
With tert-Butyl peroxybenzoate; tetra-(n-butyl)ammonium iodide; Trimethylacetic acid In dimethyl sulfoxide at 80℃; for 8h; Inert atmosphere;70%
771-50-6

1H-indole-3-carboxylic acid

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With D-Glucose; Escherichia coli endogenous alcohol dehydrogenase; Segniliparus rugosus carboxylic acid reductase; dimethyl sulfoxide; magnesium chloride In aq. phosphate buffer at 30℃; for 7h; pH=8; Reagent/catalyst; Enzymatic reaction;85%
Stage #1: 1H-indole-3-carboxylic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; Inert atmosphere;
Stage #2: With manganese(IV) oxide In acetonitrile at 20℃; Inert atmosphere;
With D-Glucose; Bacillus subtilis glucose dehydrogenase; Segniliparus rugosus carboxylic acid reductase; nicotinamide adenine dinucleotide phosphate; dimethyl sulfoxide; ATP; magnesium chloride In aq. phosphate buffer at 30℃; for 18h; pH=7.5; Enzymatic reaction;
With 2,6-dimethylpyridine; nickel(II) bromide trihydrate; phenylsilane; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc; dimethyl dicarbonate In ethyl acetate at 60℃; for 24h; Schlenk technique; Inert atmosphere;54 %Chromat.
36104-60-6

3-(1,3-dithiolan-2-yl)-1H-indole

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; water; mercury(II) oxide In tetrahydrofuran for 1h; Ambient temperature;84%
120-72-9

indole

100-61-8

N-methylaniline

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With tert-Butyl peroxybenzoate; Trimethylacetic acid In dimethyl sulfoxide at 80℃; for 8h; Inert atmosphere;82%
With tert.-butylhydroperoxide; ruthenium(III)chloride hydrate; trimethylpyruvic acid In N-methyl-acetamide at 25℃; for 24h; Inert atmosphere; regioselective reaction;81%

bis(2,2,2-trichloroethyl) 2-(1H-indol-3-yl)-1H-imidazole-1,3(2H)-dicarboxylate

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With water; ammonium chloride; zinc In methanol at 60℃; for 2h;82%
120-72-9

indole

39687-95-1

isocyanoacetic acid methyl ester

68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

487-89-8

Indole-3-carboxaldehyde

B

81467-45-0

methyl (Z)-2-(dimethylaminomethyleneamino)-3-<3(1H)-indolyl>acrylate

Conditions
ConditionsYield
With sodium carbonate; trichlorophosphate In methanol at 25℃; for 24h; (One-pot);A 9%
B 80%
369644-20-2

1-(2-azido-ethyl)-1H-indole-3-carbaldehyde

A

487-89-8

Indole-3-carboxaldehyde

B

2,3-dihydro-1H-imidazo[1,2-a]indole-9-carbaldehyde

Conditions
ConditionsYield
In various solvent(s) at 180℃;A 20%
B 80%
40614-43-5

4-carboxyquinoline 1-oxide

A

487-89-8

Indole-3-carboxaldehyde

B

15733-89-8

2-quinolone-4-carboxylic acid

Conditions
ConditionsYield
In methanol for 0.666667h; Irradiation;A 6.3%
B 79%
In methanol for 0.666667h; Irradiation;A 6.3%
B 79%

indole-3-carbaldehyde dimethylhydrazone

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate; diethylazodicarboxylate In acetonitrile at 60℃; for 11h;77%
120-72-9

indole

110-18-9

N,N,N,N,-tetramethylethylenediamine

487-89-8

Indole-3-carboxaldehyde

Conditions
ConditionsYield
With water; iodine; oxygen; sodium carbonate In 1,4-dioxane at 100℃; under 760.051 Torr; for 36h; Schlenk technique; Sealed tube;75%
With water; oxygen; potassium iodide In acetonitrile at 25℃; under 750.075 Torr; for 48h; Irradiation;67%
With water; oxygen; rose bengal; potassium iodide In acetonitrile at 60℃; for 48h; Irradiation;52%
With potassium carbonate; copper dichloride In acetonitrile for 1h; Reflux;43%
With water; oxygen; potassium iodide In acetonitrile at 25℃; under 750.075 Torr; for 36h; Irradiation;35%
487-89-8

Indole-3-carboxaldehyde

79-24-3

Nitroethane

64252-02-4

3-(β-nitro-β-methylvinyl)indole

Conditions
ConditionsYield
With ammonium acetate for 6h; Henry reaction; Reflux;100%
With ethylenediamine for 3h; Reflux;95%
With ammonium acetate In benzene Reflux;94%
487-89-8

Indole-3-carboxaldehyde

74-89-5

methylamine

22980-06-9

3-(N-methylformimidoyl)-1H-indole

Conditions
ConditionsYield
With magnesium sulfate In methanol; dichloromethane for 7h; Heating;100%
With water
In water 1.) 40 - 45 deg C, 15 min, 2.) room temp., 4 h; Yield given;
487-89-8

Indole-3-carboxaldehyde

700-06-1

indole-3-carbinol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; for 1h;100%
With formic acid In ethanol at 80℃; for 12h; Catalytic behavior;91%
With ammonia; calcium In tetrahydrofuran at -33℃; for 2h; other reagents: lithium, sodium, liq. ammonia;80%
487-89-8

Indole-3-carboxaldehyde

14267-92-6

1-chloro-4-pentyne

110206-34-3

1-(4-pentenyl)-1H-indole-3-carboxaldehyde

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 75℃; for 5h; Alkylation;100%
With sodium hydride 1.) DMF, 70 deg C, 30 min, 2.) DMF, RT, 1 h; Yield given. Multistep reaction;
With sodium hydride 1.) DMF, RT, 10 min, 2.) DMF, from 70 to 80 deg C, 2 h; Multistep reaction;
Stage #1: 1-chloro-4-pentyne With sodium iodide In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere;
Stage #2: Indole-3-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil for 48h; Inert atmosphere;
487-89-8

Indole-3-carboxaldehyde

24424-99-5

di-tert-butyl dicarbonate

57476-50-3

1-tert-butoxycarbonyl-3-formylindole

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at 0℃; for 1.83333h; Substitution;100%
With dmap; triethylamine In dichloromethane at 20℃;100%
With dmap; triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere;100%
487-89-8

Indole-3-carboxaldehyde

105-36-2

ethyl bromoacetate

27065-94-7

(3-formylindol-1-yl)acetic acid ethyl ester

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 15 - 20℃; for 16.5h;100%
Stage #1: Indole-3-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide
Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide at 20℃; for 16h;
100%
With sodium hydride In DMF (N,N-dimethyl-formamide) at 15 - 20℃; for 16.5h;100%
487-89-8

Indole-3-carboxaldehyde

501-53-1

benzyl chloroformate

74639-50-2

N-benzyloxycarbonyl-indole-3-carbaldehyde

Conditions
ConditionsYield
With dmap; sodium carbonate In water; acetonitrile at 20℃; for 24h;100%
With triethylamine In tetrahydrofuran 1) 3-5 deg C, 0.5 h; 2) room temperature, 2 h;96%
Stage #1: Indole-3-carboxaldehyde With triethylamine In dichloromethane at 0 - 20℃; for 1h;
Stage #2: benzyl chloroformate In dichloromethane for 18h;
92%
487-89-8

Indole-3-carboxaldehyde

22259-53-6

3-aminomethylindole

Conditions
ConditionsYield
Stage #1: Indole-3-carboxaldehyde With hydrogenchloride; ammonia In methanol; water for 5h;
Stage #2: With hydrogen; Raney nickel In methanol; water under 3102.97 Torr;
100%
With ammonium acetate; sodium cyanoborohydride; acetic acid
Stage #1: Indole-3-carboxaldehyde With ammonia; ammonium chloride In methanol for 5h;
Stage #2: With hydrogen; nickel In methanol; water under 3102.89 Torr;
487-89-8

Indole-3-carboxaldehyde

75-36-5

acetyl chloride

22948-94-3

1-acetyl-3-indolylcarbaldehyde

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane Heating;100%
With triethylamine In dichloromethane for 1h; Acetylation; Heating;98%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane90%
With triethylamine In tetrahydrofuran at 20℃; for 3h;
487-89-8

Indole-3-carboxaldehyde

benzyl halide

benzyl halide

10511-51-0

1-Benzylindole-3-carboxaldehyde

Conditions
ConditionsYield
Stage #1: Indole-3-carboxaldehyde With sodium hydride In acetonitrile
Stage #2: benzyl halide In acetonitrile
100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;87%
With potassium carbonate In acetone Alkylation;85%
487-89-8

Indole-3-carboxaldehyde

79-22-1

methyl chloroformate

111168-43-5

1-methoxycarbonylindole-3-carboxaldehyde

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane Heating;100%
Stage #1: Indole-3-carboxaldehyde With sodium hydride In acetonitrile; mineral oil at 20℃; for 0.0833333h;
Stage #2: methyl chloroformate In acetonitrile; mineral oil for 0.166667h;
85%
Stage #1: Indole-3-carboxaldehyde With sodium hydride In acetonitrile; mineral oil at 20℃; for 0.0833333h;
Stage #2: methyl chloroformate In acetonitrile; mineral oil at 20℃; for 0.166667h;
85%
487-89-8

Indole-3-carboxaldehyde

539-74-2

Ethyl 3-bromopropionate

503829-88-7

3-(3-formyl-indol-1-yl)-propionic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 48h; Heating / reflux;100%
With potassium carbonate In acetonitrile for 48h; Heating / reflux;100%
With potassium carbonate In acetonitrile for 48h; Heating / reflux;100%
With potassium carbonate In acetonitrile for 48h; Heating / reflux;100%
With potassium carbonate In acetonitrile for 48h;
487-89-8

Indole-3-carboxaldehyde

6272-26-0

6-hydroxybenzofuran-3-one

(2Z)-6-hydroxy-2-(1H-indol-3-ylmethylene)-1-benzofuran-3(2H)-one

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 75℃; for 5h;100%
With hydrogenchloride In methanol
487-89-8

Indole-3-carboxaldehyde

74-89-5

methylamine

C10H10N2

Conditions
ConditionsYield
at 20℃; for 12h;100%
With sodium sulfate In chloroform at 20℃; for 48h;
487-89-8

Indole-3-carboxaldehyde

2,6-dichlorobenzoyl halide

2,6-dichlorobenzoyl halide

336187-82-7

C16H9Cl2NO2

Conditions
ConditionsYield
Stage #1: Indole-3-carboxaldehyde With sodium hydride In acetonitrile
Stage #2: 2,6-dichlorobenzoyl halide In acetonitrile
100%
487-89-8

Indole-3-carboxaldehyde

4-chlorobenzoyl halide

4-chlorobenzoyl halide

62189-77-9

1-(4-chlorobenzoyl)indole-3-carbaldehyde

Conditions
ConditionsYield
Stage #1: Indole-3-carboxaldehyde With sodium hydride In acetonitrile
Stage #2: 4-chlorobenzoyl halide In acetonitrile
100%
487-89-8

Indole-3-carboxaldehyde

allyl halide

allyl halide

111480-86-5

1-Allyl-1H-indole-3-carboxaldehyde

Conditions
ConditionsYield
Stage #1: Indole-3-carboxaldehyde With sodium hydride In acetonitrile
Stage #2: allyl halide In acetonitrile
100%
Stage #1: Indole-3-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h;
Stage #2: allyl halide In N,N-dimethyl-formamide; mineral oil for 2h;
45%
Stage #1: Indole-3-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h;
Stage #2: allyl halide In N,N-dimethyl-formamide; mineral oil
45%
487-89-8

Indole-3-carboxaldehyde

benzoyl halide

benzoyl halide

27092-42-8

1-benzoyl-1H-indole-3-carbaldehyde

Conditions
ConditionsYield
Stage #1: Indole-3-carboxaldehyde With sodium hydride In acetonitrile
Stage #2: benzoyl halide In acetonitrile
100%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane; water
487-89-8

Indole-3-carboxaldehyde

cinnamyl halide

cinnamyl halide

1257094-79-3

C18H15NO

Conditions
ConditionsYield
Stage #1: Indole-3-carboxaldehyde With sodium hydride In acetonitrile
Stage #2: cinnamyl halide In acetonitrile
100%
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  • Indole-3-carboxaldehyde       CAS: 487-89-8

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    Indole-3-carboxaldehyde CAS: 487-89-8

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    Indole-3-carboxaldehyde

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Chemistry

Molecular Structure of 3-Formylindole (CAS No.487-89-8):

Molecular Formula: C9H7NO
Molecular Weight: 145.157980
IUPAC Name: 1H-Indole-3-carbaldehyde
CAS No: 487-89-8
EINECS: 207-665-8
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 32.86 Å2
Index of Refraction: 1.729
Molar Refractivity: 45.28 cm3
Molar Volume: 113.5 cm3
Surface Tension: 59.8 dyne/cm
Density: 1.278 g/cm3
Flash Point: 166.8 °C
Enthalpy of Vaporization: 58.25 kJ/mol
Boiling Point: 339.1 °C at 760 mmHg
Vapour Pressure: 9.42E-05 mmHg at 25°C
Melting Point: 193-198 °C(lit.)
Storage Temp.: Keep Cold
Sensitive: Air Sensitive
Appearance: Off-white to beige-brown crystalline powder
Classification Code: Drug/Therapeutic Agent
Product Categories: Aldehyde;Aldehydes;blocks;IndolesOxindoles;indole derivative;Indoles and derivatives;Pyrroles Indoles;Indoles;Simple Indoles;Pyrroles Indoles;Building Blocks;Heterocyclic Building Blocks

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo intraperitoneal 600mg/kg (600mg/kg) AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)"

BEHAVIORAL: ANTICONVULSANT

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Pharmaceutical Chemistry Journal Vol. 6, Pg. 33, 1972.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Safety Information of 3-Formylindole (CAS No.487-89-8):
Hazard Codes: IrritantXi
Safety Statements: 22-24/25 
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: NL5993600
F: 9-23
Hazard Note: Irritant/Keep Cold
HazardClass: IRRITANT
HS Code: 29339990

Specification

  3-Formylindole (CAS No.487-89-8), it also can be called Indol-3-carboxaldehyde ; Indole-3-aldehyde ; beta-Indolylaldehyde ; 1H-Indole-3-carboxaldehyde .
  Storage of 3-Formylindole (487-89-8): Store in a cool dry place. Keep container closed.