5-Chloroindole-3-carboxaldehyde Chemical Properties

Melting point:

213-216 °C (lit.)

Boiling point:

373.4±22.0 °C(Predicted)

Density 

1.431±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

14.59±0.30(Predicted)

form 

powder

color 

Light orange

Sensitive 

Air Sensitive

BRN 

123794

InChI

InChI=1S/C9H6ClNO/c10-7-1-2-9-8(3-7)6(5-12)4-11-9/h1-5,11H

InChIKey

YXEXOIGXNYITQH-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(Cl)C=C2)C(C=O)=C1

CAS DataBase Reference

827-01-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36-36/37/39-22

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

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

5-Chloroindole-3-carboxaldehyde Usage And Synthesis

Chemical Properties

Yellow to beige solid

Uses

5-Chloroindole-3-carboxaldehyde (5-Chloro-1H-indole-3-carboxaldehyde) may be used in the preparation of:

• 5-chloroindole-3-carboxaldehyde isonicotinoyl hydrazine
• 2′-[(5-chloro-1H-indol-3-yl)methyl-ene]-2-(1H-indol-3-yl)acetohydrazide
• 5-chloro-3-(2,2-dibromovinyl)-1-(2-trimethylsilylethoxymethyl)indole

It may also be used in the preparation of the following hydrazone derivatives:

• 5-chloroindole-3-carboxaldehyde 3-chlorobenzoylhydrazone
• 5-chloroindole-3-carboxaldehyde 4-nitrobenzoylhydrazone
• 5-chloroindole-3-carboxaldehyde 3-methylbenzoylhydrazone
• 5-chloroindole-3-carboxaldehyde 4-methylbenzoylhydrazone

General Description

5-Chloroindole-3-carboxaldehyde, also known as 5-chloro-1H-indole-3-carboxaldehyde, is an indole derivative.

Synthesis

The general procedure for the synthesis of 5-chloroindole-3-carbaldehyde from 5-chloroindole was as follows: phosphorus trichloride (4.6 mL, 49 mmol) was added slowly and dropwise to stirred dimethylformamide (20 mL) at 0 °C. After the dropwise addition, the reaction mixture was continued to be stirred for 10 minutes. Subsequently, a solution of 5-chloroindole (5.0 g, 33 mmol) dissolved in dimethylformamide (5 mL) was added slowly dropwise. After completion of the dropwise addition, the reaction mixture was heated to 40°C and kept at this temperature for 45 minutes. After completion of the reaction, the mixture was cooled to room temperature and then treated with a solution of sodium hydroxide (5.9 g, 148 mmol) in water (20 mL). Next, the mixture was heated to 50°C, held for 10 minutes and then cooled to room temperature. The reaction mixture was poured into crushed ice (100 mL) and the precipitate was collected by filtration. Finally, the filter cake was recrystallized by methanol to give the white solid product 5-chloroindole-3-carboxaldehyde (3.5 g, 59% yield) with a melting point of 215-216 °C. Elemental analysis measured values: C, 60.13; H, 3.40; N, 7.75%. Consistent with theoretical values (C9H6ClNO): C, 60.19; H, 3.37; N, 7.79%.

References

[1] Patent: US6433175, 2002, B1
[2] Patent: US3953442, 1976, A

5-Chloroindole-3-carboxaldehyde(827-01-0)Related Product Information

• Indometacin
• 5-Chloroindole-3-carboxylic acid
• 5-Bromoindole
• Indole-3-acetic acid
• Indole-3-butyric acid
• 5-Chloroindole
• Indole
• 5-CHLORO-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER
• 5-CHLOROINDOLE-3-ACETIC ACID
• Methyl 2-(5-chloro-1H-indol-3-yl)acetate
• 5-CHLOROTRYPTOPHOL
• 5-CHLOROISOINDOLINE HYDROCHLORIDE
• Ethyl 5-chloroiMidazo[1,2-a]pyrazine-2-carboxylate
• 5-ChloroiMidazo[1,2-a]pyrazine-2-carboxylic acid
• 5-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER
• Difluorochloromethane
• 5-BROMO-1H-INDOLE-2-CARBALDEHYDE
• Indole-3-carboxaldehyde