| Identification | More | [Name]
5-Chloroindole-3-carboxaldehyde | [CAS]
827-01-0 | [Synonyms]
5-CHLORO-1H-INDOLE-3-CARBALDEHYDE
5-CHLORO-1H-INDOLE-3-CARBOXALDEHYDE
5-CHLOROINDOLE-3-ALDEHYDE
5-CHLOROINDOLE-3-CARBOXALDEHYDE
TIMTEC-BB SBB003756
5-Chloro-3-formylindole
5-Chloro-3-indolecarboxaldehyde | [EINECS(EC#)]
627-809-7 | [Molecular Formula]
C9H6ClNO | [MDL Number]
MFCD00175291 | [Molecular Weight]
179.6 | [MOL File]
827-01-0.mol |
| Chemical Properties | Back Directory | [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 | [form ]
powder | [pka]
14.59±0.30(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [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 |
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