| Identification | More | [Name]
5-FLUOROINDOLE-3-CARBOXALDEHYDE | [CAS]
2338-71-8 | [Synonyms]
5-FLUORO-1H-INDOLE-3-CARBALDEHYDE
5-FLUORO-1H-INDOLE-3-CARBOXALDEHYDE
5-FLUOROINDOLE-3-ALDEHYDE
5-FLUOROINDOLE-3-CARBALDEHYDE
5-FLUOROINDOLE-3-CARBOXALDEHYDE
AKOS JY2083653
TIMTEC-BB SBB002930
5-Fluoro-3-formylindole
5-Fluoro-3-indolecarboxaldehyde | [Molecular Formula]
C9H6FNO | [MDL Number]
MFCD00022719 | [Molecular Weight]
163.15 | [MOL File]
2338-71-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
164°C | [Boiling point ]
342.4±22.0 °C(Predicted) | [density ]
1.385±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [form ]
crystalline
| [pka]
14.66±0.30(Predicted) | [color ]
yellow to green
| [Sensitive ]
Air Sensitive | [BRN ]
1449216 | [InChI]
1S/C9H6FNO/c10-7-1-2-9-8(3-7)6(5-12)4-11-9/h1-5,11H | [InChIKey]
YUAJKGBLPVLADK-UHFFFAOYSA-N | [SMILES]
Fc1ccc2[nH]cc(C=O)c2c1 | [CAS DataBase Reference]
2338-71-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
5-Fluoroindole-3-carboxaldehyde is used as a reagent in the synthetic preparation of compounds requiring an indole group or more specifically a fluoroindole group. | [Synthesis]
GENERAL METHOD: Phosphoryl chloride (0.42 g, 2.74 mmol) was slowly added dropwise to a solution of N,N-dimethylformamide (0.84 g, 11.4 mmol) of 5-fluoroindole (0.30 g, 2.29 mmol) at 0 °C, the dropwise process lasted for 30 min. Subsequently, the reaction mixture was warmed up to 40 °C and kept for 1 hour. Upon completion of the reaction, ice was added to the reaction vessel followed by 2 M sodium hydroxide solution. The mixture was refluxed for 40 minutes. After the reaction solution was cooled to room temperature, it was extracted with ethyl acetate. The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with the eluent being a mixed solvent of petroleum ether-ethyl acetate to give the target compound 5-fluoroindole-3-carboxaldehyde [19]. | [References]
[1] Archiv der Pharmazie, 2017, vol. 350, # 1,
[2] Journal of the American Chemical Society, 2009, vol. 131, # 31, p. 10796 - 10797
[3] Marine Drugs, 2014, vol. 12, # 4, p. 1757 - 1772
[4] Patent: WO2015/90233, 2015, A1. Location in patent: Paragraph 00263
[5] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 344 - 367 |
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