5-METHYLINDOLE-3-CARBOXALDEHYDE

Bezeichnung:5-METHYLINDOLE-3-CARBOXALDEHYDE

CAS-Nr52562-50-2

Englisch Name:5-METHYLINDOLE-3-CARBOXALDEHYDE

CBNumberCB8438360

SummenformelC10H9NO

Molgewicht159.18

MOL-Datei52562-50-2.mol

5-METHYLINDOLE-3-CARBOXALDEHYDE physikalisch-chemischer Eigenschaften

Schmelzpunkt	148-151 °C(lit.)
Siedepunkt	348.2±22.0 °C(Predicted)
Dichte	1.226±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
pka	15.68±0.30(Predicted)
Aussehen	Off-white to pink Solid
InChI	1S/C10H9NO/c1-7-2-3-10-9(4-7)8(6-12)5-11-10/h2-6,11H,1H3
InChIKey	ZTNQWTPWKNDRNF-UHFFFAOYSA-N
SMILES	Cc1ccc2[nH]cc(C=O)c2c1
CAS Datenbank	52562-50-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	3
HazardClass	IRRITANT
HS Code	2933998090
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

5-METHYLINDOLE-3-CARBOXALDEHYDE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Verwenden
5-Methyl-1H-indole-3-carbaldehyde (cas# 52562-50-2) is a useful reagent for regio- and enantioselective preparation of N-alkylated indole- and pyrrole-3-carbaldehydes.
Verwenden
5-Methylindole-3-carboxaldehyde was used in the synthesis of novel flexible tripodal ligand derived from 3-methylindole and its mononuclear Zn(II),Cu(II), Ni(II), Hg(II) and Pd(II) complexes.
Synthese

614-96-0

68-12-2

52562-50-2

GENERAL STEPS: Oxalyl chloride (0.3 mL) was slowly added dropwise to cooled (ice bath) N,N-dimethylformamide (DMF, 3 mL) under stirring conditions. The reaction mixture was stirred continuously at 0 °C for 1 hour. Subsequently, a solution of 5-methylindole (4 mmol) dissolved in DMF (1.5 mL) was added slowly dropwise to the above reaction mixture. The resulting mixture was stirred and reacted at room temperature for 5 hours. Upon completion of the reaction, 2N sodium hydroxide solution (2 mL) was added and the mixture was heated to 100 °C and maintained for 10 min. The reaction solution was cooled and extracted with ethyl acetate (3 x 50 mL). The organic phases were combined and washed sequentially with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by fast column chromatography with the eluent of ethyl acetate/petroleum ether (3:1, v/v) to finally obtain the purified 5-methyl-1H-indole-3-carbaldehyde.
Einzelnachweise
[1] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 158 - 167
[2] Patent: EP1932833, 2008, A1. Location in patent: Page/Page column 11; 12
[3] Chemistry - A European Journal, 2016, vol. 22, # 2, p. 716 - 723
[4] Marine Drugs, 2014, vol. 12, # 4, p. 1757 - 1772
[5] European Journal of Medicinal Chemistry, 2012, vol. 52, p. 70 - 81

5-METHYLINDOLE-3-CARBOXALDEHYDE Upstream-Materialien And Downstream Produkte

5-METHYLINDOLE-3-CARBOXALDEHYDE Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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