Indole-4-carboxaldehyde

Bezeichnung:Indole-4-carboxaldehyde

CAS-Nr1074-86-8

Englisch Name:Indole-4-carboxaldehyde

CBNumberCB0217303

SummenformelC9H7NO

Molgewicht145.16

MOL-Datei1074-86-8.mol

Indole-4-carboxaldehyde physikalisch-chemischer Eigenschaften

Schmelzpunkt	139-143 °C(lit.)
Siedepunkt	339.1±15.0 °C(Predicted)
Dichte	1.278±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	DMF: 10 mg/ml; DMSO: 3 mg/ml; Ethanol: 10 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
Aggregatzustand	powder to crystal
pka	15.84±0.30(Predicted)
Farbe	Light yellow to Brown
Wasserlöslichkeit	Soluble in ethanol and acetone. Insoluble in water.
Sensitive	Air Sensitive
InChI	InChI=1S/C9H7NO/c11-6-7-2-1-3-9-8(7)4-5-10-9/h1-6,10H
InChIKey	JFDDFGLNZWNJTK-UHFFFAOYSA-N
SMILES	N1C2=C(C(C=O)=CC=C2)C=C1
CAS Datenbank	1074-86-8(CAS DataBase Reference)
NIST chemische Informationen	1H-indole-4-carboxaldehyde(1074-86-8)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	22-36-43
S-Sätze:	26-36/37
WGK Germany	3
Hazard Note	Irritant/Keep Cold
HazardClass	IRRITANT
HS Code	29333990

Gefahreninformationscode (GHS)

Indole-4-carboxaldehyde Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36:Reizt die Augen.
R43:Sensibilisierung durch Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
Chemische Eigenschaften
White to dark brown solid
Verwenden
4-Indolecarbaldehyde is a synthetic intermediate used for pharmaceutical synthesis. Also used as reactant in Biginelli reaction, synthesis of aurora kinase A inhibitors, preparation of antitumor agents, intermolecular Friedel-Crafts acylation, preparation of inhibitors of cell division in E. coli and synthesis of Hantzsch pyridine-containing Schiff bases.
Verwenden
Indole-4-carboxaldehyde is usually used as reactant in Biginelli reaction,preparation of antitumor agents,intramolecular Friedel-Crafts acylation,preparation of inhibitors of cell division in E. Coli,synthesis of Hantzsch pyridine-containing Schiff bases.
Definition
ChEBI: Indole-4-carbaldehyde is a heteroarenecarbaldehyde that is indole in which the hydrogen at position 4 has been replaced by a formyl group. It has a role as an algal metabolite. It is a member of indoles and a heteroarenecarbaldehyde.
Synthesis Reference(s)
The Journal of Organic Chemistry, 46, p. 1752, 1981 DOI: 10.1021/jo00321a053
Tetrahedron, 39, p. 3695, 1983 DOI: 10.1016/S0040-4020(01)88608-7
Allgemeine Beschreibung
Indole-4-carboxaldehyde participates in the synthesis of arcyriacyanin A. Synthesis of 4-indole-4-carboxaldehyde has been reported. Intramolecular Friedel-Crafts (FC) acylation of indole-4-carboxaldehyde has been reported.
Synthese
Tetrapropylammonium perruthenate (0.3 g, 0.85 mmol) was added in portions to a mixture of alcohol product from 1H-Indole-4-Methanol (2.5 g, 17 mmol), N-methylmorpholine N-oxide (3.0 g, 25 mmol) and 4 A molecular sieves (3.0 g) in anhydrous methylene chloride (30 mL) at room temperature. The mixture was stirred at room temperature under nitrogen for 1 h and then filtered. The filtrate was concentrated in vacuo, and the residue was purified by chromatography (SiO2, CH2Cl2) to provide Indole-4-carboxaldehyde as a white powder (2.0 g, 80percent): 1H NMR (300 MHz, CDCl3) δ10.2 (s, 1H), 8.52 (br s, 1H), 7.64-7.69 (m, 2H), 7.31-7.44 (m, 3H), CI MS m/z=146 [C9H7NO+H]+.

Indole-4-carboxaldehyde Upstream-Materialien And Downstream Produkte

Indole-4-carboxaldehyde Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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