Indol-2-carbonsure

Bezeichnung:Indol-2-carbonsure

CAS-Nr1477-50-5

Englisch Name:Indole-2-carboxylic acid

CBNumberCB7728231

SummenformelC9H7NO2

Molgewicht161.16

MOL-Datei1477-50-5.mol

Synonyma

Indol-2-carbonsure

Indol-2-carbonsure physikalisch-chemischer Eigenschaften

Schmelzpunkt	202-206 °C(lit.)
Siedepunkt	287.44°C (rough estimate)
Dichte	1.2480 (rough estimate)
Brechungsindex	1.5050 (estimate)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	Soluble in clear yellow solution 5% in ethanol, dimethyl sulfoxide and methanol.
pka	4.44±0.30(Predicted)
Aggregatzustand	Crystalline Powder or Crystals
Farbe	Off-white to yellow to brown
BRN	124132
InChI	InChI=1S/C9H7NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h1-5,10H,(H,11,12)
InChIKey	HCUARRIEZVDMPT-UHFFFAOYSA-N
SMILES	N1C2=C(C=CC=C2)C=C1C(O)=O
CAS Datenbank	1477-50-5(CAS DataBase Reference)
NIST chemische Informationen	Indole-2-carboxylic acid(1477-50-5)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	36/37/38-21/22
S-Sätze:	22-24/25
WGK Germany	3
RTECS-Nr.	NK7882812
HazardClass	IRRITANT
HS Code	29339990
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

Indole-2-carboxylic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R21/22:Gesundheitsschädlich bei Berührung mit der Haut und beim Verschlucken.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
Yellow Crystalline Powder
Verwenden
Reactant for total synthesis of (±)-dibromophakellin and analogs, synthesis of the pyrrolizidine alkaloid (±)-trachelanthamidine, stereo selective preparation of renieramycin G analogs, preparation of spirooxoindolepyrrolidines via reduction of indole-2-carboxylic acid followed by oxidation, condensation, reduction, amidation and Kharasch radical cyclization, Pd-catalyzed cyclization and N,N-(pentane)diylbis[indolecarboxamide] and N,N-[phenylenebis(methylene)]bis[indolecarboxamide] derivatives.
Verwenden
• ;Reactant for total synthesis of (±)-dibromophakellin and analogs1• ;Reactant for synthesis of the pyrrolizidine alkaloid (±)-trachelanthamidine2• ;Reactant for stereoselective preparation of renieramycin G analogs3• ;Reactant for preparation of spirooxoindolepyrrolidines via reduction of indole-2-carboxylic acid followed by oxidation, condensation, reduction, amidation and Kharasch radical cyclization4• ;Reactant for Pd-catalyzed cyclization5• ;Reactant for preparation of N,N′-(pentane)diylbis[indolecarboxamide] and N,N′-[phenylenebis(
Definition
ChEBI: Indole-2-carboxylic acid is an indolyl carboxylic acid.
Synthesis Reference(s)
Tetrahedron Letters, 33, p. 7961, 1992 DOI: 10.1016/S0040-4039(00)74789-7
Synthese
Indole-2-carboxylic acid is prepared by a two-step condensation–reductive cyclization route: starting from 1-methyl-2-nitrobenzene (1) and diethyl oxalate (2), the intermediate sodium salt of 3-(2-nitrophenyl)-2-oxopropanoic acid (3) is first obtained by condensation, which is then reduced and cyclized to give the target product indole-2-carboxylic acid (4) [1].
IC 50
NMDA Receptor; Human Endogenous Metabolite
Einzelnachweise
[1] Jiang, T., Liu, N., Jiang, Y.-W., Ye, P.-P., Xu, W.-M. (2017). A Practical Synthesis of Indole-2-carboxylic Acid. Organic Preparations and Procedures International, 49(5), 476–478. https://doi.org/10.1080/00304948.2017.1374138

Indole-2-carboxylic acid Upstream-Materialien And Downstream Produkte

Indol-2-carbonsure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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