Indol-5-carbonsure

1H-Indole-5-Carboxylic Acid

HCID 74280CAS 1670-81-1

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Grundinformationen

Standard-SMILES: O=C(O)c1ccc2[nH]ccc2c1
InChIKey: IENZCGNHSIMFJE-UHFFFAOYSA-N
Summenformel: C9H7NO2
Durchschnittliche Molmasse: 161,16 g/mol
Monoisotopische Masse: 161,04767846

Überblick

Indole-5-carboxylic acid is an indolecarboxylic acid in which the carboxy group is the only substituent and is located at position 5. It has a role as a plant metabolite.

Namen und Bezeichner

Bevorzugter Name: 1H-Indole-5-Carboxylic Acid
IUPAC: 1H-indole-5-carboxylic acid
Lokaler Name: Indol-5-carbonsure
Englischer Name: Indole-5-carboxylic acid
Summenformel: C9H7NO2
Molmasse: 161.16

Namen und Synonyme

Indole-5-carboxylic acid1H-indole-5-carboxylic acid1670-81-15-indolecarboxylic acidDTXSID80168218CHEBI:131778RefChem:790973DTXCID5090709216-799-65-Carboxyindole142396-03-0MFCD00005678

Weitere Namen anzeigen

JACS-1670-81-15-Carboxy-1H-indoleRARECHEM AL BO 0206TIMTEC-BB SBB003951Indolecarboxylicacid,5-INDOLE-5-CARBOXYLIC AICD

Indole-5-carboxylic acid, 98%5-indole carboxylic acid1H-Indole-5-carboxylic acid, radical ion(1+)SCHEMBL105928CHEMBL20181585-Carboxyindole;AKOS000265424EN300-69795

Datenbank-Bezeichner

CAS: 1670-81-1
PubChem CID: 74280
DTXSID: DTXSID80168218
ChEMBL: CHEMBL2018158
ChEBI: CHEBI:131778
EC Number: 216-799-6
Nikkaji: J195.309E

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,5
Polarare Oberfläche (TPSA): 53,1 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 1
Schwere Atome: 12
Formalladung: 0
Komplexität: 193

Physikochemische Eigenschaften

Schmelzpunkt: 211 · 211-213 °C (lit.)
Siedepunkt: 287.44 °C · 287.44°C (rough estimate)
Dichte: 1.248 · 1.2480 (rough estimate)
Brechungsindex: 1.505 · 1.5050 (estimate)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit: Soluble in ethanol (50 mg/ml), dimethyl sulfoxide and methanol.
Aggregatzustand: Powder
pka: 4.4 · 4.40±0.30(Predicted)
Farbe: Light beige to yellow
BRN: 124391 · 124391
InChI: InChI=1S/C9H7NO2/c11-9(12)7-1-2-8-6(5-7)3-4-10-8/h1-5,10H,(H,11,12)
InChIKey: IENZCGNHSIMFJE-UHFFFAOYSA-N
SMILES: N1C2=C(C=C(C(O)=O)C=C2)C=C1
CAS Datenbank: 1670 · 1670-81-1(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 8 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (25%)

Sicherheitsdaten

wgk: 3
hs_code: 29339990
risk_code: 36/37/38-21/22
hazard_code: Xn,Xi
safety_code: 22-24/25-36/37/39-26
hazard_class: IRRITANT
Speicherklasse: 13 - Non Combustible Solids

Chemie und Industrie

Anwendungen · 1 Eintrag

VerwendenIndole-5-carboxylic acid is the suitable reagent used to study the intermolecular excited state proton transfer in indole-2-carboxylic acid and indole-5-carboxylic acid in various solvents in acidic, basic, and neutral media by steady state and time resolved fluorescence spectroscopy. It may be used in the electrochemical synthesis of poly(indole-5-carboxylic acid) (PICA) films. Also used as reactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles, as potential anticancer immunomodulators, synthesis of indirubin derivatives and amide conjugates with ketoprofen, as inhibitors of Gli1-mediated transcription in Hedgehog pathway.