5-Methoxyindol-2-carbonsure

5-Methoxyindole-2-carboxylic acid

HCID 20401CAS 4382-54-1

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Grundinformationen

Standard-SMILES: COc1ccc2[nH]c(C(=O)O)cc2c1
InChIKey: YEBJVSLNUMZXRJ-UHFFFAOYSA-N
Summenformel: C10H9NO3
Durchschnittliche Molmasse: 191,18 g/mol
Monoisotopische Masse: 191,05824315

Überblick

5-methoxyindole-2-carboxylic acid is an indolecarboxylic acid that is indole-2-carboxylic acid carrying an additional methoxy substituent at position 5. It has a role as an EC 1.8.1.4 (dihydrolipoyl dehydrogenase) inhibitor, a hypoglycemic agent and a plant metabolite. It is an aromatic ether and an indolecarboxylic acid.

Namen und Bezeichner

Bevorzugter Name: 5-Methoxyindole-2-carboxylic acid
IUPAC: 5-methoxy-1H-indole-2-carboxylic acid
Lokaler Name: 5-Methoxyindol-2-carbonsure
Englischer Name: 5-METHOXYINDOLE-2-CARBOXYLIC ACID
Summenformel: C10H9NO3
Molmasse: 191.18

Namen und Synonyme

5-Methoxyindole-2-carboxylic acid4382-54-15-Methoxy-1H-indole-2-carboxylic acidINDOLE-2-CARBOXYLIC ACID, 5-METHOXY-NSC 30927EINECS 224-487-6AFK8L54HA2NSC-30927CHEBI:133222DTXSID401959445-Methoxy-2-indolateRefChem:103063

Weitere Namen anzeigen

5-MeO-ICAAKOS JY2083529TIMTEC-BB SBB0036355-METHOXYINDOL-2-CARBOXYLIC ACID5-methoxy-indole-2-carboxylicaci5-methoxy-2-indolecarboxylicacid5-Methoxy-2-indolecarboxylic acid

5-Methoxy-2-indolecarboxylate5-Methoxyindole-2-carboxylateDTXCID80101847DTXCID80118435224-487-61H-Indole-2-carboxylic acid, 7-methoxy-24610-33-1DTXSID50179356

Datenbank-Bezeichner

CAS: 4382-54-1
PubChem CID: 20401
DTXSID: DTXSID40195944
ChEMBL: CHEMBL23961
ChEBI: CHEBI:133222
UNII: AFK8L54HA2
EC Number: 224-487-6
Nikkaji: J41.036E

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,3
Polarare Oberfläche (TPSA): 62,3 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 2
Schwere Atome: 14
Formalladung: 0
Komplexität: 231

Physikochemische Eigenschaften

Schmelzpunkt: 199 · 199-201 °C (lit.)
Siedepunkt: 326.92 °C · 326.92°C (rough estimate)
Dichte: 1.2722 · 1.2722 (rough estimate)
Brechungsindex: 1.531 · 1.5310 (estimate)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
pka: 4.38 · 4.38±0.30(Predicted)
Aggregatzustand: Powder
Farbe: Light yellow to brownish
BRN: 157478 · 157478
InChI: InChI=1S/C10H9NO3/c1-14-7-2-3-8-6(4-7)5-9(11-8)10(12)13/h2-5,11H,1H3,(H,12,13)
InChIKey: YEBJVSLNUMZXRJ-UHFFFAOYSA-N
SMILES: N1C2=C(C=C(OC)C=C2)C=C1C(O)=O
CAS Datenbank: 4382 · 4382-54-1(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.

Warning

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]

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

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (50%)

Sicherheitsdaten

wgk: 3
hs_code: 29339900
RTECS-Nr.: NL6005000
safety_code: 22-24/25
hazard_class: IRRITANT
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Anwendungen

Verwenden5-Methoxyindole-2-carboxylic Acid is a very useful synthetic intermediate. It is a reactant used to prepare anticancer agents, Indoleamine 2,3-dioxygenase (IDO) inhibitors, and potent antitumor bifunctional DNA alkylating agents.