1H-Indole-5-Carboxylic Acid

HCID 74280CAS 1670-81-1

Basic information

Standard SMILES
O=C(O)c1ccc2[nH]ccc2c1
InChIKey
IENZCGNHSIMFJE-UHFFFAOYSA-N
Molecular formula
C9H7NO2
Average molar mass
161.16 g/mol
Monoisotopic mass
161.04767846

Overview

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.

Names & identifiers

Preferred name
1H-Indole-5-Carboxylic Acid
IUPAC
1H-indole-5-carboxylic acid
English name
Indole-5-carboxylic acid
Molecular formula
C9H7NO2
Molecular weight
161.16

Names & synonyms

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

Database identifiers

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

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
53.1 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
12

Physicochemical properties

Melting point
211 · 211-213 °C (lit.)
Boiling point
287.44 °C · 287.44°C (rough estimate)
Density
1.248 · 1.2480 (rough estimate)
refractive index
1.505 · 1.5050 (estimate)
storage temp.
Keep in dark place,Sealed in dry,Room Temperature
solubility
Soluble in ethanol (50 mg/ml), dimethyl sulfoxide and methanol.

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (25%)

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
hs_code
29339990
risk_code
36/37/38-21/22
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Applications · 4 items

UsesReactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles, as potential anticancer immunomodulators 1 Reactant for preparation of indolyl-quinolines via metal- and solvent-free autoxidative coupling reaction 2 Reactant for preparation of anthranilic acids using bromamine-B oxidant and palladium chloride catalyst 3 Reactant for synthesis of indirubin derivatives 4 Reactant for preparation of amide conjugates with ketoprofen, as inhibitors of Gli1-mediated transcription in Hedgehog pathway 5 Reactant for preparation of piperazine-bisamide analogs as human growth hormone secretagogue receptor antagonists for treatment of obesity.

UsesIndole-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.

UsesIndole-5-carboxylic acid is the suitable reagent used to study the intramolecular 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.

General DescriptionIndole-5-carboxylic acid is an indole derivative. On electropolymerization, it affords electroactive polymer film of poly(indole-5-carboxylic-acid). Different concentrations of indole-5-carboxylic acid in sulfuric acid solution has been investigated for the preventive action against mild steel corrosion. On electropolymerization it affords a trimeric product. Characterization studies of the trimeric product by 1H NMR and various one- and two-dimensional NMR techniques have been reported.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes

DefinitionChEBI: 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.

Related reactions

195 records

Linked notes

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