1H-Indole-5-Carboxylic Acid
Basic information
- CAS
1670-81-1- Standard SMILES
O=C(O)c1ccc2[nH]ccc2c1- InChIKey
IENZCGNHSIMFJE-UHFFFAOYSA-N- Molecular formula
- C9H7NO2
- Average molar mass
- 161.16 g/mol
- Monoisotopic mass
- 161.04767847
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%1H-Indole-5-carboxylic acid, radical ion(1+)indol-5-carboxylic acid5-indole carboxylic acidSCHEMBL105928CHEMBL20181585-Carboxyindole;AKOS000265424
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
- Formal charge
- 0
- Complexity
- 193
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.
- form
- Powder
- pka
- 4.4 · 4.40±0.30(Predicted)
- color
- 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 DataBase Reference
- 1670 · 1670-81-1(CAS DataBase Reference)
- Comptox DTXSID
- 80168218 · DTXSID80168218
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
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
- 2933990099
- risk_code
- 36/37/38-21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- safety_code
- 22-24/25-36/37/39-26
- hazard_class
- IRRITANT
- Storage Class
- 13 - Non Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Applications
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.
Upstream & downstream products
Upstream raw materials
Related reactions
195 records
Compound notes
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