Indole-2-carboxylic acid
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Basic information
- CAS
1477-50-5- Standard SMILES
O=C(O)c1cc2ccccc2[nH]1- InChIKey
HCUARRIEZVDMPT-UHFFFAOYSA-N- Molecular formula
- C9H7NO2
- Average molar mass
- 161.16 g/mol
- Monoisotopic mass
- 161.04767846
Overview
Indole-2-carboxylic acid is an indolyl carboxylic acid.
Names & identifiers
- Preferred name
- Indole-2-carboxylic acid
- IUPAC
- 1H-indole-2-carboxylic acid
- English name
- Indole-2-carboxylic acid
- Molecular formula
- C9H7NO2
- Molecular weight
- 161.16
Names & synonyms
Indole-2-carboxylic acid1H-Indole-2-carboxylic acid1477-50-5DTXSID20163782RefChem:790959DTXCID9086273216-030-42-Carboxyindole2-Indolecarboxylic acidMFCD00005611Indol-2-Carboxylic Acidcarboxyindole
Show more names
Indole-2-carboxylicNSC 16598e-2-carboxyLAKOS JY2082713Indol-2-carbonsure2-Carboxy-1H-indoleTIMTEC-BB SBB003953
2-INDOLYLFORMIC ACIDSpectrum_0014851H-2-indolecarboxylic acid1H-indole-2-carboxylicacidCHEMBL278390KBio2_004533SMR000112260EN300-16592
Database identifiers
- CAS
1477-50-5- PubChem CID
- 72899
- DTXSID
DTXSID20163782- ChEMBL
CHEMBL278390- ChEBI
CHEBI:169990- EC Number
- 216-030-4
- Nikkaji
- J132E
Properties
Computed structural propertiesFilling in
- XLogP
- 2.3
- 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
Experimental & physicochemical properties
SpringerMaterials PropertiesChemical shift
LogP
2.31
2.31
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 202 · 202-206 °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
- 5 % · Soluble in clear yellow solution 5% in ethanol, dimethyl sulfoxide and methanol.
- pka
- 4.44 · 4.44±0.30(Predicted)
- form
- Crystalline Powder or Crystals
- color
- Off-white to yellow to brown
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 (83.3%): 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 6 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 1H-Indole-2-carboxylic acid
1H-Indole-2-carboxylic acid: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazard Classes and CategoriesAcute Tox. 4 (83.3%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- NK7882812
- hs_code
- 29339990
- risk_code
- 36/37/38-21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS06
- hazard_code
- Xn,Xi
- safety_code
Chemistry & industry
Applications
Uses• ;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(
UsesReactant 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.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
304 records
Compound notes
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