Indole-2-carboxylic acid

HCID 72899CAS 1477-50-5
Substructure searchFind similar structures

Basic information

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 properties

XLogP
2.3
Topological polar surface area
53.1 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
12

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift
LogP · 2 items

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.

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 2 items

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

Chemistry & industry

Applications · 2 items

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

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]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes

DefinitionChEBI: Indole-2-carboxylic acid is an indolyl carboxylic acid.

Related reactions

304 records
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Linked notes

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