Indole-2-carboxylic acid

Synonym(s):2-Carboxyindole;2-Indolylformic acid;NSC 16598

CAS NO.：1477-50-5
Empirical Formula: C9H7NO2
Molecular Weight: 161.16
MDL number: MFCD00005611
EINECS: 216-030-4
SAFETY DATA SHEET (SDS)
Update Date: 2024-08-21 22:41:43

What is Indole-2-carboxylic acid?

Chemical properties

Yellow Crystalline Powder

The Uses of Indole-2-carboxylic acid

• ;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(

The Uses of Indole-2-carboxylic acid

Reactant 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.

Definition

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

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 7961, 1992 DOI: 10.1016/S0040-4039(00)74789-7

Properties of Indole-2-carboxylic acid

Melting point:	202-206 °C(lit.)
Boiling point:	287.44°C (rough estimate)
Density	1.2480 (rough estimate)
refractive index	1.5050 (estimate)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	Soluble in clear yellow solution 5% in ethanol, dimethyl sulfoxide and methanol.
pka	4.44±0.30(Predicted)
form	Crystalline Powder or Crystals
color	Off-white to yellow to brown
BRN	124132
CAS DataBase Reference	1477-50-5(CAS DataBase Reference)
NIST Chemistry Reference	Indole-2-carboxylic acid(1477-50-5)

Safety information for Indole-2-carboxylic acid

Signal word	Warning
Pictogram(s)	Skull and Crossbones Acute Toxicity GHS06
GHS Hazard Statements	H301:Acute toxicity,oral H311:Acute toxicity,dermal H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up.