Indolyl

Indole

Names
IUPAC name Indole
Other names 2,3-Benzopyrrole, ketole, 1-benzazole
Identifiers
CAS Number	120-72-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:16881 Y
ChemSpider	776 Y
ECHA InfoCard	100.004.019
KEGG	C00463 Y
PubChem CID	798
RTECS number	NL2450000
UNII	8724FJW4M5 Y
InChI InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H Y Key: SIKJAQJRHWYJAI-UHFFFAOYSA-N Y InChI=1/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H Key: SIKJAQJRHWYJAI-UHFFFAOYAI
SMILES C12=C(C=CN2)C=CC=C1
Properties
Chemical formula	C8H7N
Molar mass	117.15 g/mol
Appearance	White solid
Odor	Feces or jasmine like
Density	1.1747 g/cm3, solid
Melting point	52 to 54 °C (126 to 129 °F; 325 to 327 K)
Boiling point	253 to 254 °C (487 to 489 °F; 526 to 527 K)
Solubility in water	0.19 g/100 ml (20 °C) Soluble in hot water
Acidity (pKa)	16.2 (21.0 in DMSO)
Basicity (pKb)	17.6
Magnetic susceptibility (χ)	-85.0·10−6 cm3/mol
Structure
Crystal structure	Pna21
Molecular shape	Planar
Dipole moment	2.11 D in benzene
Hazards
Safety data sheet	[1]
R/S statement (outdated)	R: 21/22-37/38-41-50/53 S: 26-36/37/39-60-61
Flash point	121 °C (250 °F; 394 K)
Related compounds
Related aromatic compounds	benzene, benzofuran, carbazole, carboline, indene, indoline, isatin, , oxindole, pyrrole, skatole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Indole is an aromatic heterocyclic organic compound with formula C₈H₇N. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Indole is widely distributed in the natural environment and can be produced by a variety of bacteria. As an intercellular signal molecule, indole regulates various aspects of bacterial physiology, including spore formation, plasmid stability, resistance to drugs, biofilm formation, and virulence. The amino acid tryptophan is an indole derivative and the precursor of the neurotransmitter serotonin.

Indole is a solid at room temperature. Indole can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal odor. At very low concentrations, however, it has a flowery smell, and is a constituent of many flower scents (such as orange blossoms) and perfumes. It also occurs in coal tar.

The corresponding substituent is called indolyl.