Indole

Indole
Names
	Preferred IUPAC name 1H-Indole
	Other names 2,3-Benzopyrrole, ketole,; 1-benzazole
Identifiers
CAS Number	120-72-9 ;
3D model (JSmol)	Interactive image;
3DMet	B01251;
Beilstein Reference	107693
ChEBI	CHEBI:16881 ;
ChEMBL	ChEMBL15844 ;
ChemSpider	776 ;
DrugBank	DB04532;
ECHA InfoCard	100.004.019
EC Number	204-420-7;
Gmelin Reference	3477
KEGG	C00463 ;
PubChem CID	798;
RTECS number	NL2450000;
UNII	8724FJW4M5 ;
CompTox Dashboard (EPA)	DTXSID0020737 ;
	InChI InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H Key: SIKJAQJRHWYJAI-UHFFFAOYSA-N ; 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	117.151 g·mol−1
Appearance	White solid
Odor	Fecal or jasmine like (at extremely low concentrations)
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
	Occupational safety and health (OHS/OSH):
Main hazards	Skin sensitising
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H311
Precautionary statements	P264, P270, P280, P301+P312, P302+P352, P312, P322, P330, P361, P363, P405, P501
Flash point	121 °C (250 °F; 394 K)
Safety data sheet (SDS)	[1]
Related compounds
Other cations	Indolium
Related aromatic; compounds	benzene, benzofuran,; carbazole, carboline,; indene, benzothiophene,; indoline,; isatin, methylindole,; oxindole, pyrrole,; skatole, benzophosphole
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Indole is an organic compound with the formula C₆H₄CCNH₃. Indole is classified as an aromatic heterocycle. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indoles are derivatives of indole where one or more of the hydrogen atoms have been replaced by substituent groups. Indoles are widely distributed in nature, most notably as amino acid tryptophan and neurotransmitter serotonin.^[2]

^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 213. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
^ Cite error: The named reference Lehninger was invoked but never defined (see the help page).

[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 213. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

[Lehninger-2] Cite error: The named reference Lehninger was invoked but never defined (see the help page).

[1]

[2]

Names



Preferred IUPAC name 1H-Indole^[1]
Other names 2,3-Benzopyrrole, ketole, 1-benzazole
Identifiers
CAS Number	120-72-9^Y
3D model (JSmol)	Interactive image
3DMet	B01251
Beilstein Reference	107693
ChEBI	CHEBI:16881^Y
ChEMBL	ChEMBL15844^Y
ChemSpider	776^Y
DrugBank	DB04532
ECHA InfoCard	100.004.019
EC Number	204-420-7
Gmelin Reference	3477
KEGG	C00463^Y
PubChem CID	798
RTECS number	NL2450000
UNII	8724FJW4M5^Y
CompTox Dashboard (EPA)	DTXSID0020737
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	117.151 g·mol⁻¹
Appearance	White solid
Odor	Fecal or jasmine like (at extremely low concentrations)
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 (pK_a)	16.2 (21.0 in DMSO)
Basicity (pK_b)	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
Occupational safety and health (OHS/OSH):
Main hazards	Skin sensitising
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H311
Precautionary statements	P264, P270, P280, P301+P312, P302+P352, P312, P322, P330, P361, P363, P405, P501
Flash point	121 °C (250 °F; 394 K)
Safety data sheet (SDS)	[1]
Related compounds
Other cations	Indolium
Related aromatic compounds	benzene, benzofuran, carbazole, carboline, indene, benzothiophene, indoline, isatin, methylindole, oxindole, pyrrole, skatole, benzophosphole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Indole

From Wikipedia, the free encyclopedia · View on Wikipedia