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Indole information


Indole
Skeletal formula with numbering scheme
Ball-and-stick model of indole
Space-filling model of indole
Names
Preferred IUPAC name
1H-Indole[1]
Other names
2,3-Benzopyrrole, ketole,
1-benzazole
Identifiers
CAS Number
  • 120-72-9 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B01251
Beilstein Reference
107693
ChEBI
  • CHEBI:16881 checkY
ChEMBL
  • ChEMBL15844 checkY
ChemSpider
  • 776 checkY
DrugBank
  • DB04532
ECHA InfoCard 100.004.019 Edit this at Wikidata
EC Number
  • 204-420-7
Gmelin Reference
3477
KEGG
  • C00463 checkY
PubChem CID
  • 798
RTECS number
  • NL2450000
UNII
  • 8724FJW4M5 checkY
CompTox Dashboard (EPA)
  • DTXSID0020737 Edit this at Wikidata
InChI
  • InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H checkY
    Key: SIKJAQJRHWYJAI-UHFFFAOYSA-N checkY
  • 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
GHS06: ToxicGHS07: Exclamation mark
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).
checkY verify (what is checkY☒N ?)
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]

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

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Indole

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Indole is an organic compound with the formula C6H4CCNH3. Indole is classified as an aromatic heterocycle. It has a bicyclic structure, consisting of a...

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Indole test

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The indole test is a biochemical test performed on bacterial species to determine the ability of the organism to convert tryptophan into indole. This...

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Skatole

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Skatole or 3-methylindole is an organic compound belonging to the indole family. It occurs naturally in the feces of mammals and birds and is the primary...

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Fischer indole synthesis

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The Fischer indole synthesis is a chemical reaction that produces the aromatic heterocycle indole from a (substituted) phenylhydrazine and an aldehyde...

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Indole alkaloid

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Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called...

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Tryptophol

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Tryptophan is first deaminated to 3-indolepyruvate. It is then decarboxylated to indole acetaldehyde by indolepyruvate decarboxylase. This latter compound is transformed...

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Drugs controlled by the UK Misuse of Drugs Act

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structurally derived from 3-(1-adamantoyl)indole or 3-(2-adamantoyl)indole by substitution at the nitrogen atom of the indole ring by alkyl, haloalkyl, alkenyl...

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IMViC

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action of enzyme tryptophanase is converted to an Indole molecule, pyruvate and ammonium. The indole is then extracted from the broth by means of xylene...

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Larock indole synthesis

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The Larock indole synthesis is a heteroannulation reaction that uses palladium as a catalyst to synthesize indoles from an ortho-iodoaniline and a disubstituted...

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Tryptophan

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contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromatic beta carbon substituent...

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Reissert indole synthesis

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The Reissert indole synthesis is a series of chemical reactions designed to synthesize indole or substituted-indoles (4 and 5) from ortho-nitrotoluene...

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Bartoli indole synthesis

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The Bartoli indole synthesis (also called the Bartoli reaction) is the chemical reaction of ortho-substituted nitroarenes and nitrosoarenes with vinyl...

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Controlled Drugs and Substances Act

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1-pentyl-3-(1-naphthoyl)indole (JWH-018) 1-butyl-3-(1-naphthoyl)indole (JWH-073) 1-pentyl-3-(4-methyl-1-naphthoyl)indole (JWH-122) 1-hexyl-3-(1-naphthoyl)indole (JWH-019)...

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