Indole
Indole (a blending of the terms indigo and oleum) is an organic compound. The chemical can be found in many places in nature. It can be produced by bacteria. At room temperature, indole is a solid.
| Indole | |
|---|---|
| |
 |
 |
1H-Indole[1] | |
| Other names | 2,3-Benzopyrrole, ketole, 1-benzazole |
| Identifiers | |
| CAS number | |
| PubChem | |
| DrugBank | DB04532 |
| KEGG | C00463 |
| ChEBI | CHEBI:16881 |
| RTECS number | NL2450000 |
| SMILES | C12=C(C=CN2)C=CC=C1 |
| Beilstein Reference | 107693 |
| Gmelin Reference | 3477 |
| 3DMet | B01251 |
| Properties | |
| Molecular formula | C8H7N |
| Molar mass | 117.15 g mol-1 |
| Appearance | White solid |
| Odor | Feces or jasmine like |
| Density | 1.1747 g/cm3, solid |
| Melting point |
52 to 54 °C, Expression error: Unrecognized word "to". K, Expression error: Unrecognized word "to". °F |
| Boiling point | |
| 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 |
| -85.0·10−6 cm3/mol | |
| Structure | |
| Crystal structure | Pna21 |
| Molecular shape | Planar |
| Dipole moment | 2.11 D in benzene |
| Hazards | |
| Main hazards | Skin sensitising |
| Related compounds | |
| Other cations | Indolium |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
Indole is found in some vegetables. They include broccoli, cauliflower and cabbage.[2] It is also in human feces. It has a strong fecal odor. In low concentration indole has a flowery smell. Indole is in perfumes.[3]
Indole Media
Baeyer's original structure for indole, 1869
Indole is produced via anthranilate and reacts further to give the amino acid tryptophan.
Reaction of aniline and ethylene glycol to give indole.
The Leimgruber–Batcho indole synthesis
The Fischer indole synthesis
One-pot microwave-assisted synthesis of indole from phenylhydrazine and pyruvic acid
The Vilsmeyer–Haack formylation of indole
Synthesis of gramine from indole
Formation and reactions of the indole anion
2-position lithiation of indole
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Related pages
References
- ↑ 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.
- ↑ "Indole as Defined". The National Cancer Institutes. Retrieved December 26, 2021.
- ↑ "Olefactory Perception with Humans". The National Centers for Biotechnology Information. Retrieved December 26, 2021.
General references
- Houlihan, W. J., ed. (1972). Indoles Part One. New York: Wiley Interscience.[ISBN missing]
- Sundberg, R. J. (1996). Indoles. San Diego: Academic Press. ISBN 978-0-12-676945-6.
- Joule, J. A.; Mills, K. (2000). Heterocyclic Chemistry. Oxford, UK: Blackwell Science. ISBN 978-0-632-05453-4.
- Joule, J. (2000). E. J., Thomas (ed.). Science of Synthesis. Vol. 10. Stuttgart: Thieme. p. 361. ISBN 978-3-13-112241-4.
- Schoenherr, H.; Leighton, J. L. (2012). "Direct and Highly Enantioselective Iso-Pictet-Spengler Reactions with α-Ketoamides: Access to Underexplored Indole Core Structures". Org. Lett. 14 (10): 2610–3. doi:10.1021/ol300922b. PMID 22540677.
Other websites
- Synthesis of indoles (overview of recent methods)
- Synthesis and properties of indoles at chemsynthesis.com
