Indole
chemical compound
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.
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
1H-Indole[1] | |||
| Other names
2,3-Benzopyrrole, ketole,
1-benzazole | |||
| Identifiers | |||
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3D model (JSmol)
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| 3DMet | |||
| Beilstein Reference | 107693 | ||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| DrugBank | |||
| ECHA InfoCard | 100.004.019 | ||
| EC Number |
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| Gmelin Reference | 3477 | ||
| KEGG | |||
PubChem CID
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| RTECS number |
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| UNII | |||
CompTox Dashboard (EPA)
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| Properties | |||
| 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 (126 to 129 °F; 325 to 327 K) | ||
| Boiling point | 253 to 254 °C (487 to 489 °F; 526 to 527 K) | ||
| 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 | |||
| Pna21 | |||
| Planar | |||
| 2.11 D in benzene | |||
| Hazards | |||
| Main hazards | Skin sensitising | ||
| Related compounds | |||
| Other cations | Indolium | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
| Infobox references | |||
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]
Related pages change
References change
- ↑ 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 change
- 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 change
Wikimedia Commons has media related to 1H-Indole.
- Synthesis of indoles (overview of recent methods)
- Synthesis and properties of indoles at chemsynthesis.com
