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 | |
|---|---|
| File:Indole 2D numbered.svg | |
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 indole structure.png
Baeyer's original structure for indole, 1869
- Tryptophan biosynthesis (en).svg
Indole is produced via anthranilate and reacts further to give the amino acid tryptophan.
Reaction of aniline and ethylene glycol to give indole.
- Leimgruber-Batcho Indole Scheme.png
The Leimgruber–Batcho indole synthesis
- Fischer indole reaction scheme.svg
The Fischer indole synthesis
- One-pot synthesis of indoles.svg
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
Related pages
References
- ↑ Lua error in Module:Citation/CS1/Utilities at line 38: bad argument #1 to 'ipairs' (table expected, got nil).
- ↑ Lua error in Module:Citation/CS1/Utilities at line 38: bad argument #1 to 'ipairs' (table expected, got nil).
- ↑ Lua error in Module:Citation/CS1/Utilities at line 38: bad argument #1 to 'ipairs' (table expected, got nil).
General references
- Lua error in Module:Citation/CS1/Utilities at line 38: bad argument #1 to 'ipairs' (table expected, got nil).[ISBN missing]
- Lua error in Module:Citation/CS1/Utilities at line 38: bad argument #1 to 'ipairs' (table expected, got nil).
- Lua error in Module:Citation/CS1/Utilities at line 38: bad argument #1 to 'ipairs' (table expected, got nil).
- Lua error in Module:Citation/CS1/Utilities at line 38: bad argument #1 to 'ipairs' (table expected, got nil).
- Lua error in Module:Citation/CS1/Utilities at line 38: bad argument #1 to 'ipairs' (table expected, got nil).
Other websites
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Wikimedia Commons has media related to Lua error in Module:Commons_link at line 62: attempt to index field 'wikibase' (a nil value).. |
- Synthesis of indoles (overview of recent methods)
- Synthesis and properties of indoles at chemsynthesis.com
