Chemistry:Quinaldine
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| Names | |
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| Preferred IUPAC name
2-Methylquinoline | |
| Other names
Quinaldine, α-methylquinoline, chinaldine, khinaldin
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| Properties | |
| C10H9N | |
| Molar mass | 143.19 g/mol |
| Appearance | colorless oil |
| Density | 1.058 g/cm3 |
| Melting point | −2 °C (28 °F; 271 K) |
| Boiling point | 248 °C (478 °F; 521 K) |
| Insoluble | |
| Hazards | |
| GHS pictograms | 
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| GHS Signal word | Warning |
| H302, H312, H319 | |
| P264, P270, P280, P301+312, P302+352, P305+351+338, P312, P322, P330, P337+313, P363, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 79 °C (174 °F; 352 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Quinaldine or 2-methylquinoline is an organic compound with the formula CH3C9H6N. It is one of the methyl derivatives of the heterocyclic compound quinoline. It is bioactive and is used in the preparation of various dyes. It is a colorless oil but commercial samples can appear colored.[1]
Production and reactions
Quinaldine is recovered from coal tar. It can be prepared from aniline and paraldehyde via Skraup synthesis or from aniline and crotonaldehyde via Doebner-von Miller variation of the Skraup reaction.[1]
Hydrogenation of quinaldine gives 2-methyltetrahydroquinoline. This reduction can be conducted enantioselectively.[2]
Properties
Quinaldine has critical point at 787 K and 4.9 MPa and its refractive index is 1.8116.[citation needed]
Uses
Quinaldine is used in manufacturing anti-malaria drugs, dyes and food colorants (e.g., Quinoline Yellows, pinacyanol). It is the precursor to the pH indicator Quinaldine Red.
Quinaldine sulfate is an anaesthetic used in fish transportation.[3] In some Caribbean islands it is used to facilitate the collection of tropical fish from reefs.
References
- ↑ 1.0 1.1 Gerd Collin; Hartmut Höke. "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_465.
- ↑ Chen, Fei; Ding, Zi-Yuan; He, Yan-Mei; Fan, Qing-Hua (2015). "Synthesis of Optically Active 1,2,3,4-Tetrahydroquinolines via Asymmetric Hydrogenation Using Iridium-Diamine Catalyst". Org. Synth. 92: 213–226. doi:10.15227/orgsyn.092.0213.
- ↑ Blasiola G. C. Jr. (1977). "Quinaldine sulphate, a new anaesthetic formulation for tropical marine fishes". Journal of Fish Biology 10 (2): 113–119(7). doi:10.1111/j.1095-8649.1977.tb04048.x.
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