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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| Identifiers | |
3D model (JSmol)
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PubChem CID
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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 labelling: | |
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| Warning | |
| H302, H312, H319 | |
| P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P312, P322, P330, P337+P313, P363, P501 | |
| NFPA 704 (fire diamond) | <imagemap>
File:NFPA 704.svg|80px|alt=NFPA 704 four-colored diamond poly 150 150 300 300 150 450 0 300 Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform poly 300 0 450 150 300 300 150 150 Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel poly 450 150 600 300 450 450 300 300 Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen poly 300 300 450 450 300 600 150 450 Special hazards (white): no code desc none </imagemap> |
| 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).
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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. "Quinoline and Isoquinoline". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_465. ISBN 978-3527306732.
- ^ 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.
External links
- MSDS at Science Lab
- Method of purifying quinaldine
- Chisholm, Hugh, ed. (1911). . Encyclopædia Britannica. Vol. 22 (11th ed.). Cambridge University Press. pp. 758–760.