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Revision as of 09:16, 9 June 2011 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits added CSID, StdInChI and StdInChIKey← Previous edit Latest revision as of 08:53, 2 September 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,127 edits added Category:Methyl compounds using HotCat 
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{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 374040900 | verifiedrevid = 433358304
| ImageFile = Quinaldine.png | ImageFile = Quinaldine.png
| ImageSize = | ImageSize =
| IUPACName = 2-Methylquinoline | PIN = 2-Methylquinoline
| OtherNames = Quinaldine, α-methylquinoline, chinaldine, khinaldin | OtherNames = Quinaldine, α-methylquinoline, chinaldine, khinaldin
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo = 91-63-4 | CASNo = 91-63-4
| CASNo_Ref = {{cascite}} | CASNo_Ref = {{cascite|correct|CAS}}
| EINECS = 202-085-1 | ChEBI = 132813
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | PubChem = 7060
| ChEMBL = 194931
⚫ | SMILES = Cc1nc2ccccc2cc1
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | InChI = 1/C10H9N/c1-8-6-7-9-4-2-3-5-10(9)11-8/h2-7H,1H3
| ChemSpiderID = 13870160 | ChemSpiderID = 13870160
| EINECS = 202-085-1
⚫ | StdInChIKey = SMUQFGGVLNAIOZ-UHFFFAOYSA-N
⚫ | PubChem = 7060
⚫ | StdInChI=1S/C10H9N/c1-8-6-7-9-4-2-3-5-10(9)11-8/h2-7H,1H3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = DVG30M0M87
⚫ | SMILES = Cc1nc2ccccc2cc1
⚫ | InChI = 1/C10H9N/c1-8-6-7-9-4-2-3-5-10(9)11-8/h2-7H,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = SMUQFGGVLNAIOZ-UHFFFAOYSA-N
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChI=1S/C10H9N/c1-8-6-7-9-4-2-3-5-10(9)11-8/h2-7H,1H3
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>10</sub>H<sub>9</sub>N | Formula = C<sub>10</sub>H<sub>9</sub>N
| MolarMass = 143.19 g/mol | MolarMass = 143.19 g/mol
| Appearance = Clear to yellow oily liquid | Appearance = colorless oil
| Density = 1.058 g/cm<sup>3</sup> | Density = 1.058 g/cm<sup>3</sup>
| MeltingPtC = -2 | MeltingPtC = -2
| BoilingPtC = 248 | BoilingPtC = 248
| Solubility = Insoluble | Solubility = Insoluble
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
⚫ | NFPA-H = 2
| MainHazards = Harmful ('''Xn'''), Corrosive ('''C''')
| NFPA-H = 2 | NFPA-F = 2
| NFPA-F = 2 | NFPA-R = 0
| NFPA-R = 0 | NFPA-S =
| GHSPictograms = {{GHS07}}
⚫ | NFPA-O =
| GHSSignalWord = Warning
| RPhrases = {{R21/22}} {{R34}}
| HPhrases = {{H-phrases|302|312|319}}
| SPhrases =
| PPhrases = {{P-phrases|264|270|280|301+312|302+352|305+351+338|312|322|330|337+313|363|501}}
| FlashPt = 79 °C
| Autoignition = | FlashPtC = 79
| AutoignitionPtC =
}} }}
}} }}


'''Quinaldine''' or '''2-methylquinoline''' is an ] with the formula CH<sub>3</sub>C<sub>9</sub>H<sub>6</sub>N. It is one of the methyl derivatives of the ] ]. It is bioactive and is used in the preparation of various dyes. It is a colorless oil but commercial samples can appear colored.<ref name=Hoke>{{Ullmann | author1 = Gerd Collin | author2 = Hartmut Höke | title = Quinoline and Isoquinoline | doi = 10.1002/14356007.a22_465}}</ref>
'''Quinaldine''' or '''2-methylquinoline''' is a simple derivative of a heterocyclic compound ].


==Production and reactions==
⚫ Quinaldine has ] at 787 K and 4.9 MPa and its refractive index is 1.8116.
⚫ Quinaldine is recovered from ]. It can be prepared from ] and ] via ] or from aniline and ] via Doebner-von Miller variation of the ].<ref name=Hoke/>


] of quinaldine gives ]. This reduction can be conducted enantioselectively.<ref>{{Cite journal |first1=Fei|last1=Chen|first2=Zi-Yuan|last2=Ding|first3=Yan-Mei|last3=He|first4=Qing-Hua|last4=Fan| title = Synthesis of Optically Active 1,2,3,4-Tetrahydroquinolines via Asymmetric Hydrogenation Using Iridium-Diamine Catalyst|journal=Org. Synth.|volume = 92 | pages = 213–226 | year = 2015 | doi = 10.15227/orgsyn.092.0213|doi-access=free}}</ref>
⚫ It can be prepared from ] and ] via ] or from aniline and ] via Doebner-von Miller variation of the ]<ref></ref> or extracted from ].

==Properties==
⚫ Quinaldine has ] at 787 K and 4.9 MPa and its ] is 1.8116.{{cn|date=November 2021}}


==Uses== ==Uses==
Quinaldine is used in anti-malaria drugs, in manufacturing dyes, food colorants (e.g. ]), pharmaceuticals, pH indicators. Quinaldine is used in manufacturing anti-malaria drugs, dyes and food colorants (e.g., ], ]). It is the precursor to the pH indicator ].
] is a popular dye derived from quinaldine.]]
], a pH indicating dye.]]


Quinaldine sulfate is an anaesthetic used in fish transportation.<ref>{{cite journal | author = Blasiola G. C. Jr. | date = 1977 | title = Quinaldine sulphate, a new anaesthetic formulation for tropical marine fishes | journal = Journal of Fish Biology | volume = 10 | issue = 2 | pages = 113–119(7) | pmid = | doi = 10.1111/j.1095-8649.1977.tb04048.x | url = http://www.blackwell-synergy.com/doi/abs/10.1111/j.1095-8649.1977.tb04048.x | accessdate = 2007-07-16 }}</ref> Quinaldine sulfate is an anaesthetic used in fish transportation.<ref>{{cite journal | author = Blasiola G. C. Jr. | year = 1977 | title = Quinaldine sulphate, a new anaesthetic formulation for tropical marine fishes | journal = Journal of Fish Biology | volume = 10 | issue = 2 | pages = 113–119(7) | doi = 10.1111/j.1095-8649.1977.tb04048.x }}</ref> In some Caribbean islands it is used to facilitate the collection of tropical fish from reefs.


==References== ==References==
<references/> <references/>
{{clear|left}}
In some islands of the Carbbean is used to facilitate the collection of tropical fishes on the reefs. It's use for this purpose could be start around the 80's when exportation of tropical fishes to the US was very popular among divers and skindivers.

==External links== ==External links==
* *
* *
* {{cite EB1911 |wstitle=Quinoline |volume=22 |pages=758–760}}
*


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