# Lepidine

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Lepidine
> Markdown URL: https://mediated.wiki/source/Lepidine.md
> Source: https://en.wikipedia.org/wiki/Lepidine
> Source revision: 1332348221
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{chembox
| Watchedfields = changed
| verifiedrevid = 462089974
| ImageFile = Lepidine.png
| ImageSize = 150px
| PIN = 4-Methylquinoline
| OtherNames = Lepidine
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 491-35-0
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 9734
| ChemSpiderID = 13854818
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 116169T3O8
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 48983
| PubChem = 10285
| EC_number = 207-734-2
| Beilstein = 110926
| SMILES = Cc1ccnc2ccccc12
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI =1S/C10H9N/c1-8-6-7-11-10-5-3-2-4-9(8)10/h2-7H,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MUDSDYNRBDKLGK-UHFFFAOYSA-N
  }}
|Section2={{Chembox Properties
| Formula = C<sub>10</sub>H<sub>9</sub>N
| MolarMass = 143.19 g/mol
| Appearance = Colorless liquid
| Density = 1.083 g/ml
| MeltingPtC = 9 to 10
| MeltingPt_notes = 
| BoilingPtC = 261 to 263
| BoilingPt_notes = 
  }}
}}

'''Lepidine''', or '''4-methylquinoline''', is an [organic compound](/source/organic_compound) with the formula {{chem2|C9H6NCH3}}.  It is one of the two commercially important methyl quinolines.  It is a colorless liquid, although impure samples can appear yellow.

Its methyl group is fairly acidic, allowing for [condensation](/source/condensation_reaction)s to occur at this position, especially when the nitrogen is [quaternized](/source/quaternized). It is used in the preparation of [cyanine dye](/source/cyanine_dye)s.<ref name=Ullmann>{{Ullmann |doi=10.1002/14356007.a16_487.pub2|title=Methine Dyes and Pigments|year=2008|last1=Berneth|first1=Horst|isbn=978-3527306732}}</ref>

Oxidation with [selenium dioxide](/source/selenium_dioxide) gives the aldehyde {{ill|4-formylquinoline|qid=Q27256940|s=1}}.<ref>{{cite journal |author=H. A. Riley, A. R. Gray|title=Phenylglyoxal |journal=Organic Syntheses |date=1935 |volume=15 |page=67 |doi=10.15227/orgsyn.015.0067}}</ref>

== See also ==
* [Quinaldine](/source/Quinaldine), the isomer with the methyl group in position 2.
* [Quinoline](/source/Quinoline)
==References==
<references />

Category:Quinolines
Category:Methyl compounds

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Adapted from the Wikipedia article [Lepidine](https://en.wikipedia.org/wiki/Lepidine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Lepidine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.