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Revision as of 17:59, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,054 edits Saving copy of the {{chembox}} taken from revid 456792964 of page 3-Methylpyridine for the Chem/Drugbox validation project (updated: 'ChEMBL').  Latest revision as of 23:46, 13 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix 
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{{Chembox
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 380162993 | verifiedrevid = 477219791
| ImageFile = 3-methylpyridine-2D-skeletal.png | ImageFile = 3-methylpyridine-2D-skeletal.png
| ImageClass = skin-invert-image
| ImageSize = 120px
| ImageSize = 120px
| OtherNames = 3-picoline
| PIN = 3-Methylpyridine
| Section1 = {{Chembox Identifiers
| OtherNames = 3-Picoline
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|Section1={{Chembox Identifiers
| ChemSpiderID = 7682
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106520
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 39922
| ChEMBL = <!-- blanked - oldvalue: 15722 -->
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| CASNo = 108-99-6
| ChEMBL = 15722
| CASNo = 108-99-6
| PubChem = 7970
| DrugBank = DB01996
| Beilstein = 1366
| Gmelin = 2450
| DTXSID = DTXSID9021897
| EINECS = 203-636-9
| RTECS = TJ5000000
| UNNumber = 2313
| UNII = B083J4KF7F
| SMILES = Cc1cccnc1
| StdInChI = 1S/C6H7N/c1-6-3-2-4-7-5-6/h2-5H,1H3
| StdInChIKey = ITQTTZVARXURQS-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>7</sub>N | Formula = C<sub>6</sub>H<sub>7</sub>N
| MolarMass = 93.13 g/mol | MolarMass = 93.13 g/mol
| Appearance = Colorless liquid | Appearance = Colorless liquid
| Density = 0.957 g/mL | Density = 0.957 g/mL
| Solubility = Miscible | Solubility = Miscible
| MeltingPt = -19 °C | MeltingPtC = -19
| MeltingPt_notes =
| BoilingPt = 144 °C
| BoilingPtC = 144
| BoilingPt_notes =
| MagSus = -59.8·10<sup>−6</sup> cm<sup>3</sup>/mol
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS06}}{{GHS07}}
| RPhrases =
| SPhrases = | GHSSignalWord = Danger
| HPhrases = {{H-phrases|226|302|311|314|315|319|331|332|335}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|270|271|280|301+312|301+330+331|302+352|303+361+353|304+312|304+340|305+351+338|310|311|312|321|322|330|332+313|337+313|361|362|363|370+378|403+233|403+235|405|501}}
}} }}
}} }}

'''3-Methylpyridine''' or '''3-picoline''', is an ] with formula 3-CH<sub>3</sub>C<sub>5</sub>H<sub>4</sub>N. It is one of three ]s of ], whose structures vary according to where the ] is attached around the ] ring. This colorless liquid is a precursor to pyridine derivatives that have applications in the pharmaceutical and agricultural industries. Like pyridine, 3-methylpyridine is a colorless liquid with a strong odor and is classified as a ].<ref name=Ull/>

==Synthesis==
3-Methylpyridine is produced industrially by the reaction of ], with ]. These ingredients are combined as gases which flows over an oxide-based ]. The reaction is multistep, culminating in cyclisation.
:2{{nbsp}} CH<sub>2</sub>CHCHO + NH<sub>3</sub> → CH<sub>3</sub>C<sub>5</sub>H<sub>4</sub>N + 2{{nbsp}}H<sub>2</sub>O
This process also affords substantial amounts of pyridine, which arises by demethylation of the 3-methylpyridine. A route that gives better control of the product starts with ], ], and ]:<ref name=Ull/>
:CH<sub>2</sub>CHCHO + CH<sub>3</sub>CH<sub>2</sub>CHO + NH<sub>3</sub> → 3-CH<sub>3</sub>C<sub>5</sub>H<sub>4</sub>N + 2 H<sub>2</sub>O + H<sub>2</sub>
It may also be obtained as a co-product of pyridine synthesis from ], ], and ] via ]. Approximately 9,000,000 kilograms were produced worldwide in 1989. It has also been prepared by dehydrogenation of 3-methylpiperidine, derived from hydrogenation of ].<ref>{{cite journal
| author = Eric F. V. Scriven
| author2 = Ramiah Murugan
| title = Pyridine and Pyridine Derivatives
| journal = Kirk-Othmer Encyclopedia of Chemical Technology
| year = 2005
| volume = XLI
| doi = 10.1002/0471238961.1625180919031809.a01.pub2
| isbn = 0471238961
}}</ref>

==Uses==
3-Picoline is a useful precursor to agrochemicals, such as ].<ref name=Ull>{{Ullmann
| author = Shinkichi Shimizu
| author2 = Nanao Watanabe
| author3 = Toshiaki Kataoka
| author4 = Takayuki Shoji
| author5 = Nobuyuki Abe
| author6 = Sinji Morishita
| author7 = Hisao Ichimura
| title = Pyridine and Pyridine Derivatives
| year = 2002
| doi = 10.1002/14356007.a22_399
| isbn = 3527306730
}}</ref> Chlorpyrifos is produced from 3,5,6-trichloro-2-pyridinol, which is generated from 3-picoline by way of cyanopyridine. This conversion involves the ] of 3-methylpyridine:
:CH<sub>3</sub>C<sub>5</sub>H<sub>4</sub>N + 1.5{{nbsp}}O<sub>2</sub> + NH<sub>3</sub> → NCC<sub>5</sub>H<sub>4</sub>N + 3{{nbsp}}H<sub>2</sub>O

] is also a precursor to ],<ref>{{cite journal|title = Nitrile Hydratase-Catalyzed Production of Nicotinamide from 3-Cyanopyridine in ''Rhodococcus rhodochrous'' J1|first1 = Toru|last1 = Nagasawa|first2 = Caluwadewa Deepal|last2 = Mathew|first3 = Jacques|last3 = Mauger|first4 = Hideaki|last4 = Yamada|journal = ]|year = 1988|volume = 54|issue = 7|pages = 1766–1769|doi = 10.1128/AEM.54.7.1766-1769.1988|pmid = 16347686|pmc = 202743| bibcode=1988ApEnM..54.1766N }}</ref><ref>{{cite book|title = White Biotechnology|editor1-first = Roland|editor1-last = Ulber|editor2-first = Dieter|editor2-last = Sell|chapter = Building Blocks|volume = 105|series = Advances in Biochemical Engineering / Biotechnology|isbn = 9783540456957|doi = 10.1007/10_033|pages = 133–173|chapter-url = https://books.google.com/books?id=_tXoG93OWHgC&pg=PA141|publisher = ]|year = 2007|pmid = 17408083|last1 = Hilterhaus|first1 = L.|last2 = Liese|first2 = A.}}</ref><ref>{{cite book|title = Biocatalysis in Organic Synthesis 1|series = Science of Synthesis|publisher = ]|year = 2015|chapter = Enzymatic Synthesis of Amides|first1 = J. W.|last1 = Schmidberger|first2 = L. J.|last2 = Hepworth|first3 = A. P.|last3 = Green|first4 = S. L.|last4 = Flitsch|pages = 329–372|isbn = 9783131766113|editor1-first = Kurt|editor1-last = Faber|editor2-first = Wolf-Dieter|editor2-last = Fessner|editor3-first = Nicholas J.|editor3-last = Turner|chapter-url = https://books.google.com/books?id=8h_wBgAAQBAJ&pg=PA362}}</ref> which is a precursor to pyridinecarbaldehydes:
:3-NCC<sub>5</sub>H<sub>3</sub>N + + catalyst → 3-HC(O)C<sub>5</sub>H<sub>4</sub>N
Pyridinecarbaldehydes are used to make antidotes for poisoning by organophosphate acetylcholinesterase inhibitors.

==Environmental behavior==
Pyridine derivatives (including 3-methylpyridine) are environmental contaminants, generally associated with processing fossil fuels, such as oil shale or coal.<ref>{{Cite journal |last1=Sims |first1=Gerald K. |last2=O'Loughlin |first2=Edward J. |last3=Crawford |first3=Ronald L. |date=January 1989 |title=Degradation of pyridines in the environment |url=http://www.tandfonline.com/doi/abs/10.1080/10643388909388372 |journal=Critical Reviews in Environmental Control |language=en |volume=19 |issue=4 |pages=309–340 |doi=10.1080/10643388909388372 |bibcode=1989CRvEC..19..309S |issn=1040-838X}}</ref> They are also found in the soluble fractions of crude oil spills. They have also been detected at legacy wood treatment sites. The high water solubility of 3-methyl pyridine increases the potential for the compound to contaminate water sources. 3-methyl pyridine is biodegradable, although it degrades more slowly and volatilize more readily from water samples than either 2-methyl- or 4-methyl-pyridine.,<ref>{{Cite journal |last1=Sims |first1=Gerald K. |last2=Sommers |first2=Lee E. |date=June 1986 |title=Biodegradation of pyridine derivatives in soil suspensions |url=https://setac.onlinelibrary.wiley.com/doi/10.1002/etc.5620050601 |journal=Environmental Toxicology and Chemistry |language=en |volume=5 |issue=6 |pages=503–509 |doi=10.1002/etc.5620050601 |issn=0730-7268}}</ref><ref>{{Cite journal |last1=Sims |first1=Gerald K. |last2=Sommers |first2=Lee E. |date=October 1985 |title=Degradation of Pyridine Derivatives in Soil |url=https://acsess.onlinelibrary.wiley.com/doi/10.2134/jeq1985.00472425001400040022x |journal=Journal of Environmental Quality |language=en |volume=14 |issue=4 |pages=580–584 |doi=10.2134/jeq1985.00472425001400040022x |bibcode=1985JEnvQ..14..580S |issn=0047-2425}}</ref>

3-Methylpyridine is the main precursor to ], one of the ]. Approximately 10,000 tons of niacin are produced annually worldwide.<ref name=Ullmann>{{cite journal
| author = Manfred Eggersdorfer
| title = Vitamins
| journal = Ullmann's Encyclopedia of Industrial Chemistry
| year = 2000
| doi = 10.1002/14356007.a27_443
| isbn = 3527306730
|display-authors=etal}}</ref>

== See also ==
* ]

==Toxicity==
Like most alkylpyridines, the ] of 2-methylpyridine is modest, being 400&nbsp;mg/kg (oral, rat).<ref name=Ullmann/>

==References==
{{reflist|35em}}

{{DEFAULTSORT:Methylpyridine, 3-}}
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