查看“︁邻甲苯胺”︁的源代码

{{NoteTA|G1=Chemistry|G2=Medicine}}
{{Medical}}
{{chembox|Name=鄰甲苯胺|ImageFile=O-Toluidin.svg|ImageSize=150px|PIN=2-Methylaniline<ref name=iupac2013>{{cite book | title =  Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 669 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = The names ‘toluidine’, ‘anisidine’, and ‘phenetidine’ for which ''o''-, ''m''-, and ''p''- have been used to distinguish isomers, and ‘xylidine’ for which numerical locants, such as 2,3-, have been used, are no longer recommended, nor are the corresponding prefixes ‘toluidine’, ‘anisidino’, ‘phenetidine’, and ‘xylidino’.}}</ref>|IUPACName=2-Methylaniline|OtherNames=鄰甲基苯胺<br />2-甲基苯胺<br />2-氨基甲苯|Section1={{Chembox Identifiers
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = B635MZ0ZLU
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13854136
| PubChem = 7242
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14403
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1381
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 95-53-4
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 66892
 }}|Section2={{Chembox Properties
| C=7|H=9|N=1
| Appearance = 無色液體
| Odor = 帶有類似苯胺的氣味
| Density = 1.004 g/cm<sup>3</sup>
| Solubility =  20&nbsp;°C 時為 0.19 g/100 ml 
| MeltingPtC = -23.68
| BoilingPtCL = 200|BoilingPtCH=202
| VaporPressure = 0.307531 mmHg (25&nbsp;°C)
| RefractIndex = 1.56987
| Viscosity = 4.4335 (20 °C)
 }}|Section7={{Chembox Hazards
| MainHazards= 易燃、有毒
| GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|301|302|319|331|350|400}}
| PPhrases = {{P-phrases|201|202|261|264|270|271|273|280|281|301+310|304+340|305+351+338|308+313|311|321|330|337+313|391|403+233|405|501}}
| ExternalSDS = 
| NFPA-H = 3
| NFPA-F = 2
| NFPA-R = 0
| FlashPtC = 85
| AutoignitionPtC = 481.67
| LD50 =  900 mg/kg（大鼠，口服）<br/>323 mg/kg（兔子，口服）
 }}|Section8={{Chembox Related
| OtherCompounds = [[甲苯胺]]
 }}}}
'''鄰甲苯胺'''，又名'''2-甲基苯胺'''，化學式<chem>C7H9N</chem>，是一種[[有机化合物|有機化合物]]。它屬於二取代苯，是[[甲苯胺]]的[[同分異構|同分異構體]]之一。對光敏感，微溶於水，可與[[乙醇]]、[[乙醚]]和[[四氯化碳|四氯甲烷]]互相混溶。<ref name="未命名-rHko-1">{{Cite web |title=o-Toluidine |url=https://ncithesaurus.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=ncit&code=C44429 |website=National Cancer Institute |access-date=2022-07-14}}</ref>可以用作有機合成中間體<ref>{{Cite web |date=2022-01-10 17:00:36 |title=邻甲苯胺 |url=https://www.chemsrc.com/cas/95-53-4_954759.html |website=化源網}}</ref>。

== 製備與反應 ==
[[甲苯]]的[[硝化反应|硝化反應]]能產生不同的[[一硝基甲苯]]。其中[[2-硝基甲苯]]的量比較多，經過蒸餾被分離出來。2-硝基甲苯其後可以經過[[氢化|氫化反應]]，被[[氧化还原反应|還原]]成鄰甲苯胺<ref name="Ullmann">{{Ullmann|first=Joseph S.|last=Bowers|title=Toluidines|doi=10.1002/14356007.a27_159}}</ref>。亦可用與酸、鐵粉與2-硝基甲苯加熱，以製備鄰甲苯胺<ref name="未命名-rHko-2">{{Cite web |title=邻甲苯胺 |url=https://www.chemicalbook.com/ChemicalProductProperty_CN_CB6854698.htm |website=ChemicalBook |language=中文 |access-date=2022-07-14 |archive-date=2022-07-14 |archive-url=https://web.archive.org/web/20220714132447/https://www.chemicalbook.com/ChemicalProductProperty_CN_CB6854698.htm }}</ref>。

由於鄰甲苯胺具備胺基，因此可以進行一般[[芳香胺]]所能進行的反應。例如它可以發生[[重氮化反应|重氮化反應]]，和[[亚硝酸|亞硝酸]]或[[亚硝酸盐|亞硝酸鹽]]及過量酸在低溫下反應，生成[[重氮盐|重氮鹽]]。<ref>{{Cite book|title=基礎有機化學|last=邢|first=其毅|year=2016|isbn=978-7-301-27943-4|location=北京|pages=864|last2=裴|first2=偉偉|last3=徐|first3=瑞秋|last4=裴|first4=堅|chapter=第18章}}</ref>而此重氮鹽可以經過[[桑德迈尔反应|桑德邁爾反應]]等不同反應轉化為[[2-溴甲苯]]、[[2-氯甲苯]]等不同化合物以及其衍生物。<ref>{{cite journal |year=1925 |title=o-Tolunitrile and p-Tolunitrile |journal=Org. Synth. |volume=4 |page=69 |doi=10.15227/orgsyn.004.0069 |authors=H. T. Clarke, R. R. Read}}</ref> <ref>{{cite journal |author=L. A. Bigelow |year=1929 |title=o-Bromotoluene |journal=Org. Synth. |volume=9 |page=22 |doi=10.15227/orgsyn.009.0022}}</ref> <ref>{{cite journal |year=1923 |title=o-Chlorotoluene and p-Chlorotoluene |journal=Org. Synth. |volume=3 |page=33 |doi=10.15227/orgsyn.003.0033 |authors=C. S. Marvel, S. M. McElvain}}</ref>胺基氮上也可以發生[[酰化反应|酰基化反應]]。<ref>{{cite journal |year=1962 |title=Indazole |journal=Org. Synth. |volume=42 |page=69 |doi=10.15227/orgsyn.042.0069 |authors=Rolf Huisgen, Klaus Bast}}</ref>

[[局部麻醉药|局部麻醉藥]][[丙胺卡因]]經過[[羧酸酯酶]]的代謝，會產生鄰甲苯胺。由於鄰甲苯胺可以將[[血红蛋白|血紅蛋白]]氧化，大劑量的丙胺卡因可引致[[正鐵血紅蛋白血症]]。<ref name="未命名-rHko-3">{{cite journal |year=2013 |title=Prilocaine- and Lidocaine-Induced Methemoglobinemia Is Caused by Human Carboxylesterase-, CYP2E1-, and CYP3A4-Mediated Metabolic Activation |journal=Drug Metab. Dispos. |volume=41 |page=1220-1230 |doi=10.1124/dmd.113.051714 |authors=Ryota Higuchi, Tatsuki Fukami, Miki Nakajima, Tsuyoshi Yokoi}}</ref><ref name="未命名-rHko-4">{{cite journal |year=2020 |title=Prilocaine-Induced Methemoglobinemia |journal=Case Rep. Acute Med. |volume=3 |page=25-28 |doi=10.1159/000508403 |doi-access=free |authors=Medetalibeyoğlu A., Koç E.S., Beyaz O., Edizer A.}}</ref>

== 用途 ==
鄰甲苯胺可以用作合成染料（如[[品红 (化合物)|鹼性品紅]]<ref>{{Cite web |title=邻甲苯胺 |url=https://www.chembk.com/cn/chem/%E9%82%BB%E7%94%B2%E8%8B%AF%E8%83%BA |website=化工百科}}</ref>等）、農藥（如[[乙草胺]]<ref name="Ullmann2">{{Ullmann|first=Joseph S.|last=Bowers|title=Toluidines|doi=10.1002/14356007.a27_159}}</ref>等）、醫藥的合成中間體。

== 健康危害 ==
鄰甲苯胺是有毒的。<ref>{{Cite web |title=o-Toluidine |url=https://pubchem.ncbi.nlm.nih.gov/compound/o-Toluidine#section=RCRA-Requirements |website=PubChem |language=英文 |access-date=2022-07-14 |archive-date=2022-07-14 |archive-url=https://web.archive.org/web/20220714135741/https://pubchem.ncbi.nlm.nih.gov/compound/o-Toluidine#section=RCRA-Requirements }}</ref>它加熱分解放出含有氮氧化物的有毒氣體。<ref name="未命名-rHko-1"/>鄰甲苯胺可以氧化[[血红蛋白|血紅蛋白]]，生產[[高铁血红蛋白|正鐵血紅蛋白]]，因此攝入、吸入和與皮膚接觸可能會引起[[正鐵血紅蛋白血症]]<ref name="未命名-rHko-3"/><ref name="未命名-rHko-4"/>，並帶來[[血尿]]等症狀<ref name="未命名-rHko-2"/>。同時，鄰甲苯胺是[[致癌物質|致癌物]]，被[[国际癌症研究机构|國際癌症研究機構]]列爲[[国际癌症研究机构一类致癌物|一類致癌物]]<ref>{{Cite web|url=http://monographs.iarc.fr/ENG/Monographs/vol99/|title=IARC Monographs|website=monographs.iarc.fr|access-date=2016-06-13|archive-date=2017-01-28|archive-url=https://web.archive.org/web/20170128175023/http://monographs.iarc.fr/ENG/Monographs/vol99/}}</ref>。

== 參考資料 ==
{{reflist|2}}

{{苯}}

[[Category:甲基苯胺]]
[[Category:有機化合物]]
[[Category:邻甲苯基化合物]]