2-甲基咪唑

化合物

2-甲基咪唑是一種有機化合物,化學式為CH3C3H2N2H。它是無色晶體,易溶於極性有機溶劑。

2-甲基咪唑
IUPAC名
2-Methyl-1H-imidazole
別名 2-MeIm
識別
CAS號 693-98-1
PubChem 12749
ChemSpider 12225
SMILES
 
  • Cc1[nH]ccn1
InChI
 
  • 1/C4H6N2/c1-4-5-2-3-6-4/h2-3H,1H3,(H,5,6)
InChIKey LXBGSDVWAMZHDD-UHFFFAOYAM
性質
化學式 C4H6N2
摩爾質量 82.10 g/mol g·mol⁻¹
外觀 無色晶體
密度 1.149 g·cm−3(−173 °C)[1]
1.062±0.06 g·cm−3(20 °C)[2]
熔點 144 °C(417 K)[3]
沸點 268 °C(541 K)[4]
溶解性 20.3 g(25 °C)[2]
相關物質
相關化學品 1-甲基咪唑
4-甲基咪唑
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

製備

編輯

2-甲基咪唑可由乙二醛乙醛的縮合反應(Debus–Radziszewski咪唑合成)製備。[5]

4,5-二氫-2-甲基咪唑的氧化反應也可得到2-甲基咪唑。[6]

反應

編輯
 
2-甲基咪唑在鹼的作用下脫質子

2-甲基咪唑可以作為配體,和金屬鹽反應得到配合物。例如,它和氟硼酸鎘反應,從溶液中可以生長出無色的Cd(2-MeIm)6(BF4)2[7];它和硝酸鋅硝酸鈷反應,可以得到配位聚合物ZIF-8吳語ZIF-8以及ZIF-67[8]

 
硝酸鋅與2-甲基咪唑製得的ZIF-8透無線電子顯微鏡圖像

2-甲基咪唑在二氯甲烷中和乙酸銀反應,可以得到4,5-二碘-2-甲基咪唑。[9]它和甲醛四氫呋喃中加熱反應,得到2-甲基咪唑基甲醇。[10]


的作用下,它可以和鹵代烴發生C-N偶聯反應,如和碘苯反應,得到2-甲基-1-苯基咪唑[11];和1-溴丁烷反應,得到1-丁基-2-甲基咪唑[12]

參考文獻

編輯
  1. ^ Hachuła, Barbara; Nowak, Maria; Kusz, Joachim. Crystal and Molecular Structure Analysis of 2-Methylimidazole. Journal of Chemical Crystallography. 2009, 40 (3): 201–206. ISSN 1074-1542. doi:10.1007/s10870-009-9634-9. 
  2. ^ 2.0 2.1 Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 ((C) 1994-2020 ACD/Labs). Retrieved from SciFinder. [2020-09-14].
  3. ^ "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2020-09-14]
  4. ^ Oakes, Merwin D. Recovery and purification of Χ-alkylimidazoles by azeotropic distillation. 1965. US 3170849.
  5. ^ Ebel, Klaus; Koehler, Hermann; Gamer, Armin O.; Jäckh, Rudolf. Imidazole and Derivatives. 2000. doi:10.1002/14356007.a13_661. 
  6. ^ Butler, Richard N.; Fitzgerald, Kevin J. 1,2- and 1,3-Diamine exchange between substituted 4,5-dihydroimidazoles and 1,4,5,6-tetrahydropyrimidines: routes to benzimidazoles, dihydroimidazoles and tetrahydropyrimidines. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1989. 1: 155-157. ISSN: 0300-922X.
  7. ^ Reedijk, J.; Verschoor, G. C. Pyrazoles and imidazoles as ligands. XX. The crystal and molecular structure of hexakis(2-methylimidazole)cadmium(II) tetrafluoroborate. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 1973, 29 (4): 721–725. ISSN 0567-7408. doi:10.1107/S0567740873003237. 
  8. ^ Gross, Adam F.; Sherman, Elena; Vajo, John J. Aqueous room temperature synthesis of cobalt and zinc sodalite zeolitic imidizolate frameworks. Dalton Transactions. 2012, 41 (18): 5458. ISSN 1477-9226. doi:10.1039/c2dt30174a. 
  9. ^ Iglesias, Manuel; Schuster, Oliver; Albrecht, Martin. A new, mild one-pot synthesis of iodinated heterocycles as suitable precursors for N-heterocyclic carbene complexes. Tetrahedron Letters. 2010, 51 (41): 5423–5425. ISSN 0040-4039. doi:10.1016/j.tetlet.2010.07.178. 
  10. ^ Lupsor, Simona; Tarcomnicu, Isabela; Aonofriesei, Florin; Iovu, Mircea. Microwave-assisted synthesis of 1-hydroxymethylazoles. Revista de Chimie (Bucharest, Romania), 2011. 62 (5): 493-498. ISSN: 0034-7752.
  11. ^ Panahi, Farhad; Daneshgar, Fatemeh; Haghighi, Fatemeh; Khalafi-Nezhad, Ali. Immobilized Pd nanoparticles on silica-starch substrate (PNP-SSS): Efficient heterogeneous catalyst in Buchwald–Hartwig C–N cross coupling reaction. Journal of Organometallic Chemistry. 2017, 851: 210–217. ISSN 0022-328X. doi:10.1016/j.jorganchem.2017.09.037. 
  12. ^ Allin, Steven M.; Barton, William R.S.; Russell Bowman, W.; Bridge (née Mann), Emma; Elsegood, Mark R.J.; McInally, Tom; McKee, Vickie. Bu3SnH-mediated radical cyclisation onto azoles. Tetrahedron. 2008, 64 (33): 7745–7758. ISSN 0040-4020. doi:10.1016/j.tet.2008.06.014.