2-甲基咪唑

2-甲基咪唑
	IUPAC名; 2-Methyl-1H-imidazole
别名	2-MeIm
识别
CAS号	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
性质
化学式	C4H6N2
摩尔质量	82.10 g/mol g·mol⁻¹
外观	无色晶体
密度	1.149 g·cm−3（−173 °C）; 1.062±0.06 g·cm−3（20 °C）
熔点	144 °C（417 K）
沸点	268 °C（541 K）
溶解性（水）	20.3 g（25 °C）
相关物质
相关化学品	1-甲基咪唑; 4-甲基咪唑
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

2-甲基咪唑是一种有机化合物，化学式为CH₃C₃H₂N₂H。它是无色晶体，易溶于极性有机溶剂。

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2-甲基咪唑可由乙二醛、氨和乙醛的缩合反应（Debus–Radziszewski咪唑合成）制备。^[5]

4,5-二氢-2-甲基咪唑的氧化反应也可得到2-甲基咪唑。^[6]

2-甲基咪唑可以作为配体，和金属盐反应得到配合物。例如，它和氟硼酸镉反应，从溶液中可以生长出无色的Cd(2-MeIm)₆(BF₄)₂^[7]；它和硝酸锌或硝酸钴反应，可以得到配位聚合物ZIF-8（吴语：ZIF-8）以及ZIF-67。^[8]

2-甲基咪唑在二氯甲烷中和碘与乙酸银反应，可以得到4,5-二碘-2-甲基咪唑。^[9]它和甲醛在四氢呋喃中加热反应，得到2-甲基咪唑基甲醇。^[10]

在碱的作用下，它可以和卤代烃发生C-N偶联反应，如和碘苯反应，得到2-甲基-1-苯基咪唑^[11]；和1-溴丁烷反应，得到1-丁基-2-甲基咪唑^[12]。

[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]
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.

[1] [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.

[ACD-2] [2]
Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 ((C) 1994-2020 ACD/Labs). Retrieved from SciFinder. [2020-09-14].

[3] [3]
"PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2020-09-14]

[4] [4]
Oakes, Merwin D. Recovery and purification of Χ-alkylimidazoles by azeotropic distillation. 1965. US 3170849.

[Ebel-5] [5]
Ebel, Klaus; Koehler, Hermann; Gamer, Armin O.; Jäckh, Rudolf. Imidazole and Derivatives. 2000. doi:10.1002/14356007.a13_661.

[6] [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] [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] [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] [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] [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] [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] [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.

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2-甲基咪唑

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2-甲基咪唑


IUPAC名 2-Methyl-1H-imidazole
别名	2-MeIm
识别
CAS号	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
性质
化学式	C₄H₆N₂
摩尔质量	82.10 g/mol g·mol⁻¹
外观	无色晶体
密度	1.149 g·cm⁻³（−173 °C）^[1] 1.062±0.06 g·cm⁻³（20 °C）^[2]
熔点	144 °C（417 K）^[3]
沸点	268 °C（541 K）^[4]
溶解性（水）	20.3 g（25 °C）^[2]
相关物质
相关化学品	1-甲基咪唑 4-甲基咪唑
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。