693-98-1 Usage
Description
2-Methylimidazole, a monomethylated imidazole, is a white or colorless solid that is highly soluble in polar organic solvents and water. It is a precursor to a range of drugs and serves as a ligand in coordination chemistry. With its amine-like odor, 2-Methylimidazole is a versatile compound that has been identified as a byproduct of fermentation and is detected in foods, mainstream, and side-stream tobacco smoke.
Uses
Used in Pharmaceutical Industry:
2-Methylimidazole is used as a raw material for the preparation of nitroimidazole antibiotics, which are effective in combating anaerobic bacterial and parasitic infections. It acts as an active pharmaceutical ingredient intermediate for drugs such as metronidazole and dimetridazole.
Used in Coordination Chemistry:
In coordination chemistry, 2-Methylimidazole serves as a ligand, playing a crucial role in the formation and stabilization of metal complexes.
Used in Biotechnology:
2-Methylimidazole is used as a catalyst for the refolding of enhanced colored fluorescent protein, which is essential in various biotechnological applications.
Used in Chemical Synthesis:
It is a building block in the synthesis of a wide range of biologically active compounds, contributing to the development of new pharmaceuticals and other bioactive substances.
Used in Epoxy Resin Industry:
2-Methylimidazole is employed as a hardener or accelerator for epoxy resin, improving the curing process and enhancing the final product's properties.
Used in Textile Industry:
It acts as an auxiliary agent for textile dyes, facilitating the dyeing process and ensuring better colorfastness and quality of the dyed fabrics.
Used in Food Industry:
As a byproduct of fermentation, 2-Methylimidazole is detected in various foods, contributing to their flavor and aroma profiles.
Chemical Properties:
2-Methylimidazole is a white to light yellow crystalline powder with an amine-like odor. It is highly soluble in polar organic solvents, easily soluble in water, alcohols, and ketones, but insoluble in ether and cold benzene. It is irritating to skin and mucous membranes, with an oral LD50 of 1400mg/kg in mice.
Preparation
2-Methylimidazole is prepared by condensation of glyoxal, ammonia and acetaldehyde, a Radziszewski reaction. It is widely used as a polymeriza tion cross-linking accelerator and a hardener for epoxy resin systems for semiconductor potting compounds and soldering masks. It is obtained by eliminating dehydrogenation of 2-methylimidazoline. 2-methylimidazoline heated to melt (melting point 107 ℃), carefully add active nickel, raise the temperature to 200-210 ℃ reaction 2h. cool down to below 150 ℃, add water to dissolve, while hot pressure filtration, separation of active nickel, the filter lookchem liquid concentrated to a temperature of 140 ℃ or more, put the material cooling that 2-methylimidazole. Use the method to produce purity of ≥ 98% of the product, 1t product consumption of ethylenediamine (95%) 1095kg, acetonitrile 975kg. better method is to use glyoxal and aldehyde as raw materials.
Hazard
Possible carcinogen.
Flammability and Explosibility
Notclassified
Purification Methods
Recrystallise 2-methylimidazole from *benzene or pet ether. The picrate has m 215o (from H2O). [Beilstein 23 III/IV 594, 23/5 V 35.]
Check Digit Verification of cas no
The CAS Registry Mumber 693-98-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,9 and 3 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 693-98:
(5*6)+(4*9)+(3*3)+(2*9)+(1*8)=101
101 % 10 = 1
So 693-98-1 is a valid CAS Registry Number.
InChI:InChI=1/C4H6N2/c1-4-5-2-3-6-4/h2-3H,1H3,(H,5,6)
693-98-1Relevant articles and documents
Identification of Intermediates and Products of 2,4,6-Trimethyl-1,3,5-Hexahydrotriazine Trihydrate and Glyoxal Reaction in an Aqueous Solution by NMR Spectroscopy
Bakibaev, A. A.,Cheltygmasheva, R. S.,Fateev, A. V.,Kotelnikov, O. A.,Kotov, A. V.,Tuguldurova, V. P.,Vodyankina, O. V.
, p. 225 - 231 (2020)
In situ formation of 2-methylimidazole as a result of 2,4,6-trimethyl-1,3,5-hexahydrotriazine trihydrate and glyoxal interaction in an aqueous solution is studied for the first time using NMR spectroscopy. In addition to the reactants and products, the reaction mixture is shown to contain stable intermediate products of the trimer decomposition as well as glycolic acid.
Imprinted Apportionment of Functional Groups in Multivariate Metal-Organic Frameworks
Feng, Liang,Wang, Kun-Yu,Lv, Xiu-Liang,Powell, Joshua A.,Yan, Tian-Hao,Willman, Jeremy,Zhou, Hong-Cai
supporting information, p. 14524 - 14529 (2019/10/02)
Sophisticated chemical processes widely observed in biological cells require precise apportionment regulation of building units, which inspires researchers to develop tailorable architectures with controllable heterogeneity for replication, recognition and information storage. However, it remains a substantial challenge to endow multivariate materials with internal sequences and controllable apportionments. Herein, we introduce a novel strategy to manipulate the apportionment of functional groups in multivariate metal-organic frameworks (MTV-MOFs) by preincorporating interlocked linkers into framework materials. As a proof of concept, the imprinted apportionment of functional groups within ZIF-8 was achieved by exchanging imine-based linker templates with original linkers initially. The removal of linker fragments by hydrolysis can be achieved via postsynthetic labilization, leading to the formation of architectures with controlled heterogeneity. The distributions of functional groups in the resulting imprinted MOFs can be tuned by judicious control of the interlocked chain length, which was further analyzed by computational methods. This work provides synthetic tools for precise control of pore environment and functionality sequences inside multicomponent materials.
Design, synthesis, structure-activity relationships study and X-ray crystallography of 3-substituted-indolin-2-one-5-carboxamide derivatives as PAK4 inhibitors
Guo, Jing,Zhao, Fan,Yin, Wenbo,Zhu, Mingyue,Hao, Chenzhou,Pang, Yu,Wu, Tianxiao,Wang, Jian,Zhao, Dongmei,Li, Haitao,Cheng, Maosheng
, p. 197 - 209 (2018/06/12)
We have previously described the identification of indolin-2-one-5-carboxamides as potent PAK4 inhibitors. This study expands the structure-activity relationships on our original series by presenting several modifications in the lead compounds, 2 and 3. A series of novel derivatives was designed, synthesized, and evaluated in biochemical and cellular assay. Most of this series displayed nanomolar biochemical activity and potent antiproliferative activity against A549 and HCT116 cells. The representative compound 10a exhibited excellent enzyme inhibition (PAK4 IC50 = 25 nM) and cellular potency (A549 IC50 = 0.58 μM, HCT116 IC50 = 0.095 μM). An X-ray structure of compound 10a bound to PAK4 was obtained. Crystallographic analysis confirmed predictions from molecular modeling and helped refine SAR results. In addition, Compound 10a displayed focused multi-targeted kinase inhibition, good calculated drug-likeness properties. Further profiling of compound 10a revealed it showed weak inhibitory activity against various isoforms of human cytochrome P450.