Silica gel

Manufactured by Qingdao Marine Chemical

Sourced in China, Sweden, Japan, United States

Silica gel is a porous, amorphous form of silicon dioxide. It is a desiccant material commonly used for moisture absorption and control in various applications.

Automatically generated - may contain errors

Lab products found in correlation

Sephadex lh 20, by Cytiva (41 mentions) Sephadex lh 20, by GE Healthcare (37 mentions) P 1020 polarimeter, by Jasco (23 mentions) Gf254, by Qingdao Marine Chemical (15 mentions) Drx 500, by Bruker (14 mentions) Sephadex lh 20, by Merck Group (13 mentions) Gf254, by Qingdao Haiyang Chemical (13 mentions) Uv 2401pc spectrometer, by Shimadzu (12 mentions) Mci gel chp 20p, by Mitsubishi (12 mentions) Mci gel, by Mitsubishi Chemical Corporation (11 mentions) Ft ir tensor 27 infrared spectrophotometer, by Bruker (10 mentions) Tensor 27 ftir spectrometer, by Bruker (10 mentions) Silica gel 60 f254, by Qingdao Marine Chemical (10 mentions) Silica gel gf254, by Qingdao Marine Chemical (10 mentions) P 1020, by Jasco (10 mentions) Avance 3 600, by Bruker (9 mentions) Uv 2401 pc spectrophotometer, by Shimadzu (9 mentions) Gf254 plates, by Qingdao Marine Chemical (9 mentions) Am 400, by Bruker (8 mentions) Autospec premier p776, by Waters Corporation (8 mentions)

260 protocols using silica gel

Synthesis of 4-Chlorobenzyl Malononitrile Oxime Ether

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Example 1

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To a solution of malononitrile oxime ether sodium salt (0.22 g, 1.86 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added p-chlorobenzyl chloride (0.3 g, 1.86 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:8) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 4 (0.21 g) as yellow oil with yield of 51%.

US10544092B2. Malononitrile oxime ether compound and use thereof (2020-01-28). SHENYANG SINOCHEM AGROCHEMICALS R&D CO., LTD. [CN]. Inventors: Xueming Cheng [CN], Lixin Zhang [CN], Liang Chen [CN], Qin Sun [CN], Junli Liu [CN], Zhinian Li [CN], Jie Zhao [CN], Jingbo Xu [CN], Hongfei Wu [CN].

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Synthesis of 1,2-Dichloro-4-(chloromethyl)benzene Derivative

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Example 5

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To a solution of malononitrile oxime ether sodium salt (0.18 g, 1.53 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added 1,2-dichloro-4-(chloromethyl)benzene (0.3 g, 1.53 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:8) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 59 (0.22 g) as yellow solid with yield of 56%.

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Synthesis of 4-(Trifluoromethoxy)benzyl-Substituted Malononitrile Oxime Ether

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Example 2

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To a solution of malononitrile oxime ether sodium salt (0.12 g, 0.98 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added 1-(bromomethyl)-4-(trifluoromethoxy)benzene (0.25 g, 0.98 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:8) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 25 (0.16 g) as white solid with yield of 61%.

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Synthesis of 4-Nitrobenzyl Malononitrile Oxime Ether

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Example 16

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To a solution of malononitrile oxime ether sodium salt (0.29 g, 2.48 mmol) dissolved in 25 mL acetonitrile in a 50 mL reaction flask was added 1-(2-chloroethoxy)-4-nitrobenzene (0.5 g, 2.48 mmol). The reaction was stirred at 80° C., and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:5) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:5; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 210 (0.26 g) as white solid with yield of 40%.

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Synthesis of 5-(Chloromethyl)pyridine Derivative

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Example 4

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To a solution of malononitrile oxime ether sodium salt (0.25 g, 2.16 mmol) dissolved in 15 mL acetonitrile in a 50 mL reaction flask was added 2-chloro-5-(chloromethyl)pyridine (0.35 g, 2.16 mmol). The reaction was stirred at room temperature, and monitored by Thin-Layer Chromatography (ethyl acetate:petroleum ether=1:8) until the reaction was over, the excessive acetonitrile was evaporated under reduced pressure, the residual was purified by column chromatography on silica gel (eluent: ethyl acetate:petroleum ether=1:10; silica gel: 100-140 mesh, Qingdao Marine Chemical Co., Ltd.) to obtain the title compound 53 (0.21 g) as yellow solid with yield of 44%.

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Isolation and Characterization of Natural Compounds

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Silica gel (100–200 and 200–300 mesh, Qingdao Marine Chemical Co., Ltd., Qingdao, China), MCI gel (75–150 μm, Mitsubishi Chemical Corporation, Tokyo, Japan) were used for column chromatography. Fractions were monitored by TLC (GF 254, Qingdao Marine Chemical Co., Ltd. Qingdao, China), and spots were visualized by heating Silica gel plates immersed in 8% H₂SO₄ in ethanol. Semi-preparative HPLC was performed on Waters 2695 HPLC with a COSMOSIL C₁₈ -MS-II (4.6ID × 250 mm) packed column. 1D and 2D NMR spectra were recorded on a Bruker DRX-600 spectrometer using TMS as an internal standard. Unless otherwise specified, chemical shifts (δ) are expressed in ppm with reference to the solvent signals. ESIMS and HRESIMS data were acquired on Agilent G6200 TOF mass spectrometer. Optical rotations were measured on a Jasco P-1020 polarimeter. UV spectra were recorded on a Shimadzu UV-2401PC spectrometer. IR spectra were recorded on a Bruker FT-IR Tensor-27 infrared spectrophotometer with KBr disks.

Zhao J.J., Li S.Y., Xia F., Hu Y.L., Nian Y, & Xu G. (2021). Isoprenylated Flavonoids as Cav3.1 Low Voltage-Gated Ca2+ Channel Inhibitors from Salvia digitaloides. Natural Products and Bioprospecting, 11(6), 671-678.

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Purification and Characterization of Insecticidal Extracts

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Based on the insecticidal activities of extracts, the most active extract was purified by the activity-tracking method combined with the separation method of silica gel column chromatography. The third set of bioassays was used to select the active fraction for subsequent evaluation. The method of the toxicity bioassay was the same as above (Section 2.3.2). The most active extract, which was subjected to silica gel column (200–300 mesh, Qingdao Marine Chemical Factory, Qingdao, China), was given four fractions by using a dichloromethane–methanol (25:1, 10:1, 5:1, 3:1, 0:1, v/v) gradient elution. Additionally, the active fraction Fr.2 was divided into four fractions by using a dichloromethane–methanol (1:0, 50:1, 25:1, 10:1, 3:1, 0:1, v/v) gradient elution (silica gel, 200–300 mesh, Qingdao Marine Chemical Factory, Qingdao, China). Additionally, the active fraction Fr.2.2 was divided into three fractions by using a petroleum-ether–ethyl-acetate (10:1, 5:1, 3:1,1:1, 0:1, v/v) gradient elution (silica gel, 300–400 mesh, Qingdao Marine Chemical Factory, Qingdao, China). The UPLC-Q-Exactive Orbitrap/MS system was employed to analyze the active fraction Fr.2.2.2.

Yue Y., Jiang M., Hu H., Wu J., Sun H., Jin H., Hou T, & Tao K. (2022). Isolation, Identification and Insecticidal Activity of the Secondary Metabolites of Talaromyces purpureogenus BS5. Journal of Fungi, 8(3), 288.

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Analytical Characterization of Methylglyoxal Derivatives

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The nuclear magnetic resonance data (¹H-NMR and ¹³C-NMR) were recorded on Bruker AV-500 (Bruker Inc., Germany). The mass spectrometry (MS) spectra were performed on Agilent 1100 Series LC-MSD-Trap/SL and Thermo TSQ Quantum LC/MS spectrometers. Silica gel (100–200 mesh, 200–300 mesh), which was used for Silica gel column chromatography and thin-layer chromatography was purchased from Qingdao Marine Chemical Factory (Qingdao, China). Sephadex LH-20 (GE Healthcare Bio-sciences AB, Uppsala, Sweden), C18 (YMC, Japan) and RP-18 F254 plates (0.25 mm, Merck, Germany) were used. Methylglyoxal was purchased from Wuhan Huameihua Co. (Wuhan, China). Aminoguanidine was purchased from Dulai Biotechnology Co. (Nanjing, China). Bovine serum albumin (BSA) was purchased from Beijing Solarbio Science and Technology Co. (Beijing, China). HPLC grade methanol was purchased from Tedia (Fairfield, USA). All other chemicals were analytical grade and purchased from Shuangling Chemical Reagent Co. (Nanjing, China).

Yang R., Wang W.X., Chen H.J., He Z.C, & Jia A.Q. (2017). The inhibition of advanced glycation end-products by five fractions and three main flavonoids from Camellia nitidissima Chi flowers. Journal of Food and Drug Analysis, 26(1), 252-259.

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Comprehensive Analytical Techniques for Chemical Characterization

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Optical rotations were recorded on an Autopol IV automatic polarimeter. The CD spectra were measured on a JASCO J-815 spectropolarimeter. UV spectra were obtained on a Persee TU-1901 UV-vis spectrometer. 1D and 2D NMR spectra were performed at 600 MHz for ¹H NMR and 150 MHz for ¹³C NMR on Bruker ARX-600 spectrometer. Chemical shifts (δ) are given in ppm, and coupling constants (J) are given in hertz (Hz). ESIMS data were recorded on a Thermo LTQ mass spectrometer. HRESIMS data were measured using a Thermo LTQ Orbitrap XL mass spectrometer. Column chromatography (CC) were carried out with silica gel (200–300 mesh, Qingdao Marine Chemical Inc. Qingdao, PR China). Analytical TLC was carried out on pre-coated silica gel GF₂₅₄ plates (Qingdao Marine Chemical Industry, Qingdao, China), and spots were visualized under UV light.

Guo Z., Zhang D., Wang Y., Bai J., Hu J., Cen S, & Yu L. (2024). An antiviral oligomerized linear thiopeptide with a nitrile group from soil-derived Streptomyces sp. CPCC 203702. RSC Advances, 14(12), 8260-8263.

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Spectroscopic Characterization of Compounds

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Optical rotations were measured on Jasco P-1020 automatic digital polarimeter. CD spectra were recorded on a Chirascan spectropolarimeter (Applied Photophysics, Leatherhead, Surrey, UK). UV data were obtained from HPLC online analysis. IR spectra were obtained on a Bruker Tensor-27 infrared spectrophotometer with KBr pellets. NMR spectra were carried out on a Bruker Avance III 600 or DRX-500 spectrometer with deuterated solvent signals used as internal standards. ESIMS and HRESIMS were measured using Agilent G6230 time-of-flight mass spectrometer. Preparative MPLC was performed on a Büchi apparatus equipped with Büchi fraction collector C-660, Büchi pump module C-605 and manager C-615. Silica gel (200–300 mesh, Qingdao Marine Chemical Inc., China), MCI gel CHP-20P (75–150 μm, Mitsubishi Chemical Corporation, Japan), Chromatorex C-18 (40–75 μm, Fuji Silysia Chemical Ltd., Japan) and Sephadex LH-20 (GE Healthcare Bio-Sciences AB, Uppsala, Sweden) were used for column chromatography. Fractions were monitored and analyzed using TLC, in combination with an Agilent 1200 series HPLC system equipped by an Extend-C18 column (5 μm, 4.6 × 150 mm).

Wang L.X., Zheng H.R., Ren F.C., Chen T.G., Li X.M., Jiang X.J, & Wang F. (2017). Polysubstituted Isoflavonoids from Spatholobus suberectus, Flemingia macrophylla, and Cudrania cochinchinensis. Natural Products and Bioprospecting, 7(2), 201-206.

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