Category: 25309-64-2

Electric Literature of 25309-64-2, These common heterocyclic compound, 25309-64-2, name is 1-Ethyl-4-iodobenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a stirred solution of aryl halides (2.0 mmol) and thiourea (1.2 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 110 C for 15 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (20 mL) was added. The combined organic extracts were dried with anhydrous Na2SO4. The solvent and volatiles were completely removed under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 9:1) to afford the corresponding coupling product in excellent yields.Recycling of the catalyst:after the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (2.0 mL) was added and CuO was removed by centrifugation. After each cycle, the catalyst was recovered by simple centrifugation, washing with deionized water and ethyl acetate and then drying in vacuo. The recovered nano CuO was used directly in the next cycle.Data of representative examples:Dip-tolylsulfane (Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Bis(4-ethylphenyl)sulfane (Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Bis(3-nitrophenyl)sulfane (Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.4,4′-Thiodianiline (Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Dithiophen-3-ylsulfane (Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Dipyrimidin-5-ylsulfane (Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; found: C, 50.45; H, 3.13; N, 29.41; S, 16.81.Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; f…

Statistics shows that 1-Ethyl-4-iodobenzene is playing an increasingly important role. we look forward to future research findings about 25309-64-2.

Reference:
Article; Reddy, K. Harsha Vardhan; Reddy, V. Prakash; Shankar; Madhav; Anil Kumar; Nageswar; Tetrahedron Letters; vol. 52; 21; (2011); p. 2679 – 2682;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 25309-64-2,Some common heterocyclic compound, 25309-64-2, name is 1-Ethyl-4-iodobenzene, molecular formula is C8H9I, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A 250 mL 3 -neck round bottom flask equipped with a thermometer and a magnetic stirring bar was charged with 4.01 g (61.3 mmol) of zinc dust and 35 mL of dimethylformamide (DMF) under a nitrogen atmosphere. The slurry was treated with 0.56 g (2.2 mmol) of iodine. The red disappeared in 90 seconds. The reaction mixture was treated with 6.00 mL (8.18 g, 42.0 mmol) of ethyl 4-bromobutyrate and heated to 800C for 4 hour. The reaction mixture was cooled to 300C and treated with 4.98 g (21.5 mmol) of 4-iodoethylbenzene and 0.48 g (0.9 mmol) of dichlorobis(triphenylphosphine)nickel(II). The reaction mixture was heated to 45C for 80 hours. The cooled reaction mixture was treated with aqueous 4% hydrochloric acid to quench the excess zinc. The mixture was extracted with methyl t-butyl ether (MTBE) (1 X 60 mL). The organic phase was washed with brine (1 X 30 mL), dried over sodium sulfate and concentrated. The crude ethyl 4-(4-ethylphenyl)butyrate was taken up in ethanol, treated with 20 mL of 2N aqueous sodium hydroxide, and heated to reflux. After 4 hours the reaction mixture was cooled to 25C and washed with MTBE (2 X 30 mL). The aqueous phase was acidified with aqueous 4% hydrochloric acid. A solid was isolated by filtration to give 1.99 g of 4-(4-ethylphenyl)butanoic acid. IH NMR (d6- DMSO): delta 11.9, bs, IH (COOH); delta 6.98, d, 2H, (arylH’s); delta 6.95, d, 2H (arylH’s); delta 2.41, m, 4H, (CH2’s alpha to aryl); delta 2.07, t, 2H (CH2 alpha to COOH); delta 1.64, m, 2H (CH2 beta to both aryl and COOH); delta 1.03, t, 3H (CH3). 13C NMR (d6-DMSO): 174.23, 141.08, 138.67, 128.20, 127.65, 33.97, 33.03, 27.73, 26.35, 15.65.

The synthetic route of 25309-64-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EMISPHERE TECHNOLOGIES, INC.; WO2008/112368; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 25309-64-2, name is 1-Ethyl-4-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 25309-64-2

General procedure: A 100 mL Schlenk flask was charged with 2-bromopyridine (1.1 mmol), phenylacetylene (0.92 mmol), Cs2CO3 (1.84 mmol), 1-Pd (0.003 mmol based on Pd), DMF (6 mL) and the reaction mixture was stirred at 100 C under air atmosphere for 12 h. The mixture was cooled to the room temperature; the solid was removed by filtration and washed twice with DMF (3 mL). The filtrate was collected, dried and the residue was extracted with ethyl acetate (3 x 3 mL) followed by purification with silica gel chromatography (petroleum ether) to give a corresponding product.

According to the analysis of related databases, 25309-64-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ezugwu, Chizoba I.; Mousavi, Bibimaryam; Asraf, Md. Ali; Luo, Zhixiong; Verpoort, Francis; Journal of Catalysis; vol. 344; (2016); p. 445 – 454;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 25309-64-2, name is 1-Ethyl-4-iodobenzene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 25309-64-2, Quality Control of 1-Ethyl-4-iodobenzene

General procedure: After standard evacuation and back-fill cycles with argon, a Schlenk tube fitted with a magnetic stirrer bar was charged with pyrazole derivative (1.29 mmol), aryl iodide (1.1 eq), K3PO4 (2 eq) and copper iodide (0.1 eq). N,N’-dimethyl-cyclohexane-1,2-diamine (0.2 eq) and anhydrous dioxane (3 mL) were then added under a stream of argon by syringe at room temperature. The sealed tube is stirred at 110 C for 24-48 h. A 28% solution of ammonia and water are added at room temperature to the reaction mixture. The resulting aqueous layer is extracted with DCM. The combined organic layers are dried on MgSO4, filtered and evaporated under reduced pressure. The residue is triturated in an appropriate solvent or purified on silica gel.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Deprez-Poulain, Rebecca; Cousaert, Nicolas; Toto, Patrick; Willand, Nicolas; Deprez, Benoit; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 3867 – 3876;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 25309-64-2, name is 1-Ethyl-4-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 25309-64-2

General procedure: To a stirred solution of aryl halides (1.0 mmol) and indoline/indoline carboxylic acid (1.0 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 80 C for 8 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was cooled to room temperature and catalyst was filtered, the crude residue was extracted with ethyl acetate (3 ¡Á 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (7:3) as eluent to give the corresponding N-substituted indoles in excellent yields. The identity and purity of the product were confirmed by 1H, 13C NMR, and mass spectra.

The synthetic route of 25309-64-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reddy, K. Harsha Vardhan; Satish; Ramesh; Karnakar; Nageswar; Tetrahedron Letters; vol. 53; 24; (2012); p. 3061 – 3065;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com