Category: 628-21-7

Some common heterocyclic compound, 628-21-7, name is 1,4-Diiodobutane, molecular formula is C4H8I2, 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. Computed Properties of C4H8I2

General procedure: Under N2 atmosphere, LHMDS (1 M in THF, 3.0 equiv) was added to a cooled solution (0 C) of tricyclic lactam (1.0 equiv) dissolved in THF (6 mL). After stirring for 1 h at 0 C, an excess of alkyl halide (3.0 equiv for methyl iodide and 5.0 equiv for ethyl iodide) was added. For the introduction of five and six membered spirocyclic rings 1,4-diiodobutane or 1,5-diiodopentane (1.0 equiv) was added at 0 C. The solution was stirred for a further 3 h at 0 C. Completion of the conversion was confirmed by TLC. Saturated NaCl solution (10 mL) was then added and the mixture was extracted with EtOAc (3 × 10 mL). The organic layer was washed with NaCl solution (10 mL) and water (10 mL) and the aqueous layer was reextracted with EtOAc (2 × 10 mL). The combined organic layers were dried (Na2SO4), filtered, and the solvent was evaporated in vacuo and the residue was purified by FC.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 628-21-7, its application will become more common.

Reference:
Article; Sarkar, Soumya; Schepmann, Dirk; Wuensch, Bernhard; Tetrahedron Asymmetry; vol. 22; 13; (2011); p. 1411 – 1422;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 628-21-7, name is 1,4-Diiodobutane, molecular formula is C4H8I2, 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. Computed Properties of C4H8I2

General procedure: Under N2 atmosphere, LHMDS (1 M in THF, 3.0 equiv) was added to a cooled solution (0 C) of tricyclic lactam (1.0 equiv) dissolved in THF (6 mL). After stirring for 1 h at 0 C, an excess of alkyl halide (3.0 equiv for methyl iodide and 5.0 equiv for ethyl iodide) was added. For the introduction of five and six membered spirocyclic rings 1,4-diiodobutane or 1,5-diiodopentane (1.0 equiv) was added at 0 C. The solution was stirred for a further 3 h at 0 C. Completion of the conversion was confirmed by TLC. Saturated NaCl solution (10 mL) was then added and the mixture was extracted with EtOAc (3 × 10 mL). The organic layer was washed with NaCl solution (10 mL) and water (10 mL) and the aqueous layer was reextracted with EtOAc (2 × 10 mL). The combined organic layers were dried (Na2SO4), filtered, and the solvent was evaporated in vacuo and the residue was purified by FC.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 628-21-7, its application will become more common.

Reference:
Article; Sarkar, Soumya; Schepmann, Dirk; Wuensch, Bernhard; Tetrahedron Asymmetry; vol. 22; 13; (2011); p. 1411 – 1422;,
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. 628-21-7, name is 1,4-Diiodobutane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 1,4-Diiodobutane

Stage 1 (0244) An oven-dried 3 L 4-neck flask fitted with an internal thermometer, N2 bubbler, overhead stirrer and oven-dried mL pressure-equalising dropping funnel was charged with 1,4-dibromo-2,5-diethylbenzene (70 g, 240 mmol) and dry THF (700 mL). The solution was cooled with stirring to <-70 C. to produce a white slurry. s-Butyllithium (335 mL, 1.4 M, 465 mmol) was charged to the dropping funnel and added dropwise over the space of 1.5 h ensuring the reaction temperature did not exceed -70 C. The slurry was stirred for 3 h after which GCMS confirmed the lithiation was complete. The dropping funnel was charged with a solution of 1,4-diiodobutane (13.8 mL, 105 mmol) in dry THF (140 mL) which was then added dropwise over 0.75 h. The resulting slurry was allowed to warm to room temperature and stirred for 12 h. The reaction was quenched by addition of water. The mixture was transferred to a separating funnel and the layers were separated. The aqueous layer was extracted with diethyl ether and the combined organics were washed with water, dried with MgSO4, filtered and concentrated to yield an orange oil. The product was triturated with 500 mL methanol for 0.5 h and filtered as a white solid before being recrystallised from toluene/IPA to yield a white powder that was dried in the oven (24.21 g, 48%). GCMS indicated a purity of 96% and the material was taken to the next stage without further purification The synthetic route of 628-21-7 has been constantly updated, and we look forward to future research findings. Reference:
Patent; Cambridge Display Technology Limited; Sumitomo Chemical Company Limited; Kamtekar, Kiran; Steudel, Annette; (30 pag.)US9812644; (2017); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 628-21-7,Some common heterocyclic compound, 628-21-7, name is 1,4-Diiodobutane, molecular formula is C4H8I2, 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.

To a solution of bis(oxazoline) 2l51 (0.100 g, 0.280 mmol) in THF (5 mL) were added TMEDA (73 muL, 0.56 mmol) and i-Pr2NH (39 muL, 0.28 mmol). The resulting mixture was then cooled at -78 C. n-BuLi (0.370 mL of a 2.5 M solution in hexanes, 0.56 mmol) was added via syringe to the cold mixture. The reaction mixture was warmed to -20 C and stirred for 20 min. The solution was cooled to -78 C and freshly distilled 1,4-diiodobutane (50 muL, 0.38 mmol) was added. After the addition, the cooling bath was removed and the mixture was allowed to stir at room temperature for 16 h. The mixture was quenched with saturated aqueous NH4Cl solution (1 mL) and diluted with water (1 mL). The resulting mixture was extracted with Et2O (2×5 mL). The combined organic layers were washed with brine (5 mL), dried over Na2SO4, and concentrated under reduced pressure to afford a dark orange oil. The desired bis(oxazoline) 2j was obtained as a white solid (87 mg, 75% yield) after flash chromatography (50% EtOAc/hexanes). Rf 0.58 (50% EtOAc/hexanes); [alpha]D25 -108.8 (c 0.50, CHCl3); mp 79-81 C; 1H NMR (400 MHz, CDCl3) delta 7.72 (d, J=8.7 Hz, 2H), 7.40 (dd, J=7.2, 2.1 Hz, 2H), 7.08-7.01 (m, 3H), 6.67 (d, J=8.7 Hz, 2H), 6.50 (s, 1H), 2.99 (dd, J=6.4, 3.6 Hz, 1H), 2.17 (d, J=6.3 Hz, 1H), 1.64 (d, J=3.5 Hz, 1H); 13C NMR (100 MHz, CDCl3) delta 160.3, 147.7, 143.6, 132.3, 129.9, 129.5, 128.0, 127.1, 123.9, 99.0, 84.4, 38.7, 35.7; IR (neat) 2955, 2924, 2856, 1741, 1603, 1515, 1346, 1323, 1305, 1288, 1222, 1181, 1136, 1019, 948, 787, 748, 698 cm-1; HMRS (ESI) calcd for C27H33N2O2 [M+H]+: 417.25365; found: 417.25428.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Diiodobutane, its application will become more common.

Reference:
Conference Paper; Lebel, Helne; Parmentier, Michael; Leogane, Olivier; Ross, Karen; Spitz, Cedric; Tetrahedron; vol. 68; 17; (2012); p. 3396 – 3409;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 628-21-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 628-21-7 as follows.

Example 38: Synthesis of 2-(2,6-Dimethyl-phenyl)-l-oxo-octahydro-isoindole-3a- carboxylic acid (3,5-bis-trifluoromethyl-phenyl)-amide[0190] a) Lithium bis(trimethylsily)amide (1.0 M in THF, 3.8 mL, 2.4 mmol) was added to a solution of l-(2,6-dimethyl-phenyl)-5-oxo-pyrrolidine-3 -carboxylic acid methyl ester (0.4 g, 1.6 mmol) in THF (16 mL) in a reaction flask at -50 C and stirred for 5 min. The reaction was then warmed to 0 C, and addition of 1,4-diiodobutane (0.79 g, 2.6 mmol) was followed. The reaction was warmed to room temperature and stirred for 1 h. The reaction quenched saturated NH4C1. The layers were separated and the aqueous layer was extracted with EtOAc (3X). The combined organic layers were dried (MgS04) and concentrated under reduced pressure. The residue was purified by flash chromatography (Si02, 0-50% hexanes/EtOAc) to give the desired compound in 63% yield (0.3 g).

According to the analysis of related databases, 628-21-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; CHARVAT, Trevor T.; CHU, Hiufung; KRASINSKI, Antoni; LANGE, Christopher W.; LELETI, Manmohan Reddy; POWERS, Jay P.; PUNNA, Sreenivas; SULLIVAN, Timothy J.; UNGASHE, Solomon; WO2011/35332; (2011); A1;,
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. 628-21-7, name is 1,4-Diiodobutane, This compound has unique chemical properties. The synthetic route is as follows., name: 1,4-Diiodobutane

A solution of 66.1 g (500 mmol) of indan-2-one [615-13-4] and 340.9 g (1100 mmol) of 1,4-diiodobutane [628-21-7] in 500 ml of THF is added dropwise over the course of 2 h to a vigorously stirred mixture of 40.0 g (1 mol) of NaOH, 40 ml of water, 18.5 g (50 mmol) of tetrabutylammonium iodide [311-28-4] and 1500 ml of THF. When the addition is complete, the mixture is stirred at room temperature for a further 14 h, the aqueous phase is separated off, and the organic phase is evaporated to dryness. The residue is taken up in 1000 ml of n-heptane, washed five times with 300 ml of water each time and dried over magnesium sulfate. The crude product obtained after removal of the n-heptane is subjected to fractional distillation in an oil-pump vacuum (about 0.2 mbar, T about 135 C.). Yield: 83.0 g (345 mmol), 69%. Purity about 95% according to1H-NMR.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 628-21-7.

Reference:
Patent; MERCK PATENT GMBH; STOESSEL, PHILIPP; KAISER, JOACHIM; KROEBER, JONAS VALENTIN; GROSSMANN, TOBIAS; (109 pag.)TW2016/30884; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 628-21-7, name is 1,4-Diiodobutane, 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. Safety of 1,4-Diiodobutane

Step (a): Synthesis of 1-(4-amino-phenyl)cyclopentanecarboxylic acid methyl esterSodium hydride (2.8 g, 60% dispersion in mineral oil) was added slowly to an ice-cold solution of (4-nitro-phenyl)-acetic acid methyl ester (6.0 g, 30.7 mmol) in anhydrous DMF (30 mL) under nitrogen atmosphere. After stirring at 0 C. for 20 min, 1,4-diiodobutane (7.86 mL, 61 mmol) was added drop wise under stirring. After complete addition, the reaction mixture was warmed to about 20-35 C. and stirring continued for an additional 3 h. The reaction was stopped by adding water drop wise followed by EtOAc. The organic layer was separated, washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The material was purified by chromatography over silica gel to afford a pale yellow viscous liquid that solidified on standing at about 20-35 C. (4.1 g, 54% yield). The solid (3.4 g, 13.6 mmol) was dissolved in anhydrous ethanol and tin (II) chloride dihydrate (13.86 g, 61 mmol) was added slowly under nitrogen atmosphere. Thereafter, the mixture was heated at 90 C. for 3 h. After evaporation of volatiles under reduced pressure the resultant mixture was diluted with ice water, and the solution was adjusted to pH 11 by adding NaOH (aq). The mixture was extracted with EtOAc (3×50 mL) and the combined organic extracts were washed with water, brine, dried over sodium sulfate, and concentrated under reduced pressure to afford the title compound as a granular light yellow solid (2.67 g, 88% yield).1H NMR (CDCl3, 300 MHz): delta 7.16 (dd, J=8.4, 1.8 Hz, 2H), 6.63 (dd, J=8.4, 1.8 Hz, 2H), 3.59 (s, 3H), 2.60-2.55 (m, 2H), 1.87-1.67 (m, 6H).LC-MSD (ES+): m/z [220 (M+H)+, 100].

The synthetic route of 1,4-Diiodobutane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dr. Reddy’s Laboratories Ltd.; US2010/144722; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 628-21-7, name is 1,4-Diiodobutane, 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 628-21-7, name: 1,4-Diiodobutane

Add in 250ml three-necked bottle19.4g anthrone (0.1mol),150ml dry THF, 1,4-diiodobutane (34.1g, 0.11mol) was added with stirringAnd 26.8g of potassium tert-butoxide (0.24mol), the reaction system was stirred at room temperature for 3 hours,The reaction was refluxed for another 3 hours. Add saturated ammonium chloride solution to quench the reaction, extract with ethyl acetate,The liquid was dried and separated by column chromatography to obtain 13.6 g of white solid with a yield of 55%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,4-Diiodobutane, and friends who are interested can also refer to it.

Reference:
Patent; Kunshan Weixinnuo Display Co., Ltd.; Tsinghua University; Beijing Weixinnuo Technology Co., Ltd.; Qiu Yong; Fan Hongtao; Duan Lian; (53 pag.)CN103172554; (2016); B;,
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. 628-21-7, name is 1,4-Diiodobutane, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C4H8I2

General procedure: At room temperature and under nitrogen atmosphere, 12.5 mmol of menthol in 25 mL of THF was added dropwise to a solution containing 24.4 mmol of oil-free KH suspended in 25 mL of THF. When hydrogen evolution had ceased, the reaction mixture was cooled to -50 C and 12.5 mmol of TCE dissolved in 15 mL of THF was slowly added. Once the addition was completed, the cooling bath was removed and the solution was stirred for 1 h at room temperature. The reaction mixture was then cooled to -78 C and a freshly titrated solution of BuLi (30.0 mmol) was added dropwise. After stirring for 30 min at -78 C and 30 min at -50 C, 40.5 mmol of HMPA was added. After stirring for 15 min, the following solution was added: 25 mmol of diiodoalkane (diiodobutane or diiodopentane) in 5.4 mL of THF. The cooling bath was removed and stirred at room temperature for 24 h under nitrogen atmosphere. The solution was then treated with 15 mL of water. The layers were separated. The aqueous phase was extracted thrice with hexanes. The combined organic layers were successively washed with water and brine, and dried over anhydrous MgSO4. Crude product was then purified with flash chromatography using hexanes as eluent.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 628-21-7.

Reference:
Article; Hanna, Rana; Daoust, Benoit; Tetrahedron; vol. 67; 1; (2011); p. 92 – 99;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 628-21-7, name is 1,4-Diiodobutane, molecular formula is C4H8I2, 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. Computed Properties of C4H8I2

Sodium hydride (60% in mineral oil, 0.10 g, 2.6 mmol) was suspended in dry THF (5 mL). After cooled down to -20 C, a solution of CAH(322 mg, 1.0 mmol) in THF (5 mL) was added slowly to the suspension.The mixture was stirred at room temperature for 1 h, then 1,4-diiodobutane(150 mg, 0.5 mmol) was added at -20 C, and further stirred atroom temperature for 6 h. The reaction was quenched by saturatedaqueous NH4Cl solution, and extracted with diethyl ether (3×30 mL).The organic layer was washed with water (3×30 mL) and dried overanhydrous MgSO4, and evaporated under reduced pressure. The residuewas purified by column chromatography on silica gel using ethylacetate/hexane (1/8, v/v) as eluent to give a pale yellow powder ofBCAC4 (164 mg, 46%). M.p.: 138.5-140.2 C. 1H NMR (400 MHz,CDCl3): delta (ppm) 8.51 (2 H, s, Ar-H), 8.43 (2 H, s, Ar-H), 8.36 (2 H, d,J=1.2 Hz, Ar-H), 8.02 (6 H, m, Ar-H), 7.67 (1 H, d, J=4 Hz, Ar-H),7.64 (1 H, d, J=2 Hz, Ar-H), 7.53 (4 H, m, Ar-H), 3.35-1.60 (20 H, br,B-H), 1.68 (4 H, d, J=2 Hz), 1.24 (4 H, q, J=8 Hz). 13C NMR(100 MHz, CDCl3): delta (ppm) 132.94, 132.46, 132.33, 130.94, 130.14,129.09, 128.25, 128.18, 127.85, 126.97, 126.66, 126.31, 126.10,126.08, 83.82, 81.92, 34.43, 28.58. HRMS: m/z calcd for[C36H46B20-H]-: m/z=693.5522. Found: m/z=693.5549.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 628-21-7, its application will become more common.

Reference:
Article; Wu, Xueyan; Guo, Jixi; Jia, Wei; Zhao, Jianzhang; Jia, Dianzeng; Shan, Huici; Dyes and Pigments; vol. 162; (2019); p. 855 – 862;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com