Month: March 2021

Reference of 20691-72-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 20691-72-9 name is 4-Iodo-2-nitroaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Synthesis of (RS)-1-(4-Iodo-2-nitrophenyl)-2-methyl-1-propanol, (R)-1-(4-Iodo-2-nitrophenyl)-2-methyl-1-propanol and (S)-1-(4-Iodo-2-nitrophenyl)-2-methyl-1-propanol1,4-Diiodo-2-nitrobenzene 4-Iodo-2-nitroaniline (6.60 g, 0.025 mol) was suspended in water (19 mL) and glacial acetic acid (17.5 mL) (Sapountzis et al., 2005, which is incorporated herein by reference). The mixture was cooled to 0 C. Sulfuric acid (17.5 mL, 0.328 mol) was added cautiously. The mixture was cooled to minus 5 C., and a solution of NaNO2 (1.90 g, 0.028 mol) in water (7.5 mL) was added dropwise at a rate that the temperature would not exceed 0 C. Upon completion of the addition the mixture was stirred for 30 minutes and was added in small portions to a boiling solution of sodium iodide (22.33 g, 0.149 mol) in water (7.5 mL) (CAUTION: vigorous nitrogen evolution). The resulting mixture was kept at 60 C. for one hour, then cooled down to room temperature, followed by addition of diethyl ether (500 mL). The ether solution was separated, washed twice with water (150 mL) and once saturated NaHCO3 (150 mL). The solution was dried over Na2SO4 and concentrated in vacuo to a solid, which was recrystallized from ethanol to yield 1,4-diiodo-2-nitrobenzene (9.30 g, 99%). 1H NMR (400 MHz, CDCl3): delta 8.15 (d, 1H, J=2.0 Hz), 7.75 (d, 1 H, J=8.3 Hz), 7.56 (dd, 1 H, J=8.3 and 2.0 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Iodo-2-nitroaniline, and friends who are interested can also refer to it.

Reference:
Patent; Lasergen, Inc.; Litosh, Vladislav A.; Hersh, Megan N.; Stupi, Brian P.; Wu, Weidong; Metzker, Michael L.; US9200319; (2015); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 612-55-5, name is 2-Iodonaphthalene, A new synthetic method of this compound is introduced below., Recommanded Product: 612-55-5

General procedure: A mixture of aryl iodide (2 mmol), aryl alkyne (2.4 mmol), Ni(OAc) 2 (10 mol %), Et3N (6 mmol) and 1,4-dioxane (15 mL) were charged into the reactor (steel bomb). The reactor was closed and pressurized to ~2bar CO and then stirred at 100 C for 4 h. The reaction Progress was monitored by TLC. The reaction mixture was cooled to room temperature, before being filtered through a pad of Celite. The filtrate was concentrated and purified by silica gel with a mixture of hexane and ethyl acetate to give the pure product. For all examples, reactions were performed on 100 mg scale of corresponding aryl iodides.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Charugandla, Renuka; Vangala, Markandeya Sarma; Chidara, Sridhar; Korupolu, Raghu Babu; Tetrahedron Letters; vol. 59; 34; (2018); p. 3283 – 3287;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 20776-54-9, A common heterocyclic compound, 20776-54-9, name is 2-Amino-4-iodobenzoic acid, molecular formula is C7H6INO2, 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.

(a) The S-acetyl-4-iodothiosalicylic acid, m.p. 184-186, was prepared from 4-iodoanthranilic acid according to the procedure described in Example 33 (a). Calcd for C9 H7 103 S: C, 33.55; H, 2.19; I, 39.40; S, 9.95%. Found: C, 33.70; H, 2.23; I, 39.20; S, 10.09%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Miles Laboratories, Inc.; US4221800; (1980); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 450412-29-0, A common heterocyclic compound, 450412-29-0, name is 1-Bromo-3-fluoro-2-iodobenzene, molecular formula is C6H3BrFI, 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.

200 g(664 mmol) 1-bromo-3-fluoro-2-iodobenzene, 101 g (664 mmol) of 2-methoxy-phenylboronicacid and sodium tetraborate 137.5 g (997 mmol) were dissolved in 1000 ml THFand 600 ml water, and degassed. 9.3 g (13.3 mmol) of bis (triphenylphosphine)palladium (II) chloride and 1 g (20 mmol) hydrazinium hydroxide was added. The reaction mixture was stirred at 70C for 48 h under a protective gas atmosphere, cooled, washed several times with water, dried and evaporated. The reaction mixture was purified by silica gel column chromatography using toluene/heptane (2:1). Yield 155 g (553 mmol), 83%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Merck Patent GMBH; Faram, Amir Hossain; Yatsi, Anya; Evemilley, Thomas; Grossman, Tobias; Krevor, Jonas Valentine; Tobelmann, Laruese; (100 pag.)KR2016/28524; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

To a solution of ethyl 2-(6-nitropyridin-3-yl)acetate (33.0 g, 157 mmol) in DMF (150 mL) was added NaH (13.2 g, 330 mmol) (60 % in oil) at 0 C. The reaction mixture was allowed to warm to RT and stirred for 15 min. The mixture was cooled to 0 C again before 1,3- diiodopropane (37.3 mL, 325 mmol) was added. The resulting mixture was stirred at 0 C for 30 min, then warmed to RT and stirred for 1 h. The mixture was quenched with sat. NH4C1 (500 mL), diluted with water (500 mL), then extracted with EtOAc (500 mLx3). The combined organic layers were washed with brine (200 mL), dried over Na2SC>4, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (Petroleum ether/ EtOAc =30/ 1 to 20/ 1) to give the title compound. MS (EI) m/z 251 [M+H]+.

The synthetic route of 627-31-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Hua; FRADERA, Xavier; HAN, Yongxin; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; WHITE, Catherine; YU, Wensheng; (89 pag.)WO2019/27856; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 608-28-6, A common heterocyclic compound, 608-28-6, name is 2-Iodo-1,3-dimethylbenzene, molecular formula is C8H9I, 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: A 10 mL flask equipped with a Teflon valve was charged with a magnetic stir bar, CuI (2 mg, 1mol%), Heteroarylamine (1.5 mmol), KOtBu (224 mg, 2.0 mmol), solid aryl halides (1.0 mmol). The tube was evacuated and backfilled with argon. Under a counter flow of argon, dioxane (1.5mL), aryl halides (1.0 mmol, if liquid) were added by syringe. The tube was sealed. The reaction mixture was allowed to stir at 110 C (X=I) or 130 C (X= Br) for 24 h. Then the mixture was cooled to room temperature and added 5.0 mL brine. Subsequently, the mixture was extracted with ethyl acetate. The organic layers were collected, dried over Na2SO4, filtered and the solvent was removed under vacuum. The residue was purified by column chromatography on silica gel.

The synthetic route of 608-28-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Deping; Kuang, Daizhi; Zhang, Fuxing; Liu, Yang; Ning, Shunhua; Tetrahedron Letters; vol. 55; 51; (2014); p. 7121 – 7123;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 123278-03-5, name is 3-Chloro-2-iodobenzoic acid, molecular formula is C7H4ClIO2, 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. Recommanded Product: 123278-03-5

Step 1; A 100-mL flask was charged with 3-chloro-2-iodobenzoic (2.43 g, 8.64 mmol, 0.90 equiv) and thionyl chloride (15 mL). The solution was vigorously stirred, then 1 drop of DMF added and the mixture heated to reflux for 4 h. During this time the acid dissolved to give a pale yellow solution. The cooled mixture was evaporated and toluene (50 mL) added, then removed in vacuo. The evaporation/dissolution with toluene/evaporation procedure was repeated twice and the pale yellow 3-chloro-2-iodobenzoyl chloride was placed on the vacuum line.In a separate flask a toluene (30 mL) solution tert-butyl 4-oxopiperidine-1-carboxylate (2.45 g, 12.32 mmol, 1.25 equiv), 4-methoxybenzylamine (1.352 g, 9.6 mmol, 1.0 equiv) and MgSO4 (20 g) were heated to reflux overnight. The mixture was filtered through a bed of Celite, the cake was washed with toluene (30 mL) and the filtrate was evaporated. The amber residue was dissolved in CH2Cl2 (100 mL) and TEA (1.94 g, 2.7 mL, 19.2 mmol, 2.0 equiv) and DMAP (117 mg, 0.96 mmol, 0.1 equiv) were added. The 3-chloro-2-iodobenzoyl chloride prepared above was dissolved in CH2Cl2 (10 mL) and the resultant solution added to the enamine solution over a 10 min period, then stirred overnight. The reaction was quenched by addition of 1.0 M aq HCl (100 mL) and the mixture was transferred to a separatory funnel. The organic layer was washed with brine, dried over Na2SO4, filtered, and evaporated. The residue was purified by flash chromatography on silica gel (120 g) eluting with 19-71% EtOAc in hexanes tert-butyl 4-(3-chloro-2-iodo-N-(4-methoxybenzyl)benzamido)-5,6-dihydropyridine-1(2H)-carboxylate (3.19 g, 5.47 mmol, 63% yield), contaminated with 5% 3-chloro-2-iodo-N-(4-methoxy]benzyl)benzamide, was isolated as a pale yellow foam.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 123278-03-5, its application will become more common.

Reference:
Patent; Claremon, David A.; Singh, Suresh B.; Tice, Colin M.; Ye, Yuanjie; Cacatian, Salvacion; He, Wei; Simpson, Robert; Xu, Zhenrong; Zhao, Wei; US2011/34455; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 13421-13-1, 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. 13421-13-1, name is 4-Chloro-2-iodobenzoic acid, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: DMF (2 drops) and oxalyl chloride (180 muL, 2.12 mmol) were added to a suspension of 4-chloro-2-iodobenzoic acid (0.400 g, 1.42mmol) in toluene (5 mL). After the acid had dissolved and evolution of gas had ceased, the mixture was concentrated under vacuum to afford the crude acyl chloride, which was used without further purification.To a soln of this crude acyl chloride in CH2Cl2 (6 mL) was added a soln of Et3N (592 muL, 4.25 mmol) and aniline (129 muL,1.42 mmol) in CH2Cl2 (6 mL). The mixture was stirred for 1 h and then sat. aq NH4Cl soln (5 mL) was added. The aq layer was extracted with CH2Cl2 (3 ¡Á 5 mL) and the combined organic layers dried (Na2SO4) and evaporated. The crude residue was purified by flash chromatography (hexanes-EtOAc, 90:10 to 85:15), to afford 5e (400 mg, 79%) as a white solid. Mp 172-173 C. IR (film): 1653 (s), 1600 (s) cm-1. 1H NMR (300.13 MHz, acetone-d6): delta = 7.18 (t, J = 7.4 Hz, 1 H), 7.41 (t, J = 7.8 Hz, 2 H), 7.57 (s, 1 H), 7.83 (d, J = 7.8 Hz, 2 H), 8.00(s, 1 H), 9.55 (s, 1 H). 13C NMR (75.47 MHz, acetone-d6): delta = 93.8 (C), 120.6 (2 ¡Á CH), 124.9 (CH), 129.1 (CH), 129.6 (2 ¡Á CH), 130.0 (CH), 136.0 (C), 139.5 (CH), 139.9 (C), 143.0 (C), 167.4 (C). MS (EI): m/z (%) = 359 (7) [37Cl, M]+, 357 (20) [35Cl, M]+, 267 (25), 265 (base). HRMS (EI): m/z [M]+ calcd for C13H935ClINO: 356.9417; found: 356.9423; m/z [M]+ calcd for C13H937ClINO: 358.9388; found: 358.9385.

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-2-iodobenzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; Madich, Youssef; Denis, J.Gabriel; Ortega, Aitor; Martinez, Claudio; Matrane, Abdellatif; Belachemi, Larbi; De Lera, Angel R.; Alvarez, Rosana; Aurrecoechea, Jose M.; Synthesis; vol. 45; 14; (2013); p. 2009 – 2017;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 3718-88-5,Some common heterocyclic compound, 3718-88-5, name is 3-Iodobenzylamine hydrochloride, molecular formula is C7H9ClIN, 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.

Example 150: Synthesis of 4-Chloro-6-[3-(3-dimethylamino-propylamino)- benzylamino]-2//-phthalazin-l-one hydroformate; (3-Iodo-benzyl)-carbamic acid tert-butyl ester; A mixture of 3-iodobenzylamine hydrochloride (3g, 11.131 mmol), CH2Cl2(6OmL) and triethylamine (3.ImL, 22.263 mmol) was stirred at room temperature. Boc- anhydride (2.6Og, 11.913 mmol) was added and the reaction stirred at room temperature for Ih. The reaction was poured onto water, extracted with CH2Cl2 and dried (Na2SO4). Preparatory HPLC afforded (3-iodo-benzyl)-carbamic acid tert-butyl ester (3.494g) as a white solid, m/z (M+l) 333.84.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Iodobenzylamine hydrochloride, its application will become more common.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; WO2008/61108; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 375-80-4, name is 1,6-Diiodoperfluorohexane, 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 375-80-4, Computed Properties of C6F12I2

General procedure: In a typical procedure (IC2F4)2 (45.40g, 0.1mol) was dissolved in 100mL of acetonitrile and 200mL of water in a 500-mL round-bottomed flask. The solution was made basic with NaHCO3 (30.00g, 0.36mol) and then fresh Na2S2O4 (50.00g 0.28mmol, the ratio is 1:2.8) was slowly added with good stirring at 22C. After 20h, fluorine-19 NMR spectroscopy indicated the reaction was complete by disappearance of the -CF2I signal. The solution (NaSO2C2F4)2 and other byproducts are light yellow.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,6-Diiodoperfluorohexane, and friends who are interested can also refer to it.

Reference:
Article; Mei, Hua; Desmarteau, Darryl D.; Journal of Fluorine Chemistry; vol. 160; (2014); p. 12 – 15;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com