Month: June 2021

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. 21304-38-1, name is 4-Iodobenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Iodobenzene-1,2-diamine

A mixture of hexaketocyclohexane octahydrate (2.21 g, 7.08 mmol) and 4-Iodo-benzene-1,2-diamine (4.97 g, 21.24 mmol) was added to a degassed acetic acid (140 mL). The mixture was heated to 110 C for 3 hrs under nitrogen. After cooled to room temperature, the solid was collected by filtration and was washed with acetic acid to give a green solid (5.35 g, 99 % yield). ¹H (300 MHz, CD3Cl/CF3COOD) No. 9.11 (br, 3H), 8.54 (br, 3H), 8.32 (br, 3 H). HRMS EI: m/z calcd for C24H913N6 761.8023, Found 761.8087.

According to the analysis of related databases, 21304-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GEORGIA TECH RESEARCH CORPORATION; WO2005/123737; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, 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 103962-05-6, Recommanded Product: 1-Iodo-4-(trifluoromethoxy)benzene

A solution of 4-bromophenol (0.173 g) in 4 mL of 1-methyl-2-pyrrolidone under argon atmosphere was treated with 4-(trifluoromethoxy)iodobenzene (0.313 mL), 2,2,6,6-tetramethylheptane-3,5-dione (0.046 mL) and caesium carbonate (0.652 g). The slurry was degassed by bubbling argon for 15 min and copper(I) chloride (0.099 g) was added. The reaction mixture was degassed by bubbling argon for 15 min, then heated to 100° C under argon for 5 h. The reaction mixture was cooled to room temperature and added dropwise to 30 mL of tert-butyl-methyl-ether. The slurry was filtered and the solids washed with tert-butyl-methyl-ether (3×20 mL). The combined filtrates were washed subsequently with 1N NaOH (50 mL), water (50 mL), 2N HCl (50 mL), 1N HCl (50 mL), water (50 mL) and brine (50 mL). The resulting organic layer was dried over Na2SO4 and concentrated to give a crude product which was purified by column chromatography on silica gel eluting with hexane to afford 0.15 g of the title compound as a colourless liquid. 1H-NMR(d, ppm, CDCl3): 7.45(m, 2H); 7.20(m, 2H); 6.99(m, 2H); 6.90(m, 2H)

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

Reference:
Patent; GLAXO GROUP LIMITED; EP1862459; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 25252-00-0,Some common heterocyclic compound, 25252-00-0, name is 2-Bromo-5-iodobenzoic acid, molecular formula is C7H4BrIO2, 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.

Oxalyl chloride (13.0 mL) is added to an ice-cold solution of 2-bromo-5-iodo-benzoic acid (49.5 g) in CH2Cl2 (200 mL). DMF (0.2 mL) is added and the solution is stirred at room temperature for 6 h. Then, the solution is concentrated under reduced pressure and the residue is dissolved in THF (100 mL). The resulting solution is cooled in an ice-bath and LiBH4 (3.4 g) is added in portions. The cooling bath is removed and the mixture is stirred at room temperature for 1 h. The reaction mixture is diluted with THF and treated with 0.1M hydrochloric acid. Then, the organic layer is separated and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried (Na2SO4) and the solvent is evaporated under reduced pressure to give the crude product. [0074] Yield: 47.0 g (99% of theory)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-5-iodobenzoic acid, its application will become more common.

Reference:
Patent; Boehringer Ingelheim Vetmedica GmbH; ECKHARDT, Matthias; BUTZ, Tanja; HIMMELSBACH, Frank; MARTIN, Hans-Juergen; US2014/31540; (2014); A1;,
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. 5326-47-6, name is 2-Amino-5-iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 5326-47-6

The starting material 2-amino-5-iodo benzoic acid (1) (15mmol, 4 . 0g) is added to 15 ml of anhydrous methanol solution, then added to this solution in 3M the mass fraction of the 70% concentrated sulfuric acid. Heating to reflux 6h, then room temperature stirring 12h. After the completion of reaction, reducing pressure and evaporating solvent, then added to the residues in the bottle 100 ml saturated sodium bicarbonate solution, ethyl acetate (3×30 ml) extraction. Obtaining organic layer, saturated salt water (3×20 ml) washing, layered takes organically phase is dried with anhydrous sodium sulfate. Filtering, by reduced pressure evaporation to dry solvent to obtain 2-amino-5-iodo benzoic acid methyl ester (2) crude 3.96g, yield: 94.5%

The synthetic route of 5326-47-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong University; Liu, Xinyong; Zhan, Peng; Kang, Dongwei; (22 pag.)CN105669653; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 627-31-6, 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. 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), This compound has unique chemical properties. The synthetic route is as follows.

A solution of methyl 2-(4-nitrophenyl)acetate (6 g, 31 mmol) in DMF (100 ml) was cooled to 0 C with an ice bath. NaH (60% in oil) (2.5 g, 63 mmol) was added portion wise. The resulting mixture was allowed to warm to RT and was stirred for 15 min at RT. After 15 min the mixture was cooled again to 0 C and 1,3-diiodopropane (6 ml, 52 mmol) was added drop wise. The resulting mixture was allowed to stir at 0 C for 30 min, and from 0 C to 10 C for 1.5 h. After 1.5 h the solution was cooled to 0 C and water was added. The reaction mixture was extracted 3 times with DCM. The combined organics were concentrated under reduced pressure and the residue was purified by flash chromatography on silica (120 g flash column, 0-20% EtOAc in hexane, 10 CV) to afford methyl 1-(4-nitrophenyl)cyclobutanecarboxylate.

The chemical industry reduces the impact on the environment during synthesis 1,3-Diiodopropane(stabilized with Copper chip). I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCGOWAN, Meredeth Ann; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; LIM, Jongwon; LIU, Kun; SCIAMMETTA, Nunzio; WHITE, Catherine, M.; YU, Wensheng; ZHANG, Hongjun; ZHOU, Hua; (109 pag.)WO2019/74747; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 156150-67-3, 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 156150-67-3 as follows.

EXAMPLE 42-(2-Chloro-4-iodorhohenylaminoV5.5-dimethyl-8-oxo-5,6J.8-tetrahvdro-4H-thienor2,3- clazepine-S-carboxylic acid ethyl ester; Caesium carbonate (2.77 g, 8.51 mmol) and 2-chloro-4-iodo-l-fluorobenzene (2.18 g, 8.51 mmol) were added to a solution of Intermediate 6 (2.0 g, 7.09 mmol) in DMF (20 mL) and heated at 650C for 18 h. Brine (100 mL) was added to the reaction and the mixture extracted with DCM (3 x 50 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residual DMF was azeotroped with heptane. The crude product was purified by chromatography (silica, 0-30% EtOAc in DCM) to give the title compound as a cream solid (916 mg, 25%). deltaeta (DMSO-d6) 10.60 (IH, s), 8.01 (IH, t, J 5.0 Hz), 7.95 (IH, d, J2.0 Hz), 7.78 (IH, dd, J 8.6, 2.0 Hz), 7.54 (IH, d, J 8.6 Hz), 4.32 (2H, q, J 7.1 Hz), 2.91 (2H, s), 2.85 (2H, d, J 5.2 Hz), 1.33 (3H, t, J 7.1 Hz), 0.99 (6H, s). LCMS (ES+) RT 3.81 minutes, 519 (M+H)+.

According to the analysis of related databases, 156150-67-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UCB PHARMA S.A.; WO2008/20206; (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. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 2-amino-5-iodobenzoate

methyl 4-amino-4′-propyl-[l,l’-biphenyl]-3-carboxylate (4a) Synthesized using reported procedure with modification (US Patent Application Publication Culshaw et al, Pub. No. US 2008/0293939 Al, Nov 27, 2008). To a round-bottom-flask under nitrogen methyl 2-amino-5-iodobenzoate (1) (831 mg, 3 mmol, 1.0 equiv.), 4- propylphenylboronic acid (541 mg, 3.3 mmol, 1.1 equiv.) and DMF (20 mL) were added, followed by addition of catalyst Pd(dppf)Cl2 (110 mg, 0.15 mmol, 0.05 equiv.) and the mixture were stirred for 15 minutes. 2M Na2CC>3 solution (7.5 mL, 15 mmol, 5.0 equiv.) was added and then the mixture was heated at 80 C for 16 hours. The reaction mixture was allowed to cool down to room temperature. The reaction mixture was filtered and concentrated under reduced pressure. H20 (20 mL) was added to the residue which was extracted with EtOAc (2 x 20 mL). All the organic extracts were combined, dried over NaSC>4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography (ethyl acetate_hexanes=20:80) on silica gel to afford 4a (418 mg, 51%) as yellow solid. XH NMR (400 MHz, CDCI3) delta 8.11 (s, 1H), 7.53-7.20 (m, 5H), 6.71 (d, J= 8.0 Hz, 1H), 5.74 (s, 2H), 3.88 (s, 3H), 2.60 (t, J= 8.0 Hz, 2H), 1.71-1.61 (m, 2H), 0.96 (t, J = 8.0 Hz, 3H); 1 C NMR (100 MHz, CDCI3) delta 168.56, 149.48, 140.96, 137.74, 132.70, 129.37, 129.23, 128.81, 126.03, 117.13, 110.90, 51.54, 37.61, 24.55, 13.82.

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 77317-55-6.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; NIKOLOVSKA-COLESKA, Zaneta; STUCKEY, Jeanne A.; MADY, Ahmed; MIAO, Lei; (140 pag.)WO2016/172218; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 624-75-9, 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. 624-75-9, name is 2-Iodoacetonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of 5-bromo-2-isopropyl-4-methoxy- phenol from step 4(0.831 g, 34 mmol) and K2C03 (0.562 g, 4.1 mmol) in 17 mE dimethyl formamide (DMF) was added iodoacetonitrile (0.594 g, 3.6 mmol). The mixture was warmed to 60 C. for 30 minutes and then allowed to cool to room temperature. After cooling to room temperature the mixture was taken up in SOmE of H20 and extracted with 1:1 toluene/ethyl acetate, washed with H20 and then with brine. The combined organic layers were dried over Na2504, filtered and concentrated in vacuo to give a crude solid. Purification via flash chromatography (1:1 hexane/CH2C12) afforded (5-bromo-2-isopropyl-4-methoxy-phenoxy)-aceto- nitrile (0.611 g, 63%) as a while solid.

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

Reference:
Patent; Ford, Anthony P.; McCarthy, Bruce G.; US2015/57299; (2015); A1;,
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

101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 101335-11-9

The 1-(2-chloro-4-fluorophenyl)-2-piperazinone used in the above procedure was prepared as follows: A suspension of 2-piperazinone (1.5 g, 15.0 mmol), 2-chloro-4-fluoro-1-iodobenzene (3.8 g, 15.0 mmol), copper(l) iodide (0.57 g, 3.0 mmol), N,N’-dimethyl-1 ,2- cyclohexanediamine (1.3 g, 6.0 mmol), and potassium phosphate (6.4 g, 44.9 mmol) in 1 ,4-dioxane (20 ml) was heated at reflux (1000C) under argon for 20 hours. The mixture was allowed to cool to room temperature and then diluted with dichloromethane and 0.88M ammonia diluted in water (1 :5). The mixture was extracted into dichloromethane (x3), and then the combined organic extracts were washed with water (x2) and dried over magnesium sulphate. The solvent was evaporated in vacuo and the crude product was purified by flash-silica gel chromatography, eluting with 5% 2M ammonia in methanol in dichloromethane, to give the product 1-(2-chloro-4-fluorophenyl)-2-piperazinone (250mg) as a brown oil which was used without further purification. LC/MS [M+H]+ = 229.

The synthetic route of 101335-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/53459; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com