Category: iodides-buliding-blocks

5100-98-1, 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. 5100-98-1 name is 3-Chloro-2-iodotoluene, 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.

General procedure: For a typical reaction, a Vapourtec 2R+ Series was used as the platform with a Vapourtec Gas/Liquid Membrane Reactor to load the carbon monoxide. The HPLC pump were both set at 0.125 mL/min, temperature of the reactor at 110 ¡ãC, pressure of CO at 15 bar with a back pressure regulator of 250 psi (17.24 bar). The system was left running for 2 h to reach steady state after which time the flow streams were switched to pass from the loops where the substrates and catalysts were loaded. The first loop (5 mL) was filled with a solution of palladium acetate (20 mg, 0.08 mmol), triphenylphosphine (48 mg, 0.168 mmol) in 6 mL of 1,4-dioxane while the second loop (5 mL) was filled with a solution made from the ortho-substituted iodoarene substrate (1.68 mmol), triethylamine (0.272 g, 0.374 mL, 2.69 mmol) and water (0.505 g, 28 mmol) in 5.8 mL of 1,4-dioxane. An Omnifit? column filled with 1.71 cm3 (r = 0.33 cm, h = 5.00 cm) of cotton was positioned just before the back pressure regulator to trap any particulate matter formed to avoid blocking of the back pressure regulator. After the substrates were passed through the system, the outlet of the flow stream was directed into a receptacle where the excess carbon monoxide gas was vented off in the fume cupboard. The reaction mixture was then evaporated to dryness, ethyl acetate (25 mL) and sodium carbonate solution (2 M, 10 mL) were added and transferred to a separating funnel. After collecting the aqueous layer, the organic layer was extracted with sodium carbonate solution (2 M, 2 ¡Á 10 mL). The combined aqueous layers were acidified by the addition of 2 M HCl solution which was then extracted with ethyl acetate (3 x 25 mL). The organic layer was dried over sodium sulfate, and the solvent evaporated under vacuum to give the crude product as a solid. The crude product was then recrystallised from the appropriate solvent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-2-iodotoluene, and friends who are interested can also refer to it.

Reference:
Article; Mallia, Carl J.; Walter, Gary C.; Baxendale, Ian R.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1503 – 1511;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

52548-14-8, 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. 52548-14-8 name is 2-Iodo-5-methylbenzoic acid, 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.

In the reactor,Add 250mL of acetone,Stirring,26.2 g of 2-iodo-5-methylbenzoic acid,Then 34.5 g of potassium carbonate was added,0.38 g copper iodide (Cul),1,2,3-triazole 7.6g.External temperature was raised to 70 C,During the heating process, a large amount of gas is generated,The reaction was refluxed for 5 hours.Then the reaction mixture was distilled under reduced pressure, the reaction system is more viscous, add 30mL of water, continue to reduce the steam distillation to no acetone (no acetone gas phase). 300mL of water was added to the residue after distillation, and 6mo 1 / L hydrochloric acid was added dropwise at room temperature to adjust the pH of the system to 1-2, resulting in a khaki-colored suspension liquid. Stirred for 15 minutes, filtered, washed with water three times,Each 50mL. The resulting solid was dried at 70 C in vacuo to dryness,Have pale green solid 19.45g,For crude compound (1-1), the purity was 95.20%.With stirring, 7.5 kg of acetone, 0.94 kg of crude compound (1-1) and 0.194 kg of sodium hydroxide were added to the reaction kettle. Stirred at 20 C-30 C for 14 hours. Centrifugation, The filter cake was washed 3 times with acetone, each time 3kg. The resulting solid was transferred to the reaction kettle , 5.65 kg of water was added, 0.14 kg of diatomaceous earth was added and stirred for 1 hour. Filtration, the filtrate was transferred to the reaction kettle, hydrochloric acid was added dropwise to adjust the pH to 1-2, a large amount of white solid formed and stirred for 1 hour. Filtered, the filter cake was washed with water three times, each time 3kg. The resulting solid was dried at 60 C in vacuo to dryness, 0.71 kg white solid, represents Compound (I-1), purity 99.97%, Isomeric compound (1-2) less than 0.1%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodo-5-methylbenzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; He Bifei; Fan Yuping; (6 pag.)CN104649983; (2018); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

13194-68-8,Some common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, molecular formula is C7H8IN, 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.

In 10 ml of acetonitrile was dissolved 1.5 g (4 mmol) of N-(1,1-dimethyl-2-methylthioethyl)-3-iodophthalisoimide, and 0.89 g (3.8 mmol) of 4-iodo-2-methylaniline was added to the solution. After 10 minutes, the crystals precipitated were collected by filtration to obtain 1.94 g of the desired compound. Physical property: m.p. 155-157C. Yield: 84%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Iodo-2-methylaniline, its application will become more common.

Reference:
Patent; Nihon Nohyaku Co., Ltd.; EP1389613; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

3032-81-3, A common compound: 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Compound was obtained following the representative procedure, using 2-phenylimidazo[1,2-a]pyridine 2 (300 mg, 1.5 mmol, 1 equiv), 1,3-dichloro-5-iodobenzene (410 mg, 1.5 mmol, 1 equiv) and heating for 12 h. The crude product was purified by silica gel chromatography using dichloromethane as eluent and trituration with methanol afforded 3-(3,5-dichlorophenyl)-2-phenylimidazo[1,2-a]pyridine 19 as a white powder (347 mg, 68percent yield). Rf = 0.60 (petroleum ether/EtOAc: 7/3); Mp = 210-211 ¡ãC. 1H NMR (400 MHz, DMSO-d6): delta 8.19 (d, 1H, 3J = 6.8 Hz, H5), 7.84 (t, 1H, 4J = 1.6 Hz, He), 7.73 (d, 1H, 3J = 9.2 Hz, H8), 7.65 (d, 2H, 4J = 1.6 Hz, Hd), 7.61 (d, 2H, 3J = 7.2 Hz, Ha), 7.42-7.32 (m, 4H, H7, Hb and Hc), 6.98 (dd, 1H, 3J = 3J’ = 6.8 Hz, H6). 13C NMR (100 MHz, DMSO-d6): delta 144.55 (C), 142.40 (C), 135.27 (2C-Cl), 133.86 (C), 133.16 (C), 129.61 (2Cd), 128.87 (Ce), 128.64 (2Cb), 127.96 (Cc), 127.85 (2Ca), 125.96 (C7), 124.43 (C5), 118.18 (C), 117.05 (C8), 113.16 (C6). IR (KBr) cm-1: 3036 (nuC-Har), 1590, 1560 (nuC=C and nuC=N), 776, 750 (nuC-Cl). MS (ESI) m/z (percent): 339.0 (100) [M + H]+, 341.0 (80) [M + H + 2]+, 343.0 (15) [M + H + 4]+. Anal. Calcd for C19H12Cl2N2: C, 67.27; H, 3.57; N, 8.26. Found: C, 67.50; H, 3.23; N, 7.98.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1,3-Dichloro-5-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Marhadour, Sophie; Marchand, Pascal; Pagniez, Fabrice; Bazin, Marc-Antoine; Picot, Carine; Lozach, Olivier; Ruchaud, Sandrine; Antoine, Maud; Meijer, Laurent; Rachidi, Najma; Le Pape, Patrice; European Journal of Medicinal Chemistry; vol. 58; (2012); p. 543 – 556;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 25252-00-0 as follows. 25252-00-0

To commercially available 2-bromo-5-iodobenzoic acid (76.5 mmol, 25 g), hydroxybenzotriazole (HOBt, 76. 5mmol, 10.4 g), triethylamine (TEA, 153 mmol, 21.3 mL) and ammonium chloride (84.1 mmol, 4.50 g), is added DMF (anhydrous, 300 mL). After dissolution of solids by stirring, 1- [3- (Dimethylamino) propyl]-3- ethylcarbodiimide hydrochloride (EDC-HCI, 84.1 mmol, 16.08 g) is added. Stirring continues with the reaction capped for 16 hours. The reaction is concentrated to half the original volume via roto-evaporation, then 1 L ethyl acetate is added and the subsequent solution is washed once with 1 M HCI (300 mL), then once with saturated NaHCO3 (300 mL), then twice with H20, and then once with saturated NaCI (100 mL). A white solid resulted on drying the ethyl acetate phase with MgS04, filtering through celite, and evaporation of volitiles. LCMS : Method [11] : Retention time at 220nm detection is 1.51 minutes and [M = 1] + = 325.8. LCMS shows nearly quantitative product (i) at >95% purity.

According to the analysis of related databases, 25252-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87751; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

364-11-4, A common compound: 364-11-4, name is 1-Bromo-4-iodo-2-(trifluoromethyl)benzene, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a solution of 1-bromo-4-iodo-2-(trifluoromethyl)benzene (246 mg, 0.701 mmol) in 1.4 mL of Et2O (C=0.5M) was added dropwise a 1.6M solution of BuLi in hexane (460muIota., 1.05 eq) at -78C. After 15 min of stirring, benzaldehyde (86muIota., 1.2 eq) was slowly added. The mixture was stirred for 4h at -75 C and then, hydrolyzed with water and with a 1M HC1 solution to acidify. The layers were separated. The aqueous layer was extracted with DCM (3>< 10mL). The combined organics were washed with brine, dried over MgSO4, filtered and solvents were removed in vacuo. The crude residue was purified by silica gel flash chromatography (cyclohexane/AcOEt 93:7 to 90: 10) to afford the desired product in 76% yield (176 mg) as an uncoloured oil. 1H NMR (300 MHz, CDC13) delta 7.76 (d, J = 2.2 Hz, 1H), 7.65 (d, J = 8.3 Hz, 1H), 7.41 - 7.27 (m, 6H), 5.81 (s, 1H), 2.36 (s, OH); 13C NMR (75 MHz, CDCI3) delta 143.5 (C), 142.8 (C), 135.1 (d, J = 2.0 Hz, CH), 131.0 (CH), 130.2 (q, J = 31.3 Hz, C), 129.0 (CH), 128.5 (CH), 126.7 (CH), 125.9 (q, J = 5.4 Hz, CH), 123.0 (q, J = 273.6 Hz, C), 1 18.9 (q, J = 2.0 Hz, C), 75.4 (CH); MS (ESI) m/z : 313.0, 315.0 [M-OH, 79Br, 81Br]+; 348.0, 350.0 [M+NH4, 79Br, 81Br]+; 680.0 [2M+NH4, 79Br, 81Br]+. In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Bromo-4-iodo-2-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see. Reference:
Patent; UNIVERSITA’ DEGLI STUDI DI MILANO – BICOCCA; UNIVERSITE DE GENEVE; UNIVERSITE CLAUDE BERNARD – LYON 1; GAMBACORTI-PASSERINI, Carlo; MOLOGNI, Luca; SCAPOZZA, Leonardo; BISSON, William; AHMED, Shaheen; GOEKJIAN, Peter; TARDY, Sebastien; ORSATO, Alexandre; GUEYRARD, David; BENOIT, Joseph; WO2013/167730; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

20691-72-9, 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. 20691-72-9, name is 4-Iodo-2-nitroaniline, A new synthetic method of this compound is introduced below.

4-Iodo-2-nitroaniline (440 mg, 1.67 mmol, 1.0 eq.) was dissolved in EtOAc (50 mL) in a 100 mL round bottom flask at room temperature, and SnCl2.2H2O (1.88 g, 8.33 mmol, 5.0 eq.) was added. The reaction mixture was stirred at reflux for 12 h and extracted upon cooling to room temperature with saturated aq. NaHCO3 (3¡Á30 mL). The combined aqueous layers were washed with EtOAc (2¡Á30 mL). The resulting organic layers were combined and dried over MgSO4, and the solvent was removed in vacuo.

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:
Patent; BLACKWELL, Helen; Frei, Reto; Breitbach, Anthony; Lynn, David M.; Broderick, Adam H.; US2013/136782; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding some certain compound to certain chemical reactions, such as: 55406-53-6, name is 3-Iodoprop-2-yn-1-yl butylcarbamate, 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 55406-53-6. 55406-53-6

EXAMPLESA solution is prepared in Dowanol TPM (tripropylene glycol methyl ether), containing 10% by weight of iodopropargyl butylcarbamate, 5% by weight of Octasoligen-Cobalt 8 (Borchers, Langenfeld, Germany) and 5% by weight of the stabilizer specified in Table 1. The compositions are stored at 40 C. The amount of IPBC was determined by means of HPLC at the beginning and after two weeks.

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 3-Iodoprop-2-yn-1-yl butylcarbamate.

Reference:
Patent; Uhr, Hermann; US2009/36555; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-75-9, The chemical industry reduces the impact on the environment during synthesis 624-75-9, name is 2-Iodoacetonitrile, I believe this compound will play a more active role in future production and life.

Cyanomethyl-trimethyl-phosphonium iodide (TJA01110) C5H11INP MW 243.03. Trimethylphosphine in THF (IM, 20.0 mL, 20.0 mmol) at 0 0C under N2 (g) was diluted with anhydrous toluene (40 mL). Iodoacetonitrile (1.40 mL, 19.4 mmol) was added dropwise with vigorous stirring forming a white ppt. The mixture was allowed to warm to r.t. and left to stir for 40 h. The mixture was filtered and washed with toluene to give a white solid which was dried under vacuum. Recrystallisation (acetonitrile) provided the title compound as a white crystalline solid (3.23 g, 66 %), 1H NMR (300 MHz, DMSO-J6) delta 2.01-2.06 (9H, d, J= 15.3 Hz, P(CHs)3), 4.01-4.07 (2H, d, J= 16.4 Hz, PCH2CN);31P NMR (121.5 MHz, DMSO-J6) delta 32.9.

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; STERIX LIMITED; WO2007/68905; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

31599-60-7, name is 1-Iodo-2,3-dimethylbenzene, 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. 31599-60-7

Under nitrogen protection, 24 g of magnesium turnings (1 mol) and 160 ml of tetrahydrofuran were added to a reaction flask and stirred at room temperature18.5 g was added dropwise2,3-dimethyliodobenzene (0.1 mol) and100 ml of tetrahydrofuran,Triggering reaction,Then, 166.5 g of 2,3-dimethyliodobenzene (0.9 mol) was added dropwise1000 ml of tetrahydrofuran mixture, drop finished, reflux reaction 1hour. The resulting Grignard reagent was cooled in an ice bath, and 73 g of N, N-dimethylformamide (1.0 mol) and 300 ml of tetrahydrofuranFuran mixture to control the reaction temperature is not higher than 30 degrees, dropping is completed at room temperature for 5 hours. After completion of the reaction1000 ml of saturated ammonium chloride solution for 1 hour hydrolysis, and then separated from the organic phase, the aqueous phase extracted with ethyl acetate aThe organic phase was washed with 500 mL of saturated brine and allowed to stand for separation. The organic phase was stirred and dried with 50 g of anhydrous sodium sulfate1 hour, filtered and the filtrate was concentrated to dryness under reduced pressure to give 2,3-dimethylbenzaldehyde in a yield of 93% and a purity of 95%

Statistics shows that 31599-60-7 is playing an increasingly important role. we look forward to future research findings about 1-Iodo-2,3-dimethylbenzene.

Reference:
Patent; Suo Anke (Shanghai) Investment Co; Mao, Zhenjun; Jiang, Xindong; Lin, Xufeng; Li, Qingpo; You, Jian; (5 pag.)CN105503551; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com