Author: Jessica.F

Reference of 6293-83-0, 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. 6293-83-0 name is 2-Iodo-4-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.

General procedure: A mixture of 2-iodoaniline 1 (0.50 mmol) and Pd/C (10 wt% palladium on activated carbon paste and 50% moisture, 10 wt% wet Pd/C based on starting material 1) in 1,4-dioxane (3 mL) was added into a Schlenk flask (25 mL) and stirred at r.t. Ethyl acrylate (100 mg, 1.0 mmol, 2.0 equiv) and Et3N (101 mg, 1.0 mmol, 2.0 equiv) were added and the mixture was stirred at 100 C until the reaction was complete. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography.

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

Reference:
Article; Zhou, Xiao-Yu; Chen, Xia; Wang, Liang-Guang; Synthesis; vol. 49; 24; (2017); p. 5364 – 5370;,
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. 66416-72-6, name is 4-Bromo-2-iodoaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 66416-72-6

Example 187 6-(5-Bromo-2-chloro-phenyl)-N*4*-(4-chloro-phenyl)-pyrimidine-2,4-diamine To a stirred suspension of copper (II) chloride (1.62 g, 12.0 mmol) and tert-butyl nitrite (15.0 mmol) in acetonitrile (40 ml), heated at 60 C., was added a solution of 4-bromo-2-iodo-phenylamine (2.98 g, 10.0 mmol) in acetonitrile (10 ml) dropwise over 50 minutes. After stirring at 60 C. for 1 hour, the mixture was poured into 20% hydrochloric acid (200 ml) and extracted with ether (2*30 ml). The crude product was purified by flash chromatography on silica gel eluding with hexane to provide 4-bromo-1-chloro-2-iodo-benzene (2.4 g, 76% yield).

According to the analysis of related databases, 66416-72-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cell Therapeutics, Inc.; US2004/204386; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 452-79-9,Some common heterocyclic compound, 452-79-9, name is 2-Fluoro-1-iodo-4-methylbenzene, molecular formula is C7H6FI, 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 solution of the corresponding boronic acid (1.2mmol) in EGME/H2O (3:1, 0.25M) were added Pd(OAc)2 (0.05mmol) and K2CO3 (1.2mmol), followed by the addition of the corresponding phenyl iodide (1.0mmol). The dark reaction mixture was stirred at rt for 15h, then diluted with EtOAc (40mL) and filtered through a pad of Celite. The resulting filtrate was washed with H2O (20mL) and a 1M solution of Na2SO3 (20mL). After separation, the organic phase was dried over Na2SO4 and concentrated under reduced pressure. The residues were purified by column chromatography (Cy/EtOAc).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-1-iodo-4-methylbenzene, its application will become more common.

Reference:
Article; Migliore, Marco; Habrant, Damien; Sasso, Oscar; Albani, Clara; Bertozzi, Sine Mandrup; Armirotti, Andrea; Piomelli, Daniele; Scarpelli, Rita; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 216 – 237;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

4387-36-4, name is 2-Iodobenzonitrile, 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. Computed Properties of C7H4IN

S1: The reaction formula of this step is as follows.The specific reaction operation is: at room temperature,Adding 100 mmol of the compound of the above formula (III) to an appropriate amount of the organic solvent N,N-dimethylacetamide (DMA),175 mmol of the above compound of formula (IV), 0.6 mmol of palladium acetate,125 mmol of tetra-n-butylammonium bromide and 175 mmol of sodium carbonate, and then the temperature was raised to 110 C with stirring.And stirring the reaction at this temperature for 20 hours;After the reaction was completed, the reaction mixture was poured into a sufficient amount of ethyl acetate.After washing with saturated brine, the organic layer and the aqueous layer were separated.After the aqueous layer is sufficiently extracted with ethyl acetate,The organic layers are combined (ie, the organic layer washed with saturated brine and the organic layer obtained by ethyl acetate extraction).Dry with anhydrous Na2SO4 and distill under reduced pressure.The residue was eluted by flash column chromatography (a mixture of petroleum ether and ethyl acetate in a volume ratio of 8:1).The eluent was collected and evaporated to remove the eluent.Thus obtaining a compound of the above formula (II) as a white solid in a yield of 88.2%

The synthetic route of 4387-36-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wenzhou Medical University Affiliated The Second Hospital ? Wenzhou Medical University Affiliated Yuying Child Hospital; Wenzhou Medical University; Wang Zhiyi; Weng Jie; Chen Chan; Wang Zhibin; Zhou Zhiliang; Ma Jianshe; Xu Tong; (18 pag.)CN108250162; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 2468-56-6, 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 2468-56-6 as follows.

Scheme 6. Preparation of HV As depicted in Scheme 6, a mixture of 4,4′-bipyridine (1.0 g, 6.4 mmol) and 6-iodo-l- hexyne (4.6 g, 22 mmol) in dry MeCN (30 mL) was heated at 105 C / 6 psi under N2 for 3 h. The reaction mixture was cooled to room temperature and the resulting reddish precipitate was filtered and washed thoroughly with MeCN. The solid was dissolved in H2O (100 mL), followed by the addition of excess of NH4PF6, resulting in the precipitation of an off-white solid which was collected by centrifugation, washed with H2O (3 x 20 mL), MeOH (1 x 20 mL) and dried in vacuo to yield HV 2PFe as a light brown solid (2.4 g) in 62% yield. NMR (500 MHz, CD3CN, 298 K) d = 8.90 (d, J= 6.4 Hz, 4H), 8.39 (d, J= 6.4 Hz, 4H), 4.65 (t, J= 7.5 Hz, 4H), 2.28 (dt, J= 2.6 Hz, J = 7.0 Hz, 4H), 2.23 (t, j = 2.6 Hz, 2H), 2.13 (p, j = 7.6 Hz, 4H), 1.60 (p, J = 7.4 Hz, 4H). 13C NMR (125 MHz, CD3CN, 298 K) d = 150.9, 146.5, 128.2, 84.2, 70.5, 62.5, 31.0, 25.5, 18.2. ESI-HRMS calcd for [M- PF6]+m/z = 463.1732, found 463.1740.

According to the analysis of related databases, 2468-56-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NORTHWESTERN UNIVERSITY; KING ABDULAZIZ CITY FOR SCIENCE AND TECHNOLOGY (KACST); NGUYEN, Minh, T.; STODDART, James, Fraser; (82 pag.)WO2019/195754; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 3058-39-7, name is 4-Iodobenzonitrile, 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 3058-39-7, Computed Properties of C7H4IN

4-Iodobenzonitrile (57 mg, 0.25 mmol) and styrene (43 muL, 0.375 mmol) were coupled using the procedure described above to give 63% conversion to (E)-4-cyanostilbene by GC analysis.

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

Reference:
Patent; Board of Trustees of The University of Alabama; Bakker, Martin G.; Sayler, Franchessa Maddox; Shaughnessy, Kevin; (19 pag.)US9233366; (2016); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 58755-70-7,Some common heterocyclic compound, 58755-70-7, name is 1-Iodo-4-methoxy-2-nitrobenzene, molecular formula is C7H6INO3, 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 4-iodo-3-nitroanisole (2.79 g, 10.0 mmol) in anhydrous THF (20 mL) at minus 40C under a nitrogen atmosphere, phenylmagnesium chloride (2 M in THF, 6.0 mL, 12 mmol) was added dropwise at a rate such that the temperature would not exceed minus 35C. Upon completion of the addition, the mixture was stirred at minus 40C for five min, followed by addition of isobutyraldehyde (1.8 mL, 20 mmol). The mixture was gradually warmed to room temperature, quenched with saturated NH4C1 solution (5.0 mL), diluted with CH2CI2 (100 mL) and washed with water (100 mL). The organic phase was separated, and the aqueous phase was extracted with CH2CI2 (50 mL) three times. The combined organic phase was washed with brine (40 mL), dried over Na2S04, concentrated in vacuo, and the residue was purified by silica gel column chromatography to yield (R/5)-l-(4- methoxy-2-nitrophenyl)-2-methyl- 1-propanol (1.5 g, 67%) as a light yellow oil. 1H NMR (400 MHz, CDCl3): delta 7.61 (d, 1 H, J = 8.8 Hz, Ph-H), 7.34 (d, 1 H, J = 2.8 Hz, Ph-H), 7.15 (dd, 1 H, J = 8.8 and 2.8 Hz, Ph-H), 4.92 (dd, 1 H, J = 5.6 and 3.2 Hz, Ph-CH), 2.46 (br s, 1 H, OH), 2.00 (m, 1 H, CH), 0.97 (d, 3 H, J= 6.4 Hz, CH3), 0.86 (d, 3 H, J= 6.8 Hz, CH3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Iodo-4-methoxy-2-nitrobenzene, its application will become more common.

Reference:
Patent; LASERGEN, INC.; STUPI, Brian, Philip; LI, Hong; WU, Weidong; HERSH, Megan, N.; HERTZOG, David; MORRIS, Sidney, E.; METZKER, Michael, L.; WO2013/40257; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 56096-89-0, 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. 56096-89-0, name is 4-Fluoro-2-iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A dry sealable vial was charged with sulfonimidamide 4a (368 mg, 2.00 mmol), 2-iodobenzoic acid (494 mg, 2.00 mmol), CuI (76 mg, 0.40 mmol), and K2CO3 (690 mg, 5.00 mmol) in anhyd DMF (5.0 mL). After heating to 100 C for 2 h, the heterogeneous mixture was cooled to r.t. The mixture was diluted with water (10 mL), acidified with 2 M HCl and extracted with EtOAc (3 ¡Á 30 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by CombiFlash chromatography (silica gel, n-hexane/EtOAc, 6:4) to afford the desired product 7a as a cream solid; yield: 633 mg (90%).

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, 4-Fluoro-2-iodobenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sen, Indira; Sasmal, Swarnendu; Hall, Roger G.; Pal, Sitaram; Synthesis; vol. 48; 21; (2016); p. 3743 – 3752;,
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. 847685-01-2, name is 4,5-Difluoro-2-iodoaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H4F2IN

General procedure: To a solution of iodoaniline 2 (5.00 mmol) and ethynyltrimethylsilane (1.47 g, 15.00 mmol) in Et3N (10 mL) in a Schlenk flask under argon were added Pd(PPh3)2Cl2 (175 mg, 0.25 mmol) and CuI (95 mg, 1.50mmol). The reaction mixture was heated at 40 C for the required period (Table 1) with stirring. Then, the mixture was diluted with CH2Cl2(10 mL). The suspension was placed directly onto a chromatography plate (silica gel) and air-dried. The trimethylsilanyl ethynylanilines 3 were isolated by TLC using EtOAc/hexane as the eluent. 4,5-Difluoro-2-[(trimethylsilyl)ethynyl]aniline (3a) Brown oil; yield: 1.00 g (89%); Rf = 0.56 (EtOAc/hexane, 1:7). IR (neat): 3485, 3388, 2960, 2901, 2148, 1628, 1599, 1516, 1437, 1348, 1298, 1252, 1227, 1182, 1122, 870, 845, 762, 629 cm-1. 1H NMR (300 MHz, acetone-d6): delta = 7.07 [dd, J (H3,F4) = 10.8 Hz, J (H3,F5) = 8.8 Hz, 1 H, H3], 6.63 [dd, J (H6,F5) = 12.7 Hz, J (H6,F4) = 7.1 Hz, 1 H, H6], 5.01 (s, 2 H, NH2), 0.26 (s, 9 H, CH3). 13C NMR (100 MHz, acetone-d6): delta = 152.0 [dd, 1J (C5,F5) = 247.3 Hz, 2J (C5,F4) = 13.8 Hz, C5], 147.9 [d, 3J (C1,F5) = 10.0 Hz, C1], 142.3 [dd,1J (C4,F4) = 235.5 Hz, 2J (C4,F5) = 13.9 Hz, C4], 120.1 [dd, 2J (C3,F4) = 19.0 Hz, 3J (C3,F5) = 2.0 Hz, C3], 103.1 [m, 3J (C2,F4) = 7.2 Hz, C2], 102.8 [d, 2J (C6,F5) = 21.0 Hz, C6], 103.1 (m, C?C), 100.3 (m, C?C), 0.0 (s, CH3). 19F NMR (282 MHz, acetone-d6): delta = -134.4 [ddd, J (F5,F4) = 22 Hz, J (F5,H6) = 12.7 Hz, J (F5,H3) = 8.8 Hz, 1 F, F5], -153.2 [ddd, J (F4,F5) = 22.4 Hz, J (F4,H3) = 10.8 Hz, J (F4,H6) = 7.1 Hz, 1 F, F4]. HRMS (EI): m/z [M]+ calcd for C11H13F2NSi: 225.0780; found: 225.0781.

According to the analysis of related databases, 847685-01-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Politanskaya, Larisa; Tretyakov, Evgeny; Synthesis; vol. 50; 3; (2018); p. 555 – 564;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 90434-01-8, name is 3-Iodo-N-methylbenzamide, 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 90434-01-8, HPLC of Formula: C8H8INO

To a solution of 1(21mg, 0.11mmol) and 2(40mg, 0.15mmol) was added Pd(dba)2(6mg, 0.01mmol), Xantphos (6mg,0.01mmol) and Cs2CO3(98mg, 0.3mmol). The suspension was degassed under vacuum and purged with N2 several times. The suspension was degassed under vacuum and purged with N2 several times. The mixture was stirred at 100 C for 1h, cooled to rt, LCMS showed the SM was consumed completely. Then the reaction mixture was diluted with EA (80mL) and washed with brine (20mL) three times. The organic solution was dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purification with prep-TLC to afford the title product (7mg, yield: 19%). LCMS: m/z, 324.2 (M+H)+; 1HNMR (400 MHz, CDCl3): delta 2.44-2.7 l(m, 2H), 2.93-3.07(s, 3H), 3.46~3.54(m, 2H), 3.76~3.83(m, 2H), 6.49-6.5 l(m, 2H), 6.64~6.66(m, 1H), 7.16-7.25 (m, 2H), 7.43-7.45 (m, 1H), 7.61~7.65(m, 1H), 8.54-8.56 (m, 1H).

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; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; BALDWIN, John J.; WU, Chengde; SHEN, Chunli; WO2014/124560; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com