Tag: M.W=200-300

Enzymes are biological catalysts that produce large increases in reaction rates and tend to be specific for certain reactants and products. 619-58-9, Name is 4-Iodobenzoic acid, molecular formula is C7H5IO2, belongs to iodides-buliding-blocks compound. In a document, author is Ai, Han-Jun, introduce the new discover, Quality Control of 4-Iodobenzoic acid.

Palladium-catalyzed Heck reaction of in-situ generated benzylic iodides and styrenes

A palladium-catalyzed Heck reaction of in-situ generated benzylic iodides and styrenes has been achieved. The reaction proceeds in a one-pot manner through 1) addition perfluoroalkyl iodides to styrenes to give benzylic iodides, 2) followed by a palladium-catalyzed Heck coupling of the resulting benzylic iodides with the same alkenes in high regio- and stereoselectivity. A variety of perfluoroalkylated alkenes were obtained in moderate to excellent yields. (C) 2017 Elsevier Ltd. All rights reserved.

Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law. In my other articles, you can also check out more blogs about 619-58-9. Quality Control of 4-Iodobenzoic acid.

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 69113-59-3 as follows. Product Details of 69113-59-3

General procedure: Vial (C2) was loaded with aryl iodide/bromide (0.5 mmol), Pd(PPh3)4 (29 mg, 5 mol %), Et3N(139 muL, 1 mmol) and cyanamide (63 mg, 1.5 mmol). To vial (C1) was added Mo(CO)6 (138mg, 0.5 mmol) and thereafter 1,4-dioxane (3+3 mL) was added to C1 and C2. The two vials were capped with a gas tight cap and DBU (224 muL, 1.5 mmol) was added to C1. The sealed double vial was heated in a heat-block (65 C for iodides and 85 C for bromides) for 20 h with vigorous stirring.

According to the analysis of related databases, 69113-59-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mane, Rajendra S.; Nordeman, Patrik; Odell, Luke R.; Larhed, Mats; Tetrahedron Letters; vol. 54; 50; (2013); p. 6912 – 6915;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 6940-76-7, name is 1-Chloro-3-iodopropane, molecular formula is C3H6ClI, 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-Chloro-3-iodopropane

EXAMPLE 14 Ethyl 4-(3-chloropropyl)-4-cyano-1-piperidinecarboxylate To a solution of ethyl 4-cyano-1-piperidinecarboxylate (6.0 g) in tetrahydrofuran (120 ml) at -70 C., under nitrogen, was added a solution of lithium diisopropylamide (4.6 g) in tetrahydrofuran (21.5 ml), dropwise, with stirring. The reaction was allowed to warm to -10 C. and after 30 min was recooled to -70 C. A solution of 1-chloro-3-iodopropane (7.4 g) in tetrahydrofuran (20 ml) was added to the mixture over 30 min. The reaction mixture was quenched with water and allowed to warm to ambient temperature. The mixture was extracted with ethyl acetate. The extracts were washed with water, saturated sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was flash chromatographed (silica), eluding with 2:1 heptane/ethyl acetate. The appropriate fractions were collected and concentrated to afford 5.5 g (64%) of product. Analysis: Calculated for C12 H19 ClN2 O2: 55.70%C 7.40%H 10.83%N Found: 55.88%C 7.67%H 10.80%N

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6940-76-7, its application will become more common.

Reference:
Patent; Hoechst Marion Roussel Inc.; US5756743; (1998); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 5876-51-7, name is 5-Iodobenzo[d][1,3]dioxole, 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 5876-51-7, HPLC of Formula: C7H5IO2

General procedure: To a solution of tetrabutylammonium bromide (1.100 g, 3.33mmol), potassium acetate (0.586 g, 3.57 mmol), and palladium acetate (0.025 g, 0.11mmol) in DMF (20 mL) were added substituted iodobenzene (2.21mmol) and substituted styrene (2.44 mmol). The reaction mixture was recharged with argon and stirred at 80C for 5 h in a sealed tube. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10:3) to afford pure product.

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:
Article; Liang, Jian-Hua; Yang, Liang; Wu, Si; Liu, Si-Si; Cushman, Mark; Tian, Jing; Li, Nuo-Min; Yang, Qing-Hu; Zhang, He-Ao; Qiu, Yun-Jie; Xiang, Lin; Ma, Cong-Xuan; Li, Xue-Meng; Qing, Hong; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 382 – 392;,
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

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

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

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

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

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