Category: 13194-73-5

Application of 13194-73-5,Some common heterocyclic compound, 13194-73-5, name is 3,5-Dibromo-4-methylaniline, molecular formula is C7H7Br2N, 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 round-bottom flask were added sulfoacetic acid (0.14g, 1.0 mmol), DMF (5 mL), HBTU (0.379g, 1 mmol), 3,5-dibromo-4- methylaniline (0.265g, 1 mmol), DIEA (0.52 mL, 3 mmol), and DMAP (0.012g, 0.1 mmol). The mixture was stirred at room temperature for 2 hours, and then it was subjected to reversed- phase HPLC purification to give product L335-M34 as a white solid (0.385g, 99% yield): 1H NMR (500 MHz, DMSO) delta 10.08 (s, 1H), 7.87 (s, 2H), 3.52 (s, 2H), 2.42 (s, 3H); 13C NMR (DMSO) delta 164.6, 138.9, 130.5, 124.1, 121.8, 59.1, 22.6; ESI-HRMS calcd for (M + H+) 385.8692, found 385.8696

The synthetic route of 13194-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH & TECHNOLOGY CORPORATION; ZHANG, Zhong-Yin; HE, Rongjun; (128 pag.)WO2016/196591; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 13194-73-5,Some common heterocyclic compound, 13194-73-5, name is 3,5-Dibromo-4-methylaniline, molecular formula is C7H7Br2N, 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 29 1,3-Dibromo-2-methylbenzene A solution of (3,5-dibromo-4-methylphenyl)amine dissolved in water (80 mL) and concentrated HCl (7.5 mL) stirring for 20 min, then the mixture was cooled to 0~5 C., and the solution of NaNO2 (3.4 g/30 mL H2O) was added. The reaction mixture was stirred for 2 h at 0~5 C., then the suspension was added to hypophosphorous acid solution (50%, 27.9 g), which was cooled to 0 C. The mixture was stirred at room temperature overnight. Then it was extracted with CH2Cl2 (100 mL*2) and the combined organic layers were washed with brine (30 mL) and dried over Na2SO4. After silica column chromatography, (eluted with petroleum ether), 3.57 g product was obtained, as colorless liquid. 1H NMR (400 MHz, CDCl3): delta 2.57 (s, 3H), 6.89 (t, J=8.0 Hz, 1H), 7.50 (d, J=8.0 Hz, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dibromo-4-methylaniline, its application will become more common.

Reference:
Patent; Glaxo Group Limited; US2009/197871; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 13194-73-5, 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. 13194-73-5, name is 3,5-Dibromo-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

Example 26 1,3-Dibromo-2-methylbenzene A solution of (3,5-dibromo-4-methylphenyl)amine dissolved in water (80 mL) and concentrated HCl (7.5 mL) stirring for 20 min, then the mixture was cooled to 0~5 C., and a solution of NaNO2 (3.4 g/40 mL H2O) was added. The reaction mixture was stirred for 2 h at 0~5 C., then the suspension was added to a solution of hypophosphorous acid (50%, 27.9 g), and the mixture was cooled to 0 C. The mixture was stirred at room temperature overnight. Then it was extracted with CH2Cl2 (100 mL*2). The organic layer was washed with brine (30 mL) and dried over Na2SO4. After silica column chomatography, (eluted with petroleum ether), 3.57 g product was obtained, as a colorless liquid. 1H NMR (400 MHz, CDCl3) delta 2.57 (s, 3H), 6.89 (t, J=8.0 Hz, 1H), 7.50 (d, J=8.0 Hz, 2H).

The chemical industry reduces the impact on the environment during synthesis 3,5-Dibromo-4-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Glaxo Group Limited; US2009/203657; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 13194-73-5,Some common heterocyclic compound, 13194-73-5, name is 3,5-Dibromo-4-methylaniline, molecular formula is C7H7Br2N, 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 1 Synthesis of Compound M1 (Step (1a)) Under an argon gas atmosphere, 3,5-dibromo-4-methylaniline (47.0 g, 177 mmol), 35 wt % hydrochloric acid (111 ml) and ion exchanged water (111 ml) were mixed in a 1000 ml flask and cooled in an ice bath, and a solution prepared by dissolving sodium nitrite (12.9 g, 186 mmol) in ion exchanged water (about 130 ml) was dropped into the cooled mixture over a period of about 30 minutes. After completion of dropping, the mixture was stirred at room temperature for about 1 hour, then, cooled in an ice bath again, then, a solution prepared by dissolving potassium iodide (30.9 g, 186 mmol) in ion exchanged water (about 130 ml) was dropped into the cooled mixture over a period of 30 minutes. After completion of dropping, the mixture was stirred at room temperature for about 3 hours, then, added slowly to a separately prepared 10 wt % sodium hydrogen carbonate aqueous solution (about 1200 ml) while stirring. Ethyl acetate (about 1000 ml) was added and extraction was performed, the organic layer was washed with a 10 wt % sodium sulfite aqueous solution (about 450 ml), dried over anhydrous magnesium sulfate (50 g), filtrated, and the filtrate was concentrated to obtain a coarse product (77 g). The above-described coarse product was dissolved in acetone (750 ml), activated carbon (10 g) was added and stirred, then, the mixture was filtrated, and the filtrate was concentrated. It was again dissolved in acetone (750 ml), activated carbon (20 g) was added and stirred, then, the mixture was filtrated, and the filtrate was concentrated, and the deposited solid was dried under reduced pressure to obtain a yellow-brown solid (about 50 g). The resultant solid was dissolved in hexane, and ethanol was added to the solution to cause crystallization, and the resultant crystal was filtrated, and dried under reduced pressure, to obtain an intermediate 2,6-dibromo-4-iodotoluene (28.4 g, yield 43%, compound M1a) as a white crystal. 1H-NMR (300 MHz, CDCl3) delta (ppm)=2.51 (s, 3H), 7.83 (s, 2H)

The synthetic route of 13194-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; US2011/272686; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 13194-73-5,Some common heterocyclic compound, 13194-73-5, name is 3,5-Dibromo-4-methylaniline, molecular formula is C7H7Br2N, 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 round-bottom flask were added sulfoacetic acid (0.14g, 1.0 mmol), DMF (5 mL), HBTU (0.379g, 1 mmol), 3,5-dibromo-4- methylaniline (0.265g, 1 mmol), DIEA (0.52 mL, 3 mmol), and DMAP (0.012g, 0.1 mmol). The mixture was stirred at room temperature for 2 hours, and then it was subjected to reversed- phase HPLC purification to give product L335-M34 as a white solid (0.385g, 99% yield): 1H NMR (500 MHz, DMSO) delta 10.08 (s, 1H), 7.87 (s, 2H), 3.52 (s, 2H), 2.42 (s, 3H); 13C NMR (DMSO) delta 164.6, 138.9, 130.5, 124.1, 121.8, 59.1, 22.6; ESI-HRMS calcd for (M + H+) 385.8692, found 385.8696

The synthetic route of 13194-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH & TECHNOLOGY CORPORATION; ZHANG, Zhong-Yin; HE, Rongjun; (128 pag.)WO2016/196591; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 13194-73-5, 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. 13194-73-5 name is 3,5-Dibromo-4-methylaniline, 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.

Step A: 2,6-Dibromo-4-iodotoluene To a solution of 3,5-dibromo-4-methylaniline (4.17 g, 15.74 mmol) in CH2I2 (10 mL) was added tert-butylnitrite (3.0 mL, 23.61 mmol) slowly at 0 C. while stirring vigorously. The ice bath was removed and the reaction mixture was stirred at rt while the reaction was very exothermic, then placed it in a 80 C. oil bath and heated for 20 min. CH2I2 was distilled off under high vacuum, and the remaining residue was purified by flash chromatography eluding with 100% hexane to gave the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dibromo-4-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; Doherty, James B.; Stelmach, John E.; Chen, Meng-Hsin; Liu, Luping; Hunt, Julianne A.; Ruzck, Rowena D.; Goulet, Joung L.; Wisnoski, David D.; Natarajan, Swaminathan Ravi; Rupprecht, Kathleen M.; Bao, Jianming; Miao, Shouwu; Hong, Xingfang; Sinclair, Peter J.; Kallashi, Florida; US2003/92712; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary