Category: 583-75-5

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. 583-75-5, name is 4-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-2-methylaniline

General procedure: A homogenous mixture of the reagent CTMATB (2 mmol) and substrate 1-9 (2 mmol) were taken in 1:1 ratio in a 50 mL round bottomed flask equipped with reflux condenser in the microwave reactor. 10 mL H2O was added to the mixture and stirred thoroughly. The reaction mixture was placed inside the microwave reactor. The reactor was switched on and kept at a controlled power of P-7 which corresponds to 595 W. Reaction temperature was recorded using the flexible temperature probe attached to the microwave reactor, immediately after the completion of the reaction, and was found to be 90 C. The progress of the reaction was monitored by TLC on silica gel HF254 using ethyl acetate-hexane solvent system (volume ratio varied for different substrates). After completion of the reaction, the product was extracted with 10 mL (2×) ethyl acetate and washed with 5 mL (2×) sodium bicarbonate solution. The crude product thus obtained was subjected to column chromatography over a pad of silica gel using ethyl acetate-hexane solvent system (volume ratio varied for different substrates) to obtain the desired products 1a-9a.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Longkumer, Naruti; Richa, Kikoleho; Karmaker, Rituparna; Kuotsu, Visekhonuo; Supong, Aola; Jamir, Latonglila; Bharali, Pranjal; Sinha, Upasana Bora; Acta Chimica Slovenica; vol. 66; 2; (2019); p. 276 – 283;,
Bromide – Wikipedia,
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Some common heterocyclic compound, 583-75-5, name is 4-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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. Computed Properties of C7H8BrN

EXAMPLE 192 1,2-Dihydro-6-(3-nitrophenyl)-2,2,4,8-tetramethylquinoline (Compound 292, structure 86 of Scheme XXII, where R1 =R3-5 =H, R2 =nitro) 4-Bromo-2-methylaniline (5.58 g, 30 mmol) was treated with iodine (0.2 g, 0.9 mmol) and acetone (150 mL) in a sealed tube at. 80 C. for 24 h to provide 6-bromo-1,2-dihydro-8-methylquinoline (Compound 85 of Scheme XXII) in 9% yield as a yellow oil (0.70g). Most of the aniline (>80%) was recovered.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 583-75-5, its application will become more common.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5696130; (1997); A;,
Bromide – Wikipedia,
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Synthetic Route of 583-75-5, 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 583-75-5 as follows.

In a 2000 ml beaker to 400 ml of 23percent aqueous HBr, 46.5 g (0.25 mol) of melted 2-methyl-4-bromoaniline was slowly added. This mixture was stirred for 20 minutes using a mechanical stirrer, cooled to -50C. Then a solution of 22.4 g (0.33 mol) Of NaNO2 in 130 ml of water was added dropwise for 1 hour at this temperature. The diazonium reagent obtained was added in several portions to a solution of 35.9 g (0.25 mmol) of CuBr in 100 ml of 47percent HBr at O0C. The resulting mixture was warmed to 7O0C, stirred for 30 minutes at this temperature, and then cooled to room temperature. The product was extracted with 3 x 200 ml of methyl-tert-butyl ether. The combined extract was dried over K2CO3 and evaporated to dryness. The crude product was purified by first using a short Silica Gel 60 column (40-63 mum, d 60 mm, 1 40 mm; eluent: hexanes). Fractional distillation gave colorless oil, b.p. 100-102°C/10 mm Hg. Yield 36.1 g (58percent). Anal. calc. for C7H6Br2: C, 33.64; H, 2.42. Found: C, 33.79; H, 2.50. 1H NMR (CDCl3): delta 7.39 (m, IH, 5-H), 7.37 (m, IH, 3-H), 7.18 (m, IH, 6- H), 2.38 (s, 3H, Me).13C NMR (CDCl3): delta 139.9, 133.6, 133.5, 130.3, 123.5, 120.9, 22.7.

According to the analysis of related databases, 583-75-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXXONMOBIL CHEMICAL PATENTS INC.; WO2007/70041; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 583-75-5, name is 4-Bromo-2-methylaniline, 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. Formula: C7H8BrN

EXAMPLE 192 1,2-Dihydro-6-(3-nitrophenyl)-2,2,4,8-tetramethylquinoline (Compound 292, structure 86 of Scheme XXII, where R1 =R3-5 =H, R2 =nitro) 4-Bromo-2-methylaniline (5.58 g, 30 mmol) was treated with iodine (0.2 g, 0.9 mmol) and acetone (150 mL) in a sealed tube at 80 C. for 24 h to provide 6-bromo-1,2-dihydro-8-methylquinoline (Compound 85 of Scheme XXII) in 9% yield as a yellow oil (0.70 g). Most of the aniline (>80%) was recovered.

The synthetic route of 4-Bromo-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688808; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 583-75-5, 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. 583-75-5, name is 4-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

6-bromo-8-methylquinoline. Glycerol (2.3 ml, 32.2 mmol) was added dropwise via syringe to a solution of 4-bromo-2-methylaniline (5.00 g, 26.8 mmol) and sodium iodide (52 mg, 0.349 mmol) in 75% aq H2SO4 (15.81 ml, 120 mmol) at 140 C. The mixture was held at this temperature for 3 hours. The reaction mixture was neutralized to a pH of 7 with aq NaOH. This mixture was extracted with EtOAc and the combined organics were washed with brine, dried over MgSO4 and concentrated. Column chromatography on silica gel (5-25% EtOAc in hexanes) afforded intermediate 11 (5.50 g, 24.7 mmol, 92%). 1H NMR (400 MHz, CDCl3) delta ppm 8.93 (dd, J=4.28, 1.76 Hz, 1H), 8.03 (dd, J=8.31, 1.76 Hz, 1H), 7.82 (d, J=2.01 Hz, 1H), 7.65 (d, J=1.01 Hz, 1H), 7.40 (dd, J=8.18, 4.15 Hz, 1H), 2.78 (s, 3H). Mass 221 [M+H]+.

The synthetic route of 4-Bromo-2-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/18163; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

583-75-5, name is 4-Bromo-2-methylaniline, belongs to bromides-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. Formula: C7H8BrN

EXAMPLE 192 1,2-Dihydro-6-(3-nitrophenyl)-2,2,4,8-tetramethylquinoline (Compound 292, structure 86 of Scheme XXII, where R1 =R3-5 =H, R2 =nitro) 4-Bromo-2-methylaniline (5.58 g, 30 mmol) was treated with iodine (0.2 g, 0.9 mmol) and acetone (150 mL) in a sealed tube at 80 C. for 24 h to provide 6-bromo-1,2-dihydro-8-methylquinoline (Compound 85 of Scheme XXII) in 9% yield as a yellow oil (0.70 g). Most of the aniline (>80%) was recovered.

The synthetic route of 583-75-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5696127; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 583-75-5, name is 4-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., Formula: C7H8BrN

Adding the compound 183a (1.0 g, 5.37 mmol),Compound 183b (2.73 g, 10.75 mmol),Potassium acetate (1.58 g, 16.12 mmol) and PdCl2 (dppf) (0.39 g, 0.54 mmol) were added to 1,4-dioxane (20 mL), replaced with nitrogen three times, and then stirred at 90 C for 4 hours. The reaction solution was cooled to room temperature and filtered.The filter cake was washed with ethyl acetate (15 mL × 2), and the filtrate was concentrated.The concentrate was purified by silica gel chromatography (ethyl acetate: petroleum ether = 0-80%) to obtain a compound 183c as a yellow solid, namely , 2-Dioxoranepentyl-2-yl) aniline (1.21 g, 96.6% yield).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Jiaxing Tekeluo Biological Technology Co., Ltd.; Xing Li; Li Guanqun; Wang Xiaolei; Cai Yuting; Jiang Xiang; Pan Xiang; Zhu Wenhao; Wang Yang; Wang Zengquan; (83 pag.)CN110627775; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 583-75-5, name is 4-Bromo-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-2-methylaniline

Preparation #4: 2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine A mixture of 4-bromo-2-methylaniline (0.250 g, 1.34 mmol), bis(pinacolato)diboron (0.442 g, 1.747 mmol), dichloro[1,1’bis(diphenylphosphino)-ferrocene]palladium (II) dichloromethane adduct (0.110 g, 0.134 mmol), and potassium acetate (0.329 g, 3.357 mmol) was heated in N,N-dimethylformamide (5 mL) at about 80 C. for about 15 h under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and was purified by flash column chromatography on silica gel using ethyl acetate/heptane (3:7) as the mobile phase to give 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine as a yellow oil (0.213 g, 0.914 mmol); RP-HPLC (25% to 100% acetonitrile/0.1 M aqueous ammonium acetate, buffered to pH 4.5, over 10 min at 1.0 mL/min; lambda=254 nm; Hypersil C18, 100 A, 5 mum, 250*4.6 mm column) Rt 11.02 min.

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 583-75-5.

Reference:
Patent; Wishart, Neil; Friedman, Michael; Arnold, Lee D.; Yang, Bryant; Fix-Stenzel, Shannon R.; Ericsson, Anna; Michaelides, Michael R.; Qian, Xiao-Dong; Holms, James H.; Steinman, Douglas H.; Tian, Zhengping; Wittenberger, Steven J.; US2006/25383; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 583-75-5, A common heterocyclic compound, 583-75-5, name is 4-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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.

To a solution of 4-bromo-2-methylaniline (1 g, 5.37 mmol,) in 1,4-dioxane (11 mL) and H2O (4 mL), at r. t. , were added Et3N (2.7 mL, 1.2 eq) and BOC20 (4.2 g, 1.2 eq). The reaction mixture was stirred at r. t. for 96 hr. Sat. aq. NH4CI and EtOAc (20 mL) were added and the phases were separated. The aqueous layer was further extracted with EtOAc (2X20 mL). The combined organic extracts were dried over anh. NA2SO4, the solids were filtered and the solvent evaporated. The residue was purified by SCX Column (Eluents : CH2CI2, MeOH and NH3 (0.5 M in MEOH)) to give the title compound as a white solid (1.22 g, 79%). NMR (‘H, DMSO-D6) : 8 8.55 (s, 1H), 7.35 (m, 1H), 7.28 (m, 2H), 2.17 (s, 3H), 1.44 (s, 9H). MS (m/z) : 230 [MH-TBU] + ; 186 [MH-BOC] +.

The synthetic route of 583-75-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SB PHARMCO PUERTO RICO INC; NEUROCRINE BIOSCIENCES INC; GLAXO GROUP LIMITED; WO2004/62665; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 583-75-5, 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. 583-75-5, name is 4-Bromo-2-methylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 70 4-bromo-2-methylaniline (10.5g, 56.3mmol) in 71 acetic acid (300mL) were added 21 NaNO2 (3.89g, 56.3mmol) and 72 water (10mL). After stirring at room temperature for 5h, the reaction mixture was concentrated in vacuo. The residue was diluted with EtOAc and washed with saturated aqueous NaHCO3 solution and brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (0-50% 73 EtOAc in hexanes) and solidified with hexanes to afford 13 6 as a brown solid (6.81g, 61% yield). 1H NMR (200MHz, CDCl3) delta ppm 7.35-7.43 (m, 1H), 7.45-7.52 (m, 1H), 7.92 (d, J=2.2Hz, 1H), 8.03 (d, J=0.9Hz, 1H); MS ESI/APCI Dual m/z 195 [M-H]-.

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-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Matsuda, Daisuke; Kobashi, Yohei; Mikami, Ayako; Kawamura, Madoka; Shiozawa, Fumiyasu; Kawabe, Kenichi; Hamada, Makoto; Nishimoto, Shinichi; Kimura, Kayo; Miyoshi, Masako; Takayama, Noriko; Kakinuma, Hiroyuki; Ohtake, Norikazu; Bioorganic and Medicinal Chemistry; vol. 25; 16; (2017); p. 4339 – 4354;,
Bromide – Wikipedia,
bromide – Wiktionary