Category: 53078-85-6

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. 53078-85-6, name is 2-Bromo-5-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 53078-85-6

The corresponding imidazopyridine (0.2 mmol) was added sequentially to a 25 ml Schlenk tube filled with oxygen and equipped with a magnetic stirrer at room temperature.Cuprous chloride (0.02 mmol), 2-bromo-5-methylaniline (0.2 mmol),1,10-azaphenanthroline (0.04 mmol), sodium carbonate (0.4 mmol), adding carbon disulfide (0.2 mmol), DMSO (2.0 mL) with a syringe under oxygen, and placing the reaction tube in a 110 C oil bath with stirring 6 hour. The obtained solution was cooled to room temperature, 2 mL of deionized water was added to the reaction liquid, and the mixture was uniformly mixed. Each time, 3 mL of ethyl acetate was used as an extracting agent, and the crude product was extracted from the reaction liquid by a liquid separation extraction operation, and the extract was combined. The solvent was removed by a rotary evaporator; the residue was purified on a silica gel column (yield: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (7:1 v/v)) to give the desired product 61.0 mg. The yield was 76%.

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 53078-85-6.

Reference:
Patent; Qingdao University of Science and Technology; Yang Daoshan; Yan Qiuli; (17 pag.)CN110294757; (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. 53078-85-6, name is 2-Bromo-5-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 53078-85-6

3-phenyl-2,2-dihydroxy-3-oxopropionic acid ethyl ester (0.05 mmol) was added to the reaction flask.2-bromo-5-methylaniline (0.05 mmol),4-phenyl-1,3-cyclohexanedione (0.05 mmol),(R)-3,3,3′,3′-tetramethylspirophosphoric acid (0.005 mmol) represented by the formula (V),Anhydrous Na2SO4 (200 mg) was poured into 1 mL of dichloromethane, and the mixture was reacted at 65 C for 16 hours. After completion of the reaction, the column was directly subjected to silica gel column chromatography, and the eluent was ethyl acetate / petroleum ether = 1:30.Corresponding optically active 1-arylindole derivative (I-7), yield 73%;

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 53078-85-6.

Reference:
Patent; Zhejiang University; Lin Xufeng; Wang Lei; Zhong Jialing; (14 pag.)CN110183373; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 53078-85-6,Some common heterocyclic compound, 53078-85-6, name is 2-Bromo-5-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.

To a suitable amount of a solvent (a mixture of 1,4-dioxane and polyethylene glycol 200 (PEG-200) in a volume ratio of 1: 2.5) was added 100 mmol of the compound of the above formula (I) (II), 6 mmol of a two-component catalyst (1.2 mmol of 1,5-cyclooctadiene (acetoacetate) iridium and 4.8 mmol of bis (tricyclohexylphosphine) nickel chloride (NiCl2(PCy3)2Proline t-butyl ester hydrochloride and 200 mmol NaHS (in the form of a 35% by mass aqueous solution), and then the temperature was raised to 90 C with stirring, and the mixture was stirred at room temperature for 10 minutes. The reaction was stirred at this temperature for 8 hours;After the completion of the reaction, the reaction solution was cooled to room temperature, filtered, and the pH of the filtrate was adjusted to neutral. The extract was shaken with n-hexane for 2-3 times. The organic phase was combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The mixture was eluted with a 2: 1 by volume mixture of chloroform and acetone. The eluate was collected, and the solvent was distilled off under reduced pressure to give the compound of the formula (III) in a yield of 97.4%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-5-methylaniline, its application will become more common.

Reference:
Patent; Wang, Jianjun; Li, Guiyan; (9 pag.)CN106083729; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 53078-85-6,Some common heterocyclic compound, 53078-85-6, name is 2-Bromo-5-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.

To a suspension of 2-bromo-5-methylaniline (9.76 g, 52.5 mmol) in 8 mL of water was added 8.8 mL of concentrated HCl. The reaction mixture was cooled in an ice/NaCl bath (approximately -5 to -10 C). Approximately 8 g of ice was added to the reaction mixture. A solution of NaNO2 (3.60 g, 52.3 mmol) in 16.2 mL of water was added slowly over 40 minutes. The solution was then stirred for an additional 30 minutes with cooling. Separately, a solution of potassium ethyl xanthogenate (10.1 g, 63.0 mmol) in 54 mL of water was prepared and heated to 60 C. The cold solution of diazonium salt was then added slowly over 20 minutes to the solution of potassium ethyl xanthogenate. The reaction mixture was stirred for an additional 30 minutes at 60 C, and then cooled to ambient temperature. It was then poured into a saturated aqueous NaHCO3 solution and extracted three times with dichloromethane. The combined organic extracts were washed with saturated brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. To this residue was added a solution of 1.8 M KOH/EtOH, and the reaction mixture was heated to reflux for 18 hours. The reaction mixture was then cooled to ambient temperature and concentrated in vacuo. The residue was dissolved in water and extracted with diethyl ether. The aqueous phase was then acidified with concentrated HCl and extracted three times with dichloromethane. The combined organic extracts were dried over anhydrous MgSO4, filtered, concentrated, and purified by silica gel chromatography using 0-5% ethyl acetate/hexanes as eluent to provide 8.26 g (78%) of the title Compound as a pale yellow oil. 1H NMR (500 MHz, CDCl3( ^ ggd: 2.25-2.28 (m, 3H) 3.96 (s, 1H) 6.81 (d, J=8.03 Hz, 1H) 7.18 (d, J=1.89 Hz, 1H) 7.40 (d, J=8.20 Hz, 1H).

The synthetic route of 53078-85-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FMC CORPORATION; XU, Ming; DEANGELIS, Andrew Jon; LAHM, George Philip; (190 pag.)WO2020/18610; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 53078-85-6,Some common heterocyclic compound, 53078-85-6, name is 2-Bromo-5-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.

To a solution of 5.0 g of 2-bromo-5-methylaniline in 17 ml of hydrochloric acid (37%) was added dropwise, at 0 C. within 30 minutes, a solution of 1.9 g of sodium nitrite in 9.6 ml of water. Subsequently, at 0 C., a solution of 16.6 g of tin chloride in 15 ml of hydrochloric acid (37%) was added dropwise, and the mixture was stirred at this temperature for a further 1.5 hours. After adding 60 ml of sodium hydroxide solution (50%) and 30 ml of ice-water (pH>10), the mixture was extracted three times with 500 ml each time of ether. The combined organic phases were washed with semisaturated sodium chloride solution and dried over sodium sulphate. The filtrate was acidified with 4.0M hydrochloric acid in 1,4-dioxane solution and the resulting precipitate was then filtered off and dried. Yield: 5.85 g of the title compound.NMR (300 MHz, DMSO-d6): delta=2.22 (3H), 6.70 (1H), 6.93 (1H), 7.39 (1H), 7.78 (1H), 10.29 (2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-5-methylaniline, its application will become more common.

Reference:
Patent; Bayer Schering Pharma AG; US2010/29598; (2010); A1;,
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. 53078-85-6, name is 2-Bromo-5-methylaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-5-methylaniline

A mixture of compound 36b (3 3 g, 17 7 mmol), glycerin (3 3 g, 35 5 mmol), nitrobenzene (2 2 g, 17 7 mmol) and 75% aqueous sulfuric acid (10 mL, 138 mmol) is stirred at 15O0C for 3 h (mixture turns black and viscous) The reaction mixture is cooled down, poured into ice-water (200 mL) and 10 N aqueous NaOH is added (30 mL, 300 mmol) The black mixture is then shaken with EtOAc (100 mL) and is centrifuged in 50 mL portions The upper EtOAc layers are combined and the bottom aqueous layers containing the black tar are shaken with EtOAc and re-cent?fuged All EtOAc extracts are combined, washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to give 4.8 g of a brown-red oil. This material is chromatographed on 80 g silica gel column (CombiFlash Companion apparatus, hexanes/EtOAc gradient). The fractions containing the compound are concentrated under vacuum to afford compound 36c as a white solid (3.26 g, 83% 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; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; CARSON, Rebekah J.; FADER, Lee; KAWAI, Stephen; LANDRY, Serge; WO2009/62288; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 53078-85-6, 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 53078-85-6 as follows.

5-methyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (2): A solution of 2-bromo-5-methylani fine (1.5 g, 8.0 mmol) in dimethyl sulfoxide (20.0 mL) was treated with bis-pinacolatodiborane(2.4 g, 9.7mmol), potassium acetate (2.4 g, 24 mmol), and [1,1 ‘Bis(diphenylphosphino)ferrocene] dichloropalladium(II) complex with dichloromethane (329 mg, 0.04 mmol) at 110 C for 6 h. After completion of the reaction, the reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to afford 2 (320 mg, 17%) as a pale yellow liquid. 1H NMR (400 MHz, DMSO-d6): delta 1.26 (s, 12H), 2.13 (s, 3H), 5.37 (s, 2H), 6.29 (d, J = 7.5 Hz, 1H), 6.37 (s, 1H), 7.23 (d, J = 7.5 Hz, 1H). MS m/z (M+H): 234.2

According to the analysis of related databases, 53078-85-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; ALEXANDER, Matthew David; MCDONALD, Joseph John; NI, Yike; NIU, Deqiang; PETTER, Russell C.; QIAO, Lixin; SINGH, Juswinder; WANG, Tao; ZHU, Zhendong; WO2014/149164; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 53078-85-6, 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. 53078-85-6, name is 2-Bromo-5-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of compound 36b (3.3 g, 17.7 mmol), glycerin (3.3 g, 35.5 mmol), nitrobenzene (2.2 g, 17.7 mmol) and 75% aqueous sulfuric acid (10 ml_, 138 mmol) is stirred at 1500C for 3 h (mixture turns black and viscous). The reaction mixture is cooled down, poured into 200 ml. ice-water and 10 N aqueous NaOH is added (30 ml_, 300 mmol). The black mixture is then shaken with 100 ml. EtOAc and is centrifuged in 50 ml_ portions. The upper EtOAc layers are combined and the bottom aqueous layers containing the black tar are shaken with EtOAc and re-centrifuged. All EtOAc extracts are combined, washed with brine, dried over Na2SO4, filtered and concentrated under vacuum to give 4.8 g of a brown-red oil. This material is chromatographed on 80 g silica gel column (CombiFlash Companion apparatus, hexanes-EtOAc gradient). The fractions containing the compound are concentrated under vacuum to afford compound 36c as a white solid (3.26 g, 83% yield).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-5-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; WO2009/62308; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 53078-85-6,Some common heterocyclic compound, 53078-85-6, name is 2-Bromo-5-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.

8-bromo-4,5-dimethylquinoline, monohydrochloride (A): At 23 C, a 2-neck500 mL round-bottom flask equipped with magnetic stuffing bar, reflux condenser, and bubbler was flushed with N2 for several minutes. The flask was placed in a bath ofaluminum beads and charged with 12 N aq. HC1 (180 mL). Molten 2-bromo-5-methyl benzenamine (50.0 g, 0.270 mol) was added steadily to the flask while the aluminum bead bath was at 23 C. Once addition ensued, an off-white chunky precipitate formed. A glass stirring rod was periodically used to pulverize the chunks. Once addition was complete, the reaction was a suspension with particulate white solid in yellow liquid.At this point, a pressure-equalizing addition funnel was attached to the flask and charged with Methyl Vinyl Ketone (26.8 mL, 0.322 mol). The reaction was heated to 120 C under N2. A circulating chiller was applied to through the reflux condenser. The bubbler was then removed and a stream of air was passed steadily over the reaction while the Methyl Vinyl Ketone was added dropwise over 10 mm. Heating wascontinued for another 30 mm, then the air stream was cut. The reaction was refitted with the bubbler and an N2 stream was applied as the reaction was cooled to 23 C. The reaction was poured into THF (1.0 L) and the sluffy was cooled to – 20 C overnight. The precipitate was collected in a Buchner funnel on filter paper and washed with 2 x 100 mL of ice-cold THF. This afforded 8-bromo-4,5-dimethylquinoline,monohydrochioride. The material was immediately used in the reaction below. LCMSESI Calc?d for C11H10BrN (M+H): 236.0 / 238.0. Found 236.1 / 238.1 (M+H)

The synthetic route of 53078-85-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; MCFADDEN, Ryan; MITCHELL, Michael, L.; WO2015/179448; (2015); A1;,
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. 53078-85-6, name is 2-Bromo-5-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 53078-85-6

The corresponding imidazopyridine (0.2 mmol) was added sequentially to a 25 ml Schlenk tube filled with oxygen and equipped with a magnetic stirrer at room temperature.Cuprous chloride (0.02 mmol), 2-bromo-5-methylaniline (0.2 mmol),1,10-azaphenanthroline (0.04 mmol), sodium carbonate (0.4 mmol), adding carbon disulfide (0.2 mmol), DMSO (2.0 mL) with a syringe under oxygen, and placing the reaction tube in a 110 C oil bath with stirring 6 hour. The obtained solution was cooled to room temperature, 2 mL of deionized water was added to the reaction liquid, and the mixture was uniformly mixed. Each time, 3 mL of ethyl acetate was used as an extracting agent, and the crude product was extracted from the reaction liquid by a liquid separation extraction operation, and the extract was combined. The solvent was removed by a rotary evaporator; the residue was purified on a silica gel column (yield: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (7:1 v/v)) to give the desired product 61.0 mg. The yield was 76%.

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 53078-85-6.

Reference:
Patent; Qingdao University of Science and Technology; Yang Daoshan; Yan Qiuli; (17 pag.)CN110294757; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary