Category: 16518-62-0

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. 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, A new synthetic method of this compound is introduced below., name: 3-Bromo-N,N-dimethylaniline

Into a 50 mL round-bottomed flask were added Pd(PPh3)2Cl2 (0.17 g, 5 mol percent) and 3-bromo-N,N-dimethylaniline (0.60 g, 3 mmol) under an argon atmosphere. Next, 10 mL of 5-(1,3-dioxolan-2-yl)-2-furanylzinc bromide (0.5 M in THF, 5 mmol) was added via a syringe. The resulting mixture was stirred at rt for 3.0 h. Quenched with saturated NH4Cl solution, then extracted with ethyl acetate (10 mL .x. 3). Washed with saturated Na2S2O3 solution and brine, then dried over anhydrous MgSO4. Purification by column chromatography on silica gel (20percent ethyl acetate/80percent heptane) afforded 3-(5-(1,3-dioxolan-2-yl)furan-2-yl)-N,N-dimethylaniline (1g, 0.71 g) in 92percent isolated 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:
Article; Rieke, Reuben D.; Kim, Seung-Hoi; Tetrahedron Letters; vol. 52; 10; (2011); p. 1128 – 1131;,
Bromide – Wikipedia,
bromide – Wiktionary

16518-62-0, name is 3-Bromo-N,N-dimethylaniline, 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. HPLC of Formula: C8H10BrN

General procedure: Bromo-N,N-dimethylaniline (400 mg, 2.0 mmol), (trimethylsilyl)acetylene (236 mg, 2.4 mmol), Pd(PPh3)4 (116 mg, 0.1 mmol), CuI (19mg, 0.1 mmol), diisopropylamine (5 mL) and toluene (15 mL) wereadded to a flask and the mixture was stirred at 80 C overnight. Thenthe reaction mixture was poured into saturated NH4Cl (50 mL) andextracted with CH2Cl2 (3 x 20 mL), the organic layer was washed withsaturated brine (1 x 50 mL) and dried over MgSO4. After filtration,solvents were removed by rotary evaporation (40-45 C ). The crudeproduct was subjected to column chromatography (SiO2; eluent,hexane/ CH2Cl2, 3:1) to give the corresponding compounds. N,N-Dimethyl-3-[(trimethylsilyl)ethynyl]aniline (3b): Pale yellow oil; yield 84%.

The synthetic route of 16518-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fang, Jing-Kun; Sun, Tengxiao; Fang, Yu; Xu, Zhimin; Zou, Hui; Liu, Yuan; Ge, Fangting; Journal of Chemical Research; vol. 39; 8; (2015); p. 487 – 491;,
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. 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 16518-62-0

3-Bromo-/V,/V-dimethylaniline (13) (3.20 g, 16.00 mmol, 2.0 eq.) was dissolved in dry Et20 (45 mL) and cooled down to -78 C. sec-BuLi (14.0 mL, 18.40 mmol, 2.3 eq., 1.3 M in cyclohexane) was added dropwise over 15 min and the mixture was stirred for 30 min at – 78 C. Dichlorodimethylsilane (14) (1.0 mL, 8.00 mmol, 1.0 eq.) was added dropwise over 10 min at -78 C. The mixture was stirred for 10 min at -78 C and then warmed up to room temperature and stirred for 1 h. The mixture was quenched with aqueous saturated NaHCC>3 solution. The aqueous layer was extracted with Et20 (3 x 150 mL) and the combined organic layers were dried over MgS04, filtered and evaporated to afford the crude product.

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 16518-62-0.

Reference:
Patent; SPIROCHROME AG; JOHNSSON, Kai; REYMOND, Luc; FREI, Michelle; PITSCH, Stefan; (71 pag.)WO2019/122269; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, molecular formula is C8H10BrN, 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 C8H10BrN

It was prepared as outlined in Scheme 1 In an oven-dried 50 mL round bottom flask under an atmosphere of anhydrous argon, THF (10 mL) was added followed by 3-bromo-N,N-dimethylaniline (5.00 mmol, 1.00 g). This clear, colourless solution was cooled to -90 °C using a Juablo cooler with a cold finger and an isopropanol bath in an appropriate sized Dewar. The aniline reagent solution was stirred at this temperature for 15 min to ensure the solution was sufficiently cold. Butyl lithium (3.44 mL, 1.60 M in hexanes) was added dropwise at -90 °C over 20 min. The resulting clear light yellow solution was stirred for 15 min at -90 °C. To this 3-lithium N,N-dimethylaniline intermediate was added N-methoxy-N-methyl-2,2,2-trifluoroacetamide (5.50 mmol, 0.857 g) dissolved in anhydrous THF (4 mL), dropwise over 15 min. The resulting solution was stirred at -90 °C for 30 min then warmed to room temperature by removing the reaction flask from the cooling bath. The resulting reaction mixture was stirred for 16 h at room temperature then extracted with 1 M HCl (3 * 10 mL). The combined aqueous layers were added to a separatory funnel and solid NaHCO3 was added until the solution stopped bubbling. During this addition a yellow liquid formed on the top of the aqueous layer. The aqueous layer was extracted with diethyl ether (3 * 15 mL). The combined organic layers were dried over Na2SO4, gravity filtered and concentrated in vacuo. The crude viscous yellow liquid was purified by flash chromatography on silica gel (5percent ethyl acetate/94percent hexanes/1percent triethylamine, Rf: 0.38) to afford the desired product as a clear yellow liquid (0.854 g, 79percent): 1HNMR (CDCl3): d 3.02 (s, 6H), 7.02?7.05 (m, 1H), 7.36?7.38 (m,3H) (Supplementary Fig. S1). 13C NMR (CDCl3): d 40.0, 112.3,116.8 (q, JC,F = 298.2 Hz), 117.9, 119.1, 129.5, 130.4, 150.5, 181.0(q, JC,F = 34.3 Hz) (Supplementary Fig. S2). IR (Neat): 2898 (m),2814 (w), 1709 (s), 1600 (s), 1573 (s), 1503 (s), 1437 (m), 1363(m), 1105 (s), 1007 (s) cm1 (Supplementary Fig. S3). LRMS m/z: 218 (M+1, 11), 217 (M+, 100), 216 (74), 148 (24), 120 (24), 119(13), 118 (10), 104 (10), 77 (11), 74 (13) (Supplementary Fig. S4). HRMS (ESI): MH+ found 218.0786, calculated for C10H11F3-NO+ = 218.0787(Supplementary Fig. S5). HPLC: retention time 2.59 min; purity 96.1percent (Supplementary Fig. S6).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16518-62-0, its application will become more common.

Reference:
Article; Jollymore-Hughes, Courtney T.; Pottie, Ian R.; Martin, Earl; Rosenberry, Terrone L.; Darvesh, Sultan; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5270 – 5279;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 16518-62-0,Some common heterocyclic compound, 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, molecular formula is C8H10BrN, 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 mixture ofpalladium(ll) acetate (3 mg, 5 molpercent), 2-dicyciohexylphosphino-2′-(A/,A/-dimethylamino)biphenyl (10 mg, 5 molpercent) and lithium bis(trimethylsilyl)amide(0.55 rnl_, 0.55 mmol, 1.1 equiv, 1.0 M solution in tetrahydrofuran) in toluene(0.5 ml) under nitrogen at-10 °C, was added a solution of 3-[5-(3,4-dichloro-10 phenyl)-1 -(2,4-dichloro-phenyl)-1 H-pyrazol-3-yl]-propionic acid tert-butyl ester(243 mg, 0.50 mmol, 1.0 equiv) in toluene (1.0 mL). This mixture was stirred at-10 °C for 10 min, then (3-bromo-phenyl)-dirnethyl-arnine (42 mg, 0.21 mmol,0.45 equiv) in toluene (0.5 ml) was added. The resulting solution was allowedto warm to room temperature then was heated to 80 °C for 3 h. The reaction15 mixture was cooled to room temperature, and the reaction was quenched withsatd aq ammonium chloride (1.0 ml). Water (10.0 ml) was added, and theresulting mixture was extracted with diethyl ether (2×10 ml). The combinedextracts were washed with brine (10 ml), dried (Na2SC>4), and concentratedunder reduced pressure. The crude material was purified by reversed-phase20 HPLC to afford the desired aryl acetic acid ester (20 mg, 16percent). MS (ESI):mass calculated for CaohbCUNaC^, 603.10; m/z found, 604.1 [M+H]+.

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

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2005/5393; (2005); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

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 16518-62-0 as follows. Safety of 3-Bromo-N,N-dimethylaniline

N,N-Diallyl-3-bromo-4-(2-bromo-4-(dimethylamino)benzyl)aniline (7) A solution of 3-bromo-N,N-dimethylaniline (7.54 g, 37.7 mmol) and 3-bromo-N,N-diallylaniline (9.51 g, 37.7 mmol) in glacial AcOH (250 mL) was treated with a 37 wt. percent solution of formaldehyde in H2O (30 mL). The resultant suspension was stirred at 80° C. for 2 h. After cooling to room temperature, the volatiles were removed under reduced pressure. The syrupy residue was dissolved in CH2Cl2 (100 mL), washed with sat. Na2CO3 (100 mL*2) and brine (100 mL), dried (Na2SO4), and concentrated under reduced pressure to afford a light brown syrup (16.9 g). 1H NMR analysis indicates that this mixture consists of approximately 30percent the desired product. The inseparable mixture was used in the subsequent step without further purification. 1H NMR (400 MHz, CDCl3): delta 6.91 (d, J=2.8 Hz, 2H), 6.82 (d, J=8.1 Hz, 2H), 6.55 (dd, J=2.8, 8.8 Hz, 2H), 5.78-5.87 (m, 2H), 5.14-5.20 (m, 4H), 3.98 (s, 2H), 3.85-3.87 (m, 4H), 3.15 (s, 6H).

According to the analysis of related databases, 16518-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHANG, Christopher J.; VAN DE BITTNER, Genevieve V.; HIRAYAMA, Tasuku; CHAN, Jefferson; US2014/51863; (2014); 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. 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, A new synthetic method of this compound is introduced below., SDS of cas: 16518-62-0

Into a 50 mL round-bottomed flask were added Pd(PPh3)2Cl2 (0.17 g, 5 mol percent) and 3-bromo-N,N-dimethylaniline (0.60 g, 3 mmol) under an argon atmosphere. Next, 10 mL of 5-(1,3-dioxolan-2-yl)-2-furanylzinc bromide (0.5 M in THF, 5 mmol) was added via a syringe. The resulting mixture was stirred at rt for 3.0 h. Quenched with saturated NH4Cl solution, then extracted with ethyl acetate (10 mL .x. 3). Washed with saturated Na2S2O3 solution and brine, then dried over anhydrous MgSO4. Purification by column chromatography on silica gel (20percent ethyl acetate/80percent heptane) afforded 3-(5-(1,3-dioxolan-2-yl)furan-2-yl)-N,N-dimethylaniline (1g, 0.71 g) in 92percent isolated 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:
Article; Rieke, Reuben D.; Kim, Seung-Hoi; Tetrahedron Letters; vol. 52; 10; (2011); p. 1128 – 1131;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, belongs to bromides-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 16518-62-0, SDS of cas: 16518-62-0

In a two-necked 200 mL round-bottom flask, Mg turnings (5.30 g, 216 mmol, 10.0 equiv) were flame-dried under vacuum. Upon cooling to room temperature, THF (55 mL), 3-bromo-N,N-dimethylaniline (6.50 g, 32.4 mmol, 1.50 equiv) as a solution in THF (55 mL) and a crystal of I2 were added. The flask was fitted with a reflux condenser and the solution vigorously stirred. Once the resulting exotherm had subsided, the reaction mixture was heated to reflux (70 ¡ãC) for 1h. This Grignard reagent was then allowed to cool to room temperature and added to a cooled solution of 2-bromobenzaldehyde (4.00 g, 21.6 mmol, 1.00 equiv) in THF (32 mL) at 0 ¡ãC via cannula over 10 mm. The reaction mixture was then allowed to reach room temperature and stirred for 12 h and quenched with sat. aq. NH4Cl (75 mL). The aqueous phase was then extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography on silica (1percent to 5percent EtOAc in hexanes) provided the desired (2-bromophenyl)(3-(dimethylamino)phenyl)methanol (S8) (6.36 g, 20.8 mmol, 96percent yield) a yellow viscous oil: Rf 0.4 (20percent EtOAc in hexanes); 1H NMR (500 MHz, CDC13) oe 7.59 (dd, J= 7.7, 1.6 Hz, 1 H), 7.53 (dd, J= 7.9, 1.1 Hz, 1 H), 7.33 (td, J= 7.5, 1.0 Hz, 1 H), 7.20 (t, J= 7.9, 1 H), 7.13 (td, J= 7.7, 1.6 Hz, 1 H), 6.84 (bs, 1 H),6.72 (d, J= 7.5, 1 H), 6.66 (dd, J= 8.2, 2.2 Hz, 1 H), 6.16 (s, 1 H), 2.93 (s, 6 H), 2.38 (bs, 1 H); 13C NMR (125 MHz, CDCl3) oe 150.8, 143.3, 142.9, 132.9, 129.3, 129.1, 128.7, 127.8, 123.1,115.3, 112.2, 111.4, 75.3, 40.8; IR (neat) 3392 (bs), 2917 (s), 2848 (s), 1604 (s), 1498 (s), 1437 (s), 1353 (s), 1018 (m), 996 (s), 744 (s) cm?; HRMS (ES) m/z calculated for C15H17NOBr [M+H] 306.0494, found 306.0492.

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; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; HOYE, Adam, T.; KIM, Won-suk; MARTINEZ-SOLORIO, Dionicio; SMITH, Amos, B.; SANCHEZ, Luis; TONG, Rongbiao; NGUYEN, Minh, Huu; WO2013/185021; (2013); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, belongs to bromides-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 16518-62-0, Recommanded Product: 16518-62-0

Step A: bis-(3-dimethylaminophenyl)amine Under dinitrogen atmosphere, 1 equivalent of 3-bromo-N,N-dimethylaniline (1 g), 1.5 equivalent of sodium tert-butylate (0.721 g), 0.1 equivalent of Pd(dba)2 (0.288 g), 0.12 equivalent of dppf (0.555 g) and 20 mL of toluene are introduced into a flask. The flask is fitted with a PTFE septum and 1.2 equivalent of N,N-dimethylbenzene-1,3-diamine (0.817 g) is added thereto using a syringe. The reaction medium is heated at 90¡ã C. for 12 hours, thereafter is cooled to room temperature and concentrated under reduced pressure. The product is purified by flash chromatography using a gradient of 5percent to 12percent of ethyl acetate in hexane (Rf: 0.33) to give 0.963 g of the expected product with a yield of 75percent.NMR 1H: (CDCl3) 7.13 (t, 2H), 6.5 (d, 2H), 6.49 (d, 2H), 6.38-6.36 (m, 2H), 5.68 (s large, 1H), 2.95 (s, 12H).MS (M+1): 256

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, 3-Bromo-N,N-dimethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMA HYDRO DEVELOPMENT – P.H.D.; US2010/204215; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, belongs to bromides-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 16518-62-0, Safety of 3-Bromo-N,N-dimethylaniline

To a solution of compoundN,N dimethyl-3-bromo aniline (10.0 g, 50.0 mmol) in AcOH (250 mL) was added 12.16 mL of 37% formaldehyde aqueous solution (4.5 g, 150.0 mmol), and the mixture was stirred at 60 C for 115 mm. After cooling to room temperature, a portion of acetic acid was removed by vacuum. Then, the reaction mixture was neutralized with saturated NaHCO3 aq. and NaOH aq., and extracted with CH2C12. The organic layer waswashed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (silica gel) to give pure 4,4?-methylenebis(3-bromo-N,N- dimethylaniline) (5.24 g, 12.7 mmol, 51% yield).

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, 3-Bromo-N,N-dimethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VISEN MEDICAL, INC.; GROVES, Kevin; BUFF, Ryan; WO2014/144793; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary