Category: 5414-21-1

Reference of 5414-21-1, These common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, 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.

CH3Se3CH3 (100 mg, 0.53 mmol, Aldrich) was added to a solution of NaBH4 (60 mg, 1.59 mmol) in 5 ml of absolute EtOH under N2. After 5 min of vigorous reaction the colour of the solution changed from yellow to white. 5-Bromopentanenitrile (0.17 g, 1.06 mmol, Acros) was then added and stirred for 2.5 h. Et2O (10 ml) was added, the reaction mixture was washed with 5 ml each of water and brine, extracted with 2 x 25 ml of Et2O, and dried (MgSO4). The solvent was removed to give 10b as a yellow oil (107 mg, 57% yield). EI-ToF-MS (Fig. 2), m/z (rel. int.): 177 [M]+ (1200), 175 (28), 173 (15), 135 (10), 109 [CH3SeCH2]+ (33), 107 (17), 96 [CH3SeH]+ (27), 94 [CH2Se]+ (21), 93 [CHSe]+ (25), 82 (22), 55 (4). 1H NMR (500 MHz, CDCl3): delta1.75-1.88 (m, 4H, CH2CH2), 2.00 (s, 3H, CH3Se), 2.38 (t, 2H, J = 6.8 Hz, CH2CN), 2.57 (t, 2H, J = 6.9 Hz, CH2Se).

The synthetic route of 5414-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Matich, Adam J.; McKenzie, Marian J.; Lill, Ross E.; Brummell, David A.; McGhie, Tony K.; Chen, Ronan K.-Y.; Rowan, Daryl D.; Phytochemistry; vol. 75; (2012); p. 140 – 152;,
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Reference of 5414-21-1, 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. 5414-21-1, name is 5-Bromovaleronitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of m-tolylmagnesium bromide 26, prepared from 416 muL of 3-bromotoluene and 83 mg of magnesium turnings in anhydrous THF (3 mL), was added dropwise under inert atmosphere to a solution of 5-bromovaleronitrile (400 muL, 3.43 mmol) in anhydrous THF (3 mL). The mixture was stirred at room temperature for 1 h, quenched with a saturated aqueous solution of NaHCO3 (3 mL) and extracted with dichloromethane (3 * 10 mL). The combined organic layers were dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (dichloromethane/methanol 95:5) to provide the compound 7 as a yellow oil (225 mg, 38% yield). Rf = 0.40 (dichloromethane/methanol 95:5). 1H NMR: delta 1.63-1.71 (m, 2H), 1.79-1.87 (m, 2H), 2.37 (s, 3H), 2.60-2.66 (m, 2H), 3.80-3.86 (m, 2H), 7.18-7.29 (m, 2H), 7.51-7.54 (m, 1H), 7.61-7.62 (m, 1H). 13C NMR: delta 20.0, 21.7, 22.1, 27.4, 50.1, 123.3, 126.8, 128.3, 130.5, 138.1, 140.4, 166.2. MS (ESI) m/z [M+H]+ Calcd for C12H16N+: 174.13. Found: 174.2.

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

Reference:
Article; Matera, Carlo; Quadri, Marta; Sciaccaluga, Miriam; Pome, Diego Yuri; Fasoli, Francesca; De Amici, Marco; Fucile, Sergio; Gotti, Cecilia; Dallanoce, Clelia; Grazioso, Giovanni; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 392 – 405;,
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Adding a certain compound to certain chemical reactions, such as: 5414-21-1, name is 5-Bromovaleronitrile, belongs to nitriles-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 5414-21-1, name: 5-Bromovaleronitrile

EXAMPLE 1 5-{4-[2-(4-Pyridinyl)-ethenyl]-phenoxy}-valeronitrile To the solution of 1.16 g (50 mmol) sodium in 250 ml 2-propanol one adds 10.0 g (50 mmol) 4-[2-(4-pyridinyl)-ethenyl]-phenol, heats under reflux for 10 min, allows to cool, adds thereto 8.1 g (50 mmol) 5-bromovaleronitrile and heats to reflux for 16 h. One evaporates, mixes with water, extracts with dichloromethane, dries the extract, evaporates and triturates the residue with ether. One obtains 11.9 g of title compound (86% of theory) of the m.p. 85-87 C.

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, 5-Bromovaleronitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Mannheim GmbH; US5399575; (1995); A;,
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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. 5414-21-1, name is 5-Bromovaleronitrile, A new synthetic method of this compound is introduced below., SDS of cas: 5414-21-1

General procedure: A stainless steel autoclave was charged with glycerol (1 mmol), base B (6 mmol), and NMP (1mL), flushed three times with CO2, and finally charged with CO2 to 0.7 MPa at room temperature.The obtained mixture was magnetically stirred at 25 C for 1 h, and an alkyl halide (10 mmol) wasadded at room temperature after CO2 evacuation, followed by repeated CO2 flushing/charging to 0.7MPa. The reaction mixture was magnetically stirred at 25 C for 18 h under 0.7 MPa pressure ofCO2. After EtOAc was added to the resulting mixture to precipitate the dissolved salt, the salt wasremoved using a Buchner funnel and washed with EtOAc. The combined filtrate was concentrated in vacuo, and the obtained product ratios were determined by 1H NMR measurements. The crudeproduct was purified by silica gel column chromatography, affording linear tricarbonates 1.Compounds 1g, 1h, and 1k were further purified by gel permeation liquid chromatography.

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; Mihara, Masatoshi; Moroga, Kaname; Iwasawa, Tetsuo; Nakai, Takeo; Ito, Takatoshi; Ohno, Toshinobu; Mizuno, Takumi; Synlett; vol. 29; 13; (2018); p. 1759 – 1764;,
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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. 5414-21-1, name is 5-Bromovaleronitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 5-Bromovaleronitrile

In a four-neck reactor equipped with a thermometer, 5.00 g (30.3 mmol) of 2-hydrazinobenzothiazole was placed in a nitrogen stream, and dissolved in DMF 100 mL.To this solution was added 20.9 g (152 mmol) of potassium carbonate,5-bromovaleronitrile 5.17 g (30.3 mmol),Stir at 60 C for 8 hours.After the reaction was completed, the reaction liquid was cooled to 20 C, and the reaction liquid was poured into water of 500 mL.It was extracted with 500 mL of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate.After sodium sulfate was filtered, ethyl acetate was distilled off under reduced pressure using a rotary evaporator to obtain a yellow solid. The yellow solid was recrystallized by hexane column chromatography (hexane: ethyl acetate = 60: 40) to yield 3.41 g of Intermediate J (yield: 45.7 mol%) as a white solid.

The synthetic route of 5414-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZEON CORPORATION; SAKAMOTO, KEI; OKUYAMA, KUMI; (157 pag.)TW2018/35058; (2018); A;,
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Electric Literature of 5414-21-1, These common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, 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.

CH3Se3CH3 (100 mg, 0.53 mmol, Aldrich) was added to a solution of NaBH4 (60 mg, 1.59 mmol) in 5 ml of absolute EtOH under N2. After 5 min of vigorous reaction the colour of the solution changed from yellow to white. 5-Bromopentanenitrile (0.17 g, 1.06 mmol, Acros) was then added and stirred for 2.5 h. Et2O (10 ml) was added, the reaction mixture was washed with 5 ml each of water and brine, extracted with 2 x 25 ml of Et2O, and dried (MgSO4). The solvent was removed to give 10b as a yellow oil (107 mg, 57% yield). EI-ToF-MS (Fig. 2), m/z (rel. int.): 177 [M]+ (1200), 175 (28), 173 (15), 135 (10), 109 [CH3SeCH2]+ (33), 107 (17), 96 [CH3SeH]+ (27), 94 [CH2Se]+ (21), 93 [CHSe]+ (25), 82 (22), 55 (4). 1H NMR (500 MHz, CDCl3): delta1.75-1.88 (m, 4H, CH2CH2), 2.00 (s, 3H, CH3Se), 2.38 (t, 2H, J = 6.8 Hz, CH2CN), 2.57 (t, 2H, J = 6.9 Hz, CH2Se).

The synthetic route of 5414-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Matich, Adam J.; McKenzie, Marian J.; Lill, Ross E.; Brummell, David A.; McGhie, Tony K.; Chen, Ronan K.-Y.; Rowan, Daryl D.; Phytochemistry; vol. 75; (2012); p. 140 – 152;,
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Electric Literature of 5414-21-1,Some common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, molecular formula is C5H8BrN, 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-hydroxy-7-((2-methyl-[l,r-biphenyl]-3-yl)methoxy)-2,3- cli hydro- 1 /7-indene-4-carbaldehyde (0.50 g, 1.39 mmol) in DMF (10 mL), potassium carbonate (0.288 g, 2.08 mmol) and 5-bromopentanenitrile (0.25 g, 1.53 mmol) were added and stirred the mixture at room temperature for 5 h. After completion, the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (3 x 30 mL). The combined organic layer was dried over sodium sulfate and concentrated. The resulting crude was purified by flash chromatography (silica gel, 12 g cartridge) using 20% EtOAc in hexanes as eluent to obtain 5-((4-formyl-7-((2-methyl-[l,l’-biphenyl]-3-yl)methoxy)- 2,3-dihydro- lH-inden-5-yl)oxy)pentanenitrile (Yield: 0.425 g, 69%) as white solid. LCMS (ES) m/z = 440.51 [M+H]+; NMR (400 MHz, DMSO-d6) d ppm: 1.74-1.80 (m, 2H), 1.86-1.90 (m, 2H), 1.97-2.01 (m, 2H), 2.21 (s, 3H), 2.59 (m, 2H), 2.69 (m, 2H), 3.11 (m, 2H), 4.20 (m, 2H), 5.31 (s, 2H), 6.79 (s, 1H), 7.22 (d, 7 = 7.6 Hz, 1H), 7.28-7.40 (m, 4H), 7.44-7.48 (m, 3H), 10.34 (s, 1H).

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

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; D A, Jeyaraj; PENDYALA, Muralidhar; SIVANANDHAN, Dhanalakshmi; RAJAGOPAL, Sridharan; (233 pag.)WO2019/175897; (2019); A1;,
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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. 5414-21-1, name is 5-Bromovaleronitrile, A new synthetic method of this compound is introduced below., Formula: C5H8BrN

Sodium hydride paste (6.16 g. of 61% w/w suspension in liquid paraffin) was added portionwise over 30 minutes to a solution of 3-nitropyrazole (17.4 g.) in dry DMF (150 ml.) with external ice cooling to maintain the temperature at 20-30. The mixture was stirred for 45 minutes and to the almost clear solution was added 5-bromovaleronitrile (25 g.) over 30 minutes, at 25-30, and the mixture was stirred for 4 hours. Water (450 ml.) and EtOAc (450 ml.) was added and the upper layer was separated, dried (MgSO4) and evaporated in vacuo to an oil which was a mixture of 5-(3-nitropyrazol-1-yl)valeronitrile and 5-(5-nitropyrazol-1-yl)valeronitrile. The oil was divided into two 15 g. portions which were fractionated on a silica column (3.5 cm diameter*100 cm long) eluted at 2 atmospheres by EtOAc/60-80 petroluem ether (3:7 v/v). The 1.5 isomer was eluted first followed by the 1:3 isomer. The 5-(3-nitropyrazol-1-yl)valeronitrile had m.p. 32-33. To a solution of 5-(3-nitropyrazol-1-yl)valeronitrile (9.16 g.) in dry tetrahydrofuran (200 ml.) was added 5% w/w palladium on carbon (1.8 g.). The mixture was stirred at 20 under an atmosphere of hydrogen. 3.2 Liters of hydrogen were absorbed over 4 hours. The catalyst was filtered off and the filtrate was evaporated in vacuo to give 5-(3-aminopyrazol-1-yl)valeronitrile as an oil.

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; Imperial Chemical Industries PLC; US4447441; (1984); A;,
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Application of 5414-21-1, The chemical industry reduces the impact on the environment during synthesis 5414-21-1, name is 5-Bromovaleronitrile, I believe this compound will play a more active role in future production and life.

General procedure: To synthesize compound 1, 2-(1H-indol-3-yl)acetic acid (3.5 g, 20 mmol) was added to a stirred suspension of NaH (4 g, 100 mmol, mixture of 60% NaH in mineral oil) in THF (80 mL) at 0C. The resulting mixture was stirred for 30 min followed by dropwise addition of ethyl iodide (5 mL, 60 mmol) in THF (30 mL), allowed to warm to room temperature (RT), and stirred overnight. The reaction mixture was then cooled to 0 C and quenched by addition of 10 mL MeOH and 20 mL H2O followed by extraction with Et2O (2 × 100 mL). The aqueous layer was acidified by addition of 6N hydrochloric acid (30 mL) and extracted with ethyl acetate (EtOAc, 2 × 100 mL). The combined organic extracts were washed with H2O (2 × 100 mL) and brine (2 × 100 mL), dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by flash chromatography (1:3 EtOAc petroleum ether, v/v) to yield 2-(1-ethyl-1H-indol-3-yl)acetic acid (1) as a colorless solid (3.87 g, 95% 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, 5-Bromovaleronitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Xia; Ma, Hongguang; Li, Lin; Chen, Yifan; Sun, Xiao; Dong, Zizheng; Liu, Jing-Yuan; Zhu, Weiming; Zhang, Jian-Ting; Oncogene; vol. 37; 18; (2018); p. 2469 – 2480;,
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Related Products of 5414-21-1, A common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, molecular formula is C5H8BrN, 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.

General procedure: To a solution of the tetrabutylammonium salt of 10-methylthio-7,8-dicarba-nido-caborane [1] (0.40 g, 0.95 mmol) in ethanol (10ml) chloroacetonitrile (0.06 ml, 0.95 mmol) was added. After stirring for 15 min, r.t., the mixture was heated under reflux for about 15 h and the solvent was evaporated under reduced pressure. The column chromatography on silica gel was used for the purification of the substance with CH2Cl2 as an eluent. Finally the solvent was removed in a vacuum to yield white solid (0.14 g, 68% yield).

The synthetic route of 5414-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Erokhina, Svetlana A.; Stogniy, Marina Yu.; Suponitsky, Kyrill Yu.; Kosenko, Irina D.; Sivaev, Igor B.; Bregadze, Vladimir I.; Polyhedron; vol. 153; (2018); p. 145 – 151;,
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