Category: nitriles-buliding-blocks

16532-79-9, A common heterocyclic compound, 16532-79-9, name is 4-Bromophenylacetonitrile, molecular formula is C8H6BrN, 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 2-(4-bromophenyl)acetonitrile (130.0 g, 0.7 mol) and iodomethane (103.9 mL, 1.7 mol) in THF (1.0 L) was added NaH (60% dispersion in mineral oil, 66.7 g, 1.7 mol) in small portions at 10 C. After completion of the addition, the mixture was stirred at 10 C. for another 2 hours. The mixture was poured into ice water (2.0 L) and extracted with EtOAc (1.5 L). The organic layer was washed with saturated aqueous NaCl, dried over anhydrous MgSO4 and concentrated to yield compound 1 (175 g, containing mineral oil) as a yellow oil, which was used directly without further purification. 1H NMR (CDCl3, 300 MHz) delta 7.52 (d, J=9.0 Hz, 2H), 7.38 (d, J=9.0 Hz, 2H), 1.72 (s, 6H).

The synthetic route of 16532-79-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERAVANCE, INC.; US2012/157383; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 15666-97-4 name is Octyl 2-cyanoacetate, 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. 15666-97-4

Octyl cyanoacetate (154 mg, 0.780 mmol) was added to a solution of 18 (390 mg, 0.300 mmol) and piperidine (0.1 mL) in dry CHCl3 (80 mL) and then the solution was stirred for 24 h under N2 at 60 C. Water was added and the reaction mixture was extracted with CHCl3, the combined extracts were washed three times with water and then dried (MgSO4). The solvent was evaporated under reduced pressure and the crude product further purified through column chromatography (SiO2, n-hexane/CHCl3 = 3:2) to afford a dark powder (0.434 g, 87%). 1H NMR (CDCl3, 400 MHz) delta ppm: 8.20 (s, 2H), 7.71 (s, 2H), 7.58 (s, 2H), 7.36 (d, J = 3.6 Hz, 2H), 7.21 (s, 2H), 6.92 (d, J = 3.6 Hz, 2H), 4.29 (t, J = 6.8 Hz, 4H), 2.89~2.81 (m, 12H), 1.79~1.63 (m, 14H), 1.47~1.26 (m, 60H), 0.97~0.87 (m, 30H).13C NMR (100 MHz, CDCl3) delta ppm: 163.15, 146.11, 146.03, 141.89, 141.66, 140.90, 140.67, 139.18, 137.00, 136.74, 136.45, 133.68, 133.52, 132.98, 131.04, 127.88, 125.55, 123.58, 122.14, 116.03, 97.77, 66.59, 41.49, 34.31, 32.55, 31.79, 31.63, 31.59, 30.58, 30.09, 29.57, 29.19, 29.11, 28.94, 28.58, 30.09, 29.57, 29.19, 29.11, 28.94, 28.58, 25.82, 25.73, 23.04, 22.65, 22.59, 14.17, 14.10, 14.08, 10.91. MS (MALDI-TOF): calcd. for C98H132N2O4S8 [M]+, 1656.79; found 1656.76.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Octyl 2-cyanoacetate, and friends who are interested can also refer to it.

Reference:
Article; Yin, Ni; Wang, Lilei; Lin, Yi; Yi, Jinduo; Yan, Lingpeng; Dou, Junyan; Yang, Hai-Bo; Zhao, Xin; Ma, Chang-Qi; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1788 – 1797;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 114772-53-1 as follows. 114772-53-1

To a sealed tube were successively added TBAF 3H2O (0.35 g, 1.10 mmol), 4 (0.42 g, 2.20 mmol) and TMSN3 (0.38 g, 3.30 mmol) and the resulting mixture was heated at 120 C for 36 h. The resulting reaction mixture was extracted with EtOAc (30 mL) and TBAF was removed by washing the organic phase with 1 M HCl aqueous solution (3 10 mL). The organic extract was dried (Na2SO4), filtered and concentrated in vacuo. Recrystallization from diisopropyl ether furnished pure 5 (77%) as a white solid: M.p. 145-147 C; Rf 0.57 (CHCl3:MeOH, 9:1); tR 11.54 min (30% MeCN / 100% MeCN in 30 min); ESI-MS (m/z): 237.0 [MH]; 1HNMR(400 MHz, CD3OD): d 7.69-7.64 (m, 2H), 7.56-7.52 (m, 2H), 7.13 (d, 2H, J . 7.8 Hz), 7.00 (d, 2H, J . 7.8 Hz), 2.33 (s, 3H) ppm; 13C NMR (160 MHz, CD3OD): d 155.42, 142.17, 137.43, 136.24, 131.05, 130.39, 130.17, 128.76, 127.27, 122.83, 19.72 ppm.

According to the analysis of related databases, 114772-53-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Agelis, George; Resvani, Amalia; Matsoukas, John; Durdagi, Serdar; Spyridaki, Katerina; Liapakis, George; Tumova, Tereza; Slaninova, Jirina; Giannopoulos, Panagiotis; Mavromoustakos, Thomas; Vlahakos, Demetrios; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 358 – 374,17;; ; Article; Agelis, George; Resvani, Amalia; Durdagi, Serdar; Spyridaki, Katerina; Tumova, Tereza; Slaninova, Jirina; Giannopoulos, Panagiotis; Vlahakos, Demetrios; Liapakis, George; Mavromoustakos, Thomas; Matsoukas, John; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 358 – 374;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

42872-74-2, 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. 42872-74-2, name is 3-Bromo-4-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 1800 muL (90%) Tris buffer (50 mM, pH 7.6) and 200 muL(10%) of methanol or acetone. In a 2 mL Eppendorf, NHase (10 mg) was added followed by Trisbuffer. Nitrile substrate (10 mg dissolved in 200 muL methanol or acetone) was added to the 2 mLEppendorf tube. (If an amine group was present on the nitrile substrate a Tris buffer of pH 9 wasused). The reaction mixture was incubated at 30 C on an ESCO Provocell microplateshaker/incubator (Esco Technologies, Halfway House, South Africa) (199 rpm). The reaction wasallowed to proceed for 24 h, 48 h or 5 d, depending on conversion, as monitored by TLC analysis.Ethyl acetate and water were added to the reaction mixture, and after separation, the organic layerwas concentrated under reduced pressure, and the resulting mixture was then purified by silica gelcolumn chromatography eluting with 20% to 90% ethyl acetate/ hexane.

The synthetic route of 3-Bromo-4-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mashweu, Adelaide R.; Chhiba?Govindjee, Varsha P.; Bode, Moira L.; Brady, Dean; Molecules; vol. 25; 1; (2020);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 16532-79-9, name is 4-Bromophenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 16532-79-9

Bromobenzeneacetonitrile (I) 0.97 g (5 mmol),1.73 g (6 mmol) of 4-boronic acid triphenylamine,Tetrakis (triphenylphosphine) palladium 0.11 g (0.1 mmol) was dissolved in a mixed solution of toluene 45 mL / tetrahydrofuran 35 mL,Aqueous sodium carbonate (2.0 M, 5 mL) was added.Under a nitrogen atmosphere,Heating to 90 reaction 36h.The reaction liquid was cooled,After evaporating the solvent under reduced pressure,Extraction with dichloromethane (60 mL x 3)The combined organic phase,Respectively, saturated aqueous sodium carbonate solution and saturated brine,Finally, dry over anhydrous magnesium sulfate.filter,The filtrate was concentrated under reduced pressure,The residue was separated by silica gel column chromatography,The eluent is a mixed solvent of petroleum ether / ethyl acetate in a volume ratio of 45/1,Collect the eluate containing the target compound,After the solvent was removed under reduced pressure and dried,1.62 g of the yellow powder triphenylamine intermediate (IV)The yield is 90%.

The synthetic route of 16532-79-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huzhou Normal College; Zhang Yujian; Zhang Qi; Yang Heyi; Qi Jun; Cao Feng; Zhang Cheng; (12 pag.)CN106883168; (2017); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, A new synthetic method of this compound is introduced below., 1835-65-0

SYNTHESIS EXAMPLE 6 Synthesis of 3-(2,6-dimethylphenoxy)-4,5-bis(phenylthio)-6-fluorophthalonitrile In a four-neck separable flask having an inner volume of 500 ml, 60 g (0.30 mol) of tetrafluorophthalonitrile, 41.8 g (0.72 mol) of potassium fluoride, and 160 ml of acetone were placed. Further, in a dropping funnel attached thereto, 33.0 g (0.60 mol) of thiophenol was charged. The thiophenol from the dropping funnel was added dropwise from the dropping funnel while kept stirred, with the speed of dropping adjusted so as to keep the reaction temperature of not more than 40¡ã C. and the stirring was subsequently continued for about two hours. Then, to this flask, 40.3 g (0.33 mol) of 2,6-dimethylphenol, 20.9 g (0.36 mol) of potassium fluoride, and 40 ml of acetonitrile were charged. The mixture was kept stirred under reflux for 8 hours. The reaction solution was cooled and filtered. The filtrate was washed with 600 ml of acetonitrile and filtered. The combined filtrate was distilled by a rotary evaporator to expel the acetonitrile and was recrystallized from methanol. The produced crystals were separated by filtration and vacuum dried to afford 113.8 g of 3-(2,6-dimethylphenoxy)-4,5-bis(phenylthio)-6-fluorophthalonitrile (yield: 78.6 mol percent).

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; Nippon Shobukai Co., Ltd.; US6323340; (2001); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

50712-68-0, 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. 50712-68-0, name is 4-Chloro-2-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 1 2-methyl-4-(2′,4′-dichlorophenoxy)benzonitrile A stirred solution of 4-chloro-2-methylbenzonitrile (7.8 g., 0.05 mole) and the potassium salt of 2,4-dichlorophenol (10.07 g., 0.05 mole) in 50 ml. of dimethyl acetamide was heated for 30 hours at 150 C. The cooled reaction mixture was diluted with 200 ml. of water to precipitate a brown oil. From this oil, an ether extract yielded 12.0 g. of an oil. A vacuum distillation of the oil gave 8.6 g. of 2-methyl-4-(2′,4′-dichlorophenoxy)benzonitrile with a boiling point of 163-166 C. at 0.05 mm Hg. and a melting point of 52-55 C.

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

Reference:
Patent; Mobil Oil Corporation; US4029493; (1977); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

6330-25-2,Some common heterocyclic compound, 6330-25-2, name is 2-Cyano-N-methyl-acetamide, molecular formula is C4H6N2O, 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 0.87 g t-BuOK (7.8 mmol) in 10 cm3 drymethanol, 2-cyanoacetamide 2a-2g (2.9 mmol) was added.The reaction mixture was stirred for 10-15 min, followed by cooling to 0 C and adding a solution of o-(azidomethyl)benzoate 1a-1c (2.6 mmol) in 5 cm3 drymethanol. After heating the reaction mixture back to room temperature, it was stirred under TLC monitoring for36-48 h and evaporated. Water (15 cm3) was added to the residue and it was acidified with HCl to pH 4-5. The resulting precipitate was filtered off and recrystallized from acetic acid.

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

Reference:
Article; Yakovenko, Georgiy G.; Yagodkina, Marta S.; Bol?but, Andriy V.; Shishkina, Svitlana V.; Vovk, Mykhailo V.; Monatshefte fur Chemie; vol. 148; 6; (2017); p. 1035 – 1041;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

31643-49-9,Some common heterocyclic compound, 31643-49-9, name is 4-Nitrophthalonitrile, molecular formula is C8H3N3O2, 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.

4-nitrophthalonitrile (1.00 g, 5.78 mmol) and 4-hydroxybenzaldehyde (0.71 g, 5.78 mmol) were dissolved inN,N-dimethylformamide (15 mL) and degassed with argon ina dual-bank vacuum-gas manifold system. After stirring for15 min, finely ground anhydrous potassium carbonate (2 g,14.45 mmol) was added portion-wise within 2 h period withthe efficient stirring. The progress of the reaction was monitoredby TLC using DCM / hexane (3/1) solvent system. Thestirring of the suspension was maintained at room temperaturefor further 24 h. The resulting mixture was poured into aniced-water/acetone mixture (5/1: v/v). The occured precipitatewas collected by filtration, washed several times with ethanoland dried in vacuo. The desired pure compound (1) was obtainedas a yellowish powder in sufficient purity. Yield 1.30 g,90 %. m.p. 154 C. FT-IR (PIKE MIRacleTM ATR) nu max/cm-1: 3105-3041(Ar, C-H), 2805-2764 (OC-H), 2237 (C?N),1691 (C=O), 1587-1506 (Ar, C=C), 1489-1309 (C-C), 1255(Ar-O-Ar), 1209, 1155, 1111, 1087, 950, 858, 839, 821. 1HNMR(CDCl3) delta (ppm) : 10.03 (s, 1H, OCH)), 8.01 (d, 2H,ArH), 7.81 (d, 1H, ArH), 7.41-7.34(m, 2H, ArH), 7.23 (d, 2H,ArH). 13C-NMR (CDCl3) delta (ppm): 190.7, 160.3, 159.1,135.9, 134.1, 132.6, 123.0, 122.9, 120.59, 118.2, 115.3,114.9, 110.6.

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

Reference:
Article; Sen, Pinar; Atmaca, Goeknur Ya?a; Erdo?mu?, Ali; Dege, Necmi; Genc, Hasan; Atalay, Yusuf; Yildiz, S. Zeki; Journal of Fluorescence; vol. 25; 5; (2015); p. 1225 – 1234;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

654-01-3, Name is 2-(2,6-Difluorophenyl)acetonitrile, 654-01-3, belongs to nitriles-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.

A mixture of 15.3 g (100 mmol) of 2-(2,6difluorophenyl)acetonitrile, 152.5 g (70 mL, 812 mmol) of dibromoethane, and 32.7 g (144 mmol) of Et3BnN+Cl- was isolated from moisture and carbon dioxide and vigorously stirred at 60. A solution prepared from 95 g (1430 mmol, ?84.5%) of KOH and 95 mL of water was then added dropwise; the mixture was stirred during 6 h at 60-65C, and left overnight. On the next day, the reaction mixture was extracted with t-BuOMe (3¡Á100 mL), the combined organic fractions were evaporated, and residual water was removed via azeotropic distillation with toluene. Then 60 mL of water and 40 mL of concentrated sulfuric acid were added to the obtained 1-(2,6-difluorophenyl)cyclopropanecarbonitrile, and the mixture was refluxed during 4 h. The reaction mass was cooled to ambient; the precipitate was filtered off and dried. Yield 17.82 g (90%), mp 156-157 (toluene). IR spectrum, nu, cm-1: 412 s, 772 m, 946 m, 994 m, 1048 s, 1246 m, 1270 m, 1306 m, 1324 m, 1414 m, 1468 m, 1474 m, 1504 s, 1624 m, 1666 m, 1726 s. 1 NMR spectrum (400.16 MHz, DMSO-d6), delta, ppm: 1.18 m (2H, 2eq, c-Pr), 1.58 m (2H, 2ax, c-Pr), 7.03 m (2H, 3,5H), 7.36 m (1H, C4H), 12.54 br.s (1H, OH). Mass spectrum (EI), m/z (Irel, %): 197.9 (100) [M]+, 153.0 (37) [M – COOH)]+, 133.0 (35) [M – COOH – HF]+, 127.2 (32) [2,6-F2C6H3CH2]+. Found, %: C 60.50; H 4.08. C10H8F2O2. Calculated, %: C 60.61; H 4.07.

Statistics shows that 2-(2,6-Difluorophenyl)acetonitrile is playing an increasingly important role. we look forward to future research findings about 654-01-3.

Reference:
Article; Novakov; Yablokov; Navrotskii; Mkrtchyan; Vernigora; Babushkin; Kachala; Ruchko; Russian Journal of General Chemistry; vol. 87; 2; (2017); p. 224 – 230; Zh. Obshch. Khim.; vol. 87; 2; (2017); p. 247 – 254,8;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts