Category: 139152-08-2

Synthetic Route of 139152-08-2, A common heterocyclic compound, 139152-08-2, name is 4,5-Dichlorophthalonitrile, molecular formula is C8H2Cl2N2, 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 mixture of 9-phenanthrol (1) (0.97 g, 5 mmol) and4,5-dichlorophthalonitrile (2) (0.985 g, 5 mmol) in 50 mLof DMSO at 25 C was added lithium hydroxide monohydrate(0.21 g, 5 mmol) within 0.5 h. The mixture was stirred for 24 h at same temperature and then it was pouredinto 100 mL of water. Then extracted with chloroform(2 × 100 mL), washed with water (1 × 100 mL), brine(1×100 mL) and dried over Na2SO4. The solvent wasremoved under reduced pressure. The resulting residuewas purified by silica-gel column chromatography usingethyl acetate:hexane (1:9) as an eluent to obtain a lightyellow solid, yield (1.45 g, 82%). 1H NMR (600 MHz,CDCl3: delta 8.79 (d, J = 82 Hz, 1H), 8.73 (d, J = 82 Hz,1H), 7.95 (s, 1H), 7.91-7.84 (m, 2H), 7.81-7.62 (m, 4H),7.44 (s, 1H), 7.06 (s , 1H) ppm; 13C NMR (150 MHz,CDCl3: delta 157.10, 146.53, 134.58, 131.30, 130.13, 128.32,128.10, 127.47, 127.24, 126.65, 126.56, 126.27, 124.28,122.46, 121.90, 120.65, 119.66, 115.24, 114.65, 113.25,108.98, 28.67 ppm; IR (KBr tablet) max/cm-1: 3104,3040, 2900, 2233, 1628, 1584, 1510, 1303, 1198, 1128;ESI-MS: 354 [M]+.

The synthetic route of 139152-08-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kim, Changkyeom; Kumar, Rangaraju Satish; Mergu, Naveen; Jun, Kun; Son, Young-A; Journal of Nanoscience and Nanotechnology; vol. 18; 5; (2018); p. 3192 – 3205;,
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These common heterocyclic compound, 139152-08-2, name is 4,5-Dichlorophthalonitrile, 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. Recommanded Product: 4,5-Dichlorophthalonitrile

0.30 g(1.5 mmol) of 4,5-dichlorophthalonitrile and 0.28 g(3.0 mmol) of phenol preliminarily crystallized fromhexane were dissolved in 15 mL of DMF and asolution of 0.42 g (3 mmol) of potassium carbonate in1 mL water was added. The reaction mixture wasstirred at 80-90 for 12 h, then the target product wasfiltered off, washed with hot water till the smell ofphenol ceased, and dried at 80-90. Yield 0.26 g(82%). Found, %: C 76.38; H 3.98; N 8.72. C20H12N22.Calculated, %: C 76.91; H 3.87; N 8.97.

The synthetic route of 4,5-Dichlorophthalonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Znoiko; Petlina; Shaposhnikov; Smirnov; Russian Journal of General Chemistry; vol. 88; 6; (2018); p. 1148 – 1153; Zh. Obshch. Khim.; vol. 88; 6; (2018); p. 968 – 973,6;,
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Application of 139152-08-2, The chemical industry reduces the impact on the environment during synthesis 139152-08-2, name is 4,5-Dichlorophthalonitrile, I believe this compound will play a more active role in future production and life.

Compound 1 (2 g, 4.04 mmol), 4,5-dichloro-1,2-dicyanobenzene(1.6 g, 8.16 mmol) and 20 mL dry DMF were stirred under nitrogenatmosphere for 15 min at 25 C and dry K2CO3 (1.41 g, 10.1 mmol)was added portion-wise for 2 h. The reaction mixture was stirredunder nitrogen atmosphere at 70 C for about 3 days. Then, it wasemptied into ice-water and filtrated. The light brown product wasrecrystallized from ethanol. The raw product was refined by columnchromatography with silica gel, using chloroform/ethanol(98:2). Yield: 1.35 g (54%). m.p.:181-190 C. Anal. calcd. forC36H30O6SN2: C, 69.89; H, 4.89; N, 4.53%. Found: C, 69.93; H, 4.83;N, 4.82%. IR, nmax/cm1 : 3097 (Ar-H), 2920-2869 (Aliph., C-H), 2234(C^N), 1274 (Ar-O-C), 1129-1017 (-OCH2), 826.1H NMR (CDCl3),(delta:ppm): 7.72 (m, 4H, ArH), 7.46 (ddd, 4H, ArH), 7.15 (d, 2H, ArH),7.01 (d, 2H, ArH), 6.84 (d, 2H, ArH), 3.98 (d, 4H, O-CH2), 3.52 (m, 4H,O-CH2), 3.27 (d, 4H, O-CH2), 3.05 (m, 4H, O-CH2). 13C NMR(CDCl3), (delta:ppm): 155.89, 135.43, 129.48, 128.05, 125.92, 124.49,120.59, 118.85, 115.32(C^N), 112.55, 108.61, 72.28, 68.71, 61.32.MS(FAB) (m/z): 615 [M 3].

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, 4,5-Dichlorophthalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Arucu, Sevinc; Sa?lam, Meltem Betuel; Oezkaya, Ali R?za; Journal of Molecular Structure; vol. 1198; (2019);,
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Synthetic Route of 139152-08-2, 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 139152-08-2 as follows.

The mixture of 1-(2-hydroxyethyl)-4-(4-methoxybenzylamino)-3-p-tolyl-1H-1,2,4-triazol-5(4H)-one (1)(1.00 g, 2.82 mmol) and 4,5-dichlorophthalonitrile (2) (0.28 g, 1.41 mmol) were dissolved in dry DMF(15 mL) under a nitrogen atmosphere and this mixture was stirred at 50 C for 10 min. After stirring,finely ground anhydrous K2CO3 (0.58 g, 4.23 mmol) was added portionwise over a period of 2 h and thereaction mixture was stirred under nitrogen at this temperature for 5 days. At the end of this time, themixture was poured into ice water (100 mL) and stirred for 30 min. The reaction mixture was extractedwith chloroform (50 mL × 3) and the organic layer was dried over anhydrous magnesium sulfate andthen solvent was removed under reduced pressure. The oily green product was dried in vacuo (P2O5).Yield: 1.00 g (85%). Calcd for C46H44N10O6: % C 66.33, % H 5.32, % N 16.82. Found: % C 66.28, % H 5.30, %N 16.85. FT-IR numax cm-1 (NaCl disk): 3259 (N-H), 3033 (Ar-H), 2935-2837 (Aliph. C-H), 2233 (C?N), and1699 (C=O), 1613, 1513, 1422, 1250, 1176, 1035, 822 and 739. 1H NMR (CDCl3) (delta: ppm): 7.79 (ArH, 4H,d), 7.28 (ArH, 4H, d), 7.18 (ArH, 4H, d), 6.79 (ArH, 4H, d), 6.75 (ArH, 2H, d), 4.93 (NH, 2H, s), 4.43 (O-CH2,4H, t), 4.11 (CH2, 8H, m), 3.78 (O-CH3, 6H, s), 2.42 (CH3, 6H, s). 13C NMR (CDCl3) (delta: ppm): 159.63, 158.24,153.75, 153.41, 144.95, 140.95, 140.80, 135.15, 130.90, 129.32, 127.46, 123.41, 117.09, 115.84, 114.08,107.89, 67.12, 61.57, 55.49, 54.48, 49.39, 44.48, and 21.77. MS (ES+), m/z: Calcd: 832.92; Found: 832.37 [M]+.

According to the analysis of related databases, 139152-08-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nas, Asiye; Journal of Coordination Chemistry; vol. 69; 8; (2016); p. 1326 – 1336;,
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Related Products of 139152-08-2, 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. 139152-08-2 name is 4,5-Dichlorophthalonitrile, 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.

4,5-Dichlorophthalonitrile (1g, 5.07 mmol) and 1,3-diazido-2-propanol (721 mg, 5.07 mmol) were dissolved in 50 mL anhydrous DMF. After stirring, anhydrous K2CO3 (1.05 g, 7.61 mmol) was added dropwise to solution over 30 minutes with continued stirring. Then the reaction mixture was stirred at 70 C for 72 h under argon atmosphere. After this time, the reaction mixture was cooled to room temperature and poured into ice-water. The formed crude product was filtered, washed with water and dried with vacuo. Then the product was purified by column chromatography on silicagel using hexane-ethyl acetate (60:40) solvent system as eluent (Rf = 0.40). Yield: 1.2 g (78%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4,5-Dichlorophthalonitrile, and friends who are interested can also refer to it.

Reference:
Article; Sari, Sait; Durmu?, Mahmut; Bulut, Mustafa; Tetrahedron Letters; vol. 57; 10; (2016); p. 1124 – 1128;,
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These common heterocyclic compound, 139152-08-2, name is 4,5-Dichlorophthalonitrile, 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. Quality Control of 4,5-Dichlorophthalonitrile

Compound 2 (1.5 g, 6.1 mmol) was dissolved in 40 mL anhydrous DMF. Anhydrous CsF (1.9 g, 12.2 mmol) was then added to the solution and the mixture was allowed to stir for 10 min at room temperature. A solution of 4,5-dichlorophthalonitrile (1.0 g, 5.1 mmol) in 10 mL anhydrous DMF was then added and the reaction mixture was stirred for 24 hrs at room temperature. After completion, the salt was filtered out using Buchner funnel and the crude mixture was diluted in 100 mL water and extracted with DCM (2¡Á50 mL). DCM was then concentrated under reduced pressure and the crude material was purified by column chromatography using (2:8) EtOAc/hexane solvent system as an eluent to obtain the desired product 5 as a white solid in 1.7 g (85% yield); mp is 106.2 C. Elemental analysis calculated (%) for C23H17ClN2O3: C, 68.23; H, 4.23; N, 6.92. Found: C, 68.03; H, 4.22; N, 6.78; FT-IR, numax/cm-1 3297.68, 2883.06, 2611.14, 2232.20; 1H-NMR (600 MHz, DMSO-d6, 25 0C): delta=2.38 (s, 3H), 3.33 (t, J=2.3 Hz, 2H), 4.02 (t, J=2.3 Hz, 4H), 4.32 (dd, J=10.9, 35.0 Hz, 4H), 7.09 (s, 1H), 7.35 (s, 2H), 8.47 (s, 1H); 13C-NMR (150 MHz, DMSO-d6, 25 0C): delta=20.5, 57.7, 77.2, 79.5, 108.5, 114.8, 114.9, 115.0, 119.9, 126.8, 130.0, 131.4, 135.6, 136.4, 146.6, 157.6; HRMS [M]+ calcd for C23H7ClN2O3: 404.0928, found: 404.0922.

The synthetic route of 4,5-Dichlorophthalonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KUWAIT UNIVERSITY; MAKHSEED, SAAD A.; HUSAIN, ALI A.; GANESAN, ASAITHAMPI; DURMUS, MAHMUT; US2020/102267; (2020); A1;,
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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. 139152-08-2 name is 4,5-Dichlorophthalonitrile, 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. 139152-08-2

4,5-Dichlorophthalonitrile (1.0g, 5.3mmol) and 13 5-hydroxy-2-methylpyridine (1.4g, 12.4mmol) were dissolved in 15mL of dry 14 N,N-dimethylformamide at 80C under N2. 15 Potassium carbonate (4.5g, 32.6mmol) was added to the reaction solution in 5 portions every 5min. The reaction mixture was heated for 3h at 80C, then cooled to room temperature, and poured into 100mL of 16 ice-water. The title compound was extracted for the reaction liquid using 50mL of 17 CHCl3 at 3 times. After filtration under vacuum, the 18 title compound was obtained as a white powder. Yield, 1.8g (97% (based on 4,5-Dichlorophthalonitrile)). Anal. Calc. for C20H14N4O2: C; 70.17, H; 4.12, N; 16.37. Found: C; 69.93, H; 4.21, N; 16.08%. HR-MS (ESI-TOF): Found 343.1190m/z. [M+H]+ (calcd. for C20H14N4O2 343.1191). 1H NMR (CD2Cl2): delta=8.31 (s, 2H, Ar-H), 7.34 (d, 2H, J=8.4Hz, Ar-H), 7.26 (d, 2H, J=8.4Hz, Ar-H), 7.23 (s, 2H, Ar-H), and 2.57ppm (s, 6H, CH3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4,5-Dichlorophthalonitrile, and friends who are interested can also refer to it.

Reference:
Article; Fujishiro, Rei; Sonoyama, Hayato; Ide, Yuki; Fujimura, Takuya; Sasai, Ryo; Nagai, Atsushi; Mori, Shigeki; Kaufman, Nichole E.M.; Zhou, Zehua; Vicente, M. Graca H.; Ikeue, Takahisa; Journal of Inorganic Biochemistry; vol. 192; (2019); p. 7 – 16;,
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139152-08-2, name is 4,5-Dichlorophthalonitrile, 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. 139152-08-2

4,5-Dichlorophthalonitrile 1 (1.00 g, 5.08 mmol) and 7-hydroxy-4-(4-methoxyphenyl)-8-methylcoumarin 2 (5.73 g, 20.32 mmol) were dissolved in anhydrous dimethylformamide (DMF) (30 mL) under N2 atmosphere. After stirring for 10 min, finely ground anhydrous K2CO3 (3.50 g, 25.37 mmol) was added by stirring. The reaction mixture was stirred at 50 C for 10 days under N2 atmosphere. Then the mixture was poured in 250 ml cold aqueous solution of 5% HCl. The formed precipitate was filtered off and washed with water. After drying in vacuum at 50 C, the crude product was purified by column chromatography with silica gel eluting with DCM. Firstly, compound 3 and then compound 4 were obtained purely by using DCM and chloroform as eluting solvents, respectively.

Statistics shows that 139152-08-2 is playing an increasingly important role. we look forward to future research findings about 4,5-Dichlorophthalonitrile.

Reference:
Article; Altun, Selcuk; Oezkaya, Ali Riza; Bulut, Mustafa; Polyhedron; vol. 48; 1; (2012); p. 31 – 42;,
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A common compound: 139152-08-2, name is 4,5-Dichlorophthalonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 139152-08-2

Amixture of 1.0 g (5.1 mmol) of 4,5-dichlorophthalonitrile,1.9 g (10.2 mmol) of 3-phenoxyphenol 2, 4.0 g(29 mmol) of K2CO3, and 30 mL of DMF was stirredfor 5 h at 110, cooled, diluted with 200 mL of water,the separated precipitate was filtered off, washed with40 mL of 2% solution of KOH, then with water till 7,and dried. Yield 2.2 g (88%), wax-like light brownsubstance, soluble in benzene, chloroform, acetone,DMF. 1 NMR spectrum, delta, ppm: 7.43-7.34 m (8),7.27 s (2), 7.21-7.04 m (10), 6.95-6.93 m (2),6.81-6.79 m (2), 6.74 s (2), 6.59-6.53 m (4). Massspectrum, m/z: 496.26 [M]+, 543.38 [M + + 2Na]+,574.45 [M + 2K]+. Found, %: C 77.57; H 4.10; N 5.36.C32H20N2O4. Calculated, %: C 77.41; H 4.06; N 5.64.M 496.14.

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, 139152-08-2, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Koptyaev; Ageeva; Galanin; Shaposhnikov; Russian Journal of Organic Chemistry; vol. 52; 2; (2016); p. 261 – 267; Zh. Org. Khim.; vol. 52; 2; (2016); p. 278 – 283,5;,
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