Tag: M.W=100-200

Reference of 453565-55-4,Some common heterocyclic compound, 453565-55-4, name is 5-Fluoroisophthalonitrile, molecular formula is C8H3FN2, 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: A mixture of aryl fluoride (51 a-d) (2.0 mmol), 5-chloro-2-methoxyphenol a (50 a) (0.32 g, 2.0 mmol) or 4-chloro-2-methoxyphenol (50 b) (0.32 g, 2.0 mmol) in DMSO (3.0 mL) and anhydrous K2C03 (0.41 g, 3.0 mmol) was heated at 120 C for 5 h. The mixture was poured into ice water and extracted with EtOAc (3 x 50 mL). The organic layer was sequentially washed with brine (2 x 75 mL), dried over anhydrous Na2S04, and concentrated in vacuo. The residue was purified by column chromatography to give 52 a-e and 36. 5-(5-chloro-2-methoxyphenoxy)isophthalonitrile (52 a): (0.28g, 50%) *H NMR (500 MHz, CDC13) 8 7.59 (d, J= 1.28 Hz, 1H), 7.32 (d, J= 1.32 Hz, 2H), 7.30 – 7.25 (m, 1H), 7.12 (d, J= 2.37 Hz, 1H), 6.99 (d, J= 8.84 Hz, 1H), 3.77 (s, 3H). 13C NMR (126 MHz, CDC13) delta 158.66, 150.14, 128.69, 127.30, 126.07, 123.27, 122.98, 118.60, 118.53, 116.32, 115.01, 113.97, 56.10.

The synthetic route of 453565-55-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YALE UNIVERSITY; WO2013/56003; (2013); A2;,
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Application of 5922-60-1, 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 5922-60-1 as follows.

Example 4 – synthesis of 4-amino-6-chloro-quinazoline; A solution of 2-amino-5-chlorobenzonitrile (1.07 g, 7.0 mmol) in formamide (20 ml) was heated at 180 0C for 6 hours. After cooling to room temperature, water (30 ml) was added to the reaction mixture. The precipitate was collected by filtration, washed with water and dried over P2O5, yielding the title compound as a grey solid (1.2 g, yield: 95 percent) which was characterized by its mass spectrum as follows: MS (m/z): 180 ([M+H]+, 100).

According to the analysis of related databases, 5922-60-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; WO2008/9078; (2008); A2;,
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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. 2973-50-4, name is 2-(2-Aminophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 2973-50-4

EXAMPLE 4 2,2,3,3,4,4,4-Heptafluoro-N-[2-(1H-tetrazol-5-ylmethyl)phenyl]butanamide A mixture of 2-aminobenzylcyanide (15 g) [Rousseau et al., JACS 72, 3047 (1950)], diisopropylethylamine (16 g) and dichloromethane (400 mL) was cooled in an ice bath under a nitrogen atmosphere. Heptafluorobutyryl chloride (28.9 g) in dichloromethane (100 mL) was added dropwise and the reaction was left to warm gradually to room temperature overnight. A 10% aqueous HCl solution was added and the organic phase was separated and dried over MgSO4. After filtration and concentration with a rotary evaporator, the crude, orange oil (42 g) was purified by high pressure liquid chromatography to give 35.4 g of 2,2,3,3,4,4,4-heptafluoro-N-[2-(cyanomethyl)phenyl]butanamide as a white solid, m.p. 76-79 C.

According to the analysis of related databases, 2973-50-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Home Products Corporation; US4764623; (1988); 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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H3ClFN

Preparation 12-Chloro-4-fluoro-3-methyl-benzonitrileTo a solution of diisopropylamine (474 mL, 3.35 mol) in anhydrous THF (5.8 L) at-5 C under a nitrogen atmosphere is added dropwise 2.5 M n-butyllithium in hexanes (1.24 L, 3.10 mol) over 3 h and the resulting mixture is stirred at -5 C for one additional hour. The LDA solution is added dropwise to a solution of 2-chloro-4-fluoro-benzonitrile (400 g, 2.58 mol) in anhydrous THF (5.8 L) at -70 C over 6 h and then stirred at -70 C overnight. lodomethane (643 mL, 10.32 mol) is added dropwise over 2.5 h and the temperature is raised to -5 C for 17 h. Saturated aqueous ammonium chloride (3 L) is added. The solution is diluted with water (3.5 L) and extracted with diethyl ether (2 x 2 L). The organic phases are separated, combined, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a black solid. The solid is purified through a silica gel pad eluting withEtOAc/hexanes (1/40) to obtain the title compound (323 g, 74%). 1H NMR (300 MHz, CDCls) delta 7.08 (dd, J= 8.6, 8.6 Hz, 1H), 7.54 (dd, J= 8.6, 5.6 Hz, 1H), 2.36 (d, J= 2.4 Hz, 3H).

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; ELI LILLY AND COMPANY; JADHAV, Prabhakar Kondaji; SAEED, Ashraf; GREEN, Jonathan Edward; KRISHNAN, Venkatesh; MATTHEWS, Donald Paul; STEPHENSON, Gregory Alan; WO2013/55577; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 868-54-2, name is 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, 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 868-54-2, name: 2-Aminoprop-1-ene-1,1,3-tricarbonitrile

General procedure: In a 20 mL reaction vial, 4-hydroxycarbazole 1{1} (0.183g, 1mmol) with benzaldehyde 2{1} (0.106g, 1mmol), and 2-aminoprop-1-ene-1,1,3-tricarbonitrile 3 (0.132g, 1mmol) and ethanol (3 mL), as well as EtONa (0.064g, 1mmol)were mixed and then capped (the automatic mode stirring helped the mixing and uniform heating of the reactants). The mixture was heated for 15 min at 80 C under microwave irradiation. Upon completion, confirmed by TLC, the reaction mixture was cooled to room temperature. The crystalline solid product was collected by Buchner filtration, subsequently washed with two different solvents of ethanol and ethylether in sequence to give the pure product 4{1,1}.

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:
Article; Zhang, Wenhui; Wang, Jianqiang; Mao, Jingpeng; Hu, Li; Wu, Xiaohua; Guo, Cheng; Tetrahedron Letters; vol. 57; 18; (2016); p. 1985 – 1989;,
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Electric Literature of 1885-38-7, The chemical industry reduces the impact on the environment during synthesis 1885-38-7, name is (E)-Cinnamonitrile, I believe this compound will play a more active role in future production and life.

General procedure: Under a nitrogen atmosphere, a mixture of [RhCl(C2H4)2]2 (1.8 mg,0.0045 mmol) and ligand L1f (3.7 mg, 0.0099 mmol) in toluene(1 mL) was stirred at r.t. for 15 min, at which time arylboronic acid(0.60 mmol) was added, followed by cyanoalkenes (0.30 mmol),aqueous KOH (0.75 M in H2O, 0.20 mL, 0.15 mmol) and toluene(1 mL). The reaction was stirred at 80 C for 12 h, after which thereaction mixture was concentrated in vacuo and purified by silica gelflash column chromatography (petroleum ether/ethyl acetate as eluent)to give the product

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, (E)-Cinnamonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xue, Feng; Zhu, Yong; Qi, Xiaolei; Journal of Chemical Research; vol. 42; 6; (2018); p. 300 – 304;,
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Application of 19472-74-3,Some common heterocyclic compound, 19472-74-3, name is 2-Bromophenylacetonitrile, molecular formula is C8H6BrN, 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 s2 in EtOH (10.0 mL) and H2O (5.0 mL) were successively added NaOH (2.94 g,73.5 mmol) and aqueous H2O2 (23 muL, 0.736 mmol) at room temperature. After the mixture washeated to reflux for 24 h, the reaction was quenched by addition of conc. HCl at 0 C. The crudemixture was extracted with EtOAc (x4) and the combined organic extracts were washed with brine,dried (Na2SO4), and concentrated in vacuo to give crude s3 (1.62 g) as pale yellow solid. Thiscrude material was used for next reaction without further purification.

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

Reference:
Article; Machida, Mizuki; Mori, Keiji; Chemistry Letters; vol. 47; 7; (2018); p. 868 – 871;,
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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. 332-25-2, name is 4-(Trifluoromethoxy)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 4-(Trifluoromethoxy)benzonitrile

A solution of lithium aluminium hydride in diethyl ether (1.0M, 69.4 ml) was added dropwise to a stirred solution of 4-(trifluoromethoxy)benzonitrile (6.0 g) in diethyl ether (120 ml) over 15 minutes. Water (2.66 ml), 10percent sodium hydroxide solution (2.66 ml) and water (7.98 ml) were then added successively, dropwise. The precipitated solid was filtered off and washed with diethyl ether. The filtrate and washings were combined and evaporated under reduced pressure to give 4-(trifluoromethoxy)benzyl alcohol, N.M.R. in deuteriochloroform: delta2.3 (1H,s), 4.65 (2H,s), 7.2 (2H,d), 7.35 (2H,d).

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; US5006543; (1991); A;,
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Application of 555-21-5, 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. 555-21-5 name is 4-Nitrophenylacetonitrile, 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-Nitrophenyl acetonitrile (20 g, 123.45 mmol), tetrabutylammonium bromide (2.15 g, 6.6 mmol) and methyl iodide (58 g, 475.41 mmol) in CH2Cl2 (150 mL) were added to NaOH (13.5 g, 337.5 mmol) in water (130 mL). The reaction mixture was stirred for 20 hours at RT. The organic layer was separated, was dried over Na2SOzJ, and was evaporated to dryness. The residue was dissolved in diethylether, was filtered over celite and solvent was evaporated to obtain the title compound. Yield: 18 g (76 %); 1H NMR (CDCl3, 300 MHz): delta 8.220-8.250 (d, 2H, J=9Hz), 7.627-7.657 (d, 2H, J=9Hz), 1.750 (s, 6H).

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

Reference:
Patent; PIRAMAL LIFE SCIENCES LIMITED; KUMAR, Sanjay; VISHWAKARMA, Ram; MUNDADA, Ramswaroop; DEORE, Vijaykumar; KUMAR, Pramod; SHARMA, Somesh; WO2011/1212; (2011); A1;,
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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. 13388-75-5, name is 2-(3,5-Dimethoxyphenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C10H11NO2

General procedure: A 50 mL round-bottomed flask was charged with 3 (0.177 g, 1 mmol), aromatic aldehyde or substituted aromatic aldehyde (1 mmol) and 10 mL methanol with stirring, and the mixture was heated to 60 C. After 30 min, sodium methoxide (0.027 g, 0.5 mmol) was added to the mixture and keep the temperature for 4-6 h. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to RT, and the precipitate was separated by filter and recrystallized from methanol to give 4a-4z and 5a-5d.

The synthetic route of 13388-75-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ma, Jun; Li, Jiajun; Tian, Yu-Shun; Bioorganic and Medicinal Chemistry Letters; vol. 27; 1; (2017); p. 81 – 85;,
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