Category: 176969-34-9

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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

PREPARATION EXAMPLES Preparation of compound No. 3 At room temperature, 70 mul (0.8 mmol) of oxal chloride and 30 mul of dimethylformamide are added to a suspension consisting of 130.0 mg (0.7 mmol) of 3-(difluoromethyl)-1-methyl-1H-pyrazol-4-carboxylic acid in 5 ml of dichloromethane. After 2 hours, this reaction mixture is added dropwise to a solution consisting of 160.0 mg (0.7 mmol) of N-cyclopropyl-2-(1,3-dimethylbutyl)aniline and 130 mul (1.0 mmol) of triethylamine in 5 ml of dichloromethane. After 48 hours of stirring at room temperature, 4 ml of water are added and the organic phase is separated off, dried over magnesium sulphate and concentrated under reduced pressure. This gives, after column chromatography (gradient cyclohexane/ethyl acetate), 202.0 mg (0.5 mmol, 72% of theory) of N-cyclopropyl-3-(difluoromethyl)-N-[2-(1,3-dimethylbutyl)phenyl]-1-methyl-1H-pyrazol-4-carboxamide [log P (pH 2.3) 3.89].

According to the analysis of related databases, 176969-34-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer CropScience AG; US2009/176844; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 176969-34-9, 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. 176969-34-9 name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, 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.

General procedure: Under nitrogen atmosphere, carboxylic acid II (3mmol), EDCI (3.3 mmol), HOBT (3.3 mmol)and Et3N (1.8 mmol) were placed in a three-necked flask with 40 mL CH2Cl2, and stirred for 2 hat 0 C; then, compound I (2.4 mmol) was added to the flask and allowed to react for 3 h at 0 C.The reaction was monitored by thin-layer chromatography (TLC) (all reactions could be completed in3 h) and, on completion of the reaction, the mixture was washed with saturated NaHCO3 solutionand water, respectively. Then, it was dried over anhydrous Na2SO4, filtered and evaporated onrotavapor in vacuum. Subsequently, crude products III-1-III-18 were purified by silica gel columnchromatography [V (CH2Cl2): V (EA) = 3:1] and crude products III-19-III-36 were purified by silicagel column chromatography [V (PE): V (EA) = 3:1]. Finally, products were recrystallized with thedichloromethane/petroleum ether to obtain pure target compounds.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Shen; Meng, Siqi; Xie, Yong; Yang, Yonggui; Zhang, Yumeng; He, Lu; Wang, Kai; Qi, Zhiqiu; Ji, Mingshan; Qin, Peiwen; Li, Xinghai; Molecules; vol. 24; 14; (2019);,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, belongs to pyrazoles-derivatives 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 176969-34-9, category: pyrazoles-derivatives

To a one-necked flask was added 53.00 g 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid and 72 mL of thionyl chloride,Heating up to the system has a reflow phenomenon,After refluxing for 2 h, the unreacted thionyl chloride was evaporated at atmospheric pressure.System cooling to 60 below, an external anhydrous calcium chloride drying tower,Water pump vacuum distillation of low boiling impurities, get red viscous liquid, placed overnight solidified into white crystals.The yield was 78.25%.

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; Zhejiang Chemical Institute Co., Ltd.; Sinochem Lantian Group Co., Ltd.; Zhu Bingchun; Peng Weili; Yuan Jing; Huang Hongying; Yu Jiping; Wei Youchang; Kong Xiaolin; Chen Jie; (36 pag.)CN106810545; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, belongs to pyrazoles-derivatives 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 176969-34-9, SDS of cas: 176969-34-9

N dichloromethane 1ml solution of 3-difluoromethyl-1-methyl -1H- pyrazole-4-carboxylic acid 176mg, added N- dimethylformamide 10mg and oxalyl chloride 381mg, I was stirred at room temperature for 1 hour.After completion of the reaction, distilling off the solvent under reduced pressure, the residue was dissolved in dichloromethane 2ml, 2- amino-1- (3,5-dichloropyridine prepared with stirring under ice-cooling, at step 5 Synthesis Example 2 2-yl) ethanone -O- dichloromethane 2ml solution of ethyl oxime 190mg, then dropped the pyridine 91mg, was continued for a further 2 hours stirring at room temperature after completion of the dropping.After completion of the reaction, and extracted with added water 10ml reaction mixture chloroform (20mlx1), after the organic layer washed with water (10mlx1), and dehydrated and dried in this order brine then anhydrous sodium sulfate, and distilling off the solvent under reduced pressure It was.The residue was ethyl acetate – hexane (1: 4 to 1: 1 gradient) was purified by silica gel column chromatography eluting with, to give a pale yellow resinous substance 165.3mg.The thing is dissolved in acetic acid 5ml, After stirring for 2 hours at 70 , distilling off the solvent under reduced pressure, the residue partitioned between ethyl acetate – hexane (1: 4 to 1: 1 gradient) and eluting with It was purified by silica gel column chromatography, and the desired compound 130.6mg obtained as a colorless resin-like substance (E / Z = 1/1).

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-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES LIMITED; Iwasa, Motoyoshi; Tomizawa, Mitsutaka; Tsuji, Keisuke; Nakamura, Toshiyuki; Mita, Takeshi; Kuwahara, Hidehito; asahi, Miho; Imanaka, Hotaka; (342 pag.)JP2016/11286; (2016); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 176969-34-9,Some common heterocyclic compound, 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, molecular formula is C6H6F2N2O2, 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.

Step 7: Production of N-[2-[3-chloro-5-(cyclopropylethynyl)pyridin-2-yl]-2-(isopropoxyimino)ethyl]-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide To a 1 ml solution of 68 mg of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid in dichloromethane, 10 mg of N,N-dimethylformamide and 66 mg of oxalyl chloride were added. After completion of the addition, the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off from the reaction mixture under reduced pressure. The obtained residue was dissolved in 1 ml of dichloromethane and, with stirring under cooling with ice, added dropwisely to a mixed solution of 100 mg of 2-amino-1-[3-chloro-5-(cyclopropylethynyl)pyridin-2-yl]ethanone-O-isopropyl oxime and 200 mg of potassium carbonate in 2 ml of dichloromethane and 2 ml of water. After completion of the dropwise addition, stirring was further continued for 1 hour at room temperature. After completion of the reaction, 10 ml of water was added to the reaction mixture, followed by extraction with dichloromethane (10 ml*1). The obtained organic layer was washed with water (10 ml*1), and then dehydrated and dried by using saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography by eluting it with ethyl acetate-hexane (2:3), to obtain 150 mg of the desired product as a pale yellow resinous substance (E/Z=2/1). 1H NMR (CDCl3, Me4Si, 300 MHz) b 8.45 and 8.43 (d, J=1.8 Hz, 1H), 7.88 and 7.82 (s, 1H), 7.68 and 7.66 (d, J=1.8 Hz, 1H), 7.12 (bs, 1H), 6.85 and 6.75 (t, J=54.2 Hz, 1H), 4.70 and 4.46 (d, J=6.1, 4.9 Hz, 2H), 4.47 and 4.36 (sep, J=6.3 Hz, 1H), 3.90 and 3.87 (s, 3H), 1.4-1.55 (m, 1H), 1.32 and 1.18 (d, J=6.3 Hz, 6H), 0.8-1.0 (m, 4H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, its application will become more common.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LTD.; KUWAHARA, Hidehito; HASUNUMA, Nakako; FUKAMI, Yasuhiro; (68 pag.)US2017/188580; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, molecular formula is C6H6F2N2O2, 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. Formula: C6H6F2N2O2

To a 200 ml single-neck round bottom flask was added 28.39 mmol 3 dissolved in 40 ml of dichloromethane, and then 31.32 mmol of triethylamine was added. Stir for 10 minutes; Further adding 31.23 mmol of EDCI and catalytic amount of DMAP to the reaction. Stir at room temperature for 30 minutes. Finally, 28.39 mmol of N,O-dimethylhydroxylamine hydrochloride was added to the system. Stir at room temperature overnight, after the reaction is completed, The mixture was suction filtered under reduced pressure and the filtrate was concentrated to remove solvent. It was dissolved in 20 ml of dichloromethane and diluted. Wash once with 30 ml of water, separate the aqueous layer and extract twice with dichloromethane (10 ml × 2). The combined organic layers were washed once with 20 ml of saturated sodium chloride solution. The aqueous layer was separated and extracted twice with dichloromethane (10 mL×2). The combined organic layers were dried over anhydrous sodium sulfate; The filtrate is concentrated to remove the solvent.With petroleum ether / ethyl acetate (2:1, volume / volume) purification by column chromatography to give a white solid 6; yield 91%;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 176969-34-9, its application will become more common.

Reference:
Patent; Nankai University; Fan Zhijin; Yu Bin; Yang Dongyan; Zhao Bin; Guo Xiaofeng; Zhang Nailou; Hao Zesheng; Wu Qifan; Zhou Shuang; Cao Lixin; (36 pag.)CN110128419; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, A new synthetic method of this compound is introduced below., Product Details of 176969-34-9

Add a 1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid (30.0 mmol) and 10 mL of sulfoxide to a 100 mL reaction flask, and heat to reflux. After waiting for the reaction solution to change from turbid to clear, continue to react for 30 minutes.Stop heating and concentrate to remove excess sulfoxide,1-methyl-3-difluoromethyl-1H-pyrazole-4-formyl chloride represented by the formula (V-1) was obtained, and it became a solid after cooling.

The synthetic route of 176969-34-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang University of Technology; Liu Xinghai; Guo Changfei; Jin Tao; Tan Chengxia; Weng Jianquan; Wu Hongke; (20 pag.)CN110615765; (2019); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid

Example A2: Preparation of 3-difluoromethyl-1-methyl-1 H-pyrazole-4-carbonyl chloride:; 69.5 g of thionyl chloride (0.58 mol, 1.17 equivalents) are added at 1100C in the course of 2 hours to a solution of 88 g of 3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxylic acid (0.5 mol) in 440 g of chlorobenzene. The reaction mixture is stirred for 1 hour at 1 100C. The reaction mixture is concentrated to a crude product solution. 190 g of 3-difluoromethyl-1- methyl-1 H-pyrazole-4-carbonyl chloride (50% in chlorobenzene, yield: 98%) is obtained. The crude product solution is used without being further purified.

The synthetic route of 176969-34-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG.; SYNGENTA LIMITED.; WO2007/31323; (2007); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

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 176969-34-9 as follows. SDS of cas: 176969-34-9

anti-Enriched 5-amino-9-isopropyl-benzonorbornene (42g, syn/anti-ratio 3:7; prepared as described in WO 04/35589 or WO 06/37632) was chromatographed on silica gel (2.1kg ) in ethyl acetate-hexane-(1:7). The last eluting fractions with antf-contents > 97% (1.2 g, g.l.c) were combined and rechromatographed on silica gel (25Og) in ethyl acetate to give 0.72g (1.96%) of a crystalline solid (m.p. 64 0C) with an antf-content of 99.2% (g.l.c).5-Amino-9-anNo.-isopropyl-benzonorbornene (0.72g, 99.2% anti, prepared as described above) was reacted with 5-difluoromethyl-2-methyl-pyrazole-4-carboxylic acid (0.76g, 1.2 eq.)tau bis-(2-oxo-3-oxazolidinyl)-phosphinic acid chloride (1.Og, 1.2 eq.) and triethylamine (0.87g, 2.4 eq.) in dichloromethane (25ml) at room temperature for 3h to give after aqueous work up with saturated NaHCO3-solution and purification on silica gel in ethyl acetate-hexane-(1 :2 ) a viscous oil. Crystallization from hexane afforded the desired product (1.18g, yield: 91.7%, m.p. 140 0C, 99.4% anti (g.l.c)). The crystalline material was analyzed by differential scanning calorimetry and x-ray diffraction and was identified as crystal modification I of anti-3-difluoromethyl-1-methyl-1 H-pyrazole-4- carboxylic acid (9-isopropyl-1 ,2,3,4-tetrahydro-1 ,4-methano-naphthalen-5-yl)-amide no presence of other crystalline forms was detected (see figures 4, 5 and 6).

According to the analysis of related databases, 176969-34-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA LIMITED; SYNGENTA PARTICIPATIONS AG; WO2008/113447; (2008); A2;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 176969-34-9, 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. 176969-34-9, name is 3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In a 50 mL eggplant-shaped bottle, add 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (0.707 g, 4.01 mmol), add dichloromethane (20 mL), and add oxalyl chloride (1.29 g , 9.96mmol), add 1 drop of N, N-dimethylformamide dropwise, stir at reflux at room temperature, you can clearly see that the reaction solution gradually changed from turbid to clear, TLC followed the reaction, and the reaction ended after 1 hour. The solvent was spin-dried to obtain Intermediate 1, which was dissolved again with dichloromethane (10 mL) and set aside.

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-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; East China University of Science and Technology; Shao Xusheng; Li Zhong; Fu Wen; Cheng Jiagao; Xu Xiaoyong; Xu Zhiping; (43 pag.)CN111087345; (2020); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics