Tag: M.W=300-400

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Zhang, Hao-Ran; Xiao, Chang; Zhang, Song-Lin; Zhang, Xiaoming researched the compound: (1,10-Phenanthroline)(trifluoromethyl)copper(I)( cas:1300746-79-5 ).Application of 1300746-79-5.They published the article 《Radical C-H Bond Trifluoromethylation of Alkenes by High-Valent Copper(III) Trifluoromethyl Compounds》 about this compound( cas:1300746-79-5 ) in Advanced Synthesis & Catalysis. Keywords: diarylalkene copper trifluoromethyl complex trifluoromethylation; alkene trifluoromethyl preparation. We’ll tell you more about this compound (cas:1300746-79-5).

A general and selective method is developed that allows direct vinylic C-H bond trifluoromethylation of 1,1-diarylalkenes 4-R1C6H5C(Ar1)=CH2 (R = H, Me, F, CN, etc.; Ar1 = Ph, 3,4-dimethylphenyl, thiophen-2-yl, etc.) and 2-methylidenetricyclo[9.4.0.0(3,8)]pentadeca-1(11),3,5,7,12,14-hexaene by a high-valent copper(III) trifluoromethyl complex, R2Cu(CF3)3 (R2 = 1,10-phenanthroline, pyridine) producing biol. active trifluoromethylated alkenes (as well as trifluoromethylated carbocyclic compounds) (E/Z)-4-R1C6H5C(Ar1)=CHCF3 and 5-(2,2,2-trifluoroethylidene)-10,11-dihydro-5H-dibenzo[a,d][7]annulene. This fundamental reactivity of Cu(III)-CF3 compounds has thus far been unknown. The presence of a tertiary amine is crucial to this reaction, acting as both a weak base and a single electron transfer (SET) promoter to abstract the vinylic hydrogen. This method starts from bulk olefins under cost-effective conditions (without the need for external noble metal photocatalyst or stoichiometric amounts of oxidant), and thus is valuable for practical and sustainable applications.

There is still a lot of research devoted to this compound(SMILES：F[C-](F)([Cu+]1[N]2=C3C4=[N]1C=CC=C4C=CC3=CC=C2)F)Application of 1300746-79-5, and with the development of science, more effects of this compound(1300746-79-5) can be discovered.

Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 1300746-79-5, is researched, SMILESS is F[C-](F)([Cu+]1[N]2=C3C4=[N]1C=CC=C4C=CC3=CC=C2)F, Molecular C13H8CuF3N2Journal, Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov’t, Angewandte Chemie, International Edition called A Broadly Applicable Copper Reagent for Trifluoromethylations and Perfluoroalkylations of Aryl Iodides and Bromides, Author is Morimoto, Hiroyuki; Tsubogo, Tetsu; Litvinas, Nichole D.; Hartwig, John F., the main research direction is copper trifluoromethylation perfluoroalkylation reagent preparation aryl iodide bromide.Computed Properties of C13H8CuF3N2.

Authors have isolated a trifluoromethylcopper(I) reagent ligated by 1,10-phenanthroline, [(Phen)CuRF] (RF = CF3 (1), CF2CF2CF3 (2)) that reacts with unprecedented range of aryl halides at room temperature to 50°. In comparison to current alternative methods for trifluoromethylation of aryl halides, this system reacts under much milder conditions, tolerates a wider range of functional groups, tolerates basic heterocycles, reacts with more hindered substrates, can be extended to perfluoroalkylation, and occurs with a low total cost of goods. On a more fundamental level, the high reactivity of complexes 1 and 2 with a broad range of iodoarenes demonstrates that a general catalytic perfluoroalkylation of aryl iodides is not limited by the reactivity of the trifluoromethylcopper intermediate.

If you want to learn more about this compound((1,10-Phenanthroline)(trifluoromethyl)copper(I))Computed Properties of C13H8CuF3N2, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(1300746-79-5).

Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Angewandte Chemie, International Edition called Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand, Author is Karmel, Caleb; Rubel, Camille Z.; Kharitonova, Elena V.; Hartwig, John F., which mentions a compound: 1300746-79-5, SMILESS is F[C-](F)([Cu+]1[N]2=C3C4=[N]1C=CC=C4C=CC3=CC=C2)F, Molecular C13H8CuF3N2, Quality Control of (1,10-Phenanthroline)(trifluoromethyl)copper(I).

The steric effects of substituents on five-membered rings are less pronounced than those on six-membered rings because of the difference in bond angles. Thus, the regioselectivities of reactions of five-membered heteroarenes that occur with selectivities dictated by steric effects, such as the borylation of C-H bonds, were poor in many cases. The authors report that the silylation of five-membered-ring heteroarenes occurs with high sterically derived regioselectivity when catalyzed by the combination of [Ir(cod)(OMe)]2 (cod = 1,5-cyclooctadiene) and a phenanthroline ligand or a new pyridyl-imidazoline ligand that further increases the regioselectivity. The silylation reactions with these catalysts produce high yields of heteroarylsilanes from functionalization at the most sterically accessible C-H bonds of these rings under conditions that the borylation of C-H bonds with previously reported catalysts formed mixtures of products or products that are unstable. The heteroarylsilane products undergo cross-coupling reactions and substitution reactions with ipso selectivity to generate heteroarenes that bear halogen, aryl, and perfluoroalkyl substituents.

If you want to learn more about this compound((1,10-Phenanthroline)(trifluoromethyl)copper(I))Quality Control of (1,10-Phenanthroline)(trifluoromethyl)copper(I), you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(1300746-79-5).

Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: (1,10-Phenanthroline)(trifluoromethyl)copper(I), is researched, Molecular C13H8CuF3N2, CAS is 1300746-79-5, about Copper-Mediated Trifluoromethylation-Allylation of Arynes, the main research direction is aryl triflate trimethylsilyl allylic bromide copper trifluoromethyl trifluoromethylation allylation; allylarene trifluoromethylated preparation.Related Products of 1300746-79-5.

An unprecedented three-component copper-mediated vicinal trifluoromethylation-allylation of arynes is described. A wide range of structurally diverse trifluoromethylated allylarenes I (R = H, 3-Me, 3-t-Bu, etc.; R1 = H, Me, dimethyl; R2 = Me, Ph, Br, etc.; R3 = H, Me; R4 = H, Me) can be quickly assembled in one step. The application of the method has been demonstrated in the expedient synthesis of the CF3-containing analog of the antispasmodic drug papaverine. The new reactivity of the [CuCF3] reagent, which is generated from the inexpensive industrial byproduct fluoroform, is revealed with unique advantages.

Here is a brief introduction to this compound(1300746-79-5)Related Products of 1300746-79-5, if you want to know about other compounds related to this compound(1300746-79-5), you can read my other articles.

Reference:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 152120-54-2, These common heterocyclic compound, 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, 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: Method B. The required amine hydrochloride salt 7 (1.5-6.0 equiv) and pyrazole-1-carboxamide 6a (1.0 equiv) were dissolved in acetonitrile or chloroform (ca. 1 mL per mmol) and triethylamine (twofold excess based on 7) was added drop-wise with stirring, together with anhydrous MgSO4 to dryness. After 16 h the mixture was filtered, evaporated and purified by column chromatography on silica.

The synthetic route of 152120-54-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Al Shuhaib, Zainab; Davies, Deiniol H.; Dennis, Mark; Evans, Daniel M.; Fletcher, Matthew D.; Franken, Herjan; Hancock, Paul; Hollinshead, Jackie; Jones, Iestyn; Kaehm, Kristina; Murphy, Patrick J.; Nash, Robert; Potter, David; Rowles, Richard; Tetrahedron; vol. 70; 29; (2014); p. 4412 – 4419;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 718632-46-3, name is 5-tert-Butyl 2-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate, 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 5-tert-Butyl 2-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate

To a solution of 9.70 g (61.3 mmol) of 1-(trimeth- ylsilyl)cyclopropanecarboxylic acid [synthesized according to the method described in J. Org. Chem., 1982(47) 5, 893-895] in 120 ml of dehydrated dichloromethane, 6.60 ml (76.9 mmol) of oxalyl chloride and 0.25 ml (3.2 mmol) of dehydrated DMF were added in this order at 00 C. in a nitrogen atmosphere and reacted at 00 C. for 2.5 hours with stirring. After completion of the reaction, the reaction solution was concentrated under reduced pressure and dried under reduced pressure. A solution of the obtained concentration residue in 30 ml of dehydrated dichloromethane was added to a solution of 19.0 ml (109 mmol) of DIPEA and 9.94 g (30.6 mmol) of 5-tert-butyl 2-ethyl 3-amino-6,6- dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate[synthesized according to the method described in Journal of Medicinal Chemistry 2012, 55 (10), 4728-4739] in 170 ml of dehydrated dichioromethane at 00 C. in a nitrogen atmosphere and reacted at 00 C. for 24 hours with stirring. After completion of the reaction, a saturated aqueous solution of sodium bicarbonate was added to the reaction solution and stirred, followed by extraction once with dichloromethane and twice with ethyl acetate. The whole organic layer thus obtained was dried over anhydrous magnesium sulfate, then filtered, and concentrated under reduced pressure. The obtained concentration residue was subjected to preparative column chromatography (apparatus 2, silica gel, elution solvent: n-hexane:ethyl acetate=90: 10-70:30 (V/V)), and a fraction containing 5-tert-butyl 2-ethyl 6,6- dimethyl-3-[1 -(trimethylsilyl)cyclopropanecarboxamido]pyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate was concentrated under reduced pressure. The concentration residue of the fraction containing impurities was subjected again to preparative column chromatography (apparatus 2, silica gel, elution solvent: n-hexane: ethyl acetate=90: 1 0-75 :25 (V/V)), combined with the preliminarily obtained fraction, concentrated under reduced pressure, and dried under reduced pressure.

The synthetic route of 5-tert-Butyl 2-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UBE INDUSTRIES, LTD.; IWASE, Noriaki; AGA, Yasuhiro; USHIYAMA, Shigeru; KONO, Shigeyuki; SUNAMOTO, Hidetoshi; MATSUSHITA, Takashi; OGI, Sayaka; UMEZAKI, Satoshi; KOJIMA, Masahiro; ONUMA, Kazuhiro; SHIRAISHI, Yusuke; OKUDO, Makoto; KIMURA, Tomio; (165 pag.)US2018/186818; (2018); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 17635-44-8, name is 3,4,5-Tribromopyrazole, 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 17635-44-8, SDS of cas: 17635-44-8

EXAMPLE 40 Preparation of 3,4,5-Tribromopyrazole-1-ethanol acetate (ester) A quantity (3.04 g., 0.01 mole) of 3,4,5-tribromopyrazole was dissolved in 70 ml. acetone and 2.76 g. (0.02 mole) solid anhydrous potassium carbonate was added. The mixture was heated at the reflux temperature with stirring for 10 minutes and after cooling, 1.85 g. (0.011 mole) of 2-bromoethyl acetate was added. This reaction mixture was heated at the reflux temperature for 12 hrs. cooled, filtered, and the acetone removed under reduced pressure. The resultant oil consisted of a mixture of the desired acetate and the corresponding alcohol. The mixture was dissolved in pyridine (15 ml.) and treated with acetic anhydride (3.06 g., 0.03 mole) at 0 C. This reaction mixture was kept at about 25 C. overnight, and then poured into 200 ml. of ice water. The precipitate that formed was collected on a filter, and washed with water. After drying and recrystallizing from hexane there was obtained 3,4,5-tribromopyrazole-1-ethanol acetate (ester) having a melting point at 64 to 67 C. Analysis: Calc’d. for C7 H7 Br3 N2 O2: C, 21.51; H, 1.81; N, 7.17; Br, 61.33. Found: C, 21.88; H, 1.95; N, 7.14; Br, 61.42.

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; The Upjohn Company; US4084955; (1978); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 120068-79-3, 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. 120068-79-3, name is 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Comparative Example 13; [0123] Direct sulfinylation of N-phenyl pyrazole starting material (III) according to known methods was tested. As such, sulfinylation was attempted using CF3SO2Na in the presence of a halogenating agent such as POCl3, SOCl2 or PBr3. (III) (II)The reaction reagents and conditions tested are provided in Table I below. Table IUl The results are provided in Table II below: Table II[0124] The reaction proceeded to the desired product, Fipronil, when SOCl2 or POCl3 were used as halogenating agents. However, PBr3 did not yield the desired product, or at least not in acceptable yield (about 6%~8% (II) in the reaction mixture, according to HPLC).

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-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VETOQUINOL; WO2009/77853; (2009); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 152120-54-2, 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. 152120-54-2, name is tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Diisopropyl azodicarboxylate (DIAD, 1.5 equiv) was added dropwise to a stirred solution of alcohol 1a-g (1-2 equiv), N,N?-bis-tert-butoxycarbonylpyrazole-1H-carboxamidine 2 (2.5 mmol, 1 equiv), and Ph3P (1.5 equiv) in THF (7 mL) at 0 C. The reaction mixture was stirred overnight (16 h) at r.t., concentrated in vacuum, and the residue was purified by flash column chromatography on silica gel (10-25% EtOAc-hexane) to give the N-alkylated guanylating agent 3a-g as colorless oils.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Tommasi, Sara; Zanato, Chiara; Carabeo, Rey; Mangoni, Arduino A.; Dall’Angelo, Sergio; Zanda, Matteo; Synthesis; vol. 47; 19; (2015); p. 3067 – 3078;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

120068-79-3, 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 120068-79-3 as follows.

Further comparative experiments are conducted employing the following preparation procedure; To a 750 ml reactor with a mechanical stirrer and a thermometer containing the amine acid complex (1.5 eq.), 147 g anhydrous toluene (6.5 eq.), and 44.8 g CF3SOCI (1.2 eq.) under an argon atmosphere at 0 0C was added vacuum dried 5-amino-1-(2,6- dichloro-4-trifluoromethyl-phenyl)-1 H-pyrazole-3-carbonitrile (1 eq., 79.5 g, 245 mmol, 99 % purity). The reaction mixture was kept at 5 0C for 60 min and then heated to 35 0C within 45 min. The temperature of 35 0C was kept for another 10 hours before quenching the reaction with 200 g of sodium hydroxide solution (10 wt.%). The resulting suspension was diluted with 176 ml of ethylacetate. After phase separation the organic layer was washed once with sodium hydroxide solution (10 wt.%). After phase separation, the organic layer was analyzed by quantitative HPLC. The product was crystallized from a mixture of ethylacetate and toluene affording the title compound as a white crystalline powder.

According to the analysis of related databases, 5-Amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carbonitrile, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; WO2008/55877; (2008); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics