Share a compound : [1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride

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[1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride, cas is 578743-87-0, it is a common heterocyclic compound, the copper-catalyst compound, its synthesis route is as follows.

Chloro[l,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) (195.1 mg, 0.4 mmol) and silver triflate (102.7 mg, 0.4 mmol) were mixed under nitrogen in 25 mL flask and 10 mL of dry THF were added. Reaction mixture was stirred at RT for 30 minutes.Solution of 2,2′-bipyridine (62.4 mg, 0.4 mmol) in dry THF (5 mL) was added. Reaction mixture turned orange and was stirred at RT overnight. Resulting mixture was filtered through Celite and solvent was evaporated on rotovap. Recrystallization from CH2CI2 by vapor diffusion of EtaO gave 215 mg (70.9%) of orange crystals. Anal, calcd. forC38H44CUF3N4O3S: C, 60.26; H, 5.86; N, 7.40; Found: C, 60.18; H, 5.82; N, 7.38. Structure was confirmed by iH-NMR spectrum of [(IPR)Cu(bipy)]OTf (CDCb, 400MHz).

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Reference£º
Patent; THE UNIVERSITY OF SOUTHERN CALIFORNIA; THOMPSON, Mark; DJUROVICH, Peter; KRYLOVA, Valentina; WO2011/63083; (2011); A1;,
Copper catalysis in organic synthesis – NCBI
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

Simple exploration of 578743-87-0

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.578743-87-0,[1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride,as a common compound, the synthetic route is as follows.

In a dry double-mouth bottle to place Ir – 2 (0.0796 g, 0.1 mmol), CuClNHC (0.0488 g, 0.1 mmol), vacuum pumping and nitrogen cycle three times, then the nitrogen flow by adding 10 ml ethanol, stirring reflux reaction for 4 hours, cooling to room temperature, then added potassium hexafluorophosphate (0.184 g, 1 mmol), stirring at the room temperature reaction 2 hours, filtered, concentrated filtrate, ethanol: dichloromethane=1:10 column, get the orange solid 0.069 g, and the yield is 50%.

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Reference£º
Patent; Jiangsu University Of Science And Technology; Shi Chao; Li Qiuxia; Zhang Xinghua; (24 pag.)CN108690096; (2018); A;,
Copper catalysis in organic synthesis – NCBI
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

Extracurricular laboratory: Synthetic route of 578743-87-0

As the rapid development of chemical substances, we look forward to future research findings about 578743-87-0

[1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride, cas is 578743-87-0, it is a common heterocyclic compound, the copper-catalyst compound, its synthesis route is as follows.

In a dry double-mouth bottle to place Ir – 3 (0.0796 g, 0.1 mmol), CuClNHC (0.0488 g, 0.1 mmol), vacuum pumping and nitrogen cycle three times, then the nitrogen flow by adding 10 ml ethanol, stirring reflux reaction for 4 hours, cooling to room temperature, then added potassium hexafluorophosphate (0.184 g, 1 mmol), stirring at the room temperature reaction 2 hours, filtered, concentrated filtrate, ethanol: dichloromethane=1:10 column, get the orange solid 0.069 g, and the yield is 50%.

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Reference£º
Patent; Jiangsu University Of Science And Technology; Shi Chao; Li Qiuxia; Zhang Xinghua; (24 pag.)CN108690096; (2018); A;,
Copper catalysis in organic synthesis – NCBI
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

Application of 7758-99-8

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A common heterocyclic compound, the copper-catalyst compound, name is Copper(II) sulfate pentahydrate,cas is 7758-99-8, mainly used in chemical industry, its synthesis route is as follows.

[0146] Sodium nitrite (2.35 g, 34.13mmol) solution (40 mL) was added dropwise to 4- Chloro-2-fluoro aniline (4. [5G,] 31mmol) in 170 mL HBr [AT-10C] bath temperature, then the mixture was stirred for 30 min at-10C bath temperature. In parallel, copper sulfate (10.22g, 24. [29MMOL)] and sodium bromide (3.79 g, 36. [8MMOL)] were mixed and the reaction mixture was heated at [60C] for 30 min. Then sodium sulfite (2.66g, 21. [2MMOL)] was added into this copper sulfate reaction mixture and heated for [95C] for 30 min. The reaction mixture was cooled to room temperature and solid formed was washed with water to afford white solid cuprous bromide. The diazonium salt was portion wise added into the freshly prepared cuprous bromide in 40 mL HBr [AT-10C] bath temperature and the reaction mixture was then warmed to room temperature. The reaction mixture was heated at [55C] for 20 min, cooled and then extracted with ethyl acetate three times. The combined organic layer was washed with water and saturated brine solution, dried over sodium sulfate and concentrated. The crude material was purified by column chromatography (5: 95 ethyl acetate: pet ether) to afford solid product.

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Reference£º
Patent; CHEMOCENTRYX, INC.; WO2003/105853; (2003); A1;,
Copper catalysis in organic synthesis – NCBI
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

Some tips on 578743-87-0

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578743-87-0, [1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride is a copper-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a flame-dried Schlenk tube under argon atmosphere, [CuCl(IPr)] (1) (0.3mmol, 150mg, 1 equiv.) and KCN (0.3mmol, 19mg, 1 equiv.) were introduced in degassed MeOH (5mL) and the reaction mixture was stirred under reflux (50C) for 4h. After returning to room temperature, the reaction mixture was concentrated to dryness under vacuum. The complex was then dissolved in dichloromethane and filtered through a pad of Celite and concentrated again under vacuum. A purification by recrystallization by slow diffusion of pentane in a THF solution of the complex led to the pure complex (4) as a white powder (143mg, 97% yield). 1H-NMR (CDCl3, 400MHz): delta 1.22 (d, J=6.9Hz, 12H), 1.27 (d, J=6.9Hz, 12H), 2.50 (sept, J=6.9Hz, 4H), 7.14 (s, 2H), 7.30 (d, J=7.8Hz, 4H), 7.50 (t, J=7.8Hz, 4H) ppm. (spectroscopic data in good agreement with the literature) [54].

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Reference£º
Article; Elie, Margaux; Mahoro, Gilbert Umuhire; Duverger, Eric; Renaud, Jean-Luc; Daniellou, Richard; Gaillard, Sylvain; Journal of Organometallic Chemistry; vol. 893; (2019); p. 21 – 31;,
Copper catalysis in organic synthesis – NCBI
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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The synthetic route of 578743-87-0 has been constantly updated, and we look forward to future research findings.

578743-87-0, [1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene]copper chloride is a copper-catalyst compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To an oven-dried screwed 20 mL vial were added (NHC)CuCl (c7 or c8, 0.2 mmol) suspended in dry THF (3 mL); in another vial, [tBu3PN]Li (1b, 42.3 mg, 0.95 eq.) was also dissolved in dry THF (3 mL), then the vial was put into glove-box fridge (-35 C) for one hour. Then the cold mixture was dropped into the (NHC)CuCl/THF suspension slowly under stirring and the suspension was turned into clear solution as the lithium salt added. After addition, the reaction mixture was kept at room temperature in glove box for 13 hours. After the reaction was completed, the volatile was removed under vacuum and dry hexane or pentane (7 mL) was added into the formed oily residue. The suspension obtained was kept stirring for another 15 mins at room temperature, then filtered through a short pad of neutral celite to get rid of precipitate. The filtrate was cooled down in the fridge (-35 C) for 3-4 hours to remove the unreacted lithium salt 1b further. Repeated once again to get the clear hexane or pentane filtrate. The filtrate was evaporated until white crystallized solid was formed, which is the catalytic active species (3 or 4). IPrCuCl (c7, 97 mg, 0.2 mmol); Obtain IPrCuNPtBu3 (3, 99 mg, 78%) as Colorless Solid; 1H NMR (C6D6, 600 MHz) delta 7.26-7.21 (br, m, 4H, m-ArH), 7.17-7.14 (br, m, 2H, p-ArH), 6.40 (s, 2H, NCH=), 2.83 (sep, 4H, J = 6.6 Hz, CH(CH3)2), 1.61 (d, 12H, J = 6.6 Hz, CH(CH3)2), 1.37 (d, 27H, J(PH) = 10.8 Hz, P(C(CH3)3)3), 1.20 (d, 12H, J = 6.6 Hz, CH(CH3)2); 13C NMR (C6D6, 151 MHz) delta 146.18, 136.50, 130.42, 128.68, 124.42, 122.05, 40.78, 40.49, 31.01, 29.33, 25.04, 24.42; 31P NMR (C6D6, 243 MHz) delta 26.35 (s); Elemental analysis calcd for [C39H63CuN3P+0.67 THF]: C, 69.84; H, 9.61; N, 5.86. Found: C, 69.48; H, 9.90; N, 6.19.

The synthetic route of 578743-87-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Bai, Tao; Yang, Yanhui; Han, Chao; Tetrahedron Letters; vol. 58; 15; (2017); p. 1523 – 1527;,
Copper catalysis in organic synthesis – NCBI
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

Application of 4-(Chloromethyl)-5-methyl-1,3-dioxol-2-one

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A common heterocyclic compound, the copper-catalyst compound, name is 5,10,15,20-Tetraphenyl-21H,23H-porphine copper(II),cas is 14172-91-9, mainly used in chemical industry, its synthesis route is as follows.

To a stirred solution of (meso-tetraphenylporphyrinato)copper(II) (1c; 237 mg, 0.35 mmol) inCHCl3 (530 mL) at room temperature, a solution of 25% aqueous nitric acid (freshly prepared fromfuming yellow HNO3, d = 1.52; large excess, 140 mL, 637 mmol) was added dropwise during ca5 min. The reaction mixture was intensively stirred under argon in a round-bottomed ask, protectedagainst light, for 30-40 min with TLC monitoring (CHCl3/n-hexane-1:1). Then, the mixture waspoured into aqueous solution of 5% NaHCO3 (200 mL), and shaken carefully in a separatory funnel.The separated organic layer was washed with water (4 200 mL), and dried with anhydrousMgSO4/Na2CO3. After evaporating the solvent, the residue was subjected to column chromatography(eluent: CHCl3/n-hexane1:1) to give (2-nitro-5,10,15,20-tetraphenylporphyrinato)copper(II) (2c; 71 mg, 28%) and a mixture of dinitro-substituted isomers (150 mg, 56%). Thedinitro-isomers were separated on preparative TLC (CHCl3/n-hexane-1:1, four times developed),allowing isolation of: (a) (2,7-dinitro-5,10,15,20-tetraphenylporphyrinato)copper(II) (3ca; 40 mg,15%); (b) (3,7-dinitro-5,10,15,20-tetraphenylporphyrinato)copper(II) (3cb; 35.5 mg, 13%); (c)(2,8-dinitro-5,10,15,20-tetra-phenylporphyrinato)copper(II) (3cc) contaminated with small amountsof (3,7-dinitro-5,10,15,20-tetraphenylporphyrinato)copper(II) (3cb) (30 mg, yield-ca 10%). 3cc can befurther purified by preparative TLC.

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Reference£º
Article; Mikus, Agnieszka; Rosa, Mariusz; Ostrowski, Stanis?aw; Molecules; vol. 24; 5; (2019);,
Copper catalysis in organic synthesis – NCBI
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

Application of 5,10,15,20-Tetraphenyl-21H,23H-porphine copper(II)

As the rapid development of chemical substances, we look forward to future research findings about 13395-16-9

A common heterocyclic compound, the copper-catalyst compound, name is Bis(acetylacetone)copper,cas is 13395-16-9, mainly used in chemical industry, its synthesis route is as follows.

General procedure: In a typical synthesis of Cu40Ag60, 0.45mmol Cu(acac)2 and 0.35 Ag (ac) was mixed with 3mL of OAm, 1 mL of OAc and 11mL of ODE. All synthesis was conducted in a four-necked glass reactor allowing the precise temperature control and inert gas atmosphere under dark conditions. Firstly, the mixture was heated to 60C and kept at this temperature for 10min. Then, the mixture was heated to 180C and kept at this temperature for 30min before it was cooled down to room temperature. After cooling, the resultant reaction mixture was collected with hexane (2mL) and the NPs were separated by centrifugation (8500rpm, 12min) after adding isopropanol (40mL). To further purify the yielded CuAg NPs, the product was centrifuged (8500rpm, 12min) one more time with ethanol (40mL). Finally, the remaining product was dispersed in hexane (10mL) for further use. By using the same recipe and varying metal precursor amounts, two different compositions of CuAg NPs were synthesized. Reductive mixing of 0.3mmol Cu(acac)2 and 0.5 Ag(ac) resulted in Cu30Ag70 NPs and mixing 0.6mmol Cu(acac)2 with 0.4 Ag (ac) led to Cu60Ag40. Synthesis of Ag NPs was conducted with the same recipe without using Cu precursor.

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Reference£º
Article; Balkan, Timucin; Kuecuekkececi, Hueseyin; Kaya, Sarp; Metin, Oender; Zarenezhad, Hamaneh; Journal of Alloys and Compounds; vol. 831; (2020);,
Copper catalysis in organic synthesis – NCBI
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

Application of 3-Piperazinobenzisothiazole hydrochloride

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A common heterocyclic compound, the copper-catalyst compound, name is Bis(acetylacetone)copper,cas is 13395-16-9, mainly used in chemical industry, its synthesis route is as follows.

The monodisperse CuPd alloy NPs with composition controlwere synthesized by using a modified version of our estab-lished recipe for the CoPd alloy NPs [14]. In a typical synthesis of Cu75Pd25NPs, copper(II) acetylacetonate (0.35 mmol, 90 mg)and palladium(II) acetylacetonate (0.1 mmol, 31 mg) were dis-solved in 3 mL of OAm in a 10 mL of glass vial. In a four-necked glass reactor that allows to study under inert atmosphere,200 mg of MB was dissolved in 3 mL of OAm and 7 mL of 1-octadecene at 80C under magnetic stirring. Next, the metal precursor mixture was quickly injected into the reactor under argon environment. The reaction was then proceed for 1 h before cooled down to room temperature. Then, the colloidal NPs mixture was transferred into two separate centrifuge tubeand acetone/ethanol (v/v = 7/3) was added into the tubes. TheNP product was separated by centrifugation at 8500 rpm for10 min.

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Reference£º
Article; Guengoermez, Kuebra; Metin, Oender; Applied Catalysis A: General; vol. 494; (2015); p. 22 – 28;,
Copper catalysis in organic synthesis – NCBI
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

Application of 1,2,3,4-Tetrahydroquinoline

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A common heterocyclic compound, the copper-catalyst compound, name is Bis(acetylacetone)copper,cas is 13395-16-9, mainly used in chemical industry, its synthesis route is as follows.

General procedure: CZTS nanoparticles were synthesized at different temperatures(220-320 C) for 3 hours and for variousreaction times (2-5 hours) at 240 C, usinghigh-temperature arrested precipitation in the coordinatingsolvent, oleylamine (OLA).15 Under the reactiontime of 3 hours, the reactants for synthesis ofCZTS nanoparticles didn?t dissolve enough in OLA.

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Reference£º
Article; Kim, Donguk; Kim, Minha; Shim, Joongpyo; Kim, Doyoung; Choi, Wonseok; Park, Yong Seob; Choi, Youngkwan; Lee, Jaehyeong; Journal of Nanoscience and Nanotechnology; vol. 16; 5; (2016); p. 5082 – 5086;,
Copper catalysis in organic synthesis – NCBI
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”