Name: 7681-65-4|Copper(I) iodide|99%
Brand: Ambeed
SKU: A531002
Price: 8.0 USD
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1
[ 588-93-2 ]
[ 7681-65-4 ]
[ 1066-54-2 ]
[ 469859-77-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; triphenylphosphine;	(i) Synthesis of 1-(4-n-propylphenyl)-2-trimethylsilylacetylene To 15.0 g (75.4 mmol) of 1-n-propyl-4-bromobenzene were added 8.8 g (89.8 mmol) of trimethylsilylacetylene and 100 ml of triethylamine (NEt3), and the reaction system was purged with argon. Next were added 81 mg (0.4 mmol) of copper (I) iodide (CuI), 324 mg (1.2 mmol) of triphenylphosphine, and 162 mg of dichlorobistriphenylphosphine palladium (II) [PdCl2(PPh3)2] to the reaction system, and the mixture was subjected to reaction for 24 hours with heating and refluxing. After completion of the reaction, the reaction mixture was poured into an iced water, and the resultant mixture was acidified by adding hydrochloric acid. After the resultant water-insoluble oil was extracted with hexane, the hexane phase was washed with water. By removing hexane from the hexane phase, 14.2 g (65.7 mmol) of 1-(4-n-propylphenyl)-2-trimethylsilylacetylene was obtained.

Reference： [1]Patent: US2003/211421,2003,A1

2
5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalene diselenide [ No CAS ]
[ 17880-61-4 ]
[ 7681-65-4 ]
methyl 5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthylselanylethynyl)pyridine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; In tetrahydrofuran; n-heptane; N,N-dimethyl-formamide;	Example 22 Methyl 5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthylselanylethynyl)-2-pyridinecarboxylate In a manner similar to that of Example 4(b), after reaction of 945 mg (1.68 mmol) of 5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalene diselenide, in 5 ml THF, with bromine (0.092 ml, 1.78 mmol), copper iodide (1.32 g; 6.95 mmol) and <strong>[17880-61-4]methyl 5-ethynyl-2-pyridinecarboxylate</strong> (500 mg; 3.1 mmol) in 10 ml of DMF are added, and after trituration from heptane, 1 g (73%) of the expected derivative is obtained in the form of a yellow solid. m.p.=52 C. 1H NMR (CDCl3) 1.27 to 1.29(m,12H); 1.68(s,4H); 2.37(s,3H); 4.02(s,3H) 7.14(s,1H); 7.71(s,1H); 7.85(dd,1H) 8.02(s,1H) 8.11(d,1H). 13C NMR (CDCl3): 20.7; CH3/31.5; 2CH3/31.6; 2CH3/33.7; Cq/34.0; Cq/34.6; 2CH2/52.7; CH3/78; Cq/98.1; Cq/123.7; Cq/124.2;CH/124.5; Cq/128.4; CH/128.5; CH/134.3;Cq/138.3; CH/144.0; Cq/144.9; Cq/145.5;Cq/151.2; CH/162.2; Cq.
	With bromine; In tetrahydrofuran; n-heptane; N,N-dimethyl-formamide;	Example 22 Methyl 5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthylselanylethynyl)-2-pyridinecarboxylate In a manner similar to that of Example 4(b), after reaction of 945 mg (1.68 mmol) of 5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalene diselenide, in 5 ml of THF, with bromine (0.092 ml, 1.78 mmol), copper iodide (1.32 g; 6.95 mmol) and <strong>[17880-61-4]methyl 5-ethynyl-2-pyridinecarboxylate</strong> (500 mg; 3.1 mmol) in 10 ml of DMF are added, and after trituration from heptane, 1 g (73%) of the expected derivative is obtained in the form of a yellow solid. m.p.=52 C. 1H NMR (CDCl3): 1.27 to 1.29(m,12H); 1.68(s,4H); 2.37(s,3H); 4.02(s,3H); 7.14(s,1H); 7.71(s,1H); 7.85(dd,1H); 8.02(s,1H); 8.11(d,1H). 13C NMR (CDCl3): 20.7; CH3/31.5; 2CH3/31.6; 2CH3/33.7; Cq/34.0; Cq/34.6; 2*CH2/52.7; CH3/78.9; Cq/98.1; Cq/123.7; Cq/124.2; CH/124.5; Cq/128.4; CH/128.5; CH/134.3; Cq/138.3; CH/144.0; Cq/144.9; Cq/145.5; Cq/151.2; CH/162.2; Cq.
	With bromine; In tetrahydrofuran; n-heptane; N,N-dimethyl-formamide;	Example 22 Methyl 5-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthylselanylethynyl)-2-pyridinecarboxylate In a manner similar to that of Example 4(b), after reaction of 945 mg (1.68 mmol) of 5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalene diselenide, in 5 ml THF, with bromine (0.092 ml, 1.78 mmol), copper iodide (1.32 g; 6.95 mmol) and <strong>[17880-61-4]methyl 5-ethynyl-2-pyridinecarboxylate</strong> (500 mg; 3.1 mmol) in 10 ml of DMF are added, and after trituration from heptane, 1 g (73%) of the expected derivative is obtained in the form of a yellow solid. m.p.=52 C. 1H NMR (CDCl3) 1.27 to 1.29(m, 12H); 1.68(s, 4H); 2.37(s, 3H); 4.02(s, 3H) 7.14(s, 1H); 7.71(s, 1H); 7.85(dd, 1H) 8.02(s, 1H) 8.11(d, 1H). -C NMR (CDCl3): 20.7; CH3/31.5; 2CH3/31.6; 2CH3/33.7; Cq/34.0; Cq/34.6; 2*CH2/52.7; CH3/78; Cq/98.1; Cq/123.7; Cq/124.2;CH/124.5; Cq/128.4; CH/128.5; CH/134.3;Cq/138.3; CH/144.0; Cq/144.9; Cq/145.5;Cq/151.2; CH/162.2; Cq.

Reference： [1]Patent: US2003/100583,2003,A1
[2]Patent: US6201019,2001,B1
[3]Patent: US6818666,2004,B2

3
[ 7681-65-4 ]
[ 1139-52-2 ]
[ 1066-54-2 ]
2,6-di-tert-butyl-4-(trimethylsilanylethynyl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;dichlorobis(triphenylphosphine)palladium[II]; In tetrahydrofuran;	2,6-Di-tert-butyl-4-trimethylsilanylethynyl-phenol: (Intermediate 167) Following General Procedure D and using 4-bromo-2,6-di-t-butyl-phenol (1.43 g, 5 mmol), triethyl amine (15 mL), anhydrous tetrahydrofuran (15 mL), copper(I)iodide (0.06 g, 0.31 mmol), trimethylsilyl acetylene (4.9 g, 50 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.18 g, 0.26 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using hexane as eluent, the title compound was obtained (1.35 g, 90percent). 1H NMR (300 MHz, CDCl3): delta7.29 (s, 2H), 5.35 (s, 1H), 1.42 (s, 18H), 0.24 (s, 9H).
	With triethylamine;dichlorobis(triphenylphosphine)palladium[II]; In tetrahydrofuran;	2,6-Di-tert-butyl-4-trimethylsilanylethynyl-phenol: (Intermediate 167) Following General Procedure D and using 4-bromo-2,6-di-t-butyl-phenol (1.43 g, 5 mmol), triethyl amine (15 mL), anhydrous tetrahydrofuran (15 mL), copper(I)iodide (0.06 g, 0.31 mmol), trimethylsilyl acetylene (4.9 g, 50 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.18 g, 0.26 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using hexane as eluent, the title compound was obtained (1.35 g, 90percent). 1H NMR (300 MHz, CDCl3): delta 7.29 (s, 2H), 5.35 (s, 1H), 1.42 (s, 18H), 0.24 (s, 9H).

Reference： [1]Patent: US6313107,2001,B1
[2]Patent: US6252090,2001,B1

4
[ 7681-65-4 ]
[ 204257-72-7 ]
[ 133532-16-8 ]
[ 345964-28-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;dichlorobis(triphenylphosphine)palladium[II]; In tetrahydrofuran; hexane;	2-Fluoro-4-(2,2,4,4-tetramethyl-chroman-6-yl-ethynyl)-benzoic acid methyl ester (Compound 29, General Formula 8) Following general procedure F and using 6-ethynyl-2,2,4,4-tetramethylchroman (0.11 g, 0.51 mmol), <strong>[204257-72-7]methyl-2-fluoro-4-iodo-benzoate</strong> (Reagent G, 0.14 g, 0.51 mmol), triethyl amine (5 mL), tetrahydrofuran(10 mL), copper(I)iodide(0.030 g, 0.16 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.110 g, 0.16 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-10% ethyl acetate in hexane as the eluent, the title compound was obtained (0.14 g, 79%). 1H NMR (300 MHz, CDCl3): delta7.82 (t, 1H, J=7.9 Hz), 7.39 (d, 1H, J=1.8 Hz), 7.25-7.16 (m, 3H), 6.69 (d, 1H, J=8.2 Hz), 3.85 (s, 3H), 1.77 (s, 2H), 1.29 (s, 6H), 1.28 (s, 6H).
	With triethylamine;dichlorobis(triphenylphosphine)palladium[II]; In tetrahydrofuran; hexane;	2-Fluoro-4-(2,2,4,4-tetramethyl-chroman-6-yl-ethynyl)-benzoic acid methyl ester (Compound 29, General Formula 8) Following general procedure F and using 6-ethynyl-2,2,4,4-tetramethylchroman (0.11 g, 0.51 mmol), <strong>[204257-72-7]methyl-2-fluoro-4-iodo-benzoate</strong> (Reagent G, 0.14 g, 0.51 mmol), triethyl amine (5 mL), tetrahydrofuran (10 mL), copper(I)iodide (0.030 g, 0.16 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.110 g, 0.16 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-10% ethyl acetate in hexane as the eluent, the title compound was obtained (0.14 g, 79%). 1H NMR (300 MHz, CDCl3): delta 7.82 (t, 1H, J=7.9 Hz), 7.39 (d, 1H, J=1.8 Hz), 7.25-7.16 (m, 3H), 6.69 (d, 1H, J=8.2 Hz), 3.85 (s, 3H), 1.77 (s, 2H), 1.29 (s, 6H), 1.28 (s, 6H).

Reference： [1]Patent: US6313107,2001,B1
[2]Patent: US6252090,2001,B1

5
[ 7681-65-4 ]
[ 204257-72-7 ]
[ 345964-54-7 ]
4-[(8-cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With triethylamine;dichlorobis(triphenylphosphine)palladium[II]; In tetrahydrofuran; hexane; ethyl acetate;	4-[(8-Cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzoic acid methyl ester (Compound 53, General Formula 1) Following general procedure F and using 8-cyclopropyl-6-ethynyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane] (Intermediate 44, 0.03 g, 0.11 mmol), <strong>[204257-72-7]methyl-2-fluoro-4-iodo-benzoate</strong> (Reagent G, 0.025 g, 0.09 mmol), triethyl amine (3 mL), tetrahydrofuran (3 mL), copper(I)iodide(0.020 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.06 g, 0.085 mmol) followed by preparative normal phase HPLC using 10% ethyl acetate in hexane as the mobile phase, the title compound was obtained as a white solid (0.019 g, 40%). 1H NMR (300 MHz, CDCl3): delta7.97 (t, 1H, J=7.8 Hz), 7.34 (d, 1H, J=1.9 Hz), 7.32-7.25 (m, 2H), 6.83 (d, 1H, J=1.9 Hz), 3.95 (s, 3H), 2.06-1.96 (m, 1H), 1.93 (s, 2H), 1.42 (s, 6H), 1.06-1.02 (m, 2H), 0.91-0.86 (m, 2H), 0.71-0.61 (m, 4H).
40%	With triethylamine;dichlorobis(triphenylphosphine)palladium[II]; In tetrahydrofuran; hexane; ethyl acetate;	4-[(8-Cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2.1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzoic acid methyl ester (Compound 53, General Formula 1) Following general procedure F and using 8-cyclopropyl-6-ethynyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane] (Intermediate 44, 0.03 g, 0.11 mmol), <strong>[204257-72-7]methyl-2-fluoro-4-iodo-benzoate</strong> (Reagent G, 0.025 g, 0.09 mmol), triethyl amine (3 mL), tetrahydrofuran (3 mL), copper(I)iodide (0.020 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.06 g, 0.085 mmol) followed by preparative normal phase HPLC using 10% ethyl acetate in hexane as the mobile phase, the title compound was obtained as a white solid (0.019 g, 40%). 1H NMR (300 MHz, CDCl3): delta 7.97 (t, 1H, J=7.8 Hz), 7.34 (d, 1H, J=1.9 Hz), 7.32-7.25 (m, 2H), 6.83 (d, 1H, J=1.9 Hz), 3.95 (s, 3H), 2.06-1.96 (m, 1H), 1.93 (s, 2H), 1.42 (s, 6H), 1.06-1.02 (m, 2H), 0.91-0.86 (m, 2H), 0.71-0.61 (m, 4H).

Reference： [1]Patent: US6313107,2001,B1
[2]Patent: US6252090,2001,B1

6
[ 98-17-9 ]
[ 7681-65-4 ]
[ 170235-18-4 ]
[ 219498-91-6 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl acetamide; water; ethyl acetate; mineral oil;	(1) <Production of 5-methoxy-6-[3-(trifluoromethyl)phenoxy] picolinic acid methyl ester as an intermediate product> 3-(trifluoromethyl) phenol (1.317 g, 0.0081 mol) was dissolved in 10 ml of dried dimethyl acetamide. While cooling the obtained solution with water, sodium hydride (0.39 g (ca. 60% in mineral oil), 0.0081*1.2 mol) was added to the solution. After completion of the foaming, a solution obtained by dissolving <strong>[170235-18-4]6-bromo-5-methoxy-2-pyridine carboxylic acid methyl ester</strong> (2.0 g, 0.0081 mol) in 10 ml of dried dimethyl acetamide, and then copper iodide (1.55 g, 0.081 mol) were successively added to the solution. The obtained mixture was heated and stirred at 120 C. for 10 hours. Thereafter, the obtained reaction solution was cooled, mixed with 50 ml of water and then with 50 ml of ethyl acetate, and filtered through a glass filter provided with Hyflo Super-Cell. The obtained filtrate was extracted with ethyl acetate to obtain an aimed product. An organic phase was separated from the product, washed with water and then dried with anhydrous sodium sulfate. The dried product was concentrated, and the obtained residues were purified by silica gel column chromatography (eluding solution: ethyl acetate/hexane). Yield weight: 0.68 g; yield percentage: 26%; solid; melting point: 116 to 118 C.; 1 H-NMR (60 MHz, CDCl3, delta): 3.76(3H, s), 3.86(3H, s), 7.16(1H, d, J=8 Hz), 7.2-7.5(4H, complex), 7.80(1H, d, J=8 Hz).

Reference： [1]Patent: US6159901,2000,A

7
[ 98-17-9 ]
[ 7681-65-4 ]
[ 1702-18-7 ]
3-chloro-2-cyano-6-[3-(trifluoromethyl)-phenoxy] pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; water; mineral oil;	(3) <Production of 3-chloro-2-cyano-6-[3-(trifluoromethyl) phenoxy] pyridine as an intermediate product> 3-(trifluoromethyl) phenol (3.09 g, 0.01731.1 mol) was dissolved in 10 ml of dried dioxane. Sodium hydride (0.728 g (ca. 60% in mineral oil), 0.001731.05 mol) was added to the obtained solution. After completion of the foaming, a solution obtained by dissolving 3,6-dichloro-2-cyano pyridine (3 g, 0.0173 mol) in 10 ml of dried dioxane, and copper iodide (0.33 g, 0.0173*0.1 mol) were successively added to the solution, and then the obtained mixture was heated and stirred in an oil bath maintained at 110 C., for 5 hours. Thereafter, the obtained reaction solution was distilled under reduced pressure. The obtained distillation residues were mixed with 30 ml of water, and filtered through a glass filter provided with Hyflo Super-Cell. The obtained filter cake was washed with ethyl acetate, and further a filtrate obtained therefrom was extracted with ethyl acetate. The resultant extract solution was distilled under reduced pressure to remove the solvent therefrom, thereby obtaining a solid product. Yield weight: 4.26 g; yield percentage: 82%; solid; melting point: 63 to 65 C.; 1 H-NMR (60 MHz, CDCl3, delta): 7.1(1H, d, J=8 Hz), 7.1-7.6(4H, complex), 7.8(1H, d, J=8 Hz).

Reference： [1]Patent: US6159901,2000,A

8
[ 7681-65-4 ]
[ 17231-51-5 ]
[ 1066-54-2 ]
2-amino-3-cyano-5-(trimethylsilylethynyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;bis(triphenylphosphine)palladium(II)-chloride; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;	Step A Synthesis of 2-amino-3-cyano-5-(trimethylsilylethynyl)pyrazine as an intermediate A solution of 3.0 grams (0.015 mole) of 2-amino-3-cyano-5-bromopyrazine and 2.1 grams (0.021 mole) of trimethylsilylacetylene in 50 mL of acetonitrile is stirred, and 10.6 mL of triethylamine, 0.13 gram of copper iodide, and 0.29 gram of bis(triphenylphosphine)palladium(II) chloride are added in order. Upon completion of addition, the reaction mixture is stirred at ambient temperature for about 20 hours. The reaction mixture is warmed to 70 C., where it is stirred for about 7.5 hours. After this time, the reaction mixture is concentrated under reduced pressure to a residue. The residue is dissolved in ethyl acetate, and the solution is washed with 50 mL of aqueous, dilute hydrochloric acid. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure to a residue. The residue is subjected to column chromatography on silica gel. Elution is accomplished using tetrahydrofuran/methylene chloride combinations. The product-containing fractions are combined and concentrated under reduced pressure, yielding 2-amino-3-cyano-5-(trimethylsilylethynyl)pyrazine.

Reference： [1]Patent: US5521190,1996,A

9
[1,1-bis(diphenylphosphino)ferrocene]dichloropalladium [ No CAS ]
[ 381248-06-2 ]
[ 312624-15-0 ]
[ 7681-65-4 ]
3-(1-Adamantyl)-5-(pyridin-2-yl)-1-phenyl-1,2-dihydropyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; In tetrahydrofuran;	Example 178. 3-(1-Adamantyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one 40mg of <strong>[381248-06-2]3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one</strong> was dissolved in 10ml of tetrahydrofuran. To the mixture were added 5mg of [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (II) and 1.2mg of copper (I) iodide. While stirring the mixture at room temperature in nitrogen atmosphere overnight, 0.4ml of 1-adamantyl zinc bromide (0.5M tetrahydrofuran solution) was added dropwise thereinto. After stirring in nitrogen atmosphere overnight, an aqueous ammonia was added thereto, followed by extracting with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 12mg of the title compound. 1H-NMR (400MHz, CDCl3); delta(ppm) 1.44-2.19(m,15H), 7.13(ddd,1H), 7.31-7.55(m,6H), 7.66(td,1H), 7.93(d,1H), 8.05(d,1H), 8.55-8.58(m,1H). ESI-Mass; 383 [M++H]

Reference： [1]Patent: EP1300396,2003,A1

10
[ 142-08-5 ]
[ 381248-06-2 ]
[ 7681-65-4 ]
3-(2-Pyridon-1-yl)-5-(pyridin-2-yl)-1-phenyl-1,2-dihydropyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; potassium carbonate; In N-methyl-acetamide;	Example 191. 3-(2-Pyridon-1-yl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one 40mg of <strong>[381248-06-2]3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one</strong> and 23mg of 2-hydroxypyridine were dissolved in 10ml of dimethylformamide. 34mg of potassium carbonate and 3mg of copper iodide were added thereto, followed by stirring at 140C overnight. After cooling the reaction mixture to room temperature, an aqueous ammonia was added thereto, followed by extracting with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (NH silica) (chloroform/methanol system), to give 10mg of the title compound. 1H-NMR (400MHz, CDCl3); delta(ppm) 6.24(td,1H), 6.69(dd,1H), 7.22(dd,1H), 7.37-7.42(m,2H), 7.45-7.57(m,6H), 7.73(td,1H), 8.33(d,1H), 8.36(d,1H), 8.58-8.60(m,1H).

Reference： [1]Patent: EP1300396,2003,A1

11
[ 381248-06-2 ]
[ 7681-65-4 ]
ammonium hydroxide [ No CAS ]
[ 108-95-2 ]
3-Phenoxy-5-(pyridin-2-yl)-1-phenyl-1,2-dihydropyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N-methyl-acetamide;	Example 175. 3-Phenoxy-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one 100mg of <strong>[381248-06-2]3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one</strong> and 58mg of phenol were dissolved in 10ml of dimethylformamide, to which 84mg of potassium carbonate and 6mg of copper iodide were added, and the mixture was stirred at 150C for 5 hours. The reaction solution was cooled to room temperature, to which ammonia water was added, and extracted with ethyl acetate. The organic layer was washed with saturated saline water and dried by magnesium sulfate anhydride, and the solvent was distilled off under a vacuum. The residue was refined by silica gel chromatography (hexane/ethyl acetate-based solvent), to obtain 66mg of the subject compound. 1H-NMR (400MHz, CDCl3); delta(ppm) 7.13-7.19(m,3H), 7.26-7.27(m,2H), 7.36-7.54(m,7H), 7.60-7.61(m,1H), 7.66-7.71(m,1H), 8.03-8.04(m,1H), 8.54-8.57(m,1H). ESI-Mass; 341 [M++H]

Reference： [1]Patent: EP1300396,2003,A1

12
tetrakis (triphenylphosphonium) palladium ⁽⁰⁾ [ No CAS ]
[ 39998-81-7 ]
[ 7681-65-4 ]
[ 109-89-7 ]
[ 115-19-5 ]
[ 195877-12-4 ]

Yield	Reaction Conditions	Operation in experiment
		The mixture of <strong>[39998-81-7]2-fluoro-4-iodotoluene</strong> (0.05 mol), 3-methyl-3-hydroxy-1-butyne (0.06 mol), tetrakis (triphenylphosphonium) palladium (0) 0.35 g, copper iodide 50 mg, and diethylamine 100 ml was refluxed for 5.5 hours. Diethylamine was distilled away under reduced pressure, the residue was extracted with diethylether, and the extract was washed with water. From the extract, diethylether was distilled away, the residue was purified by column chromatography (elution liquid: heptane-ethyl acetate) to obtain colorless oily 2-fluoro-4-(3-methyl-3-hydroxy-1-butynyl)toluene (0.035 mol).

Reference： [1]Patent: US6168728,2001,A

13
[ 7681-65-4 ]
[ 104-71-2 ]
Cu₂I₂(C₆H₅CHNC₂H₄NCHC₆H₅)2 [ No CAS ]

Reference： [1]Inorganic Chemistry,1985,vol. 24,p. 648 - 653
[2]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1987,vol. 26,p. 574 - 576

14
[ 7681-65-4 ]
[ 104-71-2 ]
[ 143-66-8 ]
[ 94249-96-4 ]

Reference： [1]Inorganic Chemistry,1985,vol. 24,p. 648 - 653

15
[ 7681-65-4 ]
[ 104-71-2 ]
[ 7175-47-5 ]
[ 94249-95-3 ]

Reference： [1]Inorganic Chemistry,1985,vol. 24,p. 648 - 653

16
[ 7681-65-4 ]
[ 104-71-2 ]
[ 94278-60-1 ]

Reference： [1]Inorganic Chemistry,1985,vol. 24,p. 648 - 653

17
[ 7681-65-4 ]
[ 4491-33-2 ]
[ 76331-95-8 ]

Reference： [1]Bulletin de la Societe Chimique de France,1980,vol. I,p. 287 - 293

18
[ 7681-65-4 ]
[ 4491-33-2 ]
[ 76331-95-8 ]

Reference： [1]Bulletin de la Societe Chimique de France,1980,vol. I,p. 287 - 293

19
[ 7681-65-4 ]
[ 2645-22-9 ]
[ 75-09-2 ]
[CuI(bis(4-pyridyl)disulfide)](CH₂Cl₂) [ No CAS ]

Reference： [1]Chemical Communications,2001,p. 1432 - 1433

20
[ 7681-65-4 ]
[ 2645-22-9 ]
[ 107-12-0 ]
[(CuI)2(bis(4-pyridyl)disulfide)]*0.5C₂H₅CN [ No CAS ]

Reference： [1]Chemical Communications,2001,p. 1432 - 1433

21
[ 7681-65-4 ]
[ 2645-22-9 ]
[ 75-05-8 ]
[CuI(bis(4-pyridyl)disulfide)](CH₃CN) [ No CAS ]

Reference： [1]Chemical Communications,2001,p. 1432 - 1433

22
[ 7681-65-4 ]
[ 2645-22-9 ]
[ 75-05-8 ]
[(CuI)2(bis(4-pyridyl)disulfide)]*0.5CH₃CN [ No CAS ]

Reference： [1]Chemical Communications,2001,p. 1432 - 1433

23
[ 7681-65-4 ]
[ 638-16-4 ]
[ 854588-94-6 ]

Reference： [1]Inorganic Chemistry,2005,vol. 44,p. 3907 - 3913

24
[ 1450-85-7 ]
[ 7681-65-4 ]
[ 854588-91-3 ]

Reference： [1]Inorganic Chemistry,2005,vol. 44,p. 3907 - 3913

25
[ 1450-85-7 ]
[ 7681-65-4 ]
[ 983-81-3 ]
[CuI(trans-1,2-bis(diphenylphosphino)ethene)(C₄H₄N₂S)]2 [ No CAS ]

Reference： [1]Polyhedron,2005,vol. 24,p. 351 - 358

26
[ 7681-65-4 ]
[ 113682-56-7 ]
[ 887918-41-4 ]

Reference： [1]Inorganic Chemistry,2006,vol. 45,p. 6179 - 6187

27
[ 7681-65-4 ]
[ 2645-22-9 ]
[Cu₄I₄(4,4'-thiodipyridine)2] [ No CAS ]

Reference： [1]Inorganic Chemistry,2007,vol. 46,p. 795 - 800

28
[ 7681-65-4 ]
[ 2645-22-9 ]
[Cu₅I₅(1-(4-pyridyl)-4-thiopyridine)2] [ No CAS ]

Reference： [1]Inorganic Chemistry,2007,vol. 46,p. 795 - 800

29
[ 7681-65-4 ]
[ 2645-22-9 ]
[Cu₆I₆(1-(4-pyridyl)-4-thiopyridine)2] [ No CAS ]

Reference： [1]Inorganic Chemistry,2007,vol. 46,p. 795 - 800

30
[ 254-60-4 ]
[ 7681-65-4 ]
[ 603-35-0 ]
[ 960123-92-6 ]

Reference： [1]Inorganic Chemistry,2007,vol. 46,p. 10032 - 10034

31
[ 7681-65-4 ]
[ 118949-61-4 ]
[Cu₄I₄((S,S)-(i)Pr-pybox)2] [ No CAS ]

Reference： [1]Inorganic Chemistry,2006,vol. 45,p. 10043 - 10045

32
[ 2033-45-6 ]
[ 7681-65-4 ]
[ 143672-34-8 ]

Reference： [1]Canadian Journal of Chemistry,1992,vol. 70,p. 1121 - 1128

33
[ 1450-85-7 ]
[ 7681-65-4 ]
[ 76144-87-1 ]
[ 1072081-59-4 ]

Reference： [1]Polyhedron,2008,vol. 27,p. 3029 - 3035

34
[ 7681-65-4 ]
[ 118949-61-4 ]
[Cu₄I₄(2,6-bis[4'-(S)-isopropyloxazolin-2'-yl]pyridine)2]*C₆H₁₄ [ No CAS ]

Reference： [1]Inorganic Chemistry,2009,vol. 48,p. 11147 - 11160

35
[ 7681-65-4 ]
[ 128249-70-7 ]
[Cu₄I₄(2,6-bis[4'-(R)-phenyloxazolin-2'-yl]pyridine)2] [ No CAS ]

Reference： [1]Inorganic Chemistry,2009,vol. 48,p. 11147 - 11160

36
[ 7681-65-4 ]
[ 837-45-6 ]
[ 68-12-2 ]
[ 1228341-20-5 ]

Reference： [1]Inorganica Chimica Acta,2010,vol. 363,p. 1377 - 1385

37
[ 1450-85-7 ]
[ 7681-65-4 ]
[ 166330-10-5 ]
[ 1258436-57-5 ]

Reference： [1]Dalton Transactions,2010,vol. 39,p. 10238 - 10248

38
[ 1450-85-7 ]
[ 7681-65-4 ]
[ 66-71-7 ]
[ 1422516-90-2 ]

Reference： [1]Dalton Transactions,2013,vol. 42,p. 2755 - 2764

39
[ 7681-65-4 ]
[ 4303-67-7 ]
[ 1253689-93-8 ]

Reference： [1]Synthetic Communications,2013,vol. 43,p. 2100 - 2109

40
[ 7681-65-4 ]
[ 75-05-8 ]
[ 739-58-2 ]
[Cu₄I₄(4-(diphenylphosphino)-N,N-dimethylaniline)₄]*CH₃CN [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2013,vol. 1,p. 4339 - 4349

41
[ 7681-65-4 ]
[ 1594-57-6 ]
[{Cu(pyridine-4-amidoxime)I}₂]_n [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	In acetonitrile; at 20℃; for 1h;	To a 20mL acetonitrile solution of copper (I) iodide (0.5mmol, 0.095g), pyridine-4-amidoxime (0.5mmol, 0.069g) was added and stirred gently at room temperature for an hour. A greenish-yellow coloured solid precipitated. The reaction mixture was filtered and the filtrate was left undisturbed at room temperature for slow evaporation. Plate shaped greenish-yellow crystals of 1 were collected after 15days. Yield: 40%, 0.065g. Anal. Calc. for C12H14Cu2I2N6O2: C, 22.00; H, 2.15; N, 12.83. Found: C, 22.03; H, 2.18; N, 12.80%.

Reference： [1]Polyhedron,2013,vol. 65,p. 252 - 261

42
[ 7681-65-4 ]
[ 66491-03-0 ]
[ 66491-04-1 ]

Yield	Reaction Conditions	Operation in experiment
640 mg		Preparation of Intermediate 7-Iodo-3,4-dihydro-2H-isoquinolin-1-one (I-32b) NaNO2 (340 mg, 4.9382 mmol) was added to a solution of <strong>[66491-03-0]7-amino-3,4-dihydro-2H-isoquinolin-1-one</strong> (I-32a: 800 mg, 4.9382 mmol) in concentrated HCl (2 mL) and water (2 mL) at 0 C. The reaction mixture was stirred at 0 C. for 15 minutes. The resulting diazonium salt solution was added portion wise to a vigorously stirred biphasic mixture of DCM (25 mL), potassium iodide (4.9 g, 29.6242 mmol), copper iodide (47 mg, 0.25 mmol) and water (8 mL). The resulting mixture was stirred at room temperature overnight. The reaction was monitored by TLC (80% ethylacetate in hexane). The reaction mixture was diluted with DCM. The organic layer was washed with 10% Na2S2SO3 solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (50% ethylacetate in hexane) afforded 640 mg of the product (44.50% yield). 1H NMR (300 MHz, CDCl3): delta 8.53-8.31 (m, 1H), 7.80-7.70 (m, 1H), 7.0 (d, 1H), 6.40-6.25 (bs, 1H), 3.70-3.51 (m, 2H), 3.0 (t, 2H) LCMS: 100%, m/z=274.0 (M+1)

Reference： [1]Patent: US2014/45872,2014,A1 .Location in patent: Paragraph 0579

43
[ 7681-65-4 ]
praseodymium(III) oxide [ No CAS ]
[ 7732-18-5 ]
[ 127-09-3 ]
[ 4385-76-6 ]
[Pr₄(acetate)₃-(H₂O)₄(4-pyridin-4-yl-benzonate)₉][Cu(μ₃-I)][Cu₁₀(μ₃-I)(μ₄-I)₆(μ₅-I)₃]·7H₂O [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 2704 - 2711

44
[ 7681-65-4 ]
neodymium(III) oxide [ No CAS ]
[ 7732-18-5 ]
[ 127-09-3 ]
[ 4385-76-6 ]
[Nd₄(acetate)₃-(H₂O)₄(4-pyridin-4-yl-benzonate)₉][Cu(μ₃-I)][Cu₁₀(μ₃-I)(μ₄-I)₆(μ₅-I)₃]·7H₂O [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 2704 - 2711

45
samarium(III) oxide [ No CAS ]
[ 7681-65-4 ]
[ 7732-18-5 ]
[ 127-09-3 ]
[ 4385-76-6 ]
[Sm₄(acetate)₃-(H₂O)₄(4-pyridin-4-yl-benzonate)₉][Cu(μ₃-I)][Cu₁₀(μ₃-I)(μ₄-I)₆(μ₅-I)₃]·7H₂O [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 2704 - 2711

46
[ 7681-65-4 ]
europium(III) oxide [ No CAS ]
[ 7732-18-5 ]
[ 127-09-3 ]
[ 4385-76-6 ]
[Eu₄(acetate)₃-(H₂O)₄(4-pyridin-4-yl-benzonate)₉][Cu(μ₃-I)][Cu₁₀(μ₃-I)(μ₄-I)₆(μ₅-I)₃]·7H₂O [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 2704 - 2711

47
dysprosium((III) oxide [ No CAS ]
[ 7681-65-4 ]
[ 7732-18-5 ]
[ 4385-76-6 ]
[Dy₅(μ₃-OH)₄(μ-H₂O)Cu₈I₈(4-pyridin-4-yl-benzoate)₁₁]*H₂O [ No CAS ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 5631 - 5636

48
[ 7681-65-4 ]
europium(III) oxide [ No CAS ]
[ 7732-18-5 ]
[ 4385-76-6 ]
[Eu₅(μ₃-OH)₄(μ-H₂O)Cu₈I₈(4-pyridin-4-yl-benzoate)₁₁]*H₂O [ No CAS ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 5631 - 5636

49
[ 7681-65-4 ]
[ 216959-91-0 ]
[(copper(I))2(iodide)2]0.5[(copper(I))2(4-(pyrimidin-5-yl)benzoate)4]0.5*2(N,N-dimethylformamide) [ No CAS ]

Reference： [1]Crystal Growth and Design,2015,vol. 15,p. 915 - 920

50
[ 7681-65-4 ]
sodium azide [ No CAS ]
[ 25372-03-6 ]
2Cu⁽¹⁺⁾*I^(1-)*C₁₀H₇N₆^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	In water; at 120℃; for 72h;High pressure;	A mixture of CuI (0.0381g, 0.2mmol), NaN3 (0.0065g, 0.1mmol), <strong>[25372-03-6]4-(1H-imidazol-1-yl)benzonitrile</strong> (0.0169g, 0.1mmol) and H2O (15mL) was sealed in a 25mL Teflon-lined stainless steel container. The reactor was heated to 120°C for 3days, and then slowly cooled down to room temperature. Colorless block crystals were isolated in 53percent yield (based on CuI). C10H7N6ICu2 (465.20): Calc. C, 26.28; H, 1.84; N, 25.54; Found C, 26.21; H, 1.87; N, 25.61percent. FT-IR (KBr pellet, cm?1): 3442(br), 1616(m), 1539(s), 1512(m), 1494(w), 1447(w), 1398(w), 1382(w), 1305(m), 1263(w), 1232(w), 1187(w), 1063(m), 953(w), 823(m), 749(m), 718(w), 652(w), 496(w).

Reference： [1]Inorganic Chemistry Communications,2015,vol. 61,p. 1 - 4

51
[ 7681-65-4 ]
[ 7601-90-3 ]
europium(III) oxide [ No CAS ]
[ 7732-18-5 ]
[ 144-62-7 ]
[ 4385-76-6 ]
Eu₆⁽¹⁸⁺⁾*Cu₉⁽⁹⁺⁾*2HO^(1-)*6I^(1-)*12C₁₂H₈NO₂^(1-)*3C₂O₄^(2-)*H₂O*ClO₄^(1-) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 15511 - 15515

52
[ 7681-65-4 ]
europium(III) oxide [ No CAS ]
[ 7732-18-5 ]
[ 127-09-3 ]
[ 4385-76-6 ]
Eu₆⁽¹⁸⁺⁾*Cu₇⁽⁷⁺⁾*7I^(1-)*12C₁₂H₈NO₂^(1-)*6C₂H₃O₂^(1-)*4H₂O [ No CAS ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 15511 - 15515

53
[ 657408-07-6 ]
[ 7681-65-4 ]
[ 811-68-7 ]
(S-Phos)CuI [ No CAS ]
(S-Phos)CuSCF₃ [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 3521 - 3528

54
[ 657408-07-6 ]
[ 7681-65-4 ]
[ 811-68-7 ]
(S-Phos)CuSCF₃ [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 3521 - 3528

55
[ 657408-07-6 ]
[ 7681-65-4 ]
(S-Phos)CuI [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 3521 - 3528

56
[ 872-50-4 ]
[ 7681-65-4 ]
copper(II) nitrate trihydrate [ No CAS ]
[ 216959-91-0 ]
[(Cu₂I₂)Cu₂(C₁₁H₇N₂O₂)₄]*(NMP)_6.4*(H₂O)_2.4 [ No CAS ]

Reference： [1]Crystal Growth and Design,2016,vol. 16,p. 722 - 727

57
[ 7681-65-4 ]
[ 7732-18-5 ]
[ 68-12-2 ]
[ 216959-91-0 ]
[(Cu₂I₂)Cu₂(C₁₁H₇N₂O₂)₄]*(DMF)_7.4*(H₂O)_4.6 [ No CAS ]

Reference： [1]Crystal Growth and Design,2016,vol. 16,p. 722 - 727

58
[ 7681-65-4 ]
[ 128249-70-7 ]
Cu₄I₇^(3-)*3C₄₆H₃₈Cu₂IN₆O₄⁽¹⁺⁾ [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 6006 - 6009

59
[ 7681-65-4 ]
[ 13885-09-1 ]
bis[2-(diphenylphosphino)biphenyl] copper(I) iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.2%	In dichloromethane; at 20℃; for 3h;	A suspension of copper(I) iodide (0.042 g, 0.22 mmol) and dpbp (0.149 g, 0.44 mmol) in 15 mL ofCH2Cl2 was stirred for 3 h at room temperature to form a white precipitate. The precipitate was filteredoff and purified by recrystallization from CH2Cl2/aectonitrile to give colorless crystals (Yield: 0.160 g,84.2percent). 1H NMR (400 M, CDCl3) delta: 7.44?7.26 (m, 26H, m,p-Ph + ?PC6H4?), 7.09?6.99 (m, 12H, o-Ph). 13CNMR (100 M, CDCl3) delta: 147.87, 147.67, 140.24, 140.16, 134.31, 134.17, 133.45, 132.17, 131.81, 131.07,130.71, 130.14, 129.90, 128.93, 128.69, 127.93, 127.26 (Ar?C). 31P NMR (240 M, CDCl3) delta ?10.16 (s). Anal.Calcd for C48H38CuIP2: C, 66.48; H, 4.42. Found: C, 66.50; H, 4.40. MS (MALDI-TOF): m/z Calcd for [M?I]+,739.1745, found 739.1874.

Reference： [1]Journal of Coordination Chemistry,2016,vol. 69,p. 3692 - 3702

60
[ 7681-65-4 ]
[ 64394-45-2 ]
cuprous ethylenetetrathiolate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; In methanol; for 12h;Inert atmosphere; Reflux;	In an argon atmosphere, 1 g of 1,3,4,6-tetrathia-cyclopentene-2,5-dione was dispersed in methanol, 2.07 g of sodium methoxide was added and refluxed for 12 h; then 3.66 g of cuprous iodide was added and Refluxed for 12 h; filtered, the resulting solid was washed sequentially with water, methanol and diethyl ether, dried in a vacuum oven (absolute pressure 0.06 Pa) at 50 C to give Ethylene copper tetrathionate reprented by formual I

Reference： [1]Patent: CN103755606,2016,B .Location in patent: Paragraph 0032; 0033

61
[ 7681-65-4 ]
[ 29949-84-6 ]
4Cu⁽¹⁺⁾*4I^(1-)*4C₂₁H₂₁O₃P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In dichloromethane; acetonitrile;	A large amount of microcrystalline the preparation of the sample: weighing 0.3mmol of cuprous iodide is dissolved in 10 ml acetonitrile to obtain solution A, weighing 0.3mmol m - anisyl3 P ligand dissolved in 10 ml dichloromethane to obtain solution B, the solution A and solution B mixed, and stirring to make fully undergo coordination reaction, and finally the resulting colorless solution is filtered, and steaming and remove all solvent, vacuum drying, to obtain the colorless crystal powder is the product, yield 96% (to Cu meter).

Reference： [1]Patent: CN104893715,2017,B .Location in patent: Paragraph 0029; 0030

62
[ 7681-65-4 ]
[ 104-71-2 ]
C₁₆H₁₆CuIN₂ [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 2345 - 2351

63
[ 7681-65-4 ]
[ 23687-25-4 ]
[ 603-35-0 ]
[CuI(PPh₃)₂(4-aminoisoquinoline)] [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2017,vol. 2017,p. 5134 - 5142

64
[ 7681-65-4 ]
[ 4731-65-1 ]
[ 75-05-8 ]
C₄₂H₄₂Cu₂I₂O₆P₂*C₂H₃N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%		Weigh 60mg CuI dissolved in 20mL of acetonitrile,Weigh 110 mg of o-anisyl3P ligand in 20 mL of acetonitrile (The molar ratio of the three reactants is 1: 1)The two solutions are mixed, And stirred to make it fully coordinate reaction, Finally, the resulting yellow reaction solution was removed by rotary evaporation of all solvents,Vacuum dried, Get the yellow crystal powder is the product,Yield 99percent (in terms of Cu).

Reference： [1]Patent: CN104830321,2016,B .Location in patent: Paragraph 0027-0028

65
[ 7681-65-4 ]
[ 118949-61-4 ]
C₁₇H₂₃CuIN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	In dichloromethane; at 20℃; for 24h;Inert atmosphere;	A 20 mL two-necked round-bottomed flask was charged with 69.2 mg (0.23 mmol, MW: 301) of pybox- ip, 87.6mg(0.46 mmol, MW: 190.45) of CuI and 5.0 mL of anhydrous CH2Cl2. A slow stream of nitrogen was passed throughthe system, and the solution was stirred well at room temperature for 24 h by means of magnetic stirring bar. Theexcess CuI was filtered off and the solvent of the filtrate was removed under reduced pressure and a yellow solid wasformed. After drying in vacuum at room temperature, the yield of F was 76.0% (85.4 mg). The structure of thiscatalyst was not confirmed.

Reference： [1]Letters in Organic Chemistry,2018,vol. 15,p. 196 - 205

66
[ 996-98-5 ]
[ 7681-65-4 ]
[ 10111-08-7 ]
3Cu⁽²⁺⁾*2I^(1-)*2C₁₀H₈N₈O₂^(2-) [ No CAS ]

Reference： [1]Inorganic Chemistry,2018,vol. 57,p. 2377 - 2380

67
[ 7681-65-4 ]
[ 13406-29-6 ]
C₈₄H₄₈Cu₄F₃₆I₄P₄ [ No CAS ]

Reference： [1]Inorganic Chemistry,2018,vol. 57,p. 4328 - 4339

68
[ 546-68-9 ]
[ 7681-65-4 ]
[ 24242-19-1 ]
Ti₃O₉C₂₄H₅₆⁽²⁺⁾*2C₆H₅N₂O₂^(1-)*0.5Cu₄I₄ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 2952 - 2961

69
[ 546-68-9 ]
[ 7681-65-4 ]
[ 4385-76-6 ]
3C₁₂H₈NO₂^(1-)*C₃₆H₈₄Cu₄I₄O_13.5Ti_4.5⁽³⁺⁾ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 2952 - 2961

70
[ 546-68-9 ]
[ 7681-65-4 ]
[ 4595-61-3 ]
3Ti₃O₉C₂₄H₅₆⁽²⁺⁾*6C₅H₃N₂O₂^(1-)*2Cu₄I₄ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 2952 - 2961

71
[ 546-68-9 ]
[ 7681-65-4 ]
[ 75-05-8 ]
[ 216959-91-0 ]
Ti₃O₉C₂₄H₅₆⁽²⁺⁾*2C₁₁H₇N₂O₂^(1-)*2C₂H₃N*Cu₈I₈ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 2952 - 2961

72
[ 7681-65-4 ]
[ 2456-81-7 ]
[ 603-35-0 ]
[Cu₂I₂(triphenylphosphine)₂(4-pyrrolidinopyridine)₂] [ No CAS ]

Reference： [1]Inorganic Chemistry,2018,vol. 57,p. 5929 - 5938

73
[ 7681-65-4 ]
[ 2456-81-7 ]
[ 6224-63-1 ]
[Cu₂I₂(tri-m-tolylphosphine)₂(4-pyrrolidinopyridine)₂] [ No CAS ]

Reference： [1]Inorganic Chemistry,2018,vol. 57,p. 5929 - 5938

74
[ 7681-65-4 ]
[ 2456-81-7 ]
[ 1038-95-5 ]
[Cu₂I₂(tri-p-tolylphosphine)₂(4-pyrrolidinopyridine)₂] [ No CAS ]

Reference： [1]Inorganic Chemistry,2018,vol. 57,p. 5929 - 5938

75
[ 7681-65-4 ]
[ 17217-57-1 ]
[ 603-35-0 ]
C₃₀H₂₇CuIN₂O₂P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In dichloromethane; for 2h;Inert atmosphere;	[CuI(PPh3) (L)] (1), L=4,4?-dimethoxy-2,2?-bipyridine). To achieve the synthesis of 1, CuI (1 mmol, 98percent from Sigma-Aldrich) was dissolved in dichloromethane (DCM, 10 mL) with magnetic stirring under a nitrogen atmosphere until complete dissolution of the CuI. Immediately after dissolution, the ligands 4,4?-dimethoxy-2,2?-bipyridine(L) (1 mmol, 97percent from Sigma-Aldrich) and triphenylphosphine(PPh3, 1 mmol, 99percent from Sigma-Aldrich) were added and the mixture was stirred under flowing nitrogen for 2 h in the dark. After this, the resulting orange precipitate was collected by filtration and dried under constant flow of N2 for 48 h. The yield was 75percent. 1H NMR spectrum(500 MHz, CD3COCD3) delta ppm 4.02 (s, 6H) 7.30?7.37 (m, 6H)7.38?7.43 (m, 3H) 7.44?7.50 (t, 6H) 7.52?7.57 (m, 2H) 7.60?7.65 (m,2H) 7.67?7.72 (m, 2H). IR (ATR): nu=493 (m), 503 (m), 523 (vs), 540(w), 574 (vw), 590 (vw), 694 (vs), 722 (w), 747 (m), 820 (w), 830 (w),845 (vw), 863 (w), 881 (vw), 900 (vw), 914 (vw), 998 (vw), 1023 (s),1044 (w), 1091 (vw), 1120 (vw), 1157 (vw), 1180 (vw), 1215 (m),1248 (m), 1270 (w), 1308 (w), 1325 (w), 1409 (w), 1422 (w), 1431(w), 1454 (vw), 1467 (vw), 1478 (vw), 1490 (w), 1560 (m), 1604 (m),2833 (vw), 2941 (vw), 2973 (vw), 2994 (vw), 3022 (vw), 3050 (vw),3068 (vw). Anal. for C30H27CuIN2O2P (668.94): C 53.78, H 4.21, N4.18; found C 53.13, H 4.19, N 4.15.

Reference： [1]Dyes and Pigments,2018,vol. 159,p. 464 - 470

76
[ 7681-65-4 ]
[ 66-71-7 ]
[ 13885-09-1 ]
C₃₆H₂₇CuIN₂P [ No CAS ]
C₃₆H₂₇Cu₂I₂N₂P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28.2%; 27.1%	In ethyl acetate; for 0.0833333h;	A solution of CuI (0.019 g, 0.1 mmol) in CH3CN(5 mL) wasadded to a stirred solution of 1,10-phenanthroline (0.018 g,0.1 mmol) and 2-(Dpp)bp (0.034 g, 0.1 mmol) in EtOAc(5 mL). The mixture was stirred for 5 min and then the precipitatewas filtered off. The resultant clear solution was setaside for evaporation in air. Orange block crystals of complex1 were obtained after 1 day and red crystals of complex2 were obtained the next day. These two different productswere separated manually under a microscope. Yield: 20.0 mg(28.2percent, based on Cu) for 1 and 24.4 mg (27.1percent, based onCu) for 2. Anal. Calc. for 1 C36H27N2P1Cu1I1:C, 60.98; H,3.81; N, 3.95. Found (percent): C, 61.04; H, 3.81; N, 3.88. IR(KBr pellet, cm?1): 3446sh, 3004s, 1789m, 1639m, 1550s,1448m, 1209w, 1120m, 716m; for 2 C36H27N2P1Cu2I2:C,48.07; H, 3.03; N, 3.12. Found (percent): C, 48.14; H, 3.04; N,3.04. IR (KBr pellet, cm?1): 3522sh, 3004s, 1639w, 1461m,1221s, 930s, 868s.

Reference： [1]Transition Metal Chemistry,2018,vol. 43,p. 517 - 527

77
[ 366-18-7 ]
[ 7681-65-4 ]
[ 13885-09-1 ]
C₃₄H₂₇CuIN₂P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63.4%	In acetonitrile; for 0.166667h;	A solution of CuI (0.019 g, 0.1 mmol) in CH3CN(5 mL) wasadded to a stirred solution of 2,2?-Bipy (0.016 g, 0.1 mmol)and 2-(Dpp)bp (0.034 g, 0.1 mmol) in CH3CN(5 mL). Themixture was stirred for 10 min, with no visible precipitation.After filtration, the clear filtrate was set aside for evaporationin air. Orange block crystals of complex 4 were obtainedafter several hours. Yield: 43.4 mg (63.4percent, based on Cu).Anal. Calc. for 4 C34H27N2P1Cu1I1:C, 59.63; H, 3.94; N,4.09. Found (percent): C, 59.64; H, 3.92; N, 3.98. IR (KBr pellet,cm?1): 3430sh, 3054vw, 1610m, 1431s, 1146w, 1103w,770, 699.

Reference： [1]Transition Metal Chemistry,2018,vol. 43,p. 517 - 527

78
[ 7681-65-4 ]
[ 1137-68-4 ]
[ 13885-09-1 ]
C₃₆H₂₈CuIN₃P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48.5%	In dichloromethane; acetonitrile; for 0.0833333h;	A solution of CuI (0.019 g, 0.1 mmol) in CH3CN(5 mL)was added to a stirred solution of 2-PBI (0.020 g, 0.1 mmol)and 2-(Dpp)bp (0.034 g, 0.1 mmol) in CH2Cl2(5 mL). Themixture was stirred for 5 min, with no visible precipitation.After filtration, the filtrate was set aside for evaporation inair. Yellow block crystals of complex 3 were obtained after3 days. Yield: 35.1 mg (48.5percent, based on Cu). Anal. Calc. for3 C36H28N3P1Cu1I1:C, 59.73; H, 3.87; N, 5.81. Found (percent):C, 59.72 H, 3.84; N, 5.78. IR (KBr pellet, cm?1): 3443sh,3077vs, 3054s, 1610w, 1491m, 1443vs, 1326m, 1114w,805m, 746vs, 711vs, 522m.

Reference： [1]Transition Metal Chemistry,2018,vol. 43,p. 517 - 527

79
[ 7681-65-4 ]
[ 75-05-8 ]
[ 13406-29-6 ]
C₁₂₈H₇₅Cu₇F₅₄I₇NP₆*8C₂H₃N [ No CAS ]

Reference： [1]Inorganic Chemistry,2018,vol. 57,p. 11961 - 11969

80
[ 7681-65-4 ]
[ 1122-28-7 ]
[ 109-89-7 ]
Cu₄I₄*C₄H₁₁N*C₅HN₄^(1-)*H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 11264 - 11267

81
[ 102-69-2 ]
[ 7681-65-4 ]
[ 1122-28-7 ]
Cu₄I₄*C₉H₂₁N*C₅HN₄^(1-)*H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 11264 - 11267

82
[ 7681-65-4 ]
[ 1122-28-7 ]
[ 111-18-2 ]
[ 7732-18-5 ]
Cu₁₆I₁₆*4C₅HN₄^(1-)*H₂O*2C₁₀H₂₄N₂*2H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 11264 - 11267

83
[ 17084-13-8 ]
diphenyl(3-bromopropyl)phosphine [ No CAS ]
[ 7681-65-4 ]
[ 4733-39-5 ]
[ 4111-54-0 ]
bis[2,9-bis{4-(diphenylphosphanyl)butyl}-4,7-diphenyl-1,10-phenanthroline copper(I)] bis-hexafluorophosphate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 17241 - 17254

84
[ 657408-07-6 ]
[ 7681-65-4 ]
[ 60556-38-9 ]
silver fluoride [ No CAS ]
[2'-dicyclohexylphosphino-2,6-dimethoxy-1,1-biphenyl₂Cu^I]⁺[Cu^III(CF₃)₄]⁻ [ No CAS ]

Reference： [1]Dalton Transactions,2019,vol. 48,p. 848 - 853

85
[ 7681-65-4 ]
[ 10034-85-2 ]
[ 140681-55-6 ]
C₂₈H₅₆Cl₄Cu₅I₆N₈⁽³⁺⁾*Cu₂I₅^(3-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; N,N-dimethyl-formamide; at 85℃; for 160h;Sealed tube;	First, add 0.05mmol CuI to the hard glass tube (Tianjin Guangfu Fine Chemical Research Institute), 0.04 mmol [C7H14N2FCl][BF4]2 (Shanghai Fluorui Fine Chemical Co., Ltd.), 0.4 mmol HI (H104605-100 ml) and 0.4 mL solvent (the solvent consists of DMF and water in a volume ratio of 1:1), The filling rate of the glass tube was 10%. The ultrasound was evenly dispersed and then sealed on an alcohol lamp (ie, the glass tube was sealed for the reaction to be in a closed state). Placed in the reaction kettle and placed in a drying oven at 85 C (no vacuum required) for 160 hours. After the reaction was completed, it was allowed to cool to room temperature naturally, and a transparent block crystal was observed in the glass tube.The inorganic-organic hybrid copper iodide is obtained by washing with acetonitrile and ethanol, respectively, followed by drying.

Reference： [1]Patent: CN109293685,2019,A .Location in patent: Paragraph 0014; 0023-0025

86
[ 7681-65-4 ]
[ 21948-70-9 ]
[Cu₂(μ₂-I)₂(2-(methylthio)pyrazine)₄] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	In acetonitrile; at 20℃; for 1h;	To a mixture of <strong>[21948-70-9]2-(methylthio)pyrazine</strong> (59 mg, 0.46 mmol) and CuI (44.5 mg,0.23 mmol), MeCN (5 mL) was added and the suspension was stirred at ambient temperature for 1 h. The precipitated redorangepowder was centrifuged and re-crystallized from acetonitrile to give 36 mg (35%) of 1. FT-IR (KBr, cm-1): 376 (w),397 (w), 413 (w), 434 (w), 484 (m), 633 (w), 648 (w), 723 (m), 762 (vs), 964 (m), 1007 (m), 1053 (m), 1094 (m), 1130 (m),1159 (s), 1263 (m), 1375 (m), 1420 (s), 1456 (s), 1560 (m), 1584 (s), 2922 (w), 2963 (w), 2982 (w), 3061 (w), 3098 (w).Anal. Calcd (%) for C20H24Cu2I2N8S4: 27.1, 2.7, N 12.6, S 14.5. Found: 27.0, 2.9, N 12.5, S 14.7.

Reference： [1]Journal of Structural Chemistry,2019,vol. 60,p. 967 - 971
Zh. Strukt. Kim.,2019,vol. 60,p. 1008 - 1012,5

87
[ 7681-65-4 ]
[ 22795-99-9 ]
(((S)-2-(aminomethyl)-1-ethylpyrrolidine))2Cu2I2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;Irradiation;	The method for preparing a chiral copper-iodine complex in this embodiment is as follows: a) In a 15ml centrifuge tube, add 10ml of absolute ethanol, 0.38mg of CuI, and 300ul of (S) -2- (aminomethyl) -1-ethylpyrrolidine ((S) -2- (Aminomethyl) -1 -ethylpyrrolidine), tighten the cap of the centrifuge tube.b) Shake until the raw materials of the two are mixed uniformly, and a yellow-green phosphor can be generated by irradiating with a 254nm ultraviolet lamp.c) The raw material solution was left to stand overnight, and colorless transparent crystals were found. Decant the ethanol in the centrifuge tube and wash the crystals with n-hexane to obtain a chiral copper-iodine complex crystal with a clean surface.d) Through single crystal X-ray characterization and OLEX software data analysis, the structure information of the chiral copper-iodine complex crystal is obtained, so as to obtain the coordination mode and two-core structure between copper iodine and chiral organic molecules, and the chemical formula is ((( S) -2- (Aminomethyl) -1-ethylpyrrolidine)) 2Cu2I2

Reference： [1]Patent: CN110105378,2019,A .Location in patent: Paragraph 0035-0040

88
[ 7681-65-4 ]
sodium azide [ No CAS ]
[ 3939-14-8 ]
Cu⁽¹⁺⁾*C₆H₃FN₅^(1-) [ No CAS ]

Reference： [1]Inorganic Chemistry,2020

Type	HazMat fee for 500 gram (Estimated)
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CAS No. :	7681-65-4	MDL No. :	MFCD00010978
Formula :	CuI	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LSXDOTMGLUJQCM-UHFFFAOYSA-M
M.W :	190.45	Pubchem ID :	6432705
Synonyms :

Signal Word:	Danger	Class:	9
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Hazard Statements:	H302-H315-H317-H318-H335-H410	Packing Group:	Ⅲ
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