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CAS No. : | 1942-30-9 | MDL No. : | |
Formula : | C14H9NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 223.23 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydrogenchloride; tin In water monomer at 60℃; for 6h; | |
93% | With nickel In N,N-dimethyl-formamide for 0.25h; Ambient temperature; | |
93% | With 4,4'-bipyridine; tetrahydroxydiborane In N,N-dimethyl-formamide at 20℃; for 0.0833333h; chemoselective reaction; |
91% | With tris(triphenylphosphine)ruthenium(II) chloride; potassium hydroxide; zinc powder In 1,4-dioxane; water monomer at 40℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction; | |
83% | With iron sulphate heptahydrate In methanol; water monomer for 11h; Reflux; | |
75% | With hydrazine hydrate monohydrate at 80℃; for 0.416667h; Microwave irradiation; chemoselective reaction; | Typical experimental procedure for microwave-induced transfer hydrogenation of nitro arenes using SS-Rh catalyst A mixture of 1e (100 mg, 0.81 mmol), hydrazine hydrate (121.5mg, 2.43 mmol), and SS-Rh (370 mg, 2 mol% Rh) were taken in an oven dried reaction tube equipped with screw cap. 0.5 ml of PEG-400 was added into the reaction mixture. The reaction was then irradiated in a microwave apparatus at 80°C , 80 W for 10 min with a pressure of 80 Psi. After cooling to ambient temperature in the microwave cavity the reaction mixture was extracted with ethyl acetate (3x2 ml) and water (1ml). The combined organic layer wasdried over anhydrous Na2SO4 and the solvent was removed under reduced pressure and afterpurification with silica gel column chromatography (hexane: EtOAc::95:5) 2e as white solid (65 mg, 75%), m.p. 124-126°C; 1H NMR (300 MHz; CD3OD) δ 6.66-6.68 (d, J = 6.75 Hz, 2H), 7.23-7.24 (d, J = 1.92, 2H), 7.26-7.36 (m, 3H), 7.43-7.46(m, 2H); 13C NMR (75 MHz; CD3OD) δ 88.35, 92.21, 113.36,116.49 (2C), 126.28, 129.33, 130.15 (2C), 132.88 (2C), 134.45 (2C), 150.56.ESI-MS: m/z (M+H).+ ESI-MS: m/zcalc. for (M+H)+ C14H11N 194.2512 and obsd. 194.2535. |
65% | With C36H56Cl3CrN2O; magnesium; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; chemoselective reaction; | |
With phenylhydrazine | ||
With stannous chloride | ||
With hydrogenchloride; zinc powder | ||
With hydrogenchloride; tin In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With potassium hydrogencarbonate In water; N,N-dimethyl-formamide at 100℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | EXAMPLE 1 2.02 g (10 mmol) of 4-bromonitrobenzene and 1.2 g (12 mmol) of phenylacetylene are heated with 10 g (0.1 mol %) of trans-di-mu-acetato-bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) in 30 ml of triethylamine for 4 hours at 90 C. The reaction solution is filtered hot to remove the quantitatively precipitated triethylammonium bromide and the product is separated off by means of fractional crystallization. Yield: 95% of 1-(4-nitrophenyl)-2-phenylethyne. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With tetrakis(triphenylphosphine) palladium(0); copper(l) chloride In N,N-dimethyl-formamide at 80℃; for 3h; | |
92% | With tetrakis(triphenylphosphine) palladium(0); copper(l) chloride In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere; | 4.3. General procedure for synthesis of unsymmetrically disubstituted ethynes with aryl iodides. Formation of (4-methoxyphenyl)(phenyl)ethyne (3a)29a General procedure: To a solution of CuCl (50 mg, 0.5 mmol, 50 mol %), tetrakis(triphenylphosphine)palladium (58 mg, 0.05 mmol, 5 mol %), and 4-iodoanisole (2a) (234 mg, 1 mmol) in DMF (5 mL) in a 20 mL of Schlenk tube was added trimethyl(phenylethynyl)silane (1a) (0.39 mL, 2 mmol). The reaction mixture was stirred for 3 h at 80 °C, quenched with 1.0 M HCl, and extracted with diethyl ether (20 mL×3). The combined ethereal layer was washed with brine and dried over MgSO4. Filtration and evaporation afforded a dark yellow oil. Column chromatography (silica gel, hexane/diethyl ether=9:1, Rf=0.14) gave the title compound (197 mg, 0.84 mmol, 84% yield) as white solid. |
76% | With Potassium benzoate; triphenylphosphine; copper(l) chloride In 1,3-dimethyl-2-imidazolidinone at 120℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 65% 2: 35% | With 5% Au/Fe2O3; hydrogen In toluene at 60℃; for 1h; Autoclave; chemoselective reaction; | |
1: 54% 2: 30% | With triethylsilane; chloro-trimethyl-silane; copper/silver activated zinc In tetrahydrofuran; methanol; water at 20℃; for 15h; stereoselective reaction; | 4.3.9 Reduction of diaryl substituted alkynes General procedure: To a suspension of the Zn(Cu/Ag)-mixture (2.0 g) in MeOH/water (1:1, 6 mL), the alkyne (0.4 mmol, 1 equiv) in THF (0.3 mL) was added followed by the addition of Et3SiH (0.8 mmol, 2 equiv) and TMSCl (0.5 mL, 4.0 mmol, 10 equiv). The reaction mixture was stirred for the specified time for each reaction. Et2O (10 mL) was added, and the reaction mixture was filtered through a short plug of silica gel and eluted with Et2O (30 mL). The combined organic phases were washed with water (10 mL). The organic layer was separated and dried (MgSO4). The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (SiO2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diiron nonacarbonyl; tributylphosphine; Triethoxysilane In tetrahydrofuran at 60℃; for 48h; Inert atmosphere; optical yield given as %de; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With anthracen-9-ylmethylene-(4-methoxyphenyl)amine; palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 100℃; for 2.5h; | General procedure: A mixture of arylboronic acid (1.0mmol), phenylacety-lene (1.2mmol), Pd(OAc) 2 (1.0mol%), L (1.0mol%) and 1,8-diazabicycloundec-7-ene (DBU) (2.0mmol) in DMF (5mL) was stirred at 100C in air for 4h. The reaction mixture was then diluted with EtOAc (20mL) and washed with water (3 × 10mL). The organic layer was dried over anhydrous Na 2 SO 4 , filtered and the solvent was removed. The residue was subjected to column chromatography on silica gel using ethyl acetate and n-hexane mixture to afford the desired product. The products were characterized by 1 H and 13 C NMR analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With {(Pd{Fe(η5-C5H5)(η5-C5H3C(CH3)=NC6H4CH3-4)}(μ-Cl))2}; potassium carbonate; XPhos In acetonitrile at 110℃; for 16h; Inert atmosphere; | |
87% | With tetrabutylammomium bromide; potassium carbonate; palladium dichloride; XPhos In water at 120℃; Inert atmosphere; Schlenk technique; Green chemistry; | Typical procedure for deacetonative coupling of aryl propargylic alcohols with aryl chlorides in water General procedure: To a 25-mL Schlenk tube equipped with magnetic stir bar, aryl chloride (0.2 mmol), aryl propargylic alcohol (0.3 mmol), K2CO3 (2.0 equiv.), TBAB (1.0 equiv.), PdCl2 (2 mol%), and Xphos (4 mol%) were added in turn, then 2 mL H2O was added, and then the solution was refluxed for 24 h under N2 atmosphere. After the reaction was completed, the mixture was extracted with EtOAc or CH2Cl2. The combined organic layer was dried with anhydrous Na2SO4 and evaporated in vacuum. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate as the eluent to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With silver fluoride; potassium hydrogencarbonate; bis(dibenzylideneacetone)-palladium(0) In acetonitrile at 20℃; for 12h; | Synthesis of internal alkynes (3-12); general procedure General procedure: Alkynyl halide 1 (0.2 mmol), aryltrialkoxysilane 2 (0.4 mmol), Pd(dba)2 (3 mol %), AgF (3 equiv.), KHCO3 (2 equiv.), all values compared to 1, and MeCN (2 mL) were added to a Schlenk tube in turn. Then the solution was stirred at room temperature for the indicated time (usually 12 h) until complete consumption of starting material as monitored by TLC and GC-MS analysis. Afterthe reaction was finished, the crude reaction mixture was filtered, poured into diethyl ether (10 mL), washed with brine (3 mL × 3), extracted with diethyl ether (5 mL × 3), dried over anhydrous Na2SO4, and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate) to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 93 %Spectr. 2: 6 %Spectr. | With [{Ir(H)((rac)-BINAP)}2(μ-Cl)3]Cl; hydrogen In 1,4-dioxane at 90℃; for 16h; | General procedure for the Ir-catalyzed semi-hydrogenation of alkynes General procedure: Iridium dinuclear complex (2.4 mol, 1.0 mol%) and alkyne (0.24 mmol) were added to a glasstube in the reactor and the tube was charged with argon gas. Dry 1,4-dioxane (1.5 mL) was addedinto a glass tube in the reactor, and replaced argon gas with H2 gas. The reaction mixture wasstirred for periodic time under optimal conditions. After removal of solvent, the mixture andphenanthrene were dissolved into CDCl3. Yield was determined by 1H NMR analysis usingphenanthrene as an internal standard and reference to literatures. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61%; 68% | In pyridine; for 3h;Reflux; | General procedure: A mixture of alkyne 1a-b, 5a-g, 7a-b (1.6 mmol) and ethylenediamine (5 ml, 75.0 mmol) in pyridine was refluxed for 1-50 h. Solvent was removed under reduced pressure and the crude reaction mixture was purified by column chromatography (toluene/ethyl acetate) to give pure products (Table 2). In the case of 2-(phenylethynyl)pyridine (7b), the reaction mixture was treated with an ethanolic solution of 2,4-dinitrophenylhydrazine to afford (Z)-2-(2-(2-(2,4-dinitrophenyl)hydrazono)-2-phenylethyl)pyridine; yield 35%, mp 196-198C (lit. 192-194C[34]). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 19% 2: 27% 3: 12% | With Oxone; silver nitrate In water; acetonitrile at 60℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With potassium hydroxide In dimethyl sulfoxide at 120℃; for 24h; Schlenk technique; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 20% 2: 28% | With palladium diacetate; sodium carbonate; triphenylphosphine; lithium chloride In N,N-dimethyl-formamide at 100℃; for 24h; Schlenk technique; Inert atmosphere; regioselective reaction; |
Tags: 1942-30-9 synthesis path| 1942-30-9 SDS| 1942-30-9 COA| 1942-30-9 purity| 1942-30-9 application| 1942-30-9 NMR| 1942-30-9 COA| 1942-30-9 structure
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