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CAS No. : | 729-17-9 | MDL No. : | MFCD01122234 |
Formula : | C15H14O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 242.27 | 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 |
---|---|---|
98% | Stage #1: With sodium hydroxide; water In tetrahydrofuran at 20℃; for 16.5 h; Heating / reflux Stage #2: With hydrogenchloride In tetrahydrofuran; water |
[0158] Step 2 : 4 -METHOXY-BIPHENYL-4-CARBOXYLIC acid. 1 N NAOH (148.5 mL, 148. 5 mmol) was added under nitrogen to a solution of 4 -METHOXY-BIPHENYL-4-CARBOXYLIC acid methyl ester (12. 0G, 49.5 mmol), prepared in the previous step, in 1 L of THF plus 250 ML of water at room temperature. After the addition the reaction was refluxed for 16.5 h (overnight). After cooling to approximately room temperature the reaction was acidified by the addition of 1 N HC1 and then concentrated under reduced pressure. The solid that formed was collected by filtration and dried under reduced pressure to give 4 -METHOXY-BIPHENYL-4-CARBOXYLIC acid (11. 11 G, 98percent) as a white solid, mp 245-250°C ; MS (ESI) M/Z 227 [M-H]-. Elemental Analysis for C14H1203 : Calc'd: C, 73.67 ; H, 5.30 ; N, 0.00 ; Found: C, 69.52 ; H, 5.01 ; N, 0.04. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | [0158] Step 2 : 4 -METHOXY-BIPHENYL-4-CARBOXYLIC acid. 1 N NAOH (148.5 mL, 148. 5 mmol) was added under nitrogen to a solution of 4 -METHOXY-BIPHENYL-4-CARBOXYLIC acid methyl ester (12. 0G, 49.5 mmol), prepared in the previous step, in 1 L of THF plus 250 ML of water at room temperature. After the addition the reaction was refluxed for 16.5 h (overnight). After cooling to approximately room temperature the reaction was acidified by the addition of 1 N HC1 and then concentrated under reduced pressure. The solid that formed was collected by filtration and dried under reduced pressure to give 4 -METHOXY-BIPHENYL-4-CARBOXYLIC acid (11. 11 G, 98%) as a white solid, mp 245-250C ; MS (ESI) M/Z 227 [M-H]-. Elemental Analysis for C14H1203 : Calc'd: C, 73.67 ; H, 5.30 ; N, 0.00 ; Found: C, 69.52 ; H, 5.01 ; N, 0.04. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium phosphate; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 100 - 110℃; Inert atmosphere; | |
96% | With trans-chloro(9-phenanthrenyl)bis(triphenylphosphine)nickel(II); potassium carbonate; triphenylphosphine In toluene at 110℃; for 18h; Inert atmosphere; | |
94% | With 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; palladium diacetate; potassium carbonate In 1,4-dioxane; 1,3,5-trimethyl-benzene at 135℃; for 24h; Inert atmosphere; |
92% | With potassium phosphate; 2-(diphenylphosphino)phenylferrocene In toluene at 110℃; for 24h; | |
89% | With potassium fluoride; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 100℃; for 4h; | |
89% | With KF In tetrahydrofuran | 104 4-methyloxycarbonyl-4'-methoxy-1,1'-biphenyl (Table 15, Entry 6) Example 104 4-methyloxycarbonyl-4'-methoxy-1,1'-biphenyl (Table 15, Entry 6) Methyl 4-chlorobenzoate (171 mg, 1.00 mmol) reacted with 4-methoxyphenylboronic acid (200 mg, 1.31 mmol) using 1/2 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 and KF (180 mg, 3.10 mmol) in THF at 100° C. for 4 h to give the title compound (210 mg, 89%) as a white solid: 1H-NMR (500 MHz, CDCl3): δ 8.09 (d, 2H, J=8.35 Hz), 7.63 (d, 2H, J=8.30 Hz), 7.59 (d, 2H, J=8.71 Hz), 7.01 (d, 2H, J=8.73 Hz), 3.95 (s, 3H), 3.88 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 167.02, 159.77, 145.14, 132.32, 130.05, 128.31, 128.16, 126.40, 114.31, 55.32, 52.03. GC/MS (EI): m/z 242 (M+), 211, 139. |
78% | With caesium carbonate at 100℃; for 20h; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; | |
In water; ethyl acetate; N,N-dimethyl-formamide | 9.1 (1) (1) Methyl 4-(4'-methoxyphenyl)benzoate A mixed solution of 4-(4'-hydroxyphenyl)benzoic acid (10.0 g, 4.67 mmol), iodomethane (19.9 g, 14.0 mmol) and N,N-dimethylformamide (80 ml) was stirred at 60° C. for 3 hours. To the obtained mixture was added ethyl acetate (200 ml) and water (150 ml), the mixture was stirred and the organic layer was separated. The organic layer was washed with 5% aqueous potassium hydrogen sulfate and water, and dried over sodium sulfate anhydride. The solvent was concentrated under reduced pressure and the object compound (10.5 g) was obtained from the residue as colorless crystals. Melting point: 177-178° C. 1H-NMR (CDCl3) δ; 3.86 (3H, s), 3.94 (3H, s), 7.00 (2H, d, J=8.8 Hz), 7.58 (2H, d, J=8.8 Hz), 7.62 (2H, d, J=8.4 Hz), 8.08 (2H, d, J=8.4 Hz). | |
With potassium carbonate In N,N-dimethyl-formamide at 25℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine; In tetrahydrofuran; at 23℃; for 12h;Inert atmosphere; Glovebox; Sealed tube;Catalytic behavior; | General procedure: 3.1 General Procedure 1 for the Cross-Coupling of 4-Methoxyphenyl Halides and Mesylates with Aryl Neopentylglycolboronates Catalyzed by Ni-Precatalysts and Mixed-Ligand Systems in Dry THF at 23 C In an oven dried test tube charged with a Teflon coated stirring bar, aryl halide or aryl mesylate (0.3 mmol), <strong>[905966-40-7]methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate</strong> (78.13 mg, 0.315 mmol), K3PO4(H2O)3.2 ((191.00 ± 1.00 mg, 0.9 mmol) and Ni-catalyst were added (in the case of NiIICl(1-naphthyl)(PCy3)2 (11.18 ± 0.0510 mg, 0.015 mmol, 5% catalyst loading) and NiIICl(1-naphthyl)(PPh3)2) (11.73 ± 0.0510 mg, 0.015 mmol, 5% catalyst loading). The test tube was brought into a nitrogen filled glove box (moisture level < 2 ppm) through three degassing cycles and PCy3 (8.4 mg, 0.03mmol, 10% loading) ligand was added. In the case of Ni(COD)2 (4.12 ± 0.0510 mg, 0.015 mmol, 5% catalyst loading), it was also added inside the glove box. Dry THF (1 mL) was added inside the glove box and the test tube was sealed by a rubber septum and left stirring at 23C.. A sample was taken by syringe and transferred outside the glove box. The sample was diluted by distilled THF (0.2 mL) and filtered through a short column of aluminum oxide. The filtrate was concentrated and the GC analysis was carried out. The reaction mixture was diluted with dichloromethane (2 mL), filtered through a layer of aluminum oxide and washed with dichloromethane (1 mL) three times. The filtrate was collected and concentrated under vacuum. The crude product was purified by column chromatography on silica gel with EtOAc/hexane mixture as eluent. The reductive elimination side-product was also isolated and characterized. |
90% | With potassium phosphate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 18h;Product distribution / selectivity; | A Schlenk tube was charged with aryl halide (0.67 mmol, 1.0 equiv), aryl boronate ester (0.81 mmol, 1.2 equiv), potassium phosphate or CsF (3.0 equiv), Pd catalyst (0.1 equiv), 2-(dicyclohexylphosphino)biphenyl (0.2 equiv) (co-ligand was used in the presence of Pd(OAc)2 as catalyst and CsF as base (see Table 8, entries 13-15); reaction was performed at rt) and a Teflon coated stirbar. The reaction mixture was evacuated three times for ten minutes under high vacuum and backfilled with N2. Dry dioxane was added via the T-neck and the reaction mixture was heated to 110 0C for 18 h. The reaction mixture was cooled to room <n="24"/>temperature and diluted with DCM (10 rnL). The solution was filtered and the filtrated washed with DCM (100 mL). The filtrate was concentrated and purified by silica gel chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine; In tetrahydrofuran; at 23℃; for 14h;Inert atmosphere; Glovebox; Sealed tube;Catalytic behavior; | General procedure: 3.1 General Procedure 1 for the Cross-Coupling of 4-Methoxyphenyl Halides and Mesylates with Aryl Neopentylglycolboronates Catalyzed by Ni-Precatalysts and Mixed-Ligand Systems in Dry THF at 23 C In an oven dried test tube charged with a Teflon coated stirring bar, aryl halide or aryl mesylate (0.3 mmol), <strong>[905966-40-7]methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate</strong> (78.13 mg, 0.315 mmol), K3PO4(H2O)3.2 ((191.00 ± 1.00 mg, 0.9 mmol) and Ni-catalyst were added (in the case of NiIICl(1-naphthyl)(PCy3)2 (11.18 ± 0.0510 mg, 0.015 mmol, 5% catalyst loading) and NiIICl(1-naphthyl)(PPh3)2) (11.73 ± 0.0510 mg, 0.015 mmol, 5% catalyst loading). The test tube was brought into a nitrogen filled glove box (moisture level < 2 ppm) through three degassing cycles and PCy3 (8.4 mg, 0.03mmol, 10% loading) ligand was added. In the case of Ni(COD)2 (4.12 ± 0.0510 mg, 0.015 mmol, 5% catalyst loading), it was also added inside the glove box. Dry THF (1 mL) was added inside the glove box and the test tube was sealed by a rubber septum and left stirring at 23C.. A sample was taken by syringe and transferred outside the glove box. The sample was diluted by distilled THF (0.2 mL) and filtered through a short column of aluminum oxide. The filtrate was concentrated and the GC analysis was carried out. The reaction mixture was diluted with dichloromethane (2 mL), filtered through a layer of aluminum oxide and washed with dichloromethane (1 mL) three times. The filtrate was collected and concentrated under vacuum. The crude product was purified by column chromatography on silica gel with EtOAc/hexane mixture as eluent. The reductive elimination side-product was also isolated and characterized. |
95% | With potassium phosphate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 110℃; for 18h;Product distribution / selectivity; | A Schlenk tube was charged with aryl halide (0.67 mmol, 1.0 equiv), aryl boronate ester (0.81 mmol, 1.2 equiv), potassium phosphate or CsF (3.0 equiv), Pd catalyst (0.1 equiv), 2-(dicyclohexylphosphino)biphenyl (0.2 equiv) (co-ligand was used in the presence of Pd(OAc)2 as catalyst and CsF as base (see Table 8, entries 13-15); reaction was performed at rt) and a Teflon coated stirbar. The reaction mixture was evacuated three times for ten minutes under high vacuum and backfilled with N2. Dry dioxane was added via the T-neck and the reaction mixture was heated to 110 0C for 18 h. The reaction mixture was cooled to room <n="24"/>temperature and diluted with DCM (10 rnL). The solution was filtered and the filtrated washed with DCM (100 mL). The filtrate was concentrated and purified by silica gel chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium phosphate;bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; In tetrahydrofuran; at 20 - 25℃; for 8 - 12h;Product distribution / selectivity; | In a glove box with N2 atmosphere, a Schlenk tube was charged with aryl halide, tosylate or mesylate (1.0 equiv), aryl neopentylglycolboronate (1.5 equiv), potassium phosphate (0.9 mmol, 3.0 equiv), Ni(COD)2 (0.018 mmol, 0.06 equiv), tricyclohexylphosphine (0.11 mmol, 0.18 equiv), and a Teflon coated stirbar. Dry THF (2 ml) was added and reaction was left stirring for 8 h at rt. The reaction mixture was diluted with DCM (10 mL) and filtered. The filtrated solid was washed with DCM (100 mL) and the organic solvent concentrated. The coupling products were precipitated in MeOH and the white crystals were filtrated and washed with cold MeOH. |
97% | With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine; In tetrahydrofuran; at 23℃; for 1h;Inert atmosphere; Glovebox; Sealed tube;Catalytic behavior; | General procedure: 3.1 General Procedure 1 for the Cross-Coupling of 4-Methoxyphenyl Halides and Mesylates with Aryl Neopentylglycolboronates Catalyzed by Ni-Precatalysts and Mixed-Ligand Systems in Dry THF at 23 C In an oven dried test tube charged with a Teflon coated stirring bar, aryl halide or aryl mesylate (0.3 mmol), <strong>[905966-40-7]methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate</strong> (78.13 mg, 0.315 mmol), K3PO4(H2O)3.2 ((191.00 ± 1.00 mg, 0.9 mmol) and Ni-catalyst were added (in the case of NiIICl(1-naphthyl)(PCy3)2 (11.18 ± 0.0510 mg, 0.015 mmol, 5% catalyst loading) and NiIICl(1-naphthyl)(PPh3)2) (11.73 ± 0.0510 mg, 0.015 mmol, 5% catalyst loading). The test tube was brought into a nitrogen filled glove box (moisture level < 2 ppm) through three degassing cycles and PCy3 (8.4 mg, 0.03mmol, 10% loading) ligand was added. In the case of Ni(COD)2 (4.12 ± 0.0510 mg, 0.015 mmol, 5% catalyst loading), it was also added inside the glove box. Dry THF (1 mL) was added inside the glove box and the test tube was sealed by a rubber septum and left stirring at 23C.. A sample was taken by syringe and transferred outside the glove box. The sample was diluted by distilled THF (0.2 mL) and filtered through a short column of aluminum oxide. The filtrate was concentrated and the GC analysis was carried out. The reaction mixture was diluted with dichloromethane (2 mL), filtered through a layer of aluminum oxide and washed with dichloromethane (1 mL) three times. The filtrate was collected and concentrated under vacuum. The crude product was purified by column chromatography on silica gel with EtOAc/hexane mixture as eluent. The reductive elimination side-product was also isolated and characterized. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With potassium phosphate;bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine; In tetrahydrofuran; at 20 - 25℃; for 8 - 12h;Product distribution / selectivity; | In a glove box with N2 atmosphere, a Schlenk tube was charged with aryl halide, tosylate or mesylate (1.0 equiv), aryl neopentylglycolboronate (1.5 equiv), potassium phosphate (0.9 mmol, 3.0 equiv), Ni(COD)2 (0.018 mmol, 0.06 equiv), tricyclohexylphosphine (0.11 mmol, 0.18 equiv), and a Teflon coated stirbar. Dry THF (2 ml) was added and reaction was left stirring for 8 h at rt. The reaction mixture was diluted with DCM (10 mL) and filtered. The filtrated solid was washed with DCM (100 mL) and the organic solvent concentrated. The coupling products were precipitated in MeOH and the white crystals were filtrated and washed with cold MeOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With potassium phosphate; C18H9F5NOP(2-)*Pd(2+)*C3H7NO In ethanol at 20℃; for 6h; Schlenk technique; Inert atmosphere; | |
89% | With potassium phosphate; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 100℃; Inert atmosphere; | |
86% | With potassium hydroxide In tetrahydrofuran; water at 60℃; for 0.0833333h; |
80% | With C21H19N2(1+)*Br(1-); palladium diacetate; potassium carbonate In toluene at 70℃; for 3h; | 3. Catalytic Coupling ReactionsGeneral procedure for Palladium(II)-catalyzed Suzuki-Miyaura reaction: General procedure: A reaction tube was charged with Pd(OAc)2 (1.34 mg, 0.006 mmol), imidazolium salt (0.0072 mmol), K2CO3 (62 mg, 0.45 mmol), and ArB(OH)2 (0.45 mmol). To the reaction tube were added toluene (2.0 mL) and aryl bromide (0.3 mmol). The mixture was stirred at 70 °C in the presence of air for 3 hours. The mixture was cooled to room temperature and directly purified through silica gel column chromatography to give the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With NHC-Pd(II)-Im; tetrabutyl ammonium fluoride In toluene at 120℃; for 3h; Inert atmosphere; | General procedure for the NHC-Pd(II)-Im complex 1 catalyzed Hiyama reaction of aryl chlorides with aryltrimethoxysilanes General procedure: Under N2 atmosphere, NHC-Pd(II)-Im 1 (1.0 mol%), dry toluene (2.0 mL), aryl chlorides 2 (0.81 mmol), aryltrimethoxysilanes 3 (2.0 equiv) and TBAF•3H2O (2.0 equiv) were successively added into a Schlenk reaction tube. Then the tube was placed in a 120 °C oil bath and stirred for 3 h. The mixture was then allowed to cool to room temperature, diluted with ethyl acetate and washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and then purified by flash chromatography to give the pure products 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine; In tetrahydrofuran; at 23℃; for 1h;Inert atmosphere; Glovebox; Sealed tube;Catalytic behavior; | General procedure: 3.1 General Procedure 1 for the Cross-Coupling of 4-Methoxyphenyl Halides and Mesylates with Aryl Neopentylglycolboronates Catalyzed by Ni-Precatalysts and Mixed-Ligand Systems in Dry THF at 23 C In an oven dried test tube charged with a Teflon coated stirring bar, aryl halide or aryl mesylate (0.3 mmol), <strong>[905966-40-7]methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate</strong> (78.13 mg, 0.315 mmol), K3PO4(H2O)3.2 ((191.00 ± 1.00 mg, 0.9 mmol) and Ni-catalyst were added (in the case of NiIICl(1-naphthyl)(PCy3)2 (11.18 ± 0.0510 mg, 0.015 mmol, 5% catalyst loading) and NiIICl(1-naphthyl)(PPh3)2) (11.73 ± 0.0510 mg, 0.015 mmol, 5% catalyst loading). The test tube was brought into a nitrogen filled glove box (moisture level < 2 ppm) through three degassing cycles and PCy3 (8.4 mg, 0.03mmol, 10% loading) ligand was added. In the case of Ni(COD)2 (4.12 ± 0.0510 mg, 0.015 mmol, 5% catalyst loading), it was also added inside the glove box. Dry THF (1 mL) was added inside the glove box and the test tube was sealed by a rubber septum and left stirring at 23C.. A sample was taken by syringe and transferred outside the glove box. The sample was diluted by distilled THF (0.2 mL) and filtered through a short column of aluminum oxide. The filtrate was concentrated and the GC analysis was carried out. The reaction mixture was diluted with dichloromethane (2 mL), filtered through a layer of aluminum oxide and washed with dichloromethane (1 mL) three times. The filtrate was collected and concentrated under vacuum. The crude product was purified by column chromatography on silica gel with EtOAc/hexane mixture as eluent. The reductive elimination side-product was also isolated and characterized. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine; In tetrahydrofuran; at 23℃; for 4h;Inert atmosphere; Glovebox; Sealed tube; | General procedure: Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ± 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ± 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; triphenylphosphine; cesium fluoride In N,N-dimethyl-formamide at 90℃; for 1h; Inert atmosphere; Green chemistry; | 2.1 Palladium cross coupling procedure General procedure: Under inert atmosphere (N2), in a 25 mL round bottom flask, Ar3Bi (0.208 mmol; 0.35 eq.), CsF (0.24 g: 1.8 mmol; 3 eq.), PPh3 (0.004 g: 0.018 mmol; 3 mol%), the aryl bromide (0.60 mmol; 1 eq.) was added to DMF (5 mL). The solution was warmed to 90 °C prior addition of PEPPSI IPr (0.012 g: 0.018 mmol; 3 mol%). The reaction was monitored by GC/MS to follow the total consumption of the aryl bromide. Cooled to room temperature (RT), the reaction mixture was diluted by addition of diethyl ether (20 mL) and aqueous HCl 6 M (30 mL). After decantation, the aqueous solution was extracted with diethylether (2 * 20 mL). The collected organic phases were then washed with HCl 6 N (2 * 25 mL), water (25 mL) and brine (25 mL) prior drying over MgSO4. After concentration under reduced pressure, the resulting crude product was subjected to purification by column chromatography leading after concentration under reduced pressure to the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine In tetrahydrofuran at 100℃; for 16h; Inert atmosphere; Glovebox; Overall yield = 82 %Spectr.; |
Tags: 729-17-9; Methyl 4'-methoxybiphenyl-4-carboxylate; Aryls
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P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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