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CAS No. : | 612-87-3 | MDL No. : | MFCD00845987 |
Formula : | C14H10O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KHZYMPDILLAIQY-UHFFFAOYSA-N |
M.W : | 242.23 | Pubchem ID : | 96533 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
With potassium permanganate | ||
With sodium hydroxide; potassium permanganate Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; | |
With sulfuric acid | ||
alkaline hydrolysis; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide; palladium on activated charcoal; Lindlar's catalyst; hydrazine hydrate at 140℃; | ||
With potassium hydroxide; palladium on activated charcoal |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trichlorophosphate | ||
With thionyl chloride for 2h; Heating; | ||
With thionyl chloride In tetrahydrofuran Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In N,N-dimethyl-formamide for 18h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) potassium iodide, nickel bromide, triphenylphosphine; 2.) zinc, nickel bromide, potassium iodide / 1.) DMF; 2.) DMF, hexamethylphosphoramide 2: alkaline hydrolysis |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2 / 2 h / Heating 2: AlCl3 / 3 h / Heating | ||
Multi-step reaction with 2 steps 1: POCl3 2: (i) CdCl2, Et2O, (ii) /BRN= 2458036/, benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: SOCl2 / 2 h / Heating 2: AlCl3 / 3 h / Heating 3: 77 percent / N2H4*H2O / ethanol / 48 h / Heating 4: 74 percent / MnO2, KOH / CH2Cl2; ethanol / 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: SOCl2 / 2 h / Heating 2: AlCl3 / 3 h / Heating 3: 77 percent / N2H4*H2O / ethanol / 48 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: diethyl ether; aqueous hydrochloric acid 2: aqueous HCl / Diazotization.Behandlung der Diazoniumsalz-Loesung mit wss. H3PO2 3: butyl lithium; diethyl ether / Aufgiessen der Reaktionsloesungen auf festes Kohlendioxid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper powder / 260 °C 2: sulfuric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: tin; aq. NaOH solution 2: diethyl ether; aqueous hydrochloric acid 3: aqueous HCl / Diazotization.Behandlung der Diazoniumsalz-Loesung mit wss. H3PO2 4: butyl lithium; diethyl ether / Aufgiessen der Reaktionsloesungen auf festes Kohlendioxid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aqueous HCl / Diazotization.Behandlung der Diazoniumsalz-Loesung mit wss. H3PO2 2: butyl lithium; diethyl ether / Aufgiessen der Reaktionsloesungen auf festes Kohlendioxid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium/charcoal 2: KMnO4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: diethyl ether 2: palladium/charcoal 3: KMnO4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: diethyl ether 2: diethyl ether 3: palladium/charcoal 4: KMnO4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: copper-powder 2: H2SO4 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: POCl3 2: (i) CdCl2, Et2O, (ii) /BRN= 2458036/, benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: POCl3 2: (i) CdCl2, Et2O, (ii) /BRN= 2458036/, benzene 3: (i) LiAlH4, THF, (ii) /BRN= 3633387/, DMF 4: (i) NaOMe, DMF, (ii) AgClO4, Et2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: POCl3 2: (i) CdCl2, Et2O, (ii) /BRN= 2458036/, benzene 3: (i) LiAlH4, THF, (ii) /BRN= 3633387/, DMF |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: POCl3 2: (i) CdCl2, Et2O, (ii) /BRN= 2458036/, benzene 3: LiAlH4 / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: POCl3 2: (i) CdCl2, Et2O, (ii) /BRN= 2458036/, benzene 3: LiAlH4 / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: POCl3 2: (i) CdCl2, Et2O, (ii) /BRN= 2458036/, benzene 3: LiAlH4 / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: POCl3 2: (i) CdCl2, Et2O, (ii) /BRN= 2458036/, benzene 3: LiAlH4 / tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With NaOH In water High Pressure; H2bdpa:dpe:Cd:NaOH=2:2:2:3 molar ratio, heated at 180°C for 72 h; cooled at room temp. for 24 h, crysts. filtered, washed (H2O), dried (air); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In toluene for 6h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5% | With dmap; 4-(dimethylamino)pyridinium tosylate; diisopropyl-carbodiimide In dichloromethane Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: thionyl chloride / tetrahydrofuran / Reflux 2.1: pyridine / tetrahydrofuran / 0.25 h / 20 °C 2.2: 15 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: thionyl chloride / tetrahydrofuran / Reflux 2.1: pyridine / tetrahydrofuran / 0.25 h / 20 °C 2.2: 15 h 3.1: methanol; triethylamine / 14 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 16 h / 20 - 90 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 14 h / 20 - 90 °C 4: water; lithium hydroxide / tetrahydrofuran; methanol / 20 °C | ||
Multi-step reaction with 3 steps 1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 14 h / 20 - 90 °C 3: water; lithium hydroxide / tetrahydrofuran; methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 16 h / 20 - 90 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 14 h / 20 - 90 °C 3: water; lithium hydroxide / tetrahydrofuran; methanol / 20 °C | ||
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane / 14 h / 20 - 90 °C 2: water; lithium hydroxide / tetrahydrofuran; methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | at 20 - 90℃; for 168h; | Synthesis of 1: A mixture of Cd(NO3)2·4H2O (0.25mmol, 0.0771g), 1,1′-biphenyl-3,3′-dicarboxylic acid (0.50mmol, 0.1211g), NaNO3 (0.25mmol, 0.0212g) was placed in a 20mL of Teflon-lined stainless steel vessel with 3mL of DME. The mixture was sealed and heated at 90°C for five days under autogeneous pressure and then cooled to room temperature in two days. Colorless crystals were collected, washed several times with ethanol and dried in air (yield 86% based on Cd). Anal. calcd for Cd3Na4C110H128N8O28 (2439.36): C, 54.11; H, 5.25; N, 4.59. Found: C, 53.96; H, 4.37; N, 4.22%. IR (KBr pellet, cm-1): 3434(w), 2978(w), 1655(vs), 1558(vs), 1386(vs), 1264(w), 1021(w), 761(s), 698(w). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With nitric acid at 110℃; for 168h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With sodium hydroxide In water at 140℃; for 72h; Autoclave; | Synthesis of compound I. A mixture of Co(NO3)2 6H2O (29.7 mg, 0.10 mmol), 3,3'H2Bpdc (24.2 mg,0.10 mmol), 2,2'Bipy (15.6 mg, 0.10 mmol), and NaOH (8.0 mg, 0.20 mmol) in a solution of H2O (7 mL) were sealed into a 23 mL Teflon-lined stainless steel container under autogenous pressure, heated at 140°C for 3 days and cooled to room temperature for 24 h. Purple prismatic single crystals suitable for X-ray analyses were obtained. The yield was 67% (based on Co(II)). IR (KBr pellet; ν, cm-1): 2968 w, 1606 w, 1560 m, 1542 s,1473 w, 1441 m, 1419 s, 1385 m, 1361 s, 1269 w, 1157 w,1081w, 1022 w, 904 w, 863 w, 757 s. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With sodium hydroxide In water at 140℃; for 72h; Autoclave; | Synthesis of compound I. General procedure: A mixture of Co(NO3)2 6H2O (29.7 mg, 0.10 mmol), 3,3'H2Bpdc (24.2 mg,0.10 mmol), 2,2'Bipy (15.6 mg, 0.10 mmol), and NaOH (8.0 mg, 0.20 mmol) in a solution of H2O (7 mL) were sealed into a 23 mL Teflon-lined stainless steel container under autogenous pressure, heated at 140°C for 3 days and cooled to room temperature for 24 h. Purple prismatic single crystals suitable for X-ray analyses were obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With sodium hydroxide In water at 120℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With sodium hydroxide In water at 140℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With sodium hydroxide In water at 160℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In water at 120℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C 1.2: 20 °C 2.1: dichloromethane / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: biphenyl-3,3'-dicarboxylic acid With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: bis(2-tert-butyloxycarbonylaminoethyl)amine With triethylamine In N,N-dimethyl-formamide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With o-fluoro-benzoic acid at 120℃; for 48h; High pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol at 140℃; for 96h; Sealed tube; Overall yield = 43 percent; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In water; acetonitrile at 90℃; for 24h; Inert atmosphere; | General Procedure A1: Preparation of 5- and 6-aryl analogues via Suzuki-Miyaura cross-coupling. General procedure: A solution of acetonitrile:water (4:1) was degassed by bubbling a stream of nitrogen through the solution for one hour. The aryl halide, boronic acid (6 eq.), caesium fluoride (3 eq.) and Pd(dppf)Cl2 (5 mol%) were added to the degassed solution (25 mL/mmol) and the suspension was heated to 90 °C under an atmosphere of nitrogen. After 16-24h the reaction mixture was partitioned between ethyl acetate and brine. The organic layer was washed with brine (x2), dried over magnesium sulfate then concentrated to the crude residue. In cases where the aryl halide or boronic acid contained a carboxylic acid the organic phase was washed with a saturated solution of sodium hydrogen carbonate (x3). The combined aqueous phases were acidified with concentrated HCl to pH 2, extracted with ethyl acetate (x3) then worked up as above to afford the crude compound. |
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