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Limited Quantity | USD 15-60 |
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CAS No. : | 3375-31-3 | MDL No. : | MFCD00012453 |
Formula : | C4H6O4Pd | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YJVFFLUZDVXJQI-UHFFFAOYSA-L |
M.W : | 224.51 | Pubchem ID : | 167845 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 23.11 |
TPSA : | 80.26 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.97 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | -0.42 |
Log Po/w (WLOGP) : | -2.49 |
Log Po/w (MLOGP) : | -0.54 |
Log Po/w (SILICOS-IT) : | -0.48 |
Consensus Log Po/w : | -0.79 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.97 |
Solubility : | 24.2 mg/ml ; 0.108 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.8 |
Solubility : | 35.5 mg/ml ; 0.158 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | 0.53 |
Solubility : | 768.0 mg/ml ; 3.42 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P362+P364-P403+P233-P501 | UN#: | 3077 |
Hazard Statements: | H302-H315-H318-H335-H410 | Packing Group: | Ⅲ |
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 |
---|---|---|
80% | at 85℃; for 5 h; Large scale | A solution of 6-chloro-2-pyrazinamine (4 kg, 31 mol, 1.00 equiv), Et3N (4.7 kg,46.5 mol, 1.50 equiv), Pd(OAc)2 (139 g, 0.62mo1, 0.02 equiv), dppf (343 g, 0.62 mol, 0.02equiv) in methanol (60 L) was placed in a 100 L pressure tank reactor(10 atm).The resulting solution was allowed to react for 5 h while maintaining the temperature at 85°C. The reaction progress was monitored by TLC (DCM: MeOH = 20: 1) until the starting material was consumed completely, and cooled to room temperature. The resulting mixture was concentrated under vacuum. The residue was washed with water 50 L. Thefilter was collected and dried. The product (3.8 kg, purity = 95 percent, 80 percent yield)obtained as a pale brown solid.1H-NIVIR (300 MHz, DMSO-d6) : 8.27(1H, s), 8.06(1H, s), 6.87(2H, b), 3.84(3H, s). LC-MS: m / z = 154(M+H) +. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | for 0.5 h; Reflux | Recycling palladium powder (10.3 g, 0.9 equiv) was added into AcOH (200 ml) and HNO3(0.5 ml), followed by refluxing for 30 min. When the reaction was stopped, the hot brownsolution was filtrated. The solution was concentrated until a little AcOH (~20 ml) was left.At room temperature, Pd(OAc)2 crystals precipitated at the bottom of beaker. Throughfiltration, we obtained recycling Pd(OAc)2 (20 g, 92percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With triethanolamine In acetonitrile | (1) Synthesis of 5-Carboethoxy-3-methylindole To a solution of 2-bromo-4-carboethoxy-N-allylaniline (J. Org. Chem., 45, 2710 (1980)) (650 mg, 2.29 mmol) in acetonitrile (10 ml), tetrakis(triphenylphosphine)palladium(0) (132 mg, 0.114 mmol), palladium (II) acetate (25.7 mg, 0.114 mmol) and TEA (0.413 ml, 2.98 mmol) were added and stirred overnight in a sealed tube at 100° C. After filtering the reaction mixture, the filtrate was evaporated under reduced pressure; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:2) to give the titled compound (340 mg, 73percent). NMR (method a, CDCl3): δ 1.43 (3H, t, J=7.2 Hz), 2.37 (3H, s), 4.41 (2H, q, J=7.2 Hz), 7.03 (1H, s), 7.34 (1H, d, J=8.6 Hz), 7.91 (1H, dd, J=1.3, 8.6 Hz), 8.08 (1H, brs), 8.36 (1H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.1% | With triphenylphosphine In triethylamine | 4-Ethynylbenzaldehyde (13): To a solution of 4-bromobenzaldehyde (10.00 g, 54.08 mmol) and triphenylphosphine (0.500 g, 1.91 mmol) in anhydrous triethylamine (80 mL) under argon were added ethynyltrimethylsilane (6.00 g, 61.09 mmol) and palladium (II) acetate (0.100 g, 0.445 mmol). The final mixture was heated to reflux for 2 hours, and was then cooled to room temperature and filtered. The filtrate was concentrated under vacuum to a thick oil, which was purified by column chromatography (dichloromethane/petroleum ether 1:4) and recrystallized from cold cyclohexane to give 10.5 g (96.1percent yield) of 4-(trimethylsilylethynyl)benzaldehyde [MS m/e 187.2 (M+); 1H-NMR (CDCl3) δ ppm: 0.27 (s, 9H, SiMe3), 7.60 (d, 2H, ArH, J=8.1 Hz), 7.82 (d, 2H, ArH, J=8.1 Hz), 10.00 (s, 1H, CHO)]. |
96.1% | With triphenylphosphine In triethylamine | 4-Ethynylbenzaldehyde (13): To a solution of 4-bromobenzaldehyde (10.00 g, 54.08 mmol) and triphenylphosphine (0.500 g, 1.91 mmol) in anhydrous triethylamine (80 mL) under argon were added ethynyltrimethylsilane (6.00 g, 61.09 mmol) and palladium (II) acetate (0.100 g, 0.445 mmol). The final mixture was heated to reflux for 2 hours, and was then cooled to room temperature and filtered. The filtrate was concentrated under vacuum to a thick oil, which was purified by column chromatography (dichloromethane/petroleum ether 1:4) and recrystallized from cold cyclohexane to give 10.5 g (96.1percent yield) of 4-(trimethylsilylethynyl)benzaldehyde [MS m/e 187.2 (M+); 1H-NMR (CDCl3) δ ppm: 0.27 (s, 9H, SiMe3), 7.60 (d, 2H, ArH, J=8.1 Hz), 7.82 (d, 2H, ArH, J=8.1 Hz), 10.00 (s, 1H, CHO)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With magnesium sulfate; potassium carbonate In ethanol; toluene | [Step 5] Synthesis of N,N',N'-triphenylbenzidine A synthesis scheme of N,N',N'-triphenylbenzidine is shown in (a-6). Into a 500 mL three-neck flask were put 4.3 g (17 mmol) of 4-bromodiphenylamine, 5 g (17 mmol) of triphenylamine-4-boronic acid, and 532 mg (1.8 mmol) of tri(o-tolyl)phosphine, and the atmosphere in the flask was replaced with nitrogen. Then, 60 mL of toluene, 40 mL of ethanol, and 14 mL of potassium carbonate aqueous solution (0.2 mol/L) were added to this mixture. After this mixture was degassed under reduced pressure, 75 mg (0.35 mmol) of palladium (II) acetate was added. This mixture was refluxed at 100° C. for 10.5 hours. After the reflux, the aqueous layer of the mixture was extracted with toluene. The extracted solution was combined with an organic layer and washed with a saturated saline, and magnesium sulfate was added thereto for drying. This mixture was filtered and the filtrate was concentrated to give an oily light-brown substance. The oily substance was dissolved in toluene of about 50 mL, and then subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). A solid obtained by concentrating the filtrate was purified by a silica gel column chromatography (developing solvent was a mixed solvent of hexane:toluene 4:6) to give a white solid. The obtained white solid was recrystallized with chloroform/hexane, so that 3.5 g of a white solid was obtained in a yield of 49percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | at 130℃; for 24 h; | [0117] 3,5-Bromo-2-methoxypyridine (XXXV) (100 mg, 1.13 mmol), palladium(II) acetate (Pd(OAc)2) (5.03 mg, 25.04 μmole), and 1,3-bis(diphenylphosphino)propane (DPPP) (14.4 mg, 45.3 μmole) were dissolved in 1.0 mL of 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim] [BF4]), and butyl vinyl ether (345 μL, 2.56 mmole) and triethylamine (TEA) (125.03 μL, 0.192 mmole) were slowly added dropwise to the resulting solution. The resulting mixture was stirred at 130 °C for 24 hrs and cooled to room temperature. 2 N hydrochloric acid (HCl) was slowly added dropwise to the mixture to adjust pH to 1∼2 and the mixture was stirred for 30 min and neutralized. The resulting solution was diluted with dichloromethane, washed with water. The organic solvent was dried over anhydrous magnesium sulfate (MgSO4), filtered, and evaporated under reduced pressure to concentrate. The resulting residue was isolated and purified by silica gel column chromatography (n-Hex/EA = 3/1) to give the title compound (53 mg, 41 percent). 1H NMR (400 MHz, CDCl3) δ 7.85 (s, 1H), 7.06 (s, 1H), 3.89 (s, 3H), 2.48 (s, 3H). |