CAS RN: 32005-36-0 | Product Number: B1374
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|Molecular Formula / Molecular Weight||C__3__4H__2__8O__2Pd = 575.02|
|Physical State (20 deg.C)||Solid|
|Store Under Inert Gas||Store under inert gas|
|Condition to Avoid||Air Sensitive|
|Packaging and Container||1G-Glass Bottle with Plastic Insert (View image)|
|PubChem Substance ID||87564299|
|SDBS (AIST Spectral DB)||50493|
|Appearance||Red to Dark blue to Black powder to crystal|
|Content (Palladium)||18.0 to 24.0 %|
|Melting Point||150 °C|
|Hazard Statements||H302 + H312 + H332 : Harmful if swallowed, in contact with skin or if inhaled.
H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
|Precautionary Statements||P501 : Dispose of contents/ container to an approved waste disposal plant.
P261 : Avoid breathing dust/ fume/ gas/ mist/ vapors/ spray.
P270 : Do not eat, drink or smoke when using this product.
P271 : Use only outdoors or in a well-ventilated area.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P362 + P364 : Take off contaminated clothing and wash it before reuse.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
P301 + P312 + P330 : IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Rinse mouth.
P302 + P352 + P312 : IF ON SKIN: Wash with plenty of water.Call a POISON CENTER/doctor if you feel unwell.
P304 + P340 + P312 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Call a POISON CENTER/doctor if you feel unwell.
Aniline (1.0 g, 10.7 mmol) and 4-chlorotoluene (1.4 g, 11.8 mmol) were dissolved in degassed toluene (10 mL) under nitrogen atmosphere. To this solution was added sodium tert-butoxide (1.54 g, 16.1 mmol), tri-tert-butylphosphonium tetrafluoroborate (31.1 mg, 0.1 mmol) and Pd(dba)2 (61.7 mg, 0.1 mmol, 1.5mol%). The reaction mixture was refluxed for 24 h and cooled to room temperature and quenched with H2O (10 mL). The organic phase was separated and washed with brine (10 mL), dried over MgSO4 (10 g), concentrated under reduced pressure to afford the crude product as a brown liquid. The crude product was purified by column chromatography on silica-gel (hexane : ethyl acetate = 95 : 5) to afford the desired product as a pale yellow crystalline solid (1.21 g, 6.6 mmol, 62%).
Toluene was degassed by bubbling with N2 gas for 30 min.
The reaction mixture was analyzed by TLC (hexane : ethyl acetate = 1 : 1, Rf = 0.30) and GC.
Analytical Data (4-Methyl-N-phenylaniline)
1H NMR (400 MHz, CDCl3); δ 7.24-7.20 (t, J = 8.7 Hz, 3H), 7.07 (d, J = 8.7 Hz, 2H), 7.00-6.88 (m, 4H), 6.88-6.84 (m, 1H), 5.58 (s, 1H), 2.29 (s, 3H).
- Tetramethoxybenzene is a Good Building Block for Molecular Wires: Insights from Photoinduced Electron Transfer
- 2-Chloro-m-xylene [C2164]
- 2-Methylphenylboronic Acid [M1313]
- Bis(dibenzylideneacetone)palladium (0) (Pd(dba)2) [B1374]
- 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) [D5036]
- Tripotassium Phosphate (K3PO4)
- Ion-exchange water
To a 3-necked flask was charged with bis(dibenzylideneacetone)palladium (0) (66 mg, 0.115 mmol, 1.5 mol%), SPhos (94 mg, 0.229 mmol, 3.0 mol%), 2-methylphenylboronic acid (1.56 g, 11.5 mmol, 1.5 equiv.), tripotassium phosphate (4.87 g, 22.9 mmol, 3.0 equiv.) degassed toluene (15 mL), and ion-exchange water (1.5 mL) under nitrogen atmosphere. The mixture was stirred at room temperature for 5 min. 2-Chloro-m-xylene (1.0 mL, 7.64 mmol, 1.0 equiv.) was added one portion. The resulting mixture was stirred at reflux for 7 h. The reaction mixture was cooled to room temperature and quenched with water (10 mL). The organic layer was washed with water (10 mL), and brine (10 mL), dried with Na2SO4 (20 g) and then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane only) to afford the corresponding compound as a colorless oil (1.46 g, 97%).
i) Toluene was degassed by bubbling with nitrogen gas for 30 min.
ii) The reaction mixture was monitored by GC.
1H NMR (400 MHz, CDCl3); δ 7.23-7.33 (m, 3H), 7.22-7.10 (m, 3H), 7.00-7.06 (m, 1H), 1.99 (s, 3H), 1.97 (s, 6H).
13C NMR (101 MHz, CDCl3); δ 141.0, 140.5, 135.8, 135.5, 129.9, 128.8, 127.2 127.0, 126.9, 126.0, 20.3, 19.4.
- Catalysts for Suzuki−Miyaura Coupling Processes: Scope and Studies of the Effect of Ligand Structure
To a 2-necked flask was charged with bis(dibenzylideneacetone)palladium (0) (36 mg, 0.0633 mmol, 1.5 mol%), XPhos (60 mg, 0.127 mmol, 3.0 mol%), sodium tert-butoxide (811 mg, 8.44 mmol, 2.0 equiv.) and toluene (5 mL) under nitrogen atmosphere. The mixture was stirred at room temperature for 5 min. 4-chlorotoluene (0.5 mL, 4.22 mmol, 1.0 equiv.), and morpholine (0.55 mL, 6.33 mmol, 1.5 equiv.) were added in one portion. The resulting mixture was stirred at reflux for 6 h. The reaction mixture was cooled to room temperature and quenched with water (10 mL). The organic layer was washed with water (10 mL), and brine (10 mL), dried with Na2SO4 (20 g) and then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane : ethyl acetate = 9 : 1) to afford the corresponding compound as an orange solid (700 mg, 94%).
Toluene was degassed by bubbling with nitrogen gas for 30 min.
The reaction mixture was monitored by GC.
Analytical Data（Compound 1）
1H NMR (400 MHz, CDCl3); δ 7.10 (d, J = 8.7 Hz, 2H), 6.84 (d, J = 8.7 Hz, 2H), 3.87 (t, J = 4.8 Hz, 4H), 3.11 (t, J = 4.8 Hz, 4H), 2.28 (s, 3H).
13C NMR (101 MHz, CDCl3); δ 149.1, 129.7, 129.5, 116.0, 66.9, 49.9, 20.4.
- Expanding Pd-Catalyzed C−N Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions
- Pd-Catalyzed Kumada－Corriu Cross-Coupling Reactions at Low Temperatures Allow the Use of Knochel-type Grignard Reagents
Safety Data Sheet (SDS)
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C of A & Other Certificates
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|Purity / Analysis Method:||>95.0%(HPLC)|