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CAS RN: 166330-10-5 | Product Number: R0301

DPEphos (HPMC encapsulated)


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Supplemental Product Information:

Contents (per one capsule)

  • DPEphos ca. 0.15 mmol

Uses of Reagent

  • Applicable to palladium-catalyzed reactions due to a ligand encapsulated in HPMC capsules

Soluble Solvents

  • Water, DMSO, DMF, 1,4-Dioxane (50°C), THF/Water mixture, 1,2-Dimethoxyethane/Water mixture

Related Product

  • B2867 Bis[2-(diphenylphosphino)phenyl] Ether

Product Number R0301
Molecular Formula / Molecular Weight C__3__6H__2__8OP__2 = 538.57 
Physical State (20 deg.C) Solid
Storage Temperature Room Temperature (Recommended in a cool and dark place, <15°C)
Store Under Inert Gas Store under inert gas
Condition to Avoid Hygroscopic
CAS RN 166330-10-5
Specifications
Appearance White to Almost white capsule
Functionality test (conversion ratio) min.90.0 %
Properties (reference)
GHS
Pictogram Pictogram
Signal Word Warning
Hazard Statements H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ 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.
P302 + P352 : IF ON SKIN: Wash with plenty of soap and water.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
P362 : Take off contaminated clothing and wash before reuse.
Related Laws:
Transport Information:
HS Number 3822.19.0080
Application
TCI Practical Example: Suzuki-Miyaura Coupling Using the Encapsulated Pd2(dba)3 and DPEphos

TCI Practical Example: Suzuki-Miyaura Coupling Using the Encapsulated Pd2(dba)3 and DPEphos

Used Chemicals

Procedure

Pd2(dba)3 (HPMC encapsulated) (one capsule) and DPEphos (HPMC encapsulated) (one capsule) were added to a solution of 2-acetamido-5-bromo-4-methylpyridine (340 mg, 1.50 mmol), cesium carbonate (540 mg, 2.0 mmol, 1.1 eq.) and phenylboronic acid (270 mg, 2.3 mmol, 1.5 eq.) in THF/water (10:1, 8.25 mL) at room temperature and the reaction mixture was stirred at 100 °C for 4 hours. The solution was then diluted with ethyl acetate (10 mL) and sat. sodium sulfate (10 mL), and filtered through Celite pad. The filtrate was separated and the organic layer was washed with water (15 mL) and brine (15 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (ethyl acetate:hexane = 1:2 - 1:1) to afford 2-acetamido-4-methyl-5-phenylpyridine (319 mg, 94% yield) as a white solid.

Experimenter’s Comments

The reaction mixture was monitored by GC.
The material of the capsule is water-soluble HPMC (hydroxypropyl methylcellulose).
The shape of the capsule is like the image below and Pd2(dba)3 (ca. 60 μmol) and DPEphos (ca. 150 μmol) are encapsulated in each capsule, respectively.

Appearance of capsule

The capsule disintegrates as shown in the image below when stirred in the solvent for about 15 minutes, releasing its content.

Capsule disintegrating

Analytical Data

2-Acetamido-4-methyl-5-phenylpyridine

1H NMR (400 MHz, CDCl3); δ 9.24-9.06 (brs, 1H), 8.16 (s, 1H), 8.10 (s, 1H), 7.46-7.36 (m, 3H), 7.30-7.29 (m, 2H), 2.32 (s, 3H), 2.21 (s, 3H).

Lead Reference

Other References


Product Documents (Note: Some products will not have analytical charts available.)
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