CAS RN: 864163-80-4 | Product Number: B4944
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|Appearance||Light yellow to Brown powder to crystal|
|Purity(HPLC)||min. 80.0 area%|
|Elemental analysis(Nitrogen)||6.00 to 6.75 %|
|Maximum Absorption Wavelength||500(CH2Cl2) nm|
|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.
P302 + P352 : IF ON SKIN: Wash with plenty of water.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P362 + P364 : Take off contaminated clothing and wash it before reuse.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
- Methyl Pentafluorobenzoate [P1418]
- (2,2'-Bipyridine)bis[2-(2,4-difluorophenyl)pyridine]iridium(III) Hexafluorophosphate (= Ir[(dFppy)2(bpy)]PF6) [B4944]
- Quinuclidine [Q0062]
- Dipotassium Hydrogenphosphate
To a solution of quinuclidine (22.4 mg, 0.201 mmol, 0.20 eq), Ir[(dFppy)2(bpy)]PF6 (18.0 mg, 0.0165 mmol, 1.7 mol%), K2HPO4 (0.358 g, 2.07 mmol, 2.1 eq) in THF (10 mL) was added methyl pentafluorobenzoate (0.146 mL, 1.00 mmol, 1.0 eq) at rt under N2. The mixture was placed at a distance of 2-3 cm from Blue LED lamp. The orange solution was stirred at rt under visible light irradiation. After 4.5 hours of irradiation, the solvent was removed in vacuo. The residue was diluted with dichloromethane and filtered through a silica gel pad. The filtrate was concentrated and purified by column chromatography (hexane : ethyl acetate on silica gel, hexane : ethyl acetate = 9 : 1 → 20 : 3), giving compound 1 as a colorless oil (125 mg, y. 45%).
Tetrahydrofuran was degassed with nitrogen for 1 hour before use.
Irradiation of visible light was performed with Kessil A160WE Tuna Blue 40W×2.
The reaction mixture was monitored by 1H NMR, TLC (hexane : ethyl acetate = 10 : 1, Rf = 0.26).
The reaction was performed at rt, however the internal temperature rose up to 40 ˚C due to the insufficient cooling. Neverthelss, the reaction proceeded without any problems.
Analytical Data（Compound 1）
- 1H NMR (400 MHz, CDCl3); δ 5.27 (t, J = 7.8 Hz, 1H), 4.09 (q, J = 7.3 Hz, 1H), 3.97 (s, 3H), 3.99−3.90 (m, 1H), 2.40−2.31 (m, 1H), 2.24−2.15 (m, 1H), 2.11-2.06 (m, 2H).
13C NMR (101 MHz, CDCl3); δ 160.2, 145.8, 143.4, 124.8, 104.5, 71.7, 69.4, 53.3, 32.4, 27.0.
19F NMR (376.5 MHz, CDCl3); δ −140.34 (d, J = 23 Hz, 2F), −142.95 (d, J = 23 Hz, 2F).
- Direct C-H Multifluoroarylation of Ethers through Hydrogen Atom Transfer Using Photoredox Catalysis
- A Retrosynthetic Approach for Photocatalysis
[Product Highlights] Visible Light Photoredox Catalysts Useful for Chemical Modifications
[TCI Practical Example] C(sp3)-H Arylation Catalyzed by the Photoredox Catalyst
Safety Data Sheet (SDS)
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