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CAS RN: 808142-88-3 | Product Number: B6258

(4,4'-Di-tert-butyl-2,2'-bipyridine-κ2N1,N1')[bis[5-fluoro-2-(5-methyl-2-pyridinyl-κN)phenyl-κC1]]iridium Hexafluorophosphate


Purity: >90.0%(HPLC)
Synonyms:
  • (4,4'-Di-tert-butyl-2,2'-bipyridine)bis[2-(4-fluorophenyl)-5-methylpyridine]iridium(III) Hexafluorophosphate
  • [Ir(p-F(Me)ppy)2-(4,4'-dtbbpy)]PF6
Documents:
200MG
€131.00
2   27  
1G
€444.00
1   26  

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Product Number B6258
Purity / Analysis Method >90.0%(HPLC)
Molecular Formula / Molecular Weight C__4__2H__4__2F__8IrN__4P = 978.00 
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 Light Sensitive,Air Sensitive
CAS RN 808142-88-3
Reaxys Registry Number 17851242
PubChem Substance ID 468591004
MDL Number

MFCD31707653

Specifications
Appearance Light yellow to Yellow powder to crystal
Purity(HPLC) min. 90.0 area%
NMR confirm to structure
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.
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.
Related Laws:
Transport Information:
HS Number 2843909000
Application
TCI Practical Example: The Deoxyfluorination of Activated Alcohols Catalyzed by a Photoredox Catalyst

The Deoxyfluorination of Activated Alcohols Catalyzed by a Photoredox Catalyst

Used Chemicals

Procedure

A 4-neck round bottom flask was charged with 2-methyl-4-phenyl-2-butanol (5 g, 30 mmol, 1 eq) and diethyl ether (300 mL, 0.1 mol/L). The solution was cooled under 5 ˚C, then oxalyl chloride (7.78 g, 60 mmol, 2 eq) was added. The reaction mixture was allowed to warm to ambient temperature and stirred for 6 h. After the reaction, the reaction mixture was cooled under 5 ˚C and quenched with ion-exchanged water (55 mL). The solution was transferred into a separatory funnel, and the aqueous layer was extracted with diethyl ether (30 mL, twice). The combined organic layers were washed with brine, dried over sodium sulfate (50 g) for about 30 minutes and then filtered. The solvent was removed in vacuo, giving compound 1 as a light yellow oil (4.91 g, y. 68.3%), which was used without further purification.
1 (1.3 g, 5.5 mmol, 1.0 eq), disodium hydrogenphosphate, dodecahydrate (3.9 g, 11 mmol, 2.0 eq), F-TEDA-BF4 (3.3 g, 9.3 mmol, 1.7 eq), [Ir(p-F(Me)ppy)2-(4,4'-dtbbpy)]PF6 (0.053 g, 0.05 mmol, 0.94 mol%) were dissolved in acetone (44 mL) and of ion-exchanged water (11 mL) at rt under N2. The reaction mixture was degassed with nitrogen for 15 minutes before irradiation. The mixture was placed at a distance of 2-3 cm from Blue LED lamp with a cooling fan. The reaction mixture was stirred at rt under visible light irradiation until 1 was completely consumed. After 6 h of irradiation, the reaction mixture was diluted with diethyl ether (50 mL) and ion-exchanged water (50 mL). The solution was transferred to a separatory funnel, and the aqueous layer was extracted with diethyl ether (30 mL, twice). The combined organic layers were washed with brine, dried over sodium sulfate (50 g) for about 30 minutes and then filtered. The solvent was removed in vacuo, giving crude as a blown oil (0.96 g). The crude was purified by silica gel column chromatography (hexane:ethyl acetate = 10:1, Rf = 0.75) to give compound 2 as a colorless oil (0.394 g, y. 43%)

Experimenter’s Comments

  • Irradiation of visible light was performed with Kessil A160WE Tuna Blue 40W×2.
  • The reaction mixture was cooled to rt with a cooling fan.
  • The reaction mixture was monitored by 1H NMR and GCMS.

Analytical Data

Compound 2

1H NMR (400 MHz, CDCl3); δ 7.32-7.27 (m, 2H), 7.20 (d, J = 7.8 Hz, 3H), 2.75-2.71 (m, 2H), 1.97-1.88 (m, 2H), 1.41 (d, J = 21.5 Hz, 6H).

13C NMR (101 MHz, CDCl3); δ 142.01, 128.42, 128.28, 125.85, 95.33 (d, JC,F = 165.0 Hz), 43.32 (d, JC,F = 22.9 Hz), 30.24 (d, JC,F = 4.8 Hz), 26.67 (d, JC,F = 24.8 Hz).

19F NMR (376 MHz, CDCl3); δ -139.87 (m, 1F).

Lead Reference

Other References


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