Maximum quantity allowed is 999
CAS RN: 1335047-34-1 | Product Number: B6254
(4,4'-Di-tert-butyl-2,2'-bipyridine-κ2N1,N1')[bis[3,5-difluoro-2-(5-methyl-2-pyridinyl-κN)phenyl-κC1]]iridium Hexafluorophosphate
Purity: >90.0%(HPLC)
- (4,4'-Di-tert-butyl-2,2'-bipyridine)bis[2-(2',4'-difluorophenyl)-5-methylpyridine]iridium(III) Hexafluorophosphate
- [Ir(dF(Me)ppy)2(dtbbpy)]PF6
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Product Number | B6254 |
Purity / Analysis Method | >90.0%(HPLC) |
Molecular Formula / Molecular Weight | C__4__2H__4__0F__1__0IrN__4P = 1,013.98 |
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 |
Packaging and Container | 1G-Glass Bottle with Plastic Insert (View image), 200MG-Glass Bottle with Plastic Insert (View image) |
CAS RN | 1335047-34-1 |
PubChem Substance ID | 468591000 |
MDL Number | MFCD31619196 |
Appearance | Light yellow to Yellow powder to crystal |
Purity(HPLC) | min. 90.0 area% |
NMR | confirm to structure |
Melting Point | 360 °C |
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. 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. |
H.S.code* | 2843.90-000 |
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Used Chemicals
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- Piperidine
- 4-Methoxystyrene [M0130]
- (4,4'-Di-tert-butyl-2,2'-bipyridine)bis[2-(2',4'-difluorophenyl)-5-methylpyridine]iridium(III) Hexafluorophosphate (= Ir[dF(Me)(ppy)2(dtbbpy)]PF6) [B6254]
- Toluene
- 2,4,6-Triisopropylbenzenethiol
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Procedure
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2,4,6-Triisopropylbenzenethiol (0.060 g, 0.25 mmol, 0.5 eq), piperidine (0.050 mL, 0.50 mmol, 1.0 eq), 4-methoxystyrene (0.10 mL, 0.75mmol, 1.5 eq), Ir[dF(Me)(ppy)2(dtbbpy)]PF6 (10 mg, 0.0099 mmol, 2.0 mol%) were dissolved in toluene (10 mL) at rt under N2. The mixture was placed at a distance of 2-3 cm from Blue LED lamp with a cooling fan. The yellow orange suspension was stirred at rt under visible light irradiation until the amine was completely consumed. After 12 h of irradiation, the reaction mixture was diluted with ethyl acetate (20 mL) and extracted with 1 mol/L HCl aq. (70 mL x 2). The combined aqueous layer was washed with diethyl ether (30 mL x 2), then neutralized with 2 mol/L NaOH aq. (78 mL) to pH 7 and then saturated sodium bicarbonate aq. (10 mL) was added to ensure slightly basic conditions. The aqueous layer was extracted with dichloromethane (50 mL x 3). The combined organic layer was dried over sodium sulfate (30 g) for about 30 minutes and then filtered. The solvent was removed in vacuo to give compound 1 as a colorless oil (39 mg, y. 35%).
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Experimenter’s Comments
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Toluene was degassed with nitrogen for 30 minutes before use.
Irradiation of visible light was performed with Kessil A160WE Tuna Blue 40Wx2.
The reaction mixture was maintained at rt by a cooling fan.
The reaction mixture was monitored by 1H NMR and GC.
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Analytical Data
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Compound 1
1H NMR (400 MHz, CDCl3); δ 7.12 (d, J = 7.8 Hz, 2H), 6.82 (d, J = 7.8 Hz, 2H), 3.78 (s, 3H), 2.79–2.75 (m, 2H), 2.56–2.49 (m, 6H), 1.46 (m, 4H), 1.25 (bs, 2H).
13C NMR (101 MHz, CDCl3); δ 157.82, 132.58, 129.57, 113.75, 61.64, 55.22, 54.51, 32.62, 25.90, 24.37.
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Lead Reference
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- Catalytic intermolecular hydroaminations of unactivated olefins with secondary alkyl amines
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Other References
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- Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines
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Specifications
C of A & Other Certificates
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