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Published TCIMAIL newest issue No.197
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CAS RN: 72914-19-3 | Product Number: D3134
4,4'-Di-tert-butyl-2,2'-bipyridyl
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Purity: >98.0%(GC)
Synonyms:
- 4,4'-Di-tert-butyl-2,2'-bipyridine
- dtbpy
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
|---|---|---|---|---|
| 1G |
36,00 €
|
1 | ≥100 |
|
| 5G |
157,00 €
|
2 | ≥40 |
|
*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).
| Product Number | D3134 |
| Purity / Analysis Method | >98.0%(GC) |
| Molecular Formula / Molecular Weight | C__1__8H__2__4N__2 = 268.40 |
| 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 | Air Sensitive |
| CAS RN | 72914-19-3 |
| Reaxys Registry Number | 792133 |
| PubChem Substance ID | 172089138 |
| MDL Number | MFCD01863731 |
Specifications
| Appearance | White to Almost white powder to crystal |
| Purity(GC) | min. 98.0 % |
| Melting point | 159.0 to 163.0 °C |
Properties (reference)
| Melting Point | 161 °C |
GHS
| 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 | 2933399990 |
Application
TCI Practical Example: Hartwig-Miyaura C-H Borylation Using an Iridium Catalyst
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Used Chemicals
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Procedure
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A solution of dtbpy (27 mg, 0.05 mmol), bis(pinacolato)diboron (1.0 g, 4.0 mmol) and [Ir(cod)OMe]2 (33 mg, 0.025 mmol) in cyclohexane (40 mL) was stirred under nitrogen at room temperature for 10 min. Benzo[1,2-b:4,5-b']dithiophene (1.0 g, 4.0 mmol) was added the mixture and stirred 80 ˚C for 18 hours. The reaction mixture was quenched with water and separated both layers, extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the crude was washed with methanol (20 mL) to give 1 as a white solid (0.771 g, 87% yield).
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Experimenter’s Comments
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The reaction mixture was monitored by NMR.
Cyclohexane was bubbled with nitrogen before use.
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Analytical Data
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Compound 1
1H NMR (270 MHz, CDCl3); δ 8.36 (s, 2H), 7.90 (s, 2H), 1.39 (s, 24H).
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Lead Reference
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- Synthesis and Transistor Application of Bis[1]benzothieno[6,7‑d:6′,7′‑d′]benzo[1,2‑b:4,5‑b′]dithiophenes
Application
Fe or Ni-catalyzed Decarboxylative C-C Couplings of Active Esters
References
- 1)Redox-active Esters in Fe-catalyzed C?C Coupling
- 2)Practical Ni-catalyzed Aryl?alkyl Cross-coupling of Secondary Redox-active Esters
- 3)A General Alkyl-alkyl Cross-coupling Enabled by Redox-active Esters and Alkylzinc Reagents
Application
ortho-Allylation of 1-Arylpyrazoles via Iron-Catalyzed C-H Bond Activation
Typical Procedure (X = H): 1-Phenylpyrazole (116 mg, 0.8 mmol) and ZnCl2-TMEDA (606 mg, 2.4 mmol) are placed in a dried Schlenk flask under argon. A solution of PhMgBr in THF (1.09 M, 4.40 mL, 4.8 mmol) is added dropwise to this mixture at 0 °C. After stirring for 3 min, allyl phenyl ether (220 µL, 1.6 mmol) and a solution of Fe(acac)3 / 4,4’-di-tert-butyl-2,2’-bipyridyl in THF (1.0 mL, 0.08 M, 80 µmol) are sequentially added. The reaction mixture is stirred at 0 °C for 48 h, and then it is diluted with Et2O, followed by the addition of a saturated aqueous solution of Rochelle salt tetrahydrate (L-(+)-tartaric acid potassium sodium salt tetrahydrate). After extraction with ethyl acetate, the combined organic layers are filtered through a pad of Florisil, and concentrated under reduced pressure. The crude product is purified by column chromatography on silica gel (eluent: hexane/AcOEt/NEt3 = 99/0.5/0.5), followed by gel-permeation chromatography (eluent: toluene) to afford 1-(2-allylphenyl)-1H-pyrazole as a colorless oil (118 mg, 80% yield).
References
PubMed Literature
Articles/Brochures
TCIMAIL
[Research Articles] Fe or Ni-catalyzed Decarboxylative C-C Couplings of Active Esters[Research Articles] ortho-Allylation of 1-Arylpyrazoles via Iron-Catalyzed C-H Bond Activation
Product Documents (Note: Some products will not have analytical charts available.)
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