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CAS RN: 72914-19-3 | Product Number: D3134

4,4'-Di-tert-butyl-2,2'-bipyridyl


Purity: >98.0%(GC)
Synonyms:
  • 4,4'-Di-tert-butyl-2,2'-bipyridine
  • dtbpy
Documents:
1G
£31.00
3   ≥40 
5G
£137.00
2   ≥40 

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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
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 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

TCI Practical Example: Hartwig-Miyaura C-H Borylation Using an Iridium Catalyst

Used Chemicals

Procedure

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).

Experimenter’s Comments

The reaction mixture was monitored by NMR.
Cyclohexane was bubbled with nitrogen before use.

Analytical Data

Compound 1

1H NMR (270 MHz, CDCl3); δ 8.36 (s, 2H), 7.90 (s, 2H), 1.39 (s, 24H).

Lead Reference


Application
Fe or Ni-catalyzed Decarboxylative C-C Couplings of Active Esters

References


Application
ortho-Allylation of 1-Arylpyrazoles via Iron-Catalyzed C-H Bond Activation

D3134

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


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