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4,4'-Di-tert-butyl-2,2'-bipyridyl
(CAS RN:72914-19-3 Product Number:D3134)

Structure

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

General Information

Product Number D3134

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Purity/Analysis Method >98.0%(GC)
Storage Temperature
M.F. / M.W. C18H24N2=268.40
CAS RN 72914-19-3
Related CAS RN
MDL Number MFCD01863731
Packaging and Container
  • Product Details
  • Safety & Regulations

Specification

Purity(GC) min. 98.0 %
Melting point 159.0 to 163.0 deg-C

References

Beilstein 25(5)8,181
Reaxys-RN 792133
PubChem SID 172089138

GHS

Pictogram
Signal Word Warning
Hazard Statements
  • H315
  • :Causes skin irritation.
  • H319
  • :Causes serious eye irritation.
Precautionary Statements
  • P264
  • :Wash hands and face thoroughly after handling.
  • P280
  • :Wear protective gloves, eye protection.
  • P302+P352+P332+P313+P362+P364
  • :IF ON SKIN: Wash with plenty of water. If skin irritation occurs: Get medical advice or attention. Take off contaminated clothing and wash it before reuse.
  • P305+P351+P338+P337+P313
  • :IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice or attention.

Transport Information

HS Number 2933399990

Application

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

I0079, B3372, D3134

References

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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