20336-15-6

Usage

Uses

2,4,6-Tritert-butylpyridine is used in the synthesis of acceptors in organic solar cells.

InChI:InChI=1/C17H29N/c1-15(2,3)12-10-13(16(4,5)6)18-14(11-12)17(7,8)9/h10-11H,1-9H3

Upstream product

• 630-18-2 tert-butyl isocyanide 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 125950-53-0 (2,6-diisopropylphenoxy)2Cl(tantalum)(η2-(N,C)-2,4,6-tri-tert-butylpyridine) 
• 125950-49-4 (((CH₃)2CH)2C₆H₃O)2Cl(Ta(C(C(CH₃)3)CHCHC(C(CH₃)3))) 
• 125950-50-7 (((CH₃)2CH)2C₆H₃O)2Cl(Ta(C(C(CH₃)3)CHCHC(C(CH₃)3))) 

Downstream Products

• 1187326-94-8 [H₂B(C₆F₅)]2 
• 1187326-96-0 [(2,4,6-tri-tert-butylpyridineH)][HB(C₆F₅)3] 

Relevant academic research and scientific papers

Photocatalyzed [2 + 2 + 2]-cycloaddition of nitriles with acetylene: An effective method for the synthesis of 2-pyridines under mild conditions

The photocatalyzed [2 + 2 + 2]-cycloaddition of nitriles with 2 equiv of acetylene to 2-pyridines can be carried out under mild conditions and represents a valuable extension to common synthetical methods. For the ideal wavelength range (350-500 nm), lamps as well as sunlight can be used. Working at room temperature and in organic solvents such as toluene or hexane as well as in water gives satisfying results in many cases. However, it is also possible to vary the solvent and the reaction temperature of the photocatalyzed synthesis and to choose, with respect to the specific substrate, specific requirements for this particular reaction and general requirements of the method. This simple and selective method derives its potential mainly from the large variety of applicable nitriles. Suitable substrates include (functionalized) aliphatic and aromatic nitriles as well as cyanamides derived from secondary amines.

REACTION OF SOME NUCLEOPHILES WITH 2,6-DI-TERT-BUTYLPYRYLIUM PERCHLORATE

The title compound IV reacted with sodium borohydride to give the 4H-pyran VIIa and the dienone VIIIa whereas its reaction with sodium cyanide afforded exclusively the dienone VIIIb.Reaction of the salt IV with tert-butylmagnesium chloride or bromide gave a mixture of the 4H-pyran VIIa and the corresponding 4-tert-butyl derivative V.Upon treatment with hydrogen sulfide and hydrogen chloride, this mixture afforded 2,4,6-tri-tert-butyl-4H-thiopyran (XI) whereas aromatization with chloranil and subsequent reaction with ammonium acetate resulted in 2,4,6-tri-tert-butylpyridine (X).Analogously, the perchlorate IV reacted with ammonium acetate to give 2,6-di-tert-butylpyridine (VI).Addition of triphenylphosphine and potassium phthalimide to IV afforded exclusively the 4H-pyran derivatives XII and XIII.A similar reaction of nitromethyl anion led to the 4,4'-bis(4H-pyran) derivative XIV.Mechanism of the studied reactions and the reasons for the low reactivity of the sterically hindered pyridine derivative VI with electrophilic and nucleophilic reagent are discussed.