36075-06-6

Basic information

• Product Name: 2-DIETHYLAMINOPYRIDINE
• Synonyms: N-(2-PYRIDYL)DIETHYLAMINE;2-DIETHYLAMINOPYRIDINE;Diethylaminopyridine;2-DIETHYL AMINOPYRIDINE 97+%;2-Pyridinamine, N,N-diethyl-;Nsc30135;2-(N,N-diethylamino)pyridine;N,N-diethyl-2-PyridinaMine
• CAS NO: 36075-06-6
• Molecular Formula: C₉H₁₄N₂
• Molecular Weight: 150.22
• Mol File: 36075-06-6.mol

Chemical Properties

• Boiling Point: 118 °C / 27mmHg
• Flash Point: 91.1°C
• Appearance: /
• Density: 0.97
• Refractive Index: 1.5380 to 1.5420
• PKA: 6.98±0.10(Predicted)
• CAS DataBase Reference: 2-DIETHYLAMINOPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-DIETHYLAMINOPYRIDINE(36075-06-6)
• EPA Substance Registry System: 2-DIETHYLAMINOPYRIDINE(36075-06-6)

Safety Data

• Hazardous Substances Data: 36075-06-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Reactions:
2-Diethylaminopyridine is used as a catalyst for the acylation of alcohols, phenols, and amines, the esterification of carboxylic acids, and the urethane formation from isocyanates. Its strong basic properties make it an effective catalyst in these reactions.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2-Diethylaminopyridine is used as a catalyst for the synthesis of various drugs. Its ability to facilitate reactions without additional solvents or reagents contributes to the efficiency and cost-effectiveness of drug production.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical industry, 2-Diethylaminopyridine is employed as a catalyst for the synthesis of agrochemicals, such as pesticides and herbicides. Its versatility in catalyzing different types of reactions makes it a valuable asset in the development of these products.
Used in Polymer Synthesis:
2-Diethylaminopyridine is also utilized in the synthesis of polymers, where it acts as a catalyst to facilitate the formation of polymer chains. Its application in this field contributes to the advancement of polymer science and the development of new materials with various applications.

Upstream product

• 107263-95-6 N-fluoropyridinium triflate 
• 109-89-7 diethylamine 

Downstream Products

• 82582-67-0 [Ir(hydrido)2(acetone)2(triphenylphosphine)2](BF4) 

Relevant articles and documents

Chemistry of heteroaryltriphenylphosphonium iodides: Preparation from iodoheteroaromatics and elimination of the phosphonium iodide group using basic solvents

α- and γ-Iodoheteroaromatics were found to react with triphenylphosphine to give heteroaromatictriphenylphosphonium iodides in excellent yields, β-lodoheteroaromatics, which are less reactive with triphenylphosphine compared to α- or γ-compounds, were con

Novel base-initiated reactions of N-substituted pyridinium salts

Reaction of N-fluoropyridinium triflate with a base in dichloromethane gave 2-chloropyridine as the major product along with 2-pyridyl triflate and 2-fluoropyridine, regardless of the nature of the base. This base-initiated reaction was also shown to take place similarly in other halogenated alkanes, ethers, a nitrile, aromatics, a ketone, vinyl ethers, alcohols and trimethylsilyl acetate as solvents to give pyridine derivatives substituted with a solvent molecule (s) at the 2-position. N-(Trifluoromethanesulfonyloxy)-and (benzenesulfonyloxy) pyridinium salts were found to undergo the same base-initiated reaction. These reactions may be explained by a postulated singlet carbene (canonical formula 11b) produced through proton abstraction of N-substituted pyridinium salts. A similar carbene reaction may thus likely occur in the thermal decomposition of thiatriazole 10. Ab initio MO calculations revealed the structure and properties of the labile deprotonated N-fluoropyridinium cation and supported the carbene intermediate reaction mechanism rather than a pyridynium or pyridyl cation mechanism. Quarroz's reports on the reactions of picolinic acid N-oxide and the reported reactions of pyridines with F2, CH3COOF or CsSO4F in solvents may be explained by this carbene mechanism.

BASE-INITIATED REACTIONS OF N-FLUOROPYRIDINIUM SALTS; A NOVEL CYCLIC CARBENE PROPOSED AS A REACTIVE SPECIES

A new type of base-initiated reactions of pyridinium salts was found and a novel cyclic carbene was proposed as the reactive species.