English Synonyms
AKOSBBS-00004314;AURORAKA-6495;26DCLPY;4-(Dimethylamino)pyridine,99%,prilled;4-(DIMETHYLAMINO)PYRIDINESOLUTION;4-(Dimethylamino)pyridine,ReagentPlus,99%;N,N'-DIMEHTYL-4-PYRIDINAMINE;4-(Dimethylamino)PyridineForSynthesis
4-Dimethylaminopyridine Properties
| Melting Point | 112 °C |
| Boiling Point | 162 °C
|
| Density | 0.906 g/mL at 25 °C |
| Vapor Pressure | 0.169 hPa at 20 °C |
| Refractive Index | n20/D 1.431 |
| Flash Point | 110 °C |
| Storage Condition | Store Below +30°C. |
| Solubility | Soluble in Methanol, Solubility 50mg/Ml, Clear |
| Acidity Coefficient (pKa) | pKa (20°): 9.7 |
| Form | Granular |
| Color | Off-White to Yellow |
| Odor | Peculiar Smell |
| PH | 11 (60g/l, H2O, 20℃) |
| Water Solubility | 76 g/L (25 ºC) |
4-Dimethylaminopyridine Usage and Synthesis
Introduction
4-Dimethylaminopyridine, commonly referred to as DMAP, is a super-strong nucleophilic acylation catalyst. The resonance between the electron-donating dimethylamino group and the parent ring (pyridine ring) in its structure can strongly activate the nitrogen atom on the ring for nucleophilic substitution, significantly catalyzing the acylation/esterification reactions of highly sterically hindered and low-reactive alcohols and amines/acids, with an activity of about 104~106 times that of pyridine. Acyl transfer is a common transformation in nature and organic synthesis, among which chiral DMAP is a common asymmetric acyl transfer catalyst. Since 1996, when Vedejs and Fu's groups reported central chirality and planar chirality of DMAP catalysts, respectively, chiral DMAP catalysts have been greatly developed. Various central chirality, planar chirality, spiral chirality and central chirality of DMAP have been reported one after another, and have been well applied in many asymmetric acyl transfer reactions.Since 1996, When Vedejs and Fu Groups Reported Central-Chirality and Planar-Chirality Dmap Catalysts Respectively, Chiral Dmap Catalysts Have Been Greatly Developed. Various Central-Chirality, Planar-Chirality, Spiral-Chirality and Central-Chirality Dmaps Have Been Reported Successively and Have Been Well Applied in Many Asymmetric Acyl Transfer Reactions.
Use
It Is Widely Used as a Catalyst in Chemical Synthesis, And in Acylation, Carbonylation, Etherification and Esterification in the Synthesis of Organic Drugs, Pesticides, Dyes, Food Additives, Etc. 4-Dimethylaminopyridine Is a New Type of High-Efficiency Catalyst Widely Used in Chemical Synthesis in Recent Years. The Resonance of the Electron-Donating Dimethylamino Group and the Parent Ring (Pyridine Ring) in Its Structure Can Strongly Activate the Nitrogen Atom on the Ring for Nucleophilic Substitution, And Significantly Catalyze the Acylation (Phosphorylation, Sulfonylation, Carbonylation) of Highly Sterically Hindered and Low-Reactive Alcohols and Amines. Its Activity Is About 104-6 Times That of Pyridine. It Has High Catalytic Ability in Various Types of Reactions Such as Acylation, Alkylation, Etherification, Esterification and Transesterification in Organic Synthesis, Drug Synthesis, Pesticides, Medicines, Dyes, Fragrances, Polymer Chemistry, Analytical Chemistry, Etc.
Production Method
Heat 4-Hydroxypyridine, Dimethylamine Hydrochloride and Hexamethylphosphoric Acid Triamide at 220℃ for 4h. Rinse the Resulting Solidified Reactant with Water, Add Hydrochloric Acid and Hydrolyze at 100℃ for 1h. Cool to Room Temperature, Add Sodium Hydroxide Aqueous Solution Under Stirring, And Then Extract with Chloroform. After Drying the Extract with Magnesium Sulfate, Evaporate the Solvent, Extract the Residue with Boiling Hexane, Filter It Hot, Concentrate It, And Crystallize It to Obtain 4-Dimethylaminopyridine. The Yield Is About 55%.
