4-Dimethylaminopyridine CAS#1122-58-3
Exceptional Catalytic Activity – Exhibits acylation and esterification activity approximately 10⁴–10⁶ times higher than pyridine.
Strong Nucleophilic Catalyst – The electron-donating dimethylamino group greatly enhances nucleophilic substitution efficiency.
Effective for Low-Reactivity Substrates – Efficiently catalyzes acylation of alcohols and amines with high steric hindrance or low reactivity.
Versatile in Organic Synthesis – Widely used in acyl transfer reactions, including asymmetric synthesis with chiral DMAP catalysts.
Products Description of 4-Dimethylaminopyridine CAS#1122-58-3
4-Dimethylaminopyridine (DMAP) is a highly effective nucleophilic acylation catalyst. The electron-donating dimethylamino group resonates with the pyridine ring, strongly activating the ring nitrogen toward nucleophilic substitution. This greatly enhances the acylation and esterification of alcohols and amines/acids, including substrates with high steric hindrance or low reactivity. Its catalytic efficiency is approximately 10⁴–10⁶ times greater than that of pyridine. Acyl transfer is a fundamental transformation in both natural processes and organic synthesis, and chiral DMAP is commonly employed as an asymmetric acyl transfer catalyst.
4-Dimethylaminopyridine Chemical 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 |
| Fp | 110 °C |
| storage temp. | Store below +30°C. |
| solubility | methanol: 50 mg/mL, clear |
| form | prilled |
| pka | pKa (20°): 9.7 |
| color | off-white to yellow |
| Odor | characteristic odor |
| PH Range | 9.7 (10% aq soln) |
| PH | 11 (60g/l, H2O, 20℃) |
| Water Solubility | 76 g/L (25 ºC) |
| Merck | 143389 |
| BRN | 110354 |
| Stability: | Stable. Incompatible with acids, oxidizing agents. |
| LogP | 1.34 at 25℃ |
| CAS DataBase Reference | 1122-58-3(CAS DataBase Reference) |
| NIST Chemistry Reference | 4-Pyridinamine, N,N-dimethyl-(1122-58-3) |
| EPA Substance Registry System | 4-(Dimethylamino)pyridine (1122-58-3) |
Safety Information
| Hazard Codes | T,C,T+,Xn,F |
| Risk Statements | 25-34-24/25-36/37/38-27-36-24-20-61-40-23/24/25-67-66-21/22-11-36/37-22-19 |
| Safety Statements | 36/37/39-45-28A-26-28-36/37-53-27-22-16 |
| RIDADR | UN 2811 6.1/PG 2 |
| WGK Germany | 3 |
| RTECS | US8400000 |
| Autoignition Temperature | 420 °C |
| Hazard Note | Toxic/Corrosive |
| TSCA | T |
| HazardClass | 8 |
| PackingGroup | II |
| HS Code | 29333999 |
| Toxicity | LD50 orally in Rabbit: 140 mg/kg LD50 dermal Rabbit 90 mg/kg |
Product Application of 4-Dimethylaminopyridine CAS#1122-58-3
It is used in water softening and the preparation of high-purity water, as well as in the refining of radioactive elements. It is also applied in iodine extraction from seaweed, antibiotic purification, and the treatment of industrial wastewater.
