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4-Dimethylaminopyridine Basic information
Chemical Properties Usage
Product Name:4-Dimethylaminopyridine
Synonyms:4-(dimethylamino)-pyridin;4-Dimethylaminepyridine;gamma-(Dimethylamino)pyridine;N,N-Dimethyl-4-aminopyridine;n,n-dimethyl-4-pyridinamin;p-Dimethylaminopyridine;Pyridine, 4-(dimethylamino)-;AURORA KA-6495
Product Categories:Pyridine;Heterocycles;Pyridines, Pyrimidines, Purines and Pteredines;Pyridines derivates;Other Reagents;Biochemistry;Condensation & Active Esterification;Reagents for Oligosaccharide Synthesis;Synthetic Organic Chemistry;Materials Science;Bases & Related Reagents;Fluorescent Labels & Indicators;Nucleotides;Amines;Aromatics
Mol File:1122-58-3.mol
4-Dimethylaminopyridine Structure
4-Dimethylaminopyridine Chemical Properties
Melting point 83-86 °C(lit.)
Boiling point 211 °C
density 0.906 g/mL at 25 °C
refractive index n20/D 1.431
Fp 110 °C
storage temp. Store in dark!
solubility methanol: 50 mg/mL, clear
form prilled
pkapKa (20°): 9.7
color off-white to yellow
PH11 (60g/l, H2O, 20℃)
Water Solubility 76 g/L (25 ºC)
Merck 14,3389
BRN 110354
Stability:Stable. Incompatible with acids, oxidizing agents.
CAS DataBase Reference1122-58-3(CAS DataBase Reference)
NIST Chemistry Reference4-Pyridinamine, N,N-dimethyl-(1122-58-3)
EPA Substance Registry System4-Pyridinamine, N,N-dimethyl-(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
Hazard Note Toxic/Corrosive
HazardClass 8
PackingGroup II
HS Code 29333999
MSDS Information
4-Dimethylaminopyridine English
SigmaAldrich English
ACROS English
ALFA English
4-Dimethylaminopyridine Usage And Synthesis
Chemical PropertiesWhite crystalline powder. The resonance between the electron-providing two-amino group and pyridine ring can strongly stimulate nucleophilic substitution of nitrogen atoms on the ring; this dramatically stimulates the acylation (phosphorylation, sulfonation, acylation) of alcohols and amines of high resistance and low reactivity, with activity at 104-6 times that of pyridine. Additionally, 4-Dimethylaminopyridine can be used as a phase transfer catalyst in interface reactions, with the following advantages: a small amount of catalyst a required, usually only 0.01-5% of the molar number of the reaction substrate; the acid produced by the reaction can be neutralized using organic or inorganic bases; reaction conditions are mild and can take place in room temperature, thus conserving energy resources; a wide variety of solvents can be used, as reactions can take place in both polar and non-polar solvents; the reaction time is minutes-short, while pyridine reactions are long, thus largely increasing production yield; it has a high yield, when reacted with sterically hindered hydroxyl compounds, which pyridine does not react with, 4-Dimethylaminopyridine has a yield of 80-90%, thus increasing reaction yield and product quality and simplifying production; it has few negative side effects, with minimal odor and waste.
Usage4-Dimethylaminopyridine is widely used in chemical syntheses as a new and highly efficient acylation and esterification catalyst. It has a high catalyzing effect in acylation, alkylation and etherification reactions in organic syntheses, drug, pesticide, dye and fragrance production, polymer chemistry, and analytical chemistry; it has a significant effect in increasing yield. 4-Dimethylaminopyridine has been successful implemented in the production of pharmaceutical ingredients such as b (c) spiramycin, succinate, and statins, improving production conditions and creating positive economic and social benefits. Additionally, it is also widely used in the synthesis of complex natural products, such as: acylation in the total synthesis of pravastatin, three-fluorine acylation in the total synthesis of tubercidin, acylation in the total synthesis of mugineic acid, benzoyl acylation in the total synthesis of terpestacin, and acylation in the total synthesis of viagar. In pesticide production, using 4-dimethylaminopyridine in tetramethrin synthesis increases yield and product purity. It also has significant catalyzing effects in synthesis of carbamates by isocyanates and synthesis of pyrethrin by acyl chloride. It also has significant effects in the synthesis of organophosphorus compounds in phosphoryl reactions.
Chemical PropertiesWhite solid
UsesA highly efficient catalyst for acylation reactions.
Uses4-Dimethylaminopyridine is a versatile hypernucleophilic acylation catalyst, it is used to improve the yield, reduce the reaction time, improving relaxation process conditions. Widely used in perfumes, dyes, pigments, pesticides, pharmaceuticals and polymer compounds and other fields. Also used as a catalyst for the synthesis of polyurethane, a curing agent and a blowing catalyst.
UsesDMAP is a useful highly basic nucleophilic catalyst for a variety of reactions such as esterifications with anhydrides, the Baylis-Hillman reaction, hydrosilylations, tritylation, the Steglich rearrangement.
UsesA highly fluorescent adenosine analogue, which in a dimethoxytrityl, phosphoramidite protected form, can be site-specifically inserted into oligonucleotides through a 3?5?phosphodiester linkage using an automated DNA synthesizer
UsesIn a wide variety of organic syntheses as a catalyst.
Purification MethodsRecrystallise DMAP from toluene [Sadownik et al. J Am Chem Soc 108 7789 1986]. [Beilstein 22 V 112.] § A polystyrene supported version (PS-DMAP) is commercially available.
4-Dimethylaminopyridine Preparation Products And Raw materials
Raw materialsAzabenzene-->Hexamethylphosphoramide-->4-Hydroxypyridine
Tag:4-Dimethylaminopyridine(1122-58-3) Related Product Information
4-DIMETHYLAMINOPYRIDINE HYDROBROMIDE PERBROMIDE 4-DIMETHYLAMINO-1-NEOPENTYLPYRIDINIUM CHLORIDE 1-(4-METHYLPHENYL)-3-(4-TETRAHYDRO-1H-PYRROL-1-YLPYRIDINIUM-1-YL)PROP-2-EN-1-ONE CHLORIDE 2-Aminopyridine 4-Dimethylaminobenzoic acid 3-Aminopyridine PYRIDINE-2,4-DIAMINE Triethylamine 3,4-Diaminopyridine Triethanolamine Bis(2-ethylhexyl)amine N-Methyl-3-pyridinamine Dibenzylamine DIMETHYLAMINOPYRIDINE ON POLYSTYRENE,DIMETHYLAMINOPYRIDINE, POLYMER-BOUND,POLYMER SUPPORTED DIMETHYLAMINOPYRIDINE,DIMETHYLAMINOPYRIDINE, 4-(SECONDARY STANDARD) 4-Dimethylaminobenzaldehyde 4-Pyridinemethaneamine 4-Dimethylaminopyridine N-Ethylmethylamine