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4-Dimethylaminopyridine

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4-Dimethylaminopyridine Basic information
"One-pot" synthesis of 4-dimethylaminopyridine Esterification catalyst Super nucleophilic acylation catalyst --4- dimethylaminopyridine Chemical Properties Uses Production method
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
CAS:1122-58-3
MF:C7H10N2
MW:122.17
EINECS:219-282-3
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
mp 83-86 °C(lit.)
bp 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
color off-white to yellow
Water Solubility 76 g/L (25 ºC)
Merck 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
TSCA T
HazardClass 8
PackingGroup II
HS Code 29333999
MSDS Information
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4-Dimethylaminopyridine English
SigmaAldrich English
ACROS English
ALFA English
4-Dimethylaminopyridine Usage And Synthesis
"One-pot" synthesis of 4-dimethylaminopyridineTake 4-cyanopyridine, 2-vinyl pyridine and dimethylamine as the main raw materials, apply one-pot method for synthesis of 4-dimethylaminopyridine. The optimum conditions obtained as follows: reactant charge ratio m (4- cyanopyridine) / m (2- vinylpyridine) = 1.5. Use the 40% aqueous NaOH solution for reflux of 2h for cleavage of intermediates with the reaction yield being 87.4%. The targeted compound is verified by IR, ^ 1HNMR and MS.
[Author] Chen Guang Zhao Xin Zhang Dayong
[Agencies] School of Life Science and Pharmacy, Nanjing University of Technology, Nanjing, Jiangsu, 210009, China; School of chemistry and environmental sciences, Nanjing Normal University Nanjing, Jiangsu, 210097, China
Esterification catalyst4-Dimethylaminopyridine is a novel efficient catalyst for being widely used in chemical synthesis. It has relative high catalytic ability in various types of reactions such as acylation, alkylation, etherification, and esterification in organic synthesis, drug synthesis, pesticides, dyes, and spices, and it has significant efficacy in improving the efficiency. As a catalyst, it is preferably to have the acylating agent being acid anhydride and in the condition of organic base. The esterification of succinate between low-grade alcohols can be carried out in an excess of alcohol with the catalysis of sulfuric acid and strong acidic cation exchange resin. However, in case of without separating the water, it will affect the conversion rate.
The above information is edited by the chemicalbook of Dai Xiongfeng.
Super nucleophilic acylation catalyst --4- dimethylaminopyridine4-dimethylaminopyridine is a novel efficient catalyst developed in recent years for widely application in chemical synthesis. In its structure, resonance between the electron donating dimethylamino group and its parent ring (pyridine ring) can strongly activate the nitrogen atom in the ring to have nucleophilic substitution and significantly catalyze the acylation (phosphorylation, sulfonylation, carbon acylation) of the high resistance, low reactivity of alcohols and amines with its activity being 6-104 time as high as the pyridine. It has strong catalyst capabilities in many types of reactions including organic synthesis, drug synthesis, pesticides, pharmaceuticals, dyes, perfumes, polymer chemistry, and the acylation, alkylation, etherification, esterification and trans-esterfication reactions in the analytical chemistry acylation, alkylation, etherification, esterification and transesterification reactions ability to significantly improve the yield. In addition, it can also be used as a phase transfer catalyst for interfacial reaction. Its advantages exhibits: a small amount of catalyst which usually take 0.01 to 5% of substrate moles. The produced acid can be subject to neutralization with organic or inorganic bases; the reaction conditions are usually mild with the reaction can be carried out under normal room temperature which save energy; it has a broad scope for choosing solvent for which both polar and non-polar organic solvent are suitable. The reaction time is also short. The reaction time is long with pyridine while only a few minutes are enough for reaction with DMAP, and thus greatly improving labor productivity; The yield is high. For hydroxy compound with large steric hindrance which almost has no reaction with pyridine, using DMAP can increase the yield up to 80-90%, and thus improving the reaction yield and product quality, and simplify the process; the side effects are small, little odor and small waste; Owing to the excellent catalytic performance of DMAP, it is known as the "super catalyst", which has become one of the most commonly used catalyst in organic synthesis workers. Domestic chemical and pharmaceutical industry have already successfully applied it to the production of B (C) acyl spiramycin, artemisinin succinate, and lipid-lowering statin drugs, improving the process conditions, and achieving good economic and social benefit. In addition, it is also widely used in complex natural product full (semi) synthesis, such as: the acetylation in the total synthesis of PRAVASTATIN, the trifluoro-acetylation in the total synthesis of TUBERCIDIN, the acetylation in the total synthesis of the MUGINEIC ACID and the benzoylation of TERPESTACIN and the acylation in the total synthesis of sildenafil (VIAGAR) etc. In the production of pesticides, applying DMAP for the synthesis of tetramethrin increases the yield and purity of the product. It also has significant catalytic activity in the reaction of using isocyanate ester for synthesis of carbamate ester and reaction of using chrysanthemoyl chloride fro synthesis of pyrethroids. In the synthesis of organic phosphorus through phosphorylation reaction, the effect is quite remarkable.
Chemical PropertiesWhite crystal powder
Uses4-Dimethylaminopyridine is a novel efficient catalyst for being widely used in chemical synthesis. It has relative high catalytic ability in various types of reactions such as acylation, alkylation, etherification, and esterification in organic synthesis, drug synthesis, pesticides, dyes, and spices, and it has significant efficacy in improving the efficiency.
It can be used as a super nucleophilic acylation catalyst.
It can be used as the highly efficient catalyst in acylation and esterification.
Production methodPut 4-hydroxypyridine, dimethylamine hydrochloride and hexamethylphosphoric triamide for heating at 220 ℃ for 4h. The generated curing reaction product was washed and rinsed with water. Add hydrochloric acid for hydrolysis at 100 ℃ for 1h. Cool to room temperature and add aqueous sodium hydroxide under stirring. Further extract with chloroform. The extract was dried by magnesium sulfate and the solvent was distilled off. The residue was extracted with boiling hexane, filtered upon hot condition, concentrated and crystallized to give 4-dimethylaminopyridine with the yield of about 55%.
Chemical PropertiesWhite solid
UsageA highly efficient catalyst for acylation reactions.
Usage4-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.
UsageA 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
4-Dimethylaminopyridine Preparation Products And Raw materials
Preparation ProductsBETA-(4-ACETOXYPHENYL)PROPIONIC ACID-->2-Chloro-4-(trifluoromethyl)pyrimidine-->1-[4-(TRIFLUOROMETHYL)PYRIMID-2-YL]PIPERAZINE-->1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-->N4-Benzoylcytosine-->3-Hydrazinyl-1-(4-methylpiperazin-1-yl)propan-1-one -->4-BROMO-5-(TRIFLUOROMETHYL)-1-PHENYL-1H-PYRAZOLE-->2-ACETAMIDOPYRIDINE-3-CARBOXYLIC ACID-->3-Hydrazinyl-1-morpholinopropan-1-one -->2-Hydrazinyl-1-(4-methylpiperazin-1-yl)ethanone -->1-TERT-BUTYL-4-BROMO-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-->2-Hydrazinyl-1-morpholinoethanone -->1-(2-PYRROLIDINOETHYL)PIPERAZINE-->4-BROMO-1-METHYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-->2-AMINO-ISONICOTINIC ACID ETHYL ESTER-->1-TERT-BUTYL-4-BROMO-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE-->5-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOLE-4-CARBALDEHYDE-->4-TRIFLUOROMETHYL-N-METHYLANILINE 97-->Aniracetam-->Docetaxel-->(2R)-(-)-Glycidyl tosylate-->METHYL 6-[(TERT-BUTOXYCARBONYL)AMINO]NICOTINATE-->2-Hydroxy-4-(trifluoromethyl)pyrimidine-->TERT-BUTYL 5-FORMYLTHIAZOL-2-YLCARBAMATE-->1-TERT-BUTYL-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBALDEHYDE-->4-BROMO-5-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOLE-->1-ACETYL-5-BROMOINDOLINE-->4-AMINOBENZANILIDE-->2-(METHYLTHIO)-4-(TRIFLUOROMETHYL)PYRIMIDINE-->Boc-L-beta-Homoproline-->1-TERT-BUTYL-3-(TRIFLUOROMETHYL)-1H-PYRAZOLE-->2'-BROMOACETANILIDE-->1-TERT-BUTYL-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE-->2-Aminoisonicotinic acid -->2,2,2-TRIFLUORO-1-(3-(TRIFLUOROMETHYL)-1-PHENYL-1H-PYRAZOL-4-YL)ETHANONE-->5-(TRIFLUOROMETHYL)-1-METHYL-1H-PYRAZOLE-->LIMAPROST-->PIPERAZINE-1,4-DICARBOXYLIC ACID TERT-BUTYL ESTER METHYL ESTER-->MONO-METHYL SUCCINATE
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