1005-31-8

Basic information

• Product Name: 4-DIMETHYLAMINOPYRIDINE N-OXIDE
• Synonyms: TIMTEC-BB SBB008470;4-Pyridinamine,N,N-dimethyl-,1-oxide;4-DIMETHYLAMINOPYRIDINE N-OXIDE;4-(DIMETHYLAMINO)PYRIDINE N-OXIDE HYDRATE;DMAPO HYDRATE;dmapo;4-DIMETHYLAMINOPYRIDINE N-OXIDE ---CRYSTALLINE---;dimethyl-(1-oxidopyridin-1-ium-4-yl)amine
• CAS NO: 1005-31-8
• Molecular Formula: C₇H₁₀N₂O
• Molecular Weight: 138.17
• Product Categories: pharmacetical
• Mol File: 1005-31-8.mol

Chemical Properties

• Melting Point: 97 °C
• Boiling Point: 316.5 °C at 760 mmHg
• Flash Point: 145.2 °C
• Appearance: /
• Density: 1.03 g/cm³
• Vapor Pressure: 0.000409mmHg at 25°C
• Refractive Index: 1.52
• Solubility: soluble in Methanol
• PKA: 3.90±0.10(Predicted)
• CAS DataBase Reference: 4-DIMETHYLAMINOPYRIDINE N-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-DIMETHYLAMINOPYRIDINE N-OXIDE(1005-31-8)
• EPA Substance Registry System: 4-DIMETHYLAMINOPYRIDINE N-OXIDE(1005-31-8)

Safety Data

• Hazardous Substances Data: 1005-31-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
4-Dimethylaminopyridine N-oxide is used as a nucleophilic catalyst for facilitating esterification and acylation reactions, which are crucial steps in the synthesis of various pharmaceutical compounds. Its ability to accelerate these reactions contributes to the efficiency and effectiveness of drug development processes.
Used in Agrochemical Production:
In the agrochemical industry, 4-Dimethylaminopyridine N-oxide serves as a catalyst to enhance the synthesis of active ingredients used in pesticides and other agricultural chemicals. This application is vital for improving the yield and purity of these compounds, thereby supporting agricultural productivity and crop protection.
Used in Organic Compound Synthesis:
4-Dimethylaminopyridine N-oxide is utilized as a catalyst in the synthesis of a wide range of organic compounds, including those used in the fragrance, flavor, and dye industries. Its catalytic properties streamline the production of these compounds, ensuring a more sustainable and cost-effective manufacturing process.
Used in Polymerization and Materials Science:
4-Dimethylaminopyridine N-oxide is explored for its potential as a catalyst in polymerization reactions and the development of new materials. Its application in this field could lead to advancements in material science, with implications for creating innovative materials with unique properties for various applications.

InChI:InChI=1/C7H10N2O/c1-8(2)7-3-5-9(10)6-4-7/h3-6H,1-2H3

Upstream product

• 1121-76-2 4-chloropyridine N-oxide 
• 124-40-3 dimethyl amine 
• 108-18-9 diisopropylamine 
• 1122-58-3 dmap 
• 26708-23-6 4-(4'-N,N-dimethylaminostyryl)pyridine N-oxide 
• 694-59-7 pyridine N-oxide 
• 118972-30-8 1-N,N-dimethylcarbamoyloxy-4-dimethylaminopyridinium tetraphenylborate 
• 1124-33-0 4-nitraminopyridine N-oxide 
• 626-61-9 4-Chloropyridine 

Downstream Products

• 1122-58-3 dmap 
• 868-84-8 S,S-dimethyl dithiocarbonate 
• 623-80-3 S,S-diethyl dithiocarbonate 
• 10596-55-1 S-Ethyl S'-methyl dithiocarbonate 
• 123457-63-6 1-ethoxy-4-dimethylaminopyridinium S-methyldithiocarbonate 
• 79322-44-4 1-benzyloxy-4-dimethylaminopyridinium bromide 
• 121-44-8 triethylamine 
• 1122-96-9 4-methoxypyridine N-oxide 
• 87748-51-4 4-Dimethylamino-1-dimethylcarbamoyloxy-pyridinium; chloride 
• 118972-30-8 1-N,N-dimethylcarbamoyloxy-4-dimethylaminopyridinium tetraphenylborate 
• 694-59-7 pyridine N-oxide 
• 118622-51-8 4-Dimethylamino-1-dimethylcarbamoyloxy-pyridinium; bromide 
• 110-86-1 pyridine 

Relevant articles and documents

A mild and efficient H2O2 oxygenation of N-heteroaromatic compounds to the amine N-oxides and KI deoxygenation back to the tertiary amine with hexaphenyloxodiphosphonium triflate

A mild and efficient method for the oxidation of N-heteroaromatic compounds to the corresponding N-oxides using H2O2 in the presence of hexaphenyloxodiphosphnium triflate (Hendrickson reagent) in EtOH at room temperature was reported. This methodology presented relatively fast and selective reactions to afford the N-oxides in good yields. The reverse reactions, deoxygenation reactions, were also carried out under the same reaction conditions by KI to produce the tertiary amines.

Renewable waste rice husk grafted oxo-vanadium catalyst for oxidation of tertiary amines to N-oxides

Low cost renewable waste rice husks (RH) have been used as a support for grafting of an oxo-vanadium Schiff base via covalent attachment for the oxidation of tertiary amines to N-oxide. The synthesis of the desired RH grafted oxo-vanadium complex involves prior functionalization of the RH support with amino-propyltrimethoxysilane (APTMS) followed by its reaction with salicylaldehyde to get an RH-functionalized Schiff base which subsequently reacted with vanadyl sulphate to get the targeted oxo-vanadium catalyst. The synthesized catalyst was found to be an efficient heterogeneous catalyst and afforded an excellent yield of corresponding N-oxides via oxidation of tertiary amines with hydrogen peroxide as an oxidant. Furthermore, the synthesized catalyst was found to be quite stable and showed consistent activity for five runs without any loss in activity.

Amines vs. N-Oxides as Organocatalysts for Acylation, Sulfonylation and Silylation of Alcohols: 1-Methylimidazole N-Oxide as an Efficient Catalyst for Silylation of Tertiary Alcohols

A comparison of the relative catalytic efficiencies of Lewis-basic amines vs. N-oxides for the acylation, sulfonylation and silylation of primary, secondary and tertiary alcohols is reported. Whilst the amines are generally superior to the N-oxides for acylation, the N-oxides are superior for sulfonylation and silylation. In particular, 1-methylimidazole N-oxide (NMI-O) is found to be a highly efficient catalyst for sulfonylation and silylation reactions. To the best of our knowledge, NMI-O is the first amine or N-oxide Lewis basic organocatalyst capable of promoting the efficient silylation of tert-alcohols in high yield with low catalyst loading under mild reaction conditions.

Highly efficient and selective phosphorylation of amino acid derivatives and polyols catalysed by 2-aryl-4-(dimethylamino)pyridine-N-oxides-towards kinase-like reactivity

The chemoselective phosphorylation of hydroxyl containing amino acid derivatives and polyols by phosphoryl chlorides catalyzed by 2-aryl-4-(dimethylamino)pyridine-N-oxides is described.

Method of synthesis of tetradentate amide macrocycle ligand and its metal-complex

A tetradendate amide based macrocyclic ligand and its Fe(III) complex which act as activators of hydrogen peroxide. The synthetic methodology to develop the ligands is new, simple and provides better yield for each step of the ligand synthesis. The Fe(III

Equilibrium of acyl transfer between pyridine N-oxides and their acylonium salts

Transfer of acyl groups from N-acyloxypyridinium salts to pyridine N-oxides in acetonitrile was studied. The equilibrium constants of acyl exchange were determined. These quantities vary in the range covering eight orders of magnitude, depending on the st

Identical acyl transfer reactions between pyridine N-oxides and their N-acylonium salts

28 identical acyl exchange reactions R-CO-Nu+, X- + Nu between pyridine N-oxides in acetonitrile were studied. Here, X- = BPh 4 - and R = methyl, N,N-dimethylamino, N,N-diethylamino, 4-morpholino, 1-piperidino, N-methyl, N-phenylamino, or N,N-diphenylamino group. The IR and NMR spectroscopic characteristics of acyloxypyridinium salts were determined, and the quantum-chemical parameters of all reagents calculated. The results were subjected to correlation analysis. It was found that the rate of identical acyl transfer reactions was controlled by the interaction of frontier orbitals in the transition state.

Rate and equilibrium constants of benzoyl group transfer between pyridine N-oxides

Kinetic characteristics of 19 transfer reactions of benzoyl group from N-benzoyloxypyridinium salts to pyridine N-oxides and 4-dimethylaminopyridine were studied in acetonitrile by the stopped-flow method. The rate of an identical reaction for 4-methoxypyridine was measured by dynamic NMR spectroscopy. For 5 other identical reactions the rates were estimated from Bronsted correlations. Equilibrium constants were estimated with the use of UV spectrophotometry (6), IR spectroscopy (2), from kinetic data (K ij = k ij /k ji ) (2), and in one case as logK i-j = logK i-x - logK j-x . The second order rate constants (k ij ) varied in the range 102-105 l mol -1 s-1, the equilibrium constants (K ij ) in the range 102-10-2; the activation parameters (ΔH ≠) were within 15-50 kJ mol-1, (-ΔS ≠) -20-110 J mol-1 K-1. The reactions under study occur in a single stage following the concerted SN2 mechanism through an early associative transition state. The benzoyl groups exchange rate and equilibrium are well described by simplified Marcus equation (omitting the quadratic term). 2005 Pleiades Publishing, Inc.

The Rate and Equilibrium Constants for N-, O-Acyl Transfer

Reactions with dimethylcarbamoyl group transfer from N-acylpyridinium salts to pyridine N-oxides and from N-acyloxypyridinium salts to pyridines in acetonirile solutions were studied. Their rate and equilibrium constants and activation parameters were determined. The reactions were shown to be one-step and to follow the SN2 mechanism. Equations relating the rate and equilibrium parameters of the N-O and O-N acyl transfer reactions to the basicity of the nucleophile and outgoing group were obtained.

Acetyl exchange between pyridine N-oxides in acetonitrile solutions: An attempt to apply the Marcus equation to acetyl transfer

Forty-three (including eight identical) reactions of acetyl transfer from N-acetyloxypyridinium salts to pyridine N-oxides in acetonitrile solutions were studied. The rate constants k2 vary in the range 107-10-1 1 mol-1 s-1; the equilibrium constants K, in the range 107-10-7; the activation enthalpy ΔH≠, in the range 17-30 kJ mol-1; the activation entropy -ΔS≠, in the range 60-85 J mol-1 K-1; and the heat of reaction -ΔH0, within ±50 kJ mol-1. All reactions occur in a single stage by the concerted SN2 mechanism with a low degree of bond cleavage in the transition state. The rate and equilibrium of the acetyl exchange are satisfactorily described by the Bronsted equation. The quality of predicting the reactivity is substantially improved by introducing into the correlation equation a second parameter, the rates of identical reactions.