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
• Article Data: 17

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

General Description

4-Dimethylaminopyridine N-oxide, also known as DMAP-N-oxide, is a chemical compound with the molecular formula C7H10N2O. It is a derivative of 4-dimethylaminopyridine (DMAP) and is commonly used as a catalyst in organic synthesis reactions. DMAP-N-oxide is a white solid that is soluble in polar solvents such as water and alcohol. It is known for its ability to facilitate esterification and acylation reactions by acting as a nucleophilic catalyst, making it a valuable tool in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. Additionally, DMAP-N-oxide has been studied for its potential applications in polymerization and materials science. Overall, this compound plays an essential role in the field of organic chemistry as a catalyst for various synthetic processes.

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

Downstream Products

• 1122-58-3 dmap 
• 118972-30-8 1-N,N-dimethylcarbamoyloxy-4-dimethylaminopyridinium tetraphenylborate 
• 889-36-1 (E)-4-[4-(dimethylamino)styryl]pyridine 
• 1219601-53-2 C₁₀H₁₁ClN₄ 
• 1219601-29-2 C₁₄H₁₆N₂O₃S 
• 1219601-28-1 C₉H₁₁N₅ 
• 1219601-52-1 C₁₃H₁₆N₄O₂ 
• 26708-23-6 4-(4'-N,N-dimethylaminostyryl)pyridine N-oxide 
• 1121-76-2 4-chloropyridine N-oxide 
• 1003-67-4 4-methylpyridine-1-oxide 
• 1122-96-9 4-methoxypyridine N-oxide 
• 694-59-7 pyridine N-oxide 
• 13296-01-0 4-(4'-methoxystyryl)pyridine-1-oxide 
• 93532-41-3 4-<4-Chlor-styryl-pyridin-N-oxid 

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.

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.

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