1193-96-0

Basic information

• Product Name: syn-2-pyridinealdoxime
• Synonyms: syn-Pyridine-2-aldoxime;syn-Pyridine-2-carboxaldehyde oxime;(E)-2-Pyridinecarbaldehyde oxime;2-Pyridinecarbaldehyde (E)-oxime;syn-2-PyridinealdoxiMe, 99+% 25GR;(E)-2-Pyridinecarboxaldehyde OxiMe;(E)-2-PyridylaldoxiMe;(E)-Picolinaldehyde OxiMe
• CAS NO: 1193-96-0
• Molecular Formula: C₆H₆N₂O
• Molecular Weight: 122.12
• EINECS: 212-849-6
• Product Categories: C6;Heterocyclic Building Blocks;Pyridines;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 1193-96-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 110-112 °C(lit.)
• Boiling Point: 233.139°C at 760 mmHg
• Flash Point: 94.799°C
• Appearance: White to very slightly pinkish/Crystalline Powder
• Density: 1.141g/cm³
• Vapor Pressure: 0.032mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: -20°C
• CAS DataBase Reference: syn-2-pyridinealdoxime(CAS DataBase Reference)
• NIST Chemistry Reference: syn-2-pyridinealdoxime(1193-96-0)
• EPA Substance Registry System: syn-2-pyridinealdoxime(1193-96-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 1193-96-0(Hazardous Substances Data)

Usage

Description

syn-2-Pyridinealdoxime is a 2-substituted pyridine derivative that exhibits inhibitory activity against prolyl-4-hydroxylase. It is characterized by its white to very slightly pinkish crystalline powder appearance. syn-2-Pyridinealdoxime is also known as the N-demethylated analogue of the acetylcholinesterase (AChE) inhibitor Pralidoxime (P701120).

Uses

1. Chemical Industry:
syn-2-Pyridinealdoxime is used as a chemical intermediate for the preparation of DNA-binding silver nitrate complexes. These complexes have potential applications in various fields, including biotechnology and nanotechnology, due to their unique properties and interactions with DNA.
2. Pharmaceutical Industry:
a) As an AChE Inhibitor:
syn-2-Pyridinealdoxime serves as an AChE inhibitor, which can be beneficial in the treatment of conditions related to the overactivity of acetylcholinesterase, such as myasthenia gravis and certain types of poisoning.
b) In the Synthesis of Pralidoxime:
Being the N-demethylated analogue of Pralidoxime, syn-2-Pyridinealdoxime plays a role in the synthesis of this AChE inhibitor, which is used as an antidote for poisoning by organophosphates and carbamates.
3. Research and Development:
syn-2-Pyridinealdoxime is utilized in research and development for studying the structure-activity relationships of pyridine derivatives and their interactions with prolyl-4-hydroxylase and other biological targets. This can lead to the discovery of new drugs and therapeutic agents.

InChI:InChI=1/C6H6N2O/c9-8-5-6-3-1-2-4-7-6/h1-5,9H/b8-5-

Upstream product

• 2110-14-7 2-hydroxyiminomethyl-pyridine 
• 1121-60-4 pyridine-2-carbaldehyde 
• 3731-51-9 2-(Aminomethyl)pyridine 
• 74231-53-1 O-acetyl-2-pyridinecarboxaldoxime 

Downstream Products

• 154-97-2 Contrathion 
• 78232-23-2 2,2'-bis-(hydroxyimino-methyl)-1,1'-hexanediyl-bis-pyridinium; dibromide 
• 3150-38-7 1-dodecyl-2-(hydroxyimino-methyl)-pyridinium; iodide 
• 74231-53-1 O-acetyl-2-pyridinecarboxaldoxime 
• 54846-16-1 1-benzyl-2-<(hydroxyimino)methyl>pyridinium bromide 
• 93583-83-6 pyridine-2-carbaldehyde-((E)-O-benzoyl oxime ) 
• 94-63-3 pralidoxime iodide 
• 3731-51-9 2-(Aminomethyl)pyridine 
• 126527-23-9 O-ethyl pyridine-2-aldoxime 
• 126527-21-7 (E)-picolinaldehyde O-benzyl oxime 
• 126527-22-8 2-pyridinecarboxaldoxime methyl ether 
• 2110-14-7 2-hydroxyiminomethyl-pyridine 
• 100-70-9 2-Cyanopyridine 

Relevant articles and documents

Cupric Ion Catalyzed Ester Hydrolysis of O-Acetyl-2-pyridinecarboxaldoxime. Nucleophilic Attack by Metal-Bound Water

The ester hydrolysis of O-acetyl-2-pyridinecarboxaldoxime is catalyzed by Cu2+.Thus, apparent rates for the hydroxide path and the water path are enhanced by 2.2x107 and 1.1x104 times, respectively.Detailed analysis indicates that the Cu2+-bound hydroxide ion or water molecule reacts with the carbonyl caarbon of the complexed ester.Thus, the catalysis includes increases in the effective concentrations of the attacking nucleophiles as well as enhancement in the leaving group ability.Besides, furhter catalysis in the attack of the coordinated water by general bases is suggested.Implications of the present results on the breakdown of the acyl carboxypeptidase A intermediate are discussed.

The effect of neutral oximes on the reactivation of human acetylcholinesterase inhibited with paraoxon

Important defense agents against chemical warfare weapons, which are reactivators of human acetylcholinesterase (huAChE) inhibited by neurotoxic organophosphorus compounds (OP), need a reasonable permeation of the hematoencephalic barrier (HB). In this wo

3-methyl-4-oxa-5-azahomoadamantane as an organocatalyst for the aerobic oxidation of primary amines to oximes in water

A simple and efficient catalytic system for the aerobic oxidation of primary amines into corresponding oximes has been developed, with 3-methyl-4-oxa-5-azahomoadamantane as catalyst, acetaldoxime as co-catalyst and water as solvent. This process, which uses oxygen (O2) as an economic and green oxidant and water as a green solvent, tolerates a wide range of substrates, affording the target oximes in moderate to excellent yields. It was found that high selectivity was achieved when 3-methyl-4-oxa-5-azahomoadamantane was used, and E-type oximes were the only detected products. A possible mechanism for this catalytic process is proposed.