59886-90-7

Basic information

• Product Name: 4-Chloro-2,3-dimethylpyridine 1-oxide
• Synonyms: 4-Chloro-2,3-dimethylpyridine-N-oxide ,98%;4-Chloro-2,3-dimethy;3-DiMethyl-4-chloropyridine N-oxide;4-chloro-2,3-diMethyl-1$l^{5}-pyridin-1-one;2,3-DiMethyl-4-chloropyridne-n-oxide;4-Chloro-2,3-lutidine N-oxide, 4-Chloro-2,3-dimethylpyridinium-1-olate;nsc 275262;2,3-DIMETHYL-4-CHLOROPYRIDINE-N-OXIDE
• CAS NO: 59886-90-7
• Molecular Formula: C₇H₈ClNO
• Molecular Weight: 157.6
• EINECS: 1806241-263-5
• Product Categories: Rabeprazole;Heterocycle-Pyridine series;Pyridines;PHARMACEUTICAL INTERMEDIATES;Intermediates of Rabeprazole;Heterocycles;Nitric Oxide Reagents
• Mol File: 59886-90-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 103-105°C
• Boiling Point: 338.5°C
• Flash Point: 158.5°C
• Appearance: Pale Yellow Solid
• Density: 1.19
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.537
• Storage Temp.: Room temperature.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 1.28±0.10(Predicted)
• CAS DataBase Reference: 4-Chloro-2,3-dimethylpyridine 1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-2,3-dimethylpyridine 1-oxide(59886-90-7)
• EPA Substance Registry System: 4-Chloro-2,3-dimethylpyridine 1-oxide(59886-90-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 59886-90-7(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

An intermediate in the synthesis of rabeprazole (R070500).

InChI:InChI=1/C7H8ClNO/c1-5-6(2)9(10)4-3-7(5)8/h3-4H,1-2H3

Upstream product

• 37699-43-7 2,3-dimethyl-4-nitropyridine N-oxide 
• 75-36-5 acetyl chloride 
• 583-61-9 2,3-Lutidine 
• 22710-07-2 2,3-dimethylpyridine 1-oxide 

Downstream Products

• 59886-84-9 (4-chloro-3-methylpyridin-2-yl)methyl acetate 
• 251345-11-6 4-(4-hydroxybutoxy)-2,3-dimethylpyridine N-oxide 
• 162280-04-8 2,3-Dimethyl-4-(2-hydroxyethylthio)pyridine-N-oxide 
• 675198-19-3 [4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanol hydrochloride 
• 112525-75-4 2-acetoxymethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine 
• 253345-80-1 C₉H₁₀F₃NO₂*ClH 
• 253345-81-2 C₈H₁₁NO₂*ClH 
• 103577-61-3 2,3-dimethyl-4-(2,2,2-trifluoroethoxy)-pyridine N-oxide 
• 1219815-69-6 2,3-dimethyl-4-(methylthio)pyridine-N-oxide 

Relevant articles and documents

1H, 13C and 15N NMR spectral and theoretical studies of some methyl and alkylamino derivatives of 4-halopyridine N-oxides

Nine new and three earlier known 4-halogen (Cl and Br) substituted pyridine N-oxides have been prepared and their 1H, 13C and 15N NMR chemical shifts assigned based on PFG 1H, X (X=13C and 15N) HMQC and HMBC experiments as well as the comparison with our earlier results for substituted pyridine N-oxide derivatives. The 15N resonances of the pyridine nitrogen are 27-40 ppm more shielded in 4-halo-2-alkylamino-6-methyl-5-nitropyridine N-oxide than in parent 4-halopyridine N-oxide. According to quantum chemical ab initio HF/6-311G** calculations the amino tautomer of 4-chloro-2- methylamino-6-methyl-5-nitropyridine N-oxide is more stable than its imino form. Using B3LYP/6-311G** optimized structures both 13C and 15N shifts were calculated by density functional B3LYP/6-311G ** CSGT methods for the amino and imino tautomers as well as for the dimeric structure for 4-chloro-2-methylamino-6-methyl-5-nitropyridine N-oxide. The 15N NMR and DFT calculations suggest the prevailing of the dimeric amino form for one congener, which is further supported by ESI-TOF MS data.

CXCR4 INHIBITORS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same.

Development of a scalable and safe process for the production of 4-chloro-2,3-dimethylpyridine- N -oxide as a key intermediate in the syntheses of proton pump inhibitors

2-(Pyridin-2-ylmethanesulfinyl)-1H-benzimidazole-based drugs belong to the most prominent and successfully applied proton pump inhibitors. To fulfill the demand for a flexible and safe procedure for the synthesis of early-stage intermediates which are known to possess a strong exothermal decomposition potential, we have developed a high-yielding telescoped procedure for the synthesis of a key intermediate in the synthesis of these drugs. This strategy turned out to be highly reproducible in laboratory as well as on pilot-plant scale. As the starting material, as well as some of the intermediates, shows a highly exothermal decomposition potential, extensive safety investigations were undertaken. The whole process was adapted in a safe and reliable manner based on the outcome of this systematic approach. Considering these precautions, no safety issues were observed, neither in the laboratory nor in the pilot plant.