26452-81-3

Basic information

• Product Name: 4-Chloro-6-methoxypyrimidine
• Synonyms: 6-CHLORO-4-PYRIMIDINYL METHYL ETHER;4-CHLORO-6-METHOXYPYRIMIDINE;Pyrimidine, 4-chloro-6-methoxy- (6CI,8CI,9CI);4-chloro-6-methoxypyrimidine(SALTDATA: FREE);4-Chloro-6-methoxypyrimidine 98+%;4-Chloro-6-methoxy-1,3-diazine;4-Chloro-6-MethoxypyriMidine, 98.0%(GC);Pyrimidine, 4-chloro-6-methoxy-
• CAS NO: 26452-81-3
• Molecular Formula: C₅H₅ClN₂O
• Molecular Weight: 144.56
• EINECS: 678-369-8
• Product Categories: PYRIMIDINE;APIs & Intermediate;API intermediates;Heterocycle-Pyrimidine series;alkyl chloride
• Mol File: 26452-81-3.mol
• Article Data: 16

Chemical Properties

• Melting Point: 34.5-35.0 °C
• Boiling Point: 80°C/18mmHg(lit.)
• Flash Point: 90.1 °C
• Appearance: /
• Density: 1.292 g/cm³
• Vapor Pressure: 0.13mmHg at 25°C
• Refractive Index: 1.52
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -1.59±0.17(Predicted)
• CAS DataBase Reference: 4-Chloro-6-methoxypyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-6-methoxypyrimidine(26452-81-3)
• EPA Substance Registry System: 4-Chloro-6-methoxypyrimidine(26452-81-3)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• Hazardous Substances Data: 26452-81-3(Hazardous Substances Data)

Usage

General Description

4-Chloro-6-methoxypyrimidine is a chemical compound with the molecular formula C5H5ClN2O. It is a derivative of pyrimidine, which is a heterocyclic compound containing nitrogen atoms in a six-membered ring. 4-Chloro-6-methoxypyrimidine is a white to light yellow solid, and it is primarily used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. Its chloro and methoxy functional groups make this compound a versatile building block for the synthesis of various bioactive molecules. It is also known for its role as a precursor in the production of various pesticides and herbicides. Overall, 4-Chloro-6-methoxypyrimidine is an important chemical with diverse applications in the production of pharmaceuticals and agrochemicals.

InChI:InChI=1/C5H5ClN2O/c1-9-5-2-4(6)7-3-8-5/h2-3H,1H3

Upstream product

• 1193-21-1 4,6-dichloropyrimidine 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 7440-44-0 pyrographite 

Downstream Products

• 869639-17-8 4-{2-[(6-methoxypyrimidin-4-yl)methylamino]ethoxy}benzaldehyde 
• 1450930-95-6 6-methoxypyrimidine-4-carbonitrile 
• 1393456-80-8 (4-chloro-6-methoxypyrimidin-5-yl)phenylmethanol 
• 1393456-83-1 1,1-dimethylethyl 4-methoxy-5-phenylthieno[2,3-d]pyrimidine-6-carboxylate 
• 1393456-82-0 4-methoxy-5-phenylthieno[2,3-d]pyrimidine-6-carbonitrile 
• 1393456-81-9 (4-chloro-6-methoxypyrimidin-5-yl)phenylmethanone 
• 1193-21-1 4,6-dichloropyrimidine 
• 17759-28-3 4-methoxy-6-phenyl-pyrimidine 
• 856694-94-5 4-methoxy-6-(p-methoxyphenyl)pyrimidine 
• 4765-77-9 6-Chloro-3,4-dihydro-4-oxopyrimidine 

Relevant articles and documents

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Three novel pyrimidinylhydrazones substituted at either the aromatic moiety or at the imine carbon atom were synthesized and characterized by standard analytical methods. All compounds were found to be toxic in the micro- to submicromolar range against a diverse panel of cancer cell lines including multidrug resistant (MDR) derivatives expressing P-glycoprotein (Pgp). UV-visible spectrophotometry experiments demonstrated that the most active compound (3) forms highly stable complexes with iron(III) and copper(II) in a wide pH range with a stronger preference towards iron(III). The redox activity of the iron and copper complexes of ligand 3 was investigated using cyclic voltammetry and was tested with cellular reductants. The impact of reactive oxygen species (ROS) on the mechanism of toxicity was assessed using the ROS-sensitive cell permeable dye 2′,7′-dichlorofluorescin diacetate (DCFDA). Our results demonstrate that the studied pyrimidinylhydrazones form redox-active iron and copper complexes that are capable of producing intracellular ROS, which might lead to cellular damage and cell death in cancer cells regardless of their resistance status.

AROMATIC RING COMPOUND

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