77146-55-5

Basic information

• Product Name: 2-Chloro-4-Nitrothioanisole
• Synonyms: 2-Chloro-4-Nitrothioanisole
• CAS NO: 77146-55-5
• Molecular Formula: C₇H₆ClNO₂S
• Molecular Weight: 203.64604
• Mol File: 77146-55-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Chloro-4-Nitrothioanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-Nitrothioanisole(77146-55-5)
• EPA Substance Registry System: 2-Chloro-4-Nitrothioanisole(77146-55-5)

Safety Data

• Hazardous Substances Data: 77146-55-5(Hazardous Substances Data)

Upstream product

• 408350-99-2 2-chloro-4-nitro-phenyl thiocyanate 
• 121-45-9 phosphorous acid trimethyl ester 
• 99-54-7 3,4-dichloronitrobenzene 
• 77-78-1 dimethyl sulfate 
• 350-30-1 3-chloro-4-fluoronitrobenzene 
• 5188-07-8 sodium thiomethoxide 
• 96-69-5 Santonox R 

Downstream Products

• 23153-12-0 3-chloro-4-(methylsulfonyl)aniline 
• 5211-01-8 3-Chloro-4-methylsulfanyl-phenylamine 

Relevant articles and documents

Phenyl heterocyclyl ethers

The invention relates to compounds of formula I

1,2-Diarylpyrroles as potent and selective inhibitors of cyclooxygenase- 2

Series of 1,2-diarylpyrroles has been synthesized and found to contain very potent and selective inhibitors of the human cyclooxygenase-2 (COX-2) enzyme. The paper describes short and practical syntheses of the target molecules utilizing the Paal-Knorr reaction. Electrophilic substitution on 1 proceeds in a regioselective fashion, and the method was used to generate a number of tetrasubstituted pyrroles. Detailed SAR on the series has been studied by modifications of the aryl rings and the substituents in the pyrrole ring. Diarylpyrrole 1 is a very potent (COX-2, IC50 = 60 nm) and selective (COX-1/COX-2 = > 1700) inhibitor whereas the isomeric 2 is completely inactive against COX-2. Modifications of the substituents on the fluorophenyl ring in 1 yields very potent inhibitors of COX-2 (IC50 = 40- 80 nm) with excellent selectivity(1200 to >2500) vs COX-1, Analog 20 containing a sulfonamide group is an excellent inhibitor of COX-2 with an IC50 of 14 nm. Tetrasubstituted pyrroles containing groups such as COCF3, SO2CF3, or CH2OAr at position 3 in the pyrrole ring give excellent inhibitors (COX-2, IC50 = 30-120 nm). In vivo testing in the carrageenan- induced paw edema model in the rat establishes that the 1,2-diarylpyrroles are orally active antiinflammatory agents. Compound 3 is the most potent inhibitor of edema with an ED50 of 4.7 mpk.