587-19-9

Basic information

• Product Name: 4-TRIFLUOROMETHYLTHIO-BENZOIC ACID ETHYL ESTER
• Synonyms: ETHYL 4-(TRIFLUOROMETHYLTHIO)BENZOATE;4-TRIFLUOROMETHYLTHIO-BENZOIC ACID ETHYL ESTER;RARECHEM AL BI 0368
• CAS NO: 587-19-9
• Molecular Formula: C₁₀H₉F₃O₂S
• Molecular Weight: 250.24
• Mol File: 587-19-9.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-TRIFLUOROMETHYLTHIO-BENZOIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 4-TRIFLUOROMETHYLTHIO-BENZOIC ACID ETHYL ESTER(587-19-9)
• EPA Substance Registry System: 4-TRIFLUOROMETHYLTHIO-BENZOIC ACID ETHYL ESTER(587-19-9)

Safety Data

• Hazardous Substances Data: 587-19-9(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 21259-75-6 mercury bis(trifluoromethanethiolate) 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 3872-23-9 Copper(I) trifluoromethanethiolate 
• 811-68-7 silver(I) trifluoromethanethiolate 
• 348-06-1 p-carboethoxybenzenediazonium tetrafluoroborate 
• 94-09-7 p-aminoethylbenzoate 
• 15223-20-8 1-methyl-4-{[(trifluoromethyl)sulfanyl]sulfonyl}benzene 
• 81290-20-2 (trifluoromethyl)trimethylsilane 

Relevant articles and documents

Transition-Metal-Free Synthesis of Aryl Trifluoromethyl Thioethers through Indirect Trifluoromethylthiolation of Sodium Arylsulfinate with TMSCF3

Herein, we report an indirect trifluoromethylthiolation of sodium arylsulfinates. This transition-metal-free reaction significantly provides an environmentally friendly and practical synthetic method for aryl trifluoromethyl thioethers using commercial Ruppert-Prakash reagent TMSCF3. This approach is also a potential alternative to the current industrial production method owing to facile substrates, excellent functional group compatibility, and operational simplicity.

Copper(I)-promoted trifluoromethylthiolation of arenediazonium salts with AgSCF3

An efficient method for trifluoromethylthiolation of arenediazonium salts has been developed in mild conditions with a stable and convenient AgSCF3. It provides a straightforward and convenient way for the synthesis of trifluoromethylthiolated compound from diazonium salts in moderate to good yields.

Copper-Catalyzed Trifluoromethylthiolation of Di(hetero)aryl-λ3-iodanes: Mechanistic Insight and Application to Synthesis of (Hetero)Aryl Trifluoromethyl Sulfides

The direct and regioselective copper/S-Phos-catalyzed trifluoromethylthiolation of symmetrical and unsymmetrical di(hetero)aryl-λ3-iodanes has been accomplished for the synthesis of various (hetero)aryl trifluoromethyl sulfides employing readily accessible silver trifluoromethylthiolate (AgSCF3) as nucleophilic trifluoromethylthiolating reagent. The developed transformation tolerates various functional groups like nitrile, enolizable ketone, ester, nitro and free carboxylic acid. Interestingly, the formal trifluoromethylthiolation of arenes was also achieved through integration of the synthesis of diaryl-λ3-iodanes from arenes with the trifluoromethylthiolation. Mechanistic investigations did not favor the radical formation and SET pathway. Based on the variable temperature 19F NMR spectroscopy, isolation of the most relevant catalytic intermediate, and stoichiometric studies supported the Cu(I)/Cu(III) catalytic cycle, wherein the oxidative addition of diaryl-λ3-iodanes was assisted by the silver salt.