Production Method 1

453-27-0

937-00-8

Reaction Conditions

1.1 Reagents: Tin ,  Hydrochloric acid

Reference

Tin

Steel, Peter J., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2006, 1, 1-7

Production Method 2

777-44-6

937-00-8

Reaction Conditions

1.1 Reagents: Zinc Solvents: Acetic acid ;  8 h, rt → reflux

Reference

Preparation method of 3-trifluoromethylthiophenol and 3-methylthiotrifluorotoluene

, China, , ,

Production Method 3

777-44-6

937-00-8

Reaction Conditions

1.1 Reagents: Dichlorodimethylsilane ,  Dimethylacetamide ,  Zinc Solvents: 1,2-Dichloroethane
1.2 Reagents: Methanol

Reference

Non-aqueous reduction of aromatic sulfonyl chlorides to thiols using a dichlorodimethylsilane-zinc-dimethylacetamide system

Uchiro, Hiromi; Kobayashi, Susumu, Tetrahedron Letters, 1999, 40(16), 3179-3182

Production Method 4

194414-34-1

937-00-8

Reaction Conditions

1.1 Reagents: Sulfur Solvents: Diethyl ether

Reference

Biosynthesis of penicillins. VII. Oxy- and mercaptoacetic acids

Soper, Quentin F.; Whitehead, Calvert W.; Behrens, Otto K.; Corse, Joseph J.; Jones, Reuben G., Journal of the American Chemical Society, 1948, 70, 2849-55

Production Method 5

777-44-6

937-00-8

Reaction Conditions

1.1 Reagents: Ammonium formate Solvents: Water ;  heated; 1 h, reflux; reflux → 200 °C; 5 h, 200 °C; 200 °C → 120 °C
1.2 Reagents: Formic acid ;  acidified

Reference

Solvent-free synthesis of thiophenol using uncatalyzed transfer hydrogenation

Zhou, Shaodong; Qian, Chao; Chen, Xinzhi, Synthetic Communications, 2012, 42(16), 2432-2439

Production Method 6

672-58-2

937-00-8

Reaction Conditions

1.1 Reagents: Potassium formate ;  5 h, rt → 200 °C; 200 °C → 80 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2

Reference

Process for preparation of thiophenol derivatives

, China, , ,

Production Method 7

937-00-8

Reaction Conditions

1.1 Reagents: Potassium ethylxanthate ,  Sodium nitrite Solvents: Water

Reference

Nonbasic character of some aminotrifluoromethyldiphenyl sulfones. Synthesis of 3-amino-5-trifluoromethyldiphenyl sulfone

Stacy, Gardner W.; Bresson, C. Richard, Journal of Organic Chemistry, 1959, 24, 1892-6

Production Method 8

777-44-6

937-00-8

Reaction Conditions

1.1 Reagents: Formic acid Catalysts: Triphenylphosphine ,  Palladium ,  Iodine ;  5 h, 60 °C

Reference

Preparation of thiophenols from substituted benzenesulfonyl chlorides

, China, , ,

Production Method 9

937-00-8

Reaction Conditions

Reference

Preparation of 3-(pyrazinylthio)carbapenems as antibacterials

, Federal Republic of Germany, , ,

Production Method 10

937-00-8

Reaction Conditions

Reference

Hydrolysis kinetics and mechanism of diarylthiocarbamates in 20% aqueous dioxane medium

Mindl, J.; Balcarek, L.; Silar, L.; Vecera, M., Collection of Czechoslovak Chemical Communications, 1980, 45(11), 3130-9

Production Method 11

401-81-0

937-00-8

Reaction Conditions

1.1 Reagents: Potassium carbonate ,  Sulfur Catalysts: Cuprous iodide Solvents: Dimethylformamide ;  8 h, 90 °C
1.2 Reagents: Sodium borohydride ;  5 h, 40 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  40 °C
1.4 Reagents: Sodium hydroxide Solvents: Water ;  rt
1.5 Reagents: Hydrochloric acid Solvents: Water ;  acidified, rt

Reference

A general and efficient approach to aryl thiols: CuI-catalyzed coupling of aryl iodides with sulfur and subsequent reduction

Jiang, Yongwen; Qin, Yuxia; Xie, Siwei; Zhang, Xiaojing; Dong, Jinhua; et al, Organic Letters, 2009, 11(22), 5250-5253

Production Method 12

118849-61-9

937-00-8

Reaction Conditions

1.1 Reagents: Tin ,  Hydrochloric acid Solvents: Water

Reference

An efficient synthetic route to aryl thiocyanates from arenesulfinates

Still, Ian W. J.; Watson, Iain D. G., Synthetic Communications, 2001, 31(9), 1355-1359

Production Method 13

1643-69-2

937-00-8

Reaction Conditions

1.1 Reagents: Isopropanol Catalysts: Triphenylphosphine ,  Palladium ,  Iodine ;  5 h, rt → reflux

Reference

preparation of arylthiols via reduction of arylsulfonic acid

, China, , ,

Production Method 14

1643-69-2

937-00-8

Reaction Conditions

1.1 Reagents: Isopropanol Catalysts: Triphenylphosphine ,  Palladium ,  Iodine ;  10 h, reflux

Reference

Catalytic transfer hydrogenation of aryl sulfo compounds

Chen, Xinzhi; Zhou, Shaodong; Qian, Chao, Journal of Sulfur Chemistry, 2012, 33(2), 179-185

Production Method 15

402-26-6

937-00-8

Reaction Conditions

Reference

Vinyl selenides and selenoxides: preparation, conversion to lithium reagents, Diels-Alder reactivity, and some comparisons with sulfur analogs

Reich, Hans J.; Willis, Willam W. Jr.; Clark, Peter D., Journal of Organic Chemistry, 1981, 46(13), 2775-84

Production Method 16

937-00-8

937-00-8

Reaction Conditions

1.1 Solvents: Ethanol ,  Dichloromethane ;  30 min, rt
1.2 Reagents: Triphenylphosphine ;  30 min, rt
1.3 Reagents: Sodium borohydride Solvents: Water ;  12 h, rt

Reference

Large-Scale Synthesis, Crystal Structure, and Optical Properties of the Ag146Br2(SR)80 Nanocluster

Song, Yongbo; Lambright, Kelly; Zhou, Meng ; Kirschbaum, Kristin; Xiang, Ji; et al, ACS Nano, 2018, 12(9), 9318-9325

Production Method 17

453-27-0

937-00-8

Reaction Conditions

1.1 Catalysts: Tin ,  Hydrochloric acid

Reference

Tin

Steel, Peter J.; Poisson, Jean-Francois, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

Production Method 18

401-78-5

937-00-8

Reaction Conditions

Reference

Product class 13: arenethiols and arenethiolates

Rakitin, O. A., Science of Synthesis, 2007, 31, 949-974

Production Method 19

937-00-8

Reaction Conditions

1.1 Catalysts: Bromocyclohexane

Reference

Donor-atom effects on relative E2 rate constants for reactions of anions with cyclohexyl bromide

Bordwell, Frederick G.; Mrozack, Susan Romberg, Journal of Organic Chemistry, 1982, 47(24), 4813-15

Production Method 20

937-00-8

Reaction Conditions

Reference

Modified amino acids containing arylthiophenols or arylselenophenols, recombinant proteins, and biosynthesis methods and applications

, China, , ,

3-(trifluoromethyl)thiophenol Raw materials

• 3-Bromobenzotrifluoride
• 3-Iodobenzotrifluoride
• Magnesium, iodo[3-(trifluoromethyl)phenyl]-
• 3-(trifluoromethyl)benzene-1-sulfonamide
• 3-(trifluoromethyl)thiophenol
• Sodium 3-(trifluoromethyl)benzene-1-sulfinate
• Benzenesulfonic acid, 3-(trifluoromethyl)-
• Benzenesulfonic acid, 3-(trifluoromethyl)-, sodium salt (1:1)
• 3-(trifluoromethyl)benzene-1-sulfonyl chloride
• m-trifluoro-methyl-phenyl-magnesium bromide

3-(trifluoromethyl)thiophenol Preparation Products

• 3-(trifluoromethyl)thiophenol (937-00-8)

• 1. Essential effect of the electrolyte on the mechanical and chemical degradation of LiNi0.8Co0.15Al0.05O2 cathodes upon long-term cycling??
  Xiaoming Liu,Zachary D. Hood,Wangda Li,Donovan N. Leonard,Arumugam Manthiram,Miaofang Chi J. Mater. Chem. A, 2021,9, 2111-2119
• 2. Evidence of pre-micellar aggregates in aqueous solution of amphiphilic PDMS–PEO block copolymer?
  Domenico Lombardo,Gianmarco Munaò,Pietro Calandra,Luigi Pasqua,Maria Teresa Caccamo Phys. Chem. Chem. Phys., 2019,21, 11983-11991
• 3. Fate of nitrogen-15 in the subsequent growing season of greenhouse tomato plants (Lycopersicon esculentum Mill) as influenced by alternate partial root-zone irrigation
  Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400
• 4. Evolution of important glucosinolates in three common Brassica vegetables during their processing into vegetable powder and in vitro gastric digestion
  Nan Fu,Naphaporn Chiewchan,Xiao Dong Chen Food Funct., 2020,11, 211-220
• 5. Fast synthesis of red Li3BaSrLn3(WO4)8:Eu3+ phosphors for white LEDs under near-UV excitation by a microwave-assisted solid state reaction method and photoluminescence studies
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Trifluoromethylbenzenes
• Pharmaceutical and Biochemical Products Medicinal Building Blocks Fluorine containing Building Blocks

Recent Advances in the Application of 3-(Trifluoromethyl)thiophenol (CAS 937-00-8) in Chemical Biology and Pharmaceutical Research

3-(Trifluoromethyl)thiophenol (CAS 937-00-8) has emerged as a versatile building block in chemical biology and pharmaceutical research due to its unique physicochemical properties. The trifluoromethyl group confers enhanced lipophilicity and metabolic stability, while the thiol moiety allows for facile functionalization. Recent studies have explored its applications in drug discovery, materials science, and bioconjugation strategies, demonstrating its broad utility across multiple disciplines.

A 2023 study published in the Journal of Medicinal Chemistry reported the use of 3-(trifluoromethyl)thiophenol as a key intermediate in the synthesis of novel kinase inhibitors. The researchers developed a series of compounds where the trifluoromethylthiophenyl group served as a bioisostere for traditional aromatic systems, resulting in improved target binding affinity and pharmacokinetic properties. Molecular docking studies revealed that the unique electronic properties of the trifluoromethyl group contributed to enhanced interactions with hydrophobic pockets in the ATP-binding site of target kinases.

In materials science, a recent breakthrough demonstrated the potential of 3-(trifluoromethyl)thiophenol as a surface modifier for gold nanoparticles. The strong Au-S bond formation combined with the hydrophobic trifluoromethyl groups created stable, self-assembled monolayers with unique interfacial properties. These modified nanoparticles showed promise in biosensing applications, particularly for the detection of low-abundance biomarkers in complex biological matrices.

Another significant application was reported in the field of bioconjugation chemistry. Researchers utilized 3-(trifluoromethyl)thiophenol as a reactive handle for site-selective protein modification. The thiol group allowed for efficient conjugation under mild conditions, while the trifluoromethyl moiety provided a convenient ¹⁹F NMR handle for real-time monitoring of conjugation efficiency and product characterization. This approach has been particularly valuable for the development of antibody-drug conjugates with improved homogeneity and stability.

Recent synthetic methodology developments have expanded the accessibility of 3-(trifluoromethyl)thiophenol derivatives. A 2024 publication in Organic Letters described a photocatalytic trifluoromethylation protocol that enables the late-stage functionalization of thiophenol derivatives. This method significantly broadens the structural diversity accessible from this important building block, opening new possibilities for structure-activity relationship studies in medicinal chemistry programs.

From a safety and regulatory perspective, recent toxicological studies have provided important insights into the handling and use of 3-(trifluoromethyl)thiophenol. While the compound demonstrates favorable stability profiles, proper precautions are recommended due to its potential reactivity as a thiol-containing compound. Updated material safety data sheets reflect these findings and provide guidance for safe laboratory practices when working with this material.

Looking forward, the unique combination of properties offered by 3-(trifluoromethyl)thiophenol positions it as a valuable tool for addressing current challenges in drug discovery and chemical biology. Its applications in the development of targeted therapies, particularly in oncology and infectious diseases, continue to expand as researchers explore novel ways to leverage its distinctive characteristics. The compound's versatility suggests it will remain an important building block in pharmaceutical research for the foreseeable future.

• 825-83-2(4-(trifluoromethyl)benzene-1-thiol)
• 13333-97-6(2-(Trifluoromethyl)thiophenol)
• 730-03-0(Benzene, 1-[(3-methylphenyl)thio]-3-(trifluoromethyl)-)
• 130783-02-7(3,5-Bis(trifluoromethyl)thiophenol)
• 329-14-6(4-Trifluoromethylthioanisole)
• 798569-87-6(Benzenethiol, 2,4-bis(trifluoromethyl)-, bismuth(3+) salt (3:1))
• 798569-86-5(Benzenethiol, 4-(trifluoromethyl)-, bismuth(3+) salt (3:1))
• 53451-90-4(4-Trifluoromethyldiphenyl sulfide)
• 798569-90-1(Benzenethiol, 2,4-bis(trifluoromethyl)-)
• 788-12-5(Benzene, 1-[(4-methylphenyl)thio]-3-(trifluoromethyl)-)