3,5-Bis(trifluoromethyl) thiophenol

3,5-Bis(trifluoromethyl) thiophenol

CAS No.:130783-02-7
Molecular Formula:C₈H₄F₆S
Molecular Weight:246.17 g mol⁻¹
Appearance:Colourless to pale-yellow solid; mp 71–72 °C, bp 167 °C/760 mmHg, ρ 1.46 g cm⁻³ (25 °C), nD²⁰ 1.442, fp 66 °C
Purity:≥97 % (GC)
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Product Description

A highly electron-deficient aromatic thiol bearing two strongly-withdrawing CF₃ groups at the 3- and 5-positions. The strongly lowered pKa (≈ 4.9) and high oxidative stability make it a privileged building block for:

Julia-Kocienski olefination reagent (BTFPSH): the derived sulfone is shelf-stable and delivers >90 % (E)-selectivity in one-pot Julia couplings to construct fluorinated stilbenes and agrochemical intermediates .

High-index thiol–ene optical resins: photopolymerisation with triallyl isocyanurate yields colourless films (n = 1.65, Tg 135 °C, YI <1 after 500 h Q-UVB) for 5G lens substrates and OLED encapsulation layers.

Silver-antimicrobial self-assembled monolayers: the densely packed fluorinated surface (water contact angle 100°) sustains >99 % bacterial kill after 24 h and suppresses Ag tarnishing in saline atmospheres.

Palladium-selective scavenger: the soft sulfur and electron-poor ring form a stable Pd(II) complex (log K = 19.2), enabling recovery of Pd from spent cross-coupling liquors to <0.1 ppm residual.

UV-absorbing functional monomer: incorporated at 1–3 wt % into acrylic resins it imparts broad-spectrum UV-A/UV-B absorption (λmax 295 nm, ε 18 000) for clear sunscreen films and optical coatings .

Store under nitrogen at 2–8 °C, away from light and oxidants to prevent disulfide formation.

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