2,4-Dimethoxy thiophenol

2,4-Dimethoxy thiophenol

CAS No.:18906-37-1
Molecular Formula:C₈H₁₀O₂S
Molecular Weight:170.23 g mol⁻¹
Appearance:Colourless to pale-yellow oil; characteristic thiophenol odour; bp 180–182 °C/10 mmHg, ρ 1.14 g cm⁻³, nD²⁰ 1.586, fp 79 °C
Purity:≥98 % (GC)
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Product Description

An electron-rich aromatic thiol bearing two methoxy donors at the 2- and 4-positions, affording high nucleophilicity (pKa 6.4) and strong π-donor character. The push–pull substitution pattern is exploited in:

Late-stage agro-chemical assembly: copper-catalysed S-arylation installs the 2,4-di-MeO-phenyl-sulfur motif into pyrazole carboxanilides, delivering potent SDHI fungicides with 2-fold improved metabolic stability versus non-methoxy analogues.

High-refractive-index optical coatings: thiol–ene photopolymerisation with triallyl isocyanurate yields colourless films (n 1.70, Tg 130 °C, YI <1 after 500 h Q-UVB) for OLED encapsulation and 5G lens substrates.

Silver-antimicrobial SAMs: self-assembled monolayers on Ag(111) give densely packed hydrophobic surfaces (water contact angle 100°) that sustain >99 % bacterial kill rates after 24 h while suppressing tarnishing in saline atmospheres.

Heavy-metal scavenger: the soft sulfur and vicinal methoxy oxygen form a bidentate S,O-binding pocket that selectively extracts Pd(II) (log K = 19.5) from spent cross-coupling liquors, enabling recovery to <0.2 ppm residual palladium.

Flavour & fragrance precursor: laccase-mediated oxidation converts the thiol into the corresponding disulfide, a long-lasting vanilla-like odorant (odour threshold 0.02 ng L⁻¹) used in beverage aromatisation.

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

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