Commonly used reagents—-phosphorus pentasulfide_industrial additives

[English name] Diphosphorus Pentasulfide&nAnti-aging agentbsp;

【Molecular formula】 P4S10

【Molecular weight】 444.55

[CA registration number] [1314-80-3]

【Structural formula】 P4S10

[Physical Properties] Phosphorus pentasulfide, light yellow crystal. mp 286~290 ℃, d 2.090 g/cm3.

【Notes】 P4S10 is highly flammable and will decompose when exposed to moisture. It should be stored in a sealed container at a low temperature and dry place.

Organosulfur reagents not only have rich reaction chemistry, but also have very important biological functions. Phosphorus pentasulfide P4S10 is a sulfiding reagent widely used in organic synthesis. It can convert carbonyl compounds into thiocarbonyl compounds to prepare various types of organic sulfides. P4S10 can also effectively activate free hydroxyl groups in alcohols or acids, and can also participate in reactions as a deoxidizer and dehydrogenation reagent.

p-Toluenesulfonic Anhydride

P4S10 can act on various types of carbonyl substrates (such as ketones, diketones, esters, amides, etc.) and convert them into the corresponding thiocarbonyl compounds (Formula 1)[1].

Lawesson’s reagent is a commonly used reagent for the synthesis of organosulfur compounds. It can be prepared by reacting P4S10 with anisole (formula 2)[2].

P4S10 can also be used to activate free hydroxyl groups in carboxylic acids or alcohol compounds, thereby generating active leaving groups, which can further undergo substitution reactions in the presence of other nucleophiles (Formula 3)[3].

P4S10 is a mild and selective deoxygenating reagent that can reduce sulfoxide compounds to sulfides (Formula 4)[4]. This type of reduction reaction does not affect other functional groups of the substrate such as ester groups, amides and ketones. Interestingly, the sulfone also remains unchanged under the action of P4S10.

P4S10 can also participate in reactions as a dehydrogenation reagent. For example, the aromatization reaction of furan Diels-Alder adducts can be effectively performed under the induction of P4S10 and carbon disulfide (Formula 5) [5].

P4S10 can also participate in reactions as an adduct, such as the adduct reaction with the steroid molecule 16-dehydropregnanolone (Formula 6)[6].

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