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- W4230307543 abstract "[324753-16-4] C13H13PS (MW 232.28) InChI = 1S/C13H13PS/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2 InChIKey = IGEZSSBBLDNMPJ-UHFFFAOYSA-N (reagent used as coupling reagent in the traceless Staudinger reaction) Solubility: soluble in alcohols, dichloromethane, chloroform, DMF. Form Supplied in: clear oil. Analysis of Reagent Purity: 1H NMR (CDCl3, 300 MHz) δ 7.41–7.38 (m, 4 H), 7.33–7.26 (m, 6 H), 3.02 (d, J = 7.8 Hz, 2 H), 1.38 (t, J = 7.5 Hz, 1 H) ppm; 13C NMR (CDCl3, 75 MHz) δ 132.5 (d, J = 17.1 Hz), 128.8, 128.3, 128.1, 20.6 (d, J = 21.7 Hz) ppm; 31P NMR (CDCl3, 121 MHz) δ −7.94 ppm. Preparative Method: (diphenylphosphino)methanethiol is synthesized from (diphenylphosphino)methyl acetyl sulphide, obtained either by reacting chloromethyldiphenylphosphine oxide with a salt of thioacetic acid1 or by reacting bromomethyl acetyl sulfide with borane–diphenylphosphine complex.2 In a representative example (eq 1), Ar(g) is bubbled through a 153 mM solution of (diphenylphosphino)methyl acetyl sulfide (1 equiv) in anhydrous methanol for 1 h at rt. Then, sodium hydroxide (2 equiv) is added and the mixture is stirred under Ar(g) for 2 h. The solvent is then removed under reduced pressure and the residue is dissolved in CH2Cl2. The resulting solution is washed with 2 N aqueous HCl and brine. The organic layer is dried over MgSO4, filtered, and evaporated to dryness under reduced pressure to afford crude (diphenylphosphino)methanethiol. (1) Purification: by flash chromatography (alumina, 25% ethyl acetate in hexanes). Handling, Storage, and Precautions: the phosphorus atom and to a lesser extent the sulfur atom are highly susceptible to oxidation. The reagent is best stored as a borane-complex intermediate and/or S-acetylated. Deprotection can be performed immediately prior to its use or even in situ during its use." @default.
- W4230307543 created "2022-05-11" @default.
- W4230307543 creator A5082373614 @default.
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- W4230307543 date "2007-03-15" @default.
- W4230307543 modified "2023-09-26" @default.
- W4230307543 title "(Diphenylphosphino)methanethiol" @default.
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- W4230307543 doi "https://doi.org/10.1002/9780470842898.rn00731" @default.
- W4230307543 hasPublicationYear "2007" @default.
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