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Accueil > Publications > Recherche par années > Années 2010 > 2010

Aucagne, V.

(9H-Fluoren-9-yl)methanethiol

In "e-EROS Encyclopedia of Reagents for Organic Synthesis" (2010) - doi : 10.1002/047084289X.rn01287

par Frapart - publié le

Abstract :

[957753-00-3] C14H12S (MW 212.32)
InChI = 1S/C14H12S/c15-9-14-12-7-3-1-5-10(12)11-6-2-4-8-13(11)14/h1-8,14-15H,9H2
InChIKey = MXHVORUHWLKKMZ-UHFFFAOYSA-N
(reagent used to introduce a masked thiocarboxylic acid through thioesterification)
Alternate Name : Fm SH.
Physical Data : no reported physical data other than NMR and MS.
Solubility : soluble in Et2O, CH2Cl2, and other common organic solvents ; insoluble in water.
Form Supplied in : pale yellow oil.
Analysis of Reagent Purity : 1H and 13C NMR.
Preparative Method : not yet commercially available. FmSH can be prepared in three steps from commercially available (9H-fluoren-9-yl)methanol (FmOH) by treatment with tosyl chloride and pyridine in chloroform at rt for 6 h,1 followed by displacement of the tosylate by potassium thioacetate and 18-crown-6 in DMF at rt for 2 h, and then reduction with DIBAL-H in Et2O at –78 °C and then at 0 °C for 30 min.2 Purification requires column chromatography.
Purification : flash column chromatography on silica gel : 98:2 hexane/ethyl acetate.
Handling, Storage, and Precautions : stable under normal pressure and temperature in the absence of air. Unpleasant odor. Store in a cool dry place under an inert atmosphere. Wash thoroughly after use and remove any contaminated clothing. The toxicological properties have not been studied.