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Bis(phenylthio)methane, 98+%, Thermo Scientific Chemicals
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Catalog number L01723.14
also known as L01723-14
Price (USD)/ Each
106.00
-
Quantity:
25 g
Price (USD)/ Each
106.00
Bis(phenylthio)methane, 98+%, Thermo Scientific Chemicals
Catalog numberL01723.14
Price (USD)/ Each
106.00
-
Chemical Identifiers
CAS3561-67-9
IUPAC Name{[(phenylsulfanyl)methyl]sulfanyl}benzene
Molecular FormulaC13H12S2
InChI KeyZHUPZVIALZHGGP-UHFFFAOYSA-N
SMILESC(SC1=CC=CC=C1)SC1=CC=CC=C1
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Specifications
Specification Sheet
Specification SheetMelting Point (clear melt)33.5-39.5?C
FormCrystals or powder or crystalline powder
Appearance (Color)White
Assay (GC)≥98.0%
Acyl anion equivalent with some advantages over 1,3-dithiane for the preparation of vinyl sulfides. Bis(phenylthio)methane is used in the synthesis of the dihydroxy thioethers.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Acyl anion equivalent with some advantages over 1,3-dithiane for the preparation of vinyl sulfides. Bis(phenylthio)methane is used in the synthesis of the dihydroxy thioethers.
Solubility
Insoluble in water.
Notes
Keep container tightly closed. Store away from oxidizing agents.
Acyl anion equivalent with some advantages over 1,3-dithiane for the preparation of vinyl sulfides. Bis(phenylthio)methane is used in the synthesis of the dihydroxy thioethers.
Solubility
Insoluble in water.
Notes
Keep container tightly closed. Store away from oxidizing agents.
RUO – Research Use Only
General References:
- Abel Mendoza.; Donald S. Matteson. Bis(phenylthio)methaneboronic esters as sources of carbanions and ketene thioacetals. J. Org. Chem. 1979, 44, (8), 1352-1354.
- Francisco Foubelo.; Ana Gutierrez.; Miguel Yus. Methane-derived polyanionic synthons from bis(phenylthio)methane. Tetrahedron Letters. 1999, 40, (46), 8177-8180.
- Acyl anion equivalent, compare 1,3-Dithiane, A10505. Can be metallated, e.g. with n-BuLi. Dimetallation requires a metal complexing agent, e.g. TMEDA, allowing dialkylation: Tetrahedron Lett., 21, 4763 (1980).
- The products of addition of the lithio-derivative to aldehydes and ketones undergo a pinacol-type rearrangement with CuOTf, with insertion of a one-carbon unit adjacent to the carbonyl group: J. Am. Chem. Soc., 97, 4749 (1975); see also: Org. Synth. Coll., 6, 737 (1988). An alternative method utilizes an alkyllithium to effect a carbenoid rearrangement, which has been applied to ring expansion: Tetrahedron Lett., 28, 20 (1987):