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3561-67-9 - Bis(phenylthio)methane, 98+% - Formaldehyde diphenyl mercapatal - L01723 - Alfa Aesar

L01723 Bis(phenylthio)methane, 98+%

CAS Number
3561-67-9
Synonyms
Formaldehyde diphenyl mercapatal

Size Price ($) Quantity Availability
5g 25.80
25g 83.00
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Bis(phenylthio)methane, 98+%

MDL
MFCD00003067
EINECS
222-624-4

Chemical Properties

Formula
C13H12S2
Formula Weight
232.36
Melting point
36-38°
Boiling Point
194°/8mm
Solubility
Insoluble in water.

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.

Notes

Keep container tightly closed. Store away from oxidizing agents.

Literature 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):

Other References

Beilstein
1874146
Harmonized Tariff Code
2930.90
TSCA
No

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