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Sigma-Aldrich

Phenylacetyl disulfide

96%

Synonym(s):

Bis(phenylacetyl) disulfide, Di(phenylacetyl) disulfide

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About This Item

Linear Formula:
(C6H5CH2COS)2
CAS Number:
15088-78-5
Molecular Weight:
302.41
MDL number:
MFCD00513572
UNSPSC Code:
12352100
PubChem Substance ID:
24879391
NACRES:
NA.22

Quality Level

200

assay

96%

form

solid

mp

59-63 °C (lit.)

SMILES string

O=C(Cc1ccccc1)SSC(=O)Cc2ccccc2

InChI

1S/C16H14O2S2/c17-15(11-13-7-3-1-4-8-13)19-20-16(18)12-14-9-5-2-6-10-14/h1-10H,11-12H2

InChI key

IXGZXXBJSZISOO-UHFFFAOYSA-N

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General description

Phenylacetyl disulphide serves as a sulfurization reagent during the preparation of phosphates.Phenyl acetyl disulfide can be synthesized by the reaction of phenyl benzenethiolsulfonate with thioacetic acid in the presence of triethylamine.

Application

Phenylacetyl disulfide (PADS) may be used as a sulphur transfer agent during the synthesis of phosphorothioate oligodeoxyribonucleotides.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Synthesis of antisense oligonucleotides: Replacement of 3H-1, 2-benzodithiol-3-one 1, 1-dioxide (Beaucage reagent) with phenylacetyl disulfide (PADS) as efficient sulfurization reagent: From bench to bulk manufacture of active pharmaceutical ingredient.
Cheruvallath ZS, et al.
Organic Process Research & Development, 4(3), 199-204 (2000)
A study on the use of phenylacetyl disulfide in the solid-phase synthesis of oligodeoxynucleoside phosphorothioates.
Roelen HCPF, et al.
J. R. Neth. Chem. Soc., 110(7-8), 325-331 (1991)
"Organic disulfides and related substances. XXIII. Unsymmetrical carbonyl disulfides and cognate compounds"
Fiel L and Buckman DJ
The Journal of Organic Chemistry, 32(11), 3467-3470 (1967)
Honglu Zhang et al.
Journal of the American Chemical Society, 128(51), 16464-16465 (2006-12-21)
The activation of phosphatidylinositol 3-kinase (PI 3-K) and subsequent production of PtdIns(3,4,5)P3 launches a signal transduction cascade that impinges on a plethora of downstream effects on cell physiology. Control of PI 3-K and PtdIns(3,4,5)P3 levels is an important therapeutic target
Use of phenylacetyl disulfide (PADS) in the synthesis of oligodeoxyribonucleotide phosphorothioates.
Cheruvallath ZS, et al.
Nucleosides, nucleotides & nucleic acids, 18(3), 485-492 (1999)
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