554324
Phenylacetyl disulfide
96%
Synonym(s):
Bis(phenylacetyl) disulfide, Di(phenylacetyl) disulfide
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About This Item
Linear Formula:
(C6H5CH2COS)2
CAS Number:
Molecular Weight:
302.41
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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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
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 Code
11 - Combustible Solids
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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