Phenylacetyl Disulfide(PADS)
CAS15088-78-5
Phenylacetyl disulfide (PADS, CAS 15088-78-5) is a sulfur-transfer reagent that converts phosphite triesters into phosphorothioate triesters during phosphoramidite oligonucleotide synthesis. Used as a 0.2 M solution in acetonitrile/3-picoline, it is an economical replacement for the Beaucage reagent and has been applied from laboratory scale to bulk antisense manufacture. KingPharm supplies research and production grade PADS with a batch-specific certificate of analysis.
- CAS No.
- 15088-78-5
- Formula
- C16H14O2S2
- Mol. weight
- 302.41 g/mol
- Appearance
- White to Off-white Powder
Product Description
Phenylacetyl disulfide (PADS) is a symmetrical diacyl disulfide, (C6H5CH2COS)2, supplied as a white to off-white crystalline solid with a reported melting point of 59-63 °C. It is used as the sulfurization reagent in solid-phase phosphoramidite synthesis of phosphorothioate (PS) oligonucleotides.
After each coupling step, the newly formed phosphite triester is treated with a PADS solution, typically 0.2 M in acetonitrile/3-picoline (1:1, v/v), which transfers a sulfur atom to phosphorus and gives the phosphorothioate triester. Studies show that solutions aged for at least 24 hours sulfurize more efficiently than freshly prepared ones, attributed to the in situ formation of a reactive polysulfide intermediate.
Compared with the Beaucage reagent, PADS is inexpensive and has been used on scales from 1 μmol to 150 mmol, which made it a common choice for large-scale antisense manufacture. With aged solutions, average stepwise sulfurization efficiencies above 99.9% have been reported, keeping phosphate diester (PO) impurities low.
For procurement, buyers usually check purity, appearance and moisture content, and whether the material is suitable for GMP oligonucleotide production. The solid should be kept tightly closed under an inert atmosphere. KingPharm provides a batch-specific COA and specification with each order.
Chemical Specifications
Identifiers
| CAS number | 15088-78-5 |
|---|---|
| Product name | Phenylacetyl Disulfide(PADS) |
| Chinese name | 苯乙酰基二硫化物 |
| IUPAC name | S-(2-phenylacetyl)sulfanyl 2-phenylethanethioate |
| Synonyms | Bis(Phenylacetyl) Disulfide; Bis(Phenylacetyl) Disulphide; Diphenylacetyl Disulfide |
| Chinese synonyms | 二硫化二苯乙酰; 苯乙酰二硫化物; 乙酰二硫化物(PADS); 双(苯乙酰基)二硫化物; 双(苯乙酰)二硫化物 |
| Molecular formula | C16H14O2S2 |
| Molecular weight | 302.41 g/mol |
| MDL number | MFCD00513572 |
| PubChem CID | 3378603 |
| InChIKey | IXGZXXBJSZISOO-UHFFFAOYSA-N |
| SMILES | C1=CC=C(C=C1)CC(=O)SSC(=O)CC2=CC=CC=C2 |
Physical and chemical properties
| Appearance | White to Off-white Powder |
|---|---|
| Melting Point | 57.0-62.0 ( ℃ ) |
Applications
PADS is used wherever phosphite triesters need to be converted into phosphorothioates during oligonucleotide synthesis.
Phosphorothioate antisense oligonucleotides
PADS is used in each synthesis cycle to sulfurize the internucleotide phosphite linkage, producing PS-modified antisense DNA.
Modified RNA and gapmer synthesis
PADS serves as the sulfur-transfer reagent when introducing phosphorothioate linkages into RNA and 2'-modified oligonucleotides.
Large-scale oligonucleotide API manufacture
Its low cost and proven performance at mmol scale make PADS suitable for bulk production of oligonucleotide drug substances.
Quality Documentation
The following documents can be provided for Phenylacetyl Disulfide(PADS) to support technical evaluation and purchasing. Documents are issued for the specific grade and batch supplied.
-
Certificate of Analysis (COA) Batch-specific test results against the specification.
-
Product specification The release specification with test items, limits and methods.
Packaging, Storage & Transport
| Available pack sizes | 25 kg, 10 kg, 1 kg, 500 g, 100 g, 25 g |
|---|
Read the current safety data sheet before handling. Packaging can be adapted to the order quantity and destination.
Frequently Asked Questions
Why should a PADS solution be aged before use?
Freshly prepared PADS solutions give lower sulfurization efficiency and more PO-diester impurity. Preparing the 0.2 M acetonitrile/3-picoline solution at least one day in advance allows a reactive polysulfide intermediate to form, giving stepwise efficiencies above 99.9%.
How does PADS compare with the Beaucage reagent?
Both convert phosphite triesters to phosphorothioates. PADS is considerably cheaper and has been scaled from μmol to over 100 mmol, so it is often chosen for process-scale synthesis; the Beaucage reagent is more common in small-scale research synthesis.
How should PADS be stored?
Store the solid in a tightly closed container under an inert atmosphere at room temperature, protected from moisture. Prepared solutions should also be kept closed and protected from moisture.
What is the CAS number of Phenylacetyl Disulfide(PADS)?
The CAS Registry Number of Phenylacetyl Disulfide(PADS) is 15088-78-5. Phenylacetyl Disulfide(PADS) is also known as Bis(Phenylacetyl) Disulfide; Bis(Phenylacetyl) Disulphide; Diphenylacetyl Disulfide.
What is the molecular formula and molecular weight of Phenylacetyl Disulfide(PADS)?
The molecular formula of Phenylacetyl Disulfide(PADS) is C16H14O2S2, and its molecular weight is 302.41 g/mol.
What is Phenylacetyl Disulfide(PADS) used for?
PADS is used wherever phosphite triesters need to be converted into phosphorothioates during oligonucleotide synthesis.
Which quality documents are available for Phenylacetyl Disulfide(PADS)?
The following documents are available for Phenylacetyl Disulfide(PADS): Certificate of Analysis (COA); Product specification. Contact KingPharm to request the documents for a specific batch.
How can I request a quotation for Phenylacetyl Disulfide(PADS)?
Send an inquiry for Phenylacetyl Disulfide(PADS) (CAS 15088-78-5) with the required quantity, target specification, destination country and any documentation requirements. KingPharm will confirm availability, packaging, lead time and price.
Related Products
Request a Quote for Phenylacetyl Disulfide(PADS)
Tell us the required quantity, target specification, destination country and any documentation requirements. We will confirm availability, packaging, lead time and price.
Page last reviewed on by Leo Xiao.