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ISOLUTE® Si-Thiol

Diverse Metal Scavenger, Suitable for a Wide Range of Applications

ISOLUTE si-thiol

ISOLUTE® Si-Thiol is the silica-bond equivalent of 1-propanethiol, which is useful for covalent scavenging of electrophiles. The main application is the use to scavenge a variety of metals used in organic chemistry including Pd, Pt, Cu, Hg, Ag and Pb.

CONSUMABLES

Part No. Description Product type Pack Size Price
9180-0010 ISOLUTE Si-Thiol, 10 g Consumables 1 Log in for price
9180-0025 ISOLUTE Si-Thiol, 25 g Consumables 1 Log in for price
9180-0100 ISOLUTE Si-Thiol, 100 g Consumables 1 Log in for price
9180-0500 ISOLUTE Si-Thiol, 500 g Consumables 1 Log in for price
9180-1000 ISOLUTE Si-Thiol 1 kg Consumables 1 Log in for price

Committed to preserving our shared environment – further details available on request.

Can be used in processes in compliance with cGMP standards.

Manufacture of consumables is accredited by the world renowned British Standards Institute.

Flexible supply chains, back up manufacturing and warehousing ensures supply risk reduction

Can be used in processes in compliance with GLP standards.

Products which are scaleable from lab or development to process scale.

Long to indefinite product shelf life, reduced process risk.

Supports pharma guidelines for reducing elemental impurities in APIs.

Further extractable information provided on request.

Raw materials certified free of materials of human or animal origin.

Chemical substances used in our manufacturing process do not require registration.

Able to withstand mechanical stirring and heating under normal reaction conditions.

Download the product note.

 

Background

Palladium-catalyzed reactions are very popular in organic synthesis. Some of the most widely practiced examples include Suzuki-Miyaura cross coupling reactions, Heck reactions, Buchwald aminations, Wacker-type oxidation, hydrogenation, allylation, reductive de-allylation and indole formation.

Removal of Metals

Despite the widespread use of these palladium-mediated reactions, removal of residual palladium during workup and product isolation remains a major problem. Reducing the palladium content to the low parts per million (ppm) levels, as is required for active pharmaceutical ingredients, is particularly challenging.

Metal Scavengers

Biotage has developed a portfolio of scavenging products designed to remove these transition metal impurities. ISOLUTE® Si-Thiol was developed to address the need for a versatile metal scavenger that can be deployed in a multitude of different cases. It is the workhorse of the scavenging world and a first port of call for many screening and process applications.

Improving Med-Chem

In 2006, Li reported a modified Palladium-catalyzed crosscoupling reaction under copper, amine and solvent free conditions. Due to the lack of other contaminating metal, we used this as a model reaction for demonstrating metal scavenging with Biotage Si-Thiol. In our example study, alkyne (5) was prepared in previously published yields and purities (Scheme 1).

however the product was found to contain high levels of contaminating palladium. This initial reaction offered a starting point for to explore removal of Pd. Simple treatments with Si-Thiol metal scavenger significantly reduced the palladium content (Figure 2).

Based on previous optimization 3 eq of scavenger was used and scavenging measured over time. In the case of the Pd(OAc)2, Si-Thiol was able to remove the Pd from solution at 3 equiv. after 960 minutes however 98.6% and 99.1% of the palladium had been removed by the 30 and 60 minute marks, respectively.