5-Benzylthio-1H-tetrazole (BTT)
CAS21871-47-6
5-Benzylthio-1H-tetrazole (BTT, CAS 21871-47-6) is a tetrazole-based activator for the coupling step of phosphoramidite oligonucleotide synthesis. BTT is more acidic than both 1H-tetrazole and ETT, which shortens coupling times for 2′-O-TBDMS and TOM-protected RNA phosphoramidites. King-Pharm supplies BTT for research and manufacturing, with a batch-specific certificate of analysis.
- CAS No.
- 21871-47-6
- Formula
- C8H8N4S
- Mol. weight
- 192.24 g/mol
- Appearance
- White to Off-white Powder
Product Description
5-Benzylthio-1H-tetrazole, commonly known as BTT (also called BMT, 5-benzylmercaptotetrazole), is a tetrazole-based activator used in phosphoramidite chemistry for oligonucleotide synthesis, particularly RNA synthesis.
During the coupling step, BTT protonates the diisopropylamino group of a nucleoside phosphoramidite and forms a reactive tetrazolide intermediate, which then couples with the free 5′-hydroxyl group of the growing oligonucleotide chain.
BTT is more acidic than ETT and 1H-tetrazole (pKa about 4.1, against about 4.3 and 4.9). With 2′-O-TBDMS RNA phosphoramidites, coupling with BTT takes about 3 minutes, while 1H-tetrazole needs 12 minutes or more. BTT also dissolves in acetonitrile up to about 0.44 M, which is higher than 1H-tetrazole.
When evaluating BTT for a process, buyers usually check the assay, the water content, the clarity of a 0.25 M solution in anhydrous acetonitrile, packaging integrity and batch-to-batch consistency.
Chemical Specifications
Identifiers
| CAS number | 21871-47-6 |
|---|---|
| Product name | 5-Benzylthio-1H-tetrazole (BTT) |
| IUPAC name | 5-benzylsulfanyl-2H-tetrazole |
| Synonyms | 5-Benzylthio-1H-tetrazole; 5-Benzylmercapto-1H-Tetrazole; 5-Benzylmercaptotetrazole; 5-[(Phenylmethyl)Thio]-1H-Tetrazole; 5-[(Phenylmethyl)Thio-1H-Tetrazole; BMT; BTT; 5-(Benzylthio)-1H-Tetrazoel; 5-((Phenylmethyl)Thio)-1H-Tetrazole |
| Molecular formula | C8H8N4S |
| Molecular weight | 192.24 g/mol |
| MDL number | MFCD00068731 |
| PubChem CID | 323185 |
| InChIKey | GXGKKIPUFAHZIZ-UHFFFAOYSA-N |
| SMILES | C1=CC=C(C=C1)CSC2=NNN=N2 |
Physical and chemical properties
| Appearance | White to Off-white Powder |
|---|---|
| Melting Point | 133.0-138.0 ( ℃ ) |
Applications
BTT is used at the coupling step of solid-phase oligonucleotide synthesis, usually as a 0.25 M solution in anhydrous acetonitrile.
RNA synthesis
BTT activates 2′-O-TBDMS and 2′-O-TOM protected RNA phosphoramidites with shorter coupling times than 1H-tetrazole.
DNA synthesis
BTT can also serve as a general activator for DNA phosphoramidites on automated synthesizers.
Modified oligonucleotides
Its higher acidity suits sterically hindered or modified phosphoramidites that couple slowly with 1H-tetrazole.
Activator solution preparation
Solid BTT lets users prepare activator solutions in-house at the concentration their process requires.
Quality Documentation
The following documents can be provided for 5-Benzylthio-1H-tetrazole (BTT) 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.
Packaging, Storage & Transport
| Storage Temp | Store at room temperature in a dry, well-ventilated place. Keep container tightly closed. ( ℃ ) |
|---|
Packaging can be adapted to the order quantity and destination.
Frequently Asked Questions
How does BTT compare with ETT and 1H-tetrazole?
BTT is the most acidic of the three (pKa about 4.1, against about 4.3 for ETT and 4.9 for 1H-tetrazole). For 2′-O-TBDMS RNA monomers, coupling with BTT takes about 3 minutes, compared with 12 minutes or more with 1H-tetrazole.
At what concentration is BTT usually used?
BTT is usually used as a 0.25 M solution in anhydrous acetonitrile. Keep the solvent dry, because water lowers coupling efficiency.
How should BTT be stored?
Keep BTT tightly sealed in a cool, dry place, protected from moisture and preferably under an inert atmosphere. Follow the storage conditions on the label and SDS.
What is the CAS number of 5-Benzylthio-1H-tetrazole (BTT)?
The CAS Registry Number of 5-Benzylthio-1H-tetrazole (BTT) is 21871-47-6. 5-Benzylthio-1H-tetrazole (BTT) is also known as 5-Benzylthio-1H-tetrazole; 5-Benzylmercapto-1H-Tetrazole; 5-Benzylmercaptotetrazole.
What is the molecular formula and molecular weight of 5-Benzylthio-1H-tetrazole (BTT)?
The molecular formula of 5-Benzylthio-1H-tetrazole (BTT) is C8H8N4S, and its molecular weight is 192.24 g/mol.
What is 5-Benzylthio-1H-tetrazole (BTT) used for?
BTT is used at the coupling step of solid-phase oligonucleotide synthesis, usually as a 0.25 M solution in anhydrous acetonitrile.
Which quality documents are available for 5-Benzylthio-1H-tetrazole (BTT)?
The following documents are available for 5-Benzylthio-1H-tetrazole (BTT): Certificate of Analysis (COA). Contact King-Pharm to request the documents for a specific batch.
How can I request a quotation for 5-Benzylthio-1H-tetrazole (BTT)?
Send an inquiry for 5-Benzylthio-1H-tetrazole (BTT) (CAS 21871-47-6) with the required quantity, target specification, destination country and any documentation requirements. King-Pharm will confirm availability, packaging, lead time and price.
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