Molecular structure of Tributyltin hydride, CAS Number: 688-73-3
Tributyltin hydride (CAS 688-73-3)
Application:
Tributyltin hydride is a reducing agent acting by radical intermediates
CAS Number:
688-73-3
Purity:
≥95%
Molecular Weight:
291.06
Molecular Formula:
C12H28Sn
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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Tributyltin hydride is a reducing agent acting by radical intermediates. Tributyltin hydride (TBT-H) is a pivotal organotin compound renowned for its role as a potent reducing agent, primarily through the mediation of radical intermediates. Its mechanism of action is distinguished by its ability to generate tributyltin radicals, which serve as key intermediates in various organic synthesis reactions. This process is initiated by the homolytic cleavage of the tin-hydrogen bond in the presence of a radical initiator, leading to the formation of highly reactive tributyltin radicals. These radicals then partake in a series of chain reactions, including the abstraction of hydrogen atoms from other molecules, effectively facilitating the reduction or radical addition processes that are critical in the synthesis of complex organic compounds.
Tributyltin hydride (CAS 688-73-3) References
- Determination of bis(tributyltin) oxide by GC--MS with on-line hydride derivatization: application to drug substance analysis. | O'Brien, TP., et al. 1999. J Pharm Biomed Anal. 19: 327-33. PMID: 10704098
- Lewis Acid-Catalyzed Hydrostannation of Acetylenes. Regio- and Stereoselective Trans-Addition of Tributyltin Hydride and Dibutyltin Dihydride. | Asao, N., et al. 1996. J Org Chem. 61: 4568-4571. PMID: 11667381
- Synthesis of Aminocyclitols by Intramolecular Reductive Coupling of Carbohydrate Derived delta- and epsilon-Functionalized Oxime Ethers Promoted by Tributyltin Hydride or Samarium Diiodide. | Marco-Contelles, J., et al. 1997. J Org Chem. 62: 7397-7412. PMID: 11671857
- Tributylgermanium hydride as a replacement for tributyltin hydride in radical reactions. | Russell Bowman, W., et al. 2004. Org Biomol Chem. 2: 585-92. PMID: 14770238
- Toxicity of tributyltin to willow trees. | Trapp, S., et al. 2004. Environ Sci Pollut Res Int. 11: 327-30. PMID: 15506636
- Thermal reactions of tributyltin hydride with alpha-azido esters: unexpected intervention of tin triazene adducts under both nonradical and radical conditions. | Benati, L., et al. 2005. J Org Chem. 70: 3046-53. PMID: 15822963
- Palladium(II)-catalyzed isomerization of olefins with tributyltin hydride. | Kim, IS., et al. 2007. J Org Chem. 72: 5424-6. PMID: 17552567
- Reduction of ribonucleosides to 2'-deoxyribonucleosides. | Robins, MJ. and Wnuk, SF. 2005. Curr Protoc Nucleic Acid Chem. Chapter 1: Unit 1.11. PMID: 18428933
- Tributyltin hydride-mediated radical cyclisation reactions: efficient construction of multiply substituted cyclopentanes. | Lei, J., et al. 2010. Org Biomol Chem. 8: 2840-4. PMID: 20431836
- The stereoselectivities of tributyltin hydride-mediated reductions of 5-bromo-D-glucuronides to L-iduronides are dependent on the anomeric substituent: syntheses and DFT calculations. | Mohamed, S., et al. 2016. Org Biomol Chem. 14: 2950-60. PMID: 26878700
- Radical Arene Addition vs Radical Reduction: Why Organometal Hydride Chain Reactions Stop and How To Make Them Go. | Bowry, VW. and Chatgilialoglu, C. 2018. J Org Chem. 83: 10037-10050. PMID: 30028610
- Aminoalkyl radicals as halogen-atom transfer agents for activation of alkyl and aryl halides. | Constantin, T., et al. 2020. Science. 367: 1021-1026. PMID: 32108109
- Synthesis and Antiproliferative Evaluation of 2-Deoxy-N-glycosylbenzotriazoles/imidazoles. | Garton, CS., et al. 2021. Molecules. 26: PMID: 34205324
- Synthesis and removal of trichloroethylidene derivatives of carbohydrates. | Jahan, N., et al. 2022. Carbohydr Res. 515: 108545. PMID: 35405392
Inhibitor of:
ATP10B.Activator of:
17β-HSD8, COUP-TF2, ephrin-B3, Gm906, MUP17, MUP18, RBMY1B, ROPN1B, SMCP, SPATA17, and TSPY8.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Tributyltin hydride, 10 g | sc-255686 | 10 g | $69.00 | |||
Tributyltin hydride, 50 g | sc-255686A | 50 g | $192.00 |