670359
Acetylthiomethyl-diphenylphosphine borane complex
≥98.0%
Synonym(s):
(T-4)-[S-[(Diphenylphosphino-κP)methyl] ethanethioate]trihydroboron
About This Item
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Assay
≥98.0%
form
solid
reaction suitability
reaction type: click chemistry
reagent type: ligand
reaction type: Staudinger Reaction
mp
52-55 °C
functional group
phosphine
storage temp.
2-8°C
SMILES string
B.CC(=O)SCP(c1ccccc1)c2ccccc2
InChI
1S/C15H15OPS.BH3/c1-13(16)18-12-17(14-8-4-2-5-9-14)15-10-6-3-7-11-15;/h2-11H,12H2,1H3;1H3
InChI key
MXPNVFCCEGQGEN-UHFFFAOYSA-N
Application
- Traceless Staudinger ligation reagent with borane protecting group.
- The borane group stabilizes the phosphine against oxidation and can be easily removed with mild basic or acidic conditions to yield the active phosphine.
- After reaction with an azide, the phosphine is eliminated in the presence of water to yield a native amide bond.
- Used in the synthesis of cyclic peptides.
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Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
Certificates of Analysis (COA)
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Related Content
Professor Ron Raines works with Sigma-Aldrich on the development of reagents and tools for chemical biology such as the traceless Staudinger ligation reagent (670359). DTBA (774405), a superior biological reducing reagent to DTT, is another technology to come out of the Raines lab.
Professor Ron Raines works with Sigma-Aldrich on the development of reagents and tools for chemical biology such as the traceless Staudinger ligation reagent (670359). DTBA (774405), a superior biological reducing reagent to DTT, is another technology to come out of the Raines lab.
Professor Ron Raines works with Sigma-Aldrich on the development of reagents and tools for chemical biology such as the traceless Staudinger ligation reagent (670359). DTBA (774405), a superior biological reducing reagent to DTT, is another technology to come out of the Raines lab.
Professor Ron Raines works with Sigma-Aldrich on the development of reagents and tools for chemical biology such as the traceless Staudinger ligation reagent (670359). DTBA (774405), a superior biological reducing reagent to DTT, is another technology to come out of the Raines lab.
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