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HBTU
Sign in to saveHBTU (hexafluorophosphate benzotriazole tetramethyl uronium) is a coupling reagent used in solid phase peptide synthesis. It was introduced in 1978 and shows resistance against racemization. It is used because of its mild activating properties.
Chemical data
- Formula
- C11H16F6N5OP
- Molecular weight
- 379.24 g/mol
- IUPAC name
- [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium hexafluorophosphate
- SMILES
- CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
- InChIKey
- UQYZFNUUOSSNKT-UHFFFAOYSA-N
- Polar surface area
- 46.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Has part
- hydrogen
- Mass
- 379.099666
Show 3 more facts
- chemical formula
- C₁₁H₁₆F₆N₅OP
- canonical SMILES
- CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
- Commons category
- HBTU
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Mechanism
- Safety
- See also
- References
HBTU (hexafluorophosphate benzotriazole tetramethyl uronium) is a coupling reagent used in solid phase peptide synthesis. It was introduced in 1978 and shows resistance against racemization. It is used because of its mild activating properties.
HBTU is prepared by reaction of hydroxybenzotriazole with TCFH under basic conditions and was assigned to a uronium type structure, presumably by analogy with the corresponding phosphonium salts, which bear a positive carbon atom instead of the phosphonium residue. Later, it was shown by X-ray analysis that salts crystallize as guanidinium rather than the corresponding uronium salts.
Excerpted from Wikipedia’s “HBTU” article, available under the CC BY-SA 4.0 licence.