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12806 Sigma-Aldrich

O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate

≥97.0% (N)

Synonym: N,N,N′,N′-Tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate, TBTU

  • CAS Number 125700-67-6

  • Linear Formula C11H16N5O · BF4

  • Molecular Weight 321.08

  •  Beilstein Registry Number 7066325

  •  MDL number MFCD00077413

  •  PubChem Substance ID 24847819

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Properties

Related Categories Chemical Biology, Chemical Synthesis, Coupling, Peptide Chemistry, Peptide Coupling,
assay   ≥97.0% (N)
mp   205 °C (dec.)(lit.)
solubility   acetonitrile: soluble0.1 g/mL, clear, colorless
storage temp.   2-8°C

Description

Application

Coupling reagent which is ideally suited for solid-phase peptide synthesis.

Other Notes

Recent studies show that crystal as well as solution structure of this coupling agent is a guanidinium N-oxide and not an uronium compound1; Coupling reagent which is ideally suited for solid-phase peptide synthesis.2

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
UN 1325 4.1 / PGII
WGK Germany 
3

Documents

Certificate of Analysis

Protocols & Articles

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Peer-Reviewed Papers

References

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1. I. Abdelmoty Lett. Pept. Sci. 1, 57, (1994)

Novel polymyxin derivatives carrying only three positive charges are effective antibacterial agents. Martti Vaara et al Antimicrob. Agents Chemother. 52, 3229-36, (2008)

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O-(BENZOTRIAZOL-1-YL)-N, N, N', N'-TETRAMETHYLURONIUM TETRAFLUOROBORATE (TBTU): A NEW REAGENT FOR THE CLEAVAGE OF TETRAHYDROPYRANYL, SILYL AND 4, 4'-D IMETHOXYTRITYL ETHERS. Ramasamy KS and Averett D. Synlett 6, 709-712, (1999)

Semiautomated T-bag peptide synthesis using 9-fluorenyl-methoxycarbonyl strategy and benzotriazol-1-yl-tetramethyl-uronium tetrafluoroborate activation. Beck-Sickinger AG, Dürr H, and Jung G Pept. Res. 4(2), 88-94, (1991)

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Automated solid-phase peptide synthesis: use of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate for coupling of tert-butyloxycarbonyl amino acids. Reid GE and Simpson RJ Anal. Biochem. 200(2), 301-9, (1992)

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2. S. Zimmer et al., C.H. Schneider and A.N. Eberle, eds. Proc. 22nd Eur. Pept. Symp.: Peptides 1992 Leiden 1993, p. 393

S. Zimmer, C.H. Schneider and A.N. Eberle, eds. Proc. 22nd Eur. Pept. Symp.: Peptides 1992 Leiden , (1993), 393

Fieser 12,44

FT-NMR 1 (3), 192:C / RegBook 1 (2), 2447:F / Structure Index 1, 387:A:6

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