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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

  • Popular Documents:  FTNMR (PDF)  

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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

Packaging

1 kg in glass bottle

5, 25, 100, 250 g in glass bottle

Price and Availability

Suggested Laboratory Gloves


Laboratory GlovesThis substance has been tested against several types of hand protection for CE compliance. Click below to find the recommended gloves for handling this product.



Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Risk Statements (Europe) 
Safety Statements (Europe) 
26-35
RIDADR 
UN 1325 4.1 / PGII
WGK Germany 
3

Protocols & Articles

Articles

COMU—Safer and More Efficient Peptide Coupling Reagent

Proteins and peptides are ubiquitous in all living systems. The chemical synthesis of peptidic structures for scientific research or drug discovery relies heavily on efficient coupling reagents. This...
Dr. Matthias Junkers
Aldrich Chemfiles, 2010 Volume 10 Article 1
Keywords: Calorimetry, Coupling reactions, Drug discovery, Epimerizations, Methods, Microwave synthesis, Peptide synthesis, Protocols, Racemizations, Reductions, Search, Sequences, Solid phase peptide synthesis, Solvents

Uronium and Guanidinium Salts

The special need of SPPS for rapid and highly efficient coupling reagents led to the development of several new reagents starting from BOP (Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluo...
Matthias Junkers
Aldrich ChemFiles 2007, 7.2, 9.
Keywords: Condensations, Cyclizations, Peptide synthesis, Racemizations, Solid phase peptide synthesis, Substitutions, Type

Related Content

COMU – Safer and More Efficient Peptide Coupling Reagent

Peptide synthesis relies heavily on efficient and reliable coupling reagents. A low tendency for racemization is a key requirement. This is especially true for solid phase peptide synthesis—quantitat...
Keywords: Building blocks, Calorimetry, Catalog, Condensations, Coupling reactions, Epimerizations, Methods, PEGylations, Peptide synthesis, Protocols, Racemizations, Search, Solid phase peptide synthesis, Solvents, Tools

Indoles, Purines, and Their Isosteres

Substituted indoles and purines have frequently been referred to as “privileged structures” since they are capable of binding to multiple receptors with high affinity, and thus have applications acro...
Keywords: Applications, Building blocks, Medicinal chemistry

Peer-Reviewed Papers

References

Set your institution to view full text papers.

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

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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