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12806

Sigma-Aldrich

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

≥97.0% (N), for peptide synthesis

Synonym(s):

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

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About This Item

Linear Formula:
C11H16N5O · BF4
CAS Number:
125700-67-6
Molecular Weight:
321.08
Beilstein:
7066325
MDL number:
MFCD00077413
UNSPSC Code:
12352100
PubChem Substance ID:
329749883
NACRES:
NA.21

product name

O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, ≥97.0% (N)

Quality Level

200

Assay

≥97.0% (N)

form

solid

mp

205 °C (dec.) (lit.)

solubility

acetonitrile: 0.1 g/mL, clear, colorless

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

F[B-](F)(F)F.CN(C)\C(On1nnc2ccccc12)=[N+](/C)C

InChI

1S/C11H16N5O.BF4/c1-14(2)11(15(3)4)17-16-10-8-6-5-7-9(10)12-13-16;2-1(3,4)5/h5-8H,1-4H3;/q+1;-1

InChI key

JKEKMBGUVUKMQB-UHFFFAOYSA-N

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

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H228,H317

Hazard Classifications

Flam. Sol. 1 - Skin Sens. 1A

Storage Class Code

4.1A - Other explosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK6007
STBK5204
WXBD6643V
WXBD3762V
WXBC9203V

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Samer Al-Gharabli et al.
Materials (Basel, Switzerland), 11(5) (2018-05-08)
Advanced ceramic materials with a well-defined nano-architecture of their surfaces were formed by applying a two-step procedure. Firstly, a primary amine was docked on the ordered nanotubular ceramic surface via a silanization process. Subsequently, single-wall carbon nanotubes (SWCNTs) were covalently
S. Zimmer et al. et al.
Proc. 22nd Eur. Pept. Symp.: Peptides 1992 null
Parvin Zakeri-Milani et al.
EXCLI journal, 16, 650-662 (2017-07-12)
Gemcitabine (Gem) is used as a single agent or in combination with other anticancer agents to treat many types of solid tumors. However, it has many limitations such as a short plasma half-life, dose-limiting toxicities and drug resistance. Cell-penetrating peptides
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)
Rajni Bala et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 196, 268-273 (2018-02-20)
In the present study, we report a highly sensitive, rapid and low cost colorimetric monitoring of malathion (an organophosphate insecticide) employing a basic hexapeptide, malathion specific aptamer (oligonucleotide) and silver nanoparticles (AgNPs) as a nanoprobe. AgNPs are made to interact
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Uronium and Guanidinium Salts for Peptide Coupling

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 hexafluorophosphate).

COMU-Safer and More Efficient Peptide Coupling Reagent

COMU is a non-explosive coupling agent suitable for solution phase & solid phase peptide synthesis. Its activity meets or exceeds that of HATU and its water-soluble by-product are easily removed.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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