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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
STBL2606
STBK6007
WXBD7007V
STBK5204
WXBD6643V

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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
S. Zimmer et al. et al.
Proc. 22nd Eur. Pept. Symp.: Peptides 1992 null
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EXCLI journal, 16, 650-662 (2017-07-12)
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Kavita Bansal et al.
Bioconjugate chemistry, 29(4), 1102-1110 (2018-03-01)
Peptide-based drug delivery systems have become a mainstay in the contemporary medicinal field, resulting in the design and development of better pharmaceutical formulations. However, most of the available reports employ tedious multiple reaction steps for the conjugation of bioactive cationic
Kiat Hwa Chan et al.
Scientific reports, 7(1), 12897-12897 (2017-10-12)
Self-assembly of small biomolecules is a prevalent phenomenon that is increasingly being recognised to hold the key to building complex structures from simple monomeric units. Small peptides, in particular ultrashort peptides containing up to seven amino acids, for which our
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