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Merck

12804

HBTU

≥98.0% (T), for peptide synthesis

Synonym(s):

N,N,N′,N′-Tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate, O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

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About This Item

Empirical Formula (Hill Notation):
C11H16F6N5OP
CAS Number:
94790-37-1
Molecular Weight:
379.24
NACRES:
NA.22
PubChem Substance ID:
57647025
UNSPSC Code:
12352107
EC Number:
423-020-5
MDL number:
MFCD00075445
Beilstein/REAXYS Number:
7328329

Key Documents

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Product Name

HBTU, ≥98.0% (T)

InChI key

UQYZFNUUOSSNKT-UHFFFAOYSA-N

InChI

1S/C11H16N5O.F6P/c1-14(2)11(15(3)4)17-16-10-8-6-5-7-9(10)12-13-16;1-7(2,3,4,5)6/h5-8H,1-4H3;/q+1;-1

SMILES string

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

assay

≥98.0% (T)

form

solid

reaction suitability

reaction type: Coupling Reactions

mp

200 °C (dec.) (lit.)

solubility

acetonitrile: 0.1 g/mL, clear

application(s)

peptide synthesis

functional group

amine

storage temp.

2-8°C

Quality Level

200

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Application

HBTU is a peptide coupling agent for peptide synthesis. It has also been used in standard Fmoc-based solid-phase peptide synthesis (SPPS) protocol.
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 for peptide synthesis; advantages are: very low racemization, simple reaction conditions, very short reaction time, and high yields.

General description

HBTU is a peptide coupling agent used in Fmoc-based solid-phase peptide synthesis.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1A

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7285V
WXBF7035V
BCCH7947
BCCG0843
BCCB6870

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Bioorganic & medicinal chemistry, 23(17), 5748-5755 (2015-08-04)
Dengue virus (DENV) and West Nile virus (WNV) are mosquito-borne arboviruses responsible for causing acute systemic diseases and severe health conditions in humans. The discovery of therapies capable to prevent infections or treat infected individuals remains an important challenge, since
Structural studies of reagents for peptide bond formation: Crystal and molecular structures of HBTU and HATU.
Abdelmoty I, et al.
Lett. Pept. Sci., 1(2), 57-67 (1994)
Some mechanistic aspects on Fmoc solid phase peptide synthesis
Pires DAT, et al.
International Journal of Peptide Research and Therapeutics, 20, 53-69 (2014)
Small molecule approach to studying protein tyrosine phosphatase.
Kumar S, et al.
Methods, 35(1), 9-21 (2005)
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