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Sigma-Aldrich

O-(3,4-Dihydro-4-oxo-1,2,3-benzotriazin-3-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate

≥95.0% (HPLC)

Synonym(s):

N,N,N′,N′-Tetramethyl-O-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl)uronium tetrafluoroborate, O-(4-Oxo-1,2,3-benzotriazin-3(4H)-yl)-N,N,N′,N′,-tetramethyluronium tetrafluoroborate, TDBTU

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About This Item

Empirical Formula (Hill Notation):
C12H16BF4N5O2
CAS Number:
125700-69-8
Molecular Weight:
349.09
MDL number:
MFCD00077730
UNSPSC Code:
12352100
PubChem Substance ID:
57649719

assay

≥95.0% (HPLC)

form

solid

solubility

acetonitrile: 0.1 g/mL, clear

storage temp.

2-8°C

SMILES string

F[B-](F)(F)F.CN(C)\C(ON1N=Nc2ccccc2C1=O)=[N+](\C)C

InChI

1S/C12H16N5O2.BF4/c1-15(2)12(16(3)4)19-17-11(18)9-7-5-6-8-10(9)13-14-17;2-1(3,4)5/h5-8H,1-4H3;/q+1;-1

InChI key

FOBCPCIJLQTYBT-UHFFFAOYSA-N

Application

O-(3,4-Dihydro-4-oxo-1,2,3-benzotriazin-3-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (2-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate, TBTU) may be used as:
  • coupling reagent in the synthesis of macrocyclic polyamine derivatives with various length of linkers
  • condensation reagent in the large-scale preparation of the hematoregulatory nonapeptide (Glp-Glu-Asp)2-DAS-(Lys)2 (2,SK&F 107647)
  • coupling reagent for peptide synthesis which best suppresses racemization during fragment condensation

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1A

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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J Hiebl et al.
The journal of peptide research : official journal of the American Peptide Society, 54(1), 54-65 (1999-08-17)
Linear and convergent routes for the large-scale preparation of the hematoregulatory nonapeptide (Glp-Glu-Asp)2-DAS-(Lys)2 (2, SK&F 107647) were investigated. A convergent approach ('3 + 2'-route employing Boc-and benzyl ester protecting groups) was selected for the preparation of multihundred-gram quantities of 2.
Convergent and sequential synthesis of dendritic, multivalent complexing agents.
Liu C, et al.
Synthesis, 10, 1398-1406 (2002)
Knorr, R, et al.
Tetrahedron Letters, 30, 1927-1927 (1989)

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