125700-69-8

Basic information

• Product Name: N,N,N',N'-Tetramethyl-O-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl)uronium tetrafluoroborate
• Synonyms: O-(3,4-DIHYDRO-4-OXO-1,2,3-BENZOTRIAZIN- 3-YL)-N,N,;O-(3,4-Dihydro-4-oxo-1,2,3-benzotriazin-3-yl)-N,N,N',N'-tetramethyluronium tetra;O-(3,4-DIHYDRO-4-OXO-1,2,3-BENZOTRIZIN-3-YL)-N,N,N',N'-TETRAMETHYLURONIUMTETRAFLUOROBORATE;TDBTU N,N,N'',N''-TETRAMETHYL-O-(3,4-DIHYDRO-4-OXO-1,2,3-BENZOTRIAZIN-3-YL) URONIUMTETRAFLUOROBORATE;N,N,N'',N''-TETRAMETHYL-O-(3,4-DIHYDRO-4-OXO-1,2,3-BENZOTRIAZIN-3-YL)URONIUM TETRAFLUOROBORATE(TDBTU);2-(3,4-DIHYDRO-4-OXO-1,2,3-BENZOTRIAZIN-3-YL)-N,N,N'',N''-TETRAMETHYLURONIUM TETRAFLUOROBORATE;2-(3,4-DIHYDRO-4-OXO-BENZOTRIAZIN-3-YL)TETRAMETHYLURONIUM TETRAFLUOROBORATE;dihydrooxobenzotriazinyl tetramethyluronium fluoroborate
• CAS NO: 125700-69-8
• Molecular Formula: C12H16BF4N5O2
• Molecular Weight: 349.09
• Product Categories: Coupling Reagent;Peptide Coupling Reagents;Peptide
• Mol File: 125700-69-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: 147 °C (dec.)
• Appearance: White to yellow/Powder or Solid
• Storage Temp.: 2-8°C
• Solubility: acetonitrile: 0.1 g/mL, clear
• Sensitive: Moisture & Light Sensitive
• CAS DataBase Reference: N,N,N',N'-Tetramethyl-O-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl)uronium tetrafluoroborate(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,N',N'-Tetramethyl-O-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl)uronium tetrafluoroborate(125700-69-8)
• EPA Substance Registry System: N,N,N',N'-Tetramethyl-O-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl)uronium tetrafluoroborate(125700-69-8)

Safety Data

• Hazard Codes: Xi
• Statements: 37-36/37/38
• Safety Statements: 22-24/25-36-26
• RIDADR: UN 1759 8/PG III
• WGK Germany: 3
• F: 8-10-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 125700-69-8(Hazardous Substances Data)

Usage

Description

N,N,N',N'-Tetramethyl-O-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl)uronium tetrafluoroborate, also known as TBTU, is a chemical compound that serves as a coupling reagent in the synthesis of various organic compounds, particularly in the field of peptide synthesis. It is known for its ability to effectively suppress racemization during fragment condensation, making it a valuable tool in the development of macrocyclic polyamine derivatives and other complex molecules.

Uses

Used in Peptide Synthesis:
N,N,N',N'-Tetramethyl-O-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl)uronium tetrafluoroborate is used as a coupling reagent for peptide synthesis, particularly in the large-scale preparation of complex peptides such as the hematoregulatory nonapeptide (Glp-Glu-Asp)2-DAS-(Lys)2 (2,SK&F 107647). Its application in this field is due to its ability to efficiently promote the formation of peptide bonds while minimizing the occurrence of racemization, which can negatively impact the biological activity of the final product.
Used in Macrocyclic Polyamine Derivatives Synthesis:
In the synthesis of macrocyclic polyamine derivatives with various lengths of linkers, N,N,N',N'-Tetramethyl-O-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl)uronium tetrafluoroborate is used as a coupling reagent. Its role in this process is to facilitate the formation of the desired macrocyclic structures, which can have diverse applications in fields such as pharmaceuticals, materials science, and chemical biology.
Used in Condensation Reactions:
N,N,N',N'-Tetramethyl-O-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl)uronium tetrafluoroborate is also used as a condensation reagent in the large-scale preparation of specific peptides and other organic compounds. Its application in this context is due to its ability to promote the formation of amide bonds, which are crucial for the structure and function of many biologically active molecules.

InChI:InChI=1/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