Name: 1,14-Diazido-3,6,9,12-tetraoxatetradecane
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Price

Stock

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$--

In stock

Purity

95%

Appearance

Clear Colorless Oil

Application

Multifunctional alkylating agent.

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

1-azido-2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethane

Synonyms

1,14-Diazido-3,6,9,12-tetraoxatetradecane

InChI Key

QTEOEACEOUNLRG-UHFFFAOYSA-N

InChI

InChI=1S/C10H20N6O4/c11-15-13-1-3-17-5-7-19-9-10-20-8-6-18-4-2-14-16-12/h1-10H2

SMILES

C(COCCOCCOCCOCCN=[N+]=[N-])N=[N+]=[N-]

1. 2-Aminotryptanthrin derivative with pyrene as a FRET-based fluorescent chemosensor for Al3+

Jun Kawakami, Kenta Kikuchi, Kazunori Chiba, Noriyuki Matsushima, Asako Yamaya, Shunji Ito, Masahiko Nagaki, Haruo Kitahara Anal Sci. 2009 Dec;25(12):1385-6. doi: 10.2116/analsci.25.1385.

1-(2-Tryptanthrinylaminoacetoxy)-14-(1-pyrenecarboxy)-3,6,9,12-tetraoxatetradecane (T2NH-P5P) was synthesized as a fluorescent chemosensor for Al3+. Excited at 325 nm, corresponding to absorption of the pyrene unit of T2NH-P5P, emission at 600 nm from the 2-aminotryptanthrin unit has been observed, indicating that intramolecular fluorescence resonance energy transfer (FRET) occurs in T2NH-P5P. However, when Al3+ is added to a solution of T2NH-P5P, the fluorescence of 2-aminotryptanthrin is quenched (FRET-off), whereas that of the pyrene group is revived. Such a FRET "on-off" behavior of T2NH-P5P is not observed for other metal cations (Ca2+, Ba2+, and Zn2+).

2. 2-Aminotryptanthrin derivative with pyrene as a FRET-based fluorescent chemosensor for metal ions

Jun Kawakami, Arisa Soma, Kenta Kikuchi, Yoh Kikuchi, Shunji Ito, Haruo Kitahara Anal Sci. 2014;30(10):949-54. doi: 10.2116/analsci.30.949.

1-(2-tryptanthrinylaminoacetoxy)-14-(1-pyrenecarboxy)-3,6,9,12-tetraoxatetradecane (T2NH-P5P) was synthesized as a fluorescent chemosensor for metal ions. We investigated the metal-ion recognition of T2NH-P5P by separately adding Mg(2+), Ca(2+), Ba(2+), Fe(2+), Fe(3+), Co(2+), Ni(2+), Cu(2+), Ag(+), Zn(2+), Cd(2+), Hg(2+), Al(3+), and Pb(2+) in an acetonitrile solution. When using excitation at 325 nm, which corresponds to the absorption of the pyrene unit of T2NH-P5P, emission at 600 nm, from the 2-aminotryptanthrin unit, was observed, indicating that intramolecular fluorescence resonance energy transfer (FRET) occurs in T2NH-P5P (FRET-on). However, when Fe(2+), Fe(3+), Ni(2+), Cu(2+), Cd(2+), Hg(2+), and Al(3+) were added to an acetonitrile solution of T2NH-P5P, the behavior changed from FRET-on to FRET-off, which means that the fluorescence of 2-aminotryptanthrin was quenched, whereas that of the pyrene group was revived (FRET-off). Especially, this behavior was remarkable for Fe(2+), Fe(3+), Cu(2+), and Hg(2+). T2NH-P5P is suitable for use as a fluorescent chemosensor for Fe(2+), Fe(3+), Cu(2+), and Hg(2+).

1,14-Diazido-3,6,9,12-tetraoxatetradecane, provides a flexible, polyether-based spacer bearing two azide termini for modular conjugation. Its ether-rich backbone supports conformational adaptability between the ligand warhead and E3-recruiting element, which can improve productive ternary complex formation. The azide handles enable widely used click-type coupling strategies, facilitating efficient synthesis of targeted protein degraders. Detailed structural and synthetic guidance is provided below.

Structure: The linker is a long, flexible diazide polyether featuring repeating ether oxygen atoms that confer polarity and conformational mobility. Two terminal azide functional groups serve as reactive handles. The molecule contains ether C–O bonds and azide N–N/N–N connectivity, with overall properties consistent with solubility in common organic media.

Reactivity: The azide groups are suited to copper-catalyzed azide–alkyne cycloaddition or related strain-promoted azide coupling, enabling attachment to alkyne-functional ligands under mild conditions. Typical approaches use Cu(I) generated in situ, appropriate ligand scaffolds, and polar aprotic solvents to promote reaction efficiency while minimizing side reactions. Mechanistically, the azide undergoes cycloaddition to form a stable triazole linkage, preserving linker integrity during PROTAC assembly.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂