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

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

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

CAS No.: 57602-02-5

Cat No.: BP-500760

Purity: 95% 4.5

1,14-Dibromo-3,6,9,12-tetraoxatetradecane is a bifunctional, ether-rich alkyl linker bearing two terminal bromides separated by a tetraethylene glycol–like oxygen sequence within a fourteen-carbon scaffold. The multiple ether oxygens confer conformational flexibility and polarity, which can improve solubility and help position two PROTAC-relevant fragments with reduced steric bias. In PROTAC construction, this linker serves as a reactive spacer that can be converted into two electrophilic handles for stepwise conjugation to nucleophilic groups on ligands (for example, via substitution with heteroatom-containing moieties such as amines or phenoxides) to generate a defined, symmetric or near-symmetric distance between the target-binding ligand and the E3 ligase recruiter. Its value for targeted protein degradation research lies in enabling systematic tuning of linker length and donor/acceptor character, supporting optimization of ternary complex formation and degradation potency while maintaining synthetic modularity for analog series.

Structure of 57602-02-5

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Category

PROTAC Linker

Molecular Formula

C10H20O4Br2

Molecular Weight

364.07

Appearance

Clear Light Yellow Liquid

* For research and manufacturing use only. Not for human or clinical use.

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Purity

95%

Solubility

Soluble in Chloroform

Appearance

Clear Light Yellow Liquid

Application

A cross-linking reagent.

Storage

Store at 2-8°C

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

1,2-bis[2-(2-bromoethoxy)ethoxy]ethane

Synonyms

Br-PEG4-Br; Bromo-PEG4-bromide; 3,6,9,12-Tetraoxatetradecane, 1,14-dibromo-; Br-PEG4-CH2CH2Br

Boiling Point

373.174±32.0°C at 760 mmHg

Density

1.483±0.1 g/cm3

InChI Key

VYNNYZUBABMNTB-UHFFFAOYSA-N

InChI

InChI=1S/C10H20Br2O4/c11-1-3-13-5-7-15-9-10-16-8-6-14-4-2-12/h1-10H2

SMILES

C(COCCOCCBr)OCCOCCBr

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

Kawakami J1, Soma A, Kikuchi K, Kikuchi Y, Ito S, Kitahara H. Anal Sci. 2014;30(10):949-54.

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+).

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

Kawakami J1, Kikuchi K, Chiba K, Matsushima N, Yamaya A, Ito S, Nagaki M, Kitahara H. Anal Sci. 2009 Dec;25(12):1385-6.

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+).

1,14-Dibromo-3,6,9,12-tetraoxatetradecane, is a difunctional bromo-terminated polyethylene glycol–like scaffold designed to connect ligands in targeted protein degradation constructs. Its ether-rich chain provides conformational flexibility and favorable solvation, supporting efficient linker-ligand conjugation while maintaining accessibility for ternary complex formation. The points below describe its structure and practical reactivity considerations for PROTAC assembly.

Structure: The linker is a linear, ether-rich chain featuring multiple internal oxygen atoms and terminal carbon–bromine substituents. It contains C–O ether linkages that confer polarity and flexibility, with a flexible aliphatic backbone suitable for spacing pharmacophores. Overall, it behaves as a brominated polyether segment with stable covalent connectivity.

Reactivity: The terminal bromides are suitable electrophilic handles for substitution-based coupling reactions commonly used in PROTAC synthesis. In practice, nucleophilic displacement is typically promoted by appropriate bases to generate reactive nucleophiles from ligand-bearing alcohol or amine groups, often in polar aprotic solvents. The mechanism follows SN-type substitution at the brominated termini, enabling stepwise installation of ligands while minimizing side reactions through controlled stoichiometry and temperature.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂