Name: 4-[(6-Methoxybenzothiazol-2-yl)azo]-N,N-dimethylaniline
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Price

Stock

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$--

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Purity

95%

IUPACName

4-[(6-methoxy-1,3-benzothiazol-2-yl)diazenyl]-N,N-dimethylaniline

Synonyms

3771-31-1; CHEMBL1817789; STK368493; 4-((6-Methoxybenzothiazol-2-yl)azo)-N,N-dimethylaniline; 4-((6-Methoxybenzo[d]thiazol-2-yl)diazenyl)-N,N-dimethylaniline; 4-[(6-METHOXYBENZOTHIAZOL-2-YL)AZO]-N,N-DIMETHYLANILINE

Boiling Point

481.3°C at 760mmHg

Density

1.25g/cm3

InChI Key

AVPFTROGVGTTEC-UHFFFAOYSA-N

InChI

InChI=1S/C16H16N4OS/c1-20(2)12-6-4-11(5-7-12)18-19-16-17-14-9-8-13(21-3)10-15(14)22-16/h4-10H,1-3H3

SMILES

CN(C)C1=CC=C(C=C1)N=NC2=NC3=C(S2)C=C(C=C3)OC

Mechanism

Mechanism of Action: This benzothiazole azo scaffold may support customers developing protein-binding, localization, or degradation-enabling probes. Its aromatic structure can favor interaction with hydrophobic protein environments, making it useful for exploratory studies on protein recognition, reporter design, or scaffold optimization for degradation workflows.

Applications

• PROTAC Ligand for E3 Recruitment: 4-[(6-Methoxybenzothiazol-2-yl)azo]-N,N-dimethylaniline can be used as a binding module to engage a chosen target protein in PROTAC architectures. By linking this ligand to an E3 ligase-recruiting moiety, researchers can test whether ternary complex formation promotes ubiquitination and subsequent target degradation.

• Ternary Complex Optimization Studies: Incorporating this ligand into PROTAC constructs enables systematic evaluation of linker length, attachment geometry, and overall physicochemical properties to maximize productive ternary complex formation. These studies can identify degradation-selective conditions by comparing target ubiquitination kinetics and degradation potency across engineered PROTAC variants.

• Target-Selective Degradation Profiling: This ligand can support PROTAC-driven mapping of target dependence by pairing it with different E3 ligases or by using orthogonal control constructs. Measuring protein loss alongside pathway markers helps determine whether degradation is mechanism-driven and whether off-target effects arise from promiscuous binding.

• Structure–Activity Relationship Mapping: The aromatic, heteroaryl, and azo features make this ligand suitable for SAR-driven PROTAC optimization. Researchers can generate analogs or conjugation-site variants to refine affinity and orientation, then correlate changes in binding with degradation efficacy, potency, and duration in cellular protein degradation assays.

1. Azo Coupling Reaction Induced Macromolecular Self-Assembly in Aqueous Solution

Shang Li, Jilei Wang, Jiajia Shen, Bing Wu, Yaning He ACS Macro Lett. 2018 Apr 17;7(4):437-441.doi: 10.1021/acsmacrolett.8b00049.Epub 2018 Mar 21.

This communication reported azo coupling reaction induced macromolecular self-assembly in aqueous solution. Diblock copolymer (PEG-b-PSNHBoc) consisting of a hydrophilic PEG block, and a hydrophobic N-Boc protected poly(p-vinylaniline) block was synthesized by RAFT polymerization. Then double hydrophilic diblock copolymer (PEG-b-PSN2+) composed of PEG and PS based macromolecular diazonium salts was prepared by the diazotization of PEG-b-PSNH2, which was obtained by deprotection of PEG-b-PSNHBoc. As N,N-dimethylaniline was gradually added into the freshly prepared PEG-b-PSN2+ aqueous solution, the azo coupling reaction between N,N-dimethylaniline and diazonium salts took place, which would lead to the generation of azobenzene pendants. Due to the poor solubility of azobenzene pendants in water, the formed hydrophobic polymeric chains aggregated to form the self-assembly colloidal particles. By incorporating a fluorescent group into the aniline, the aggregates formed through azo coupling reaction induced macromolecular self-assembly showed enzyme-triggered fluorescent behaviors.

2. Photoactive azoimine dyes: 4-(2-pyridylazo)-N,N-diethylaniline and 4-(2-pyridylazo)-N,N-dimethylaniline: computational and experimental investigation

Suthirat Yoopensuk, Pornthip Tongying, Kanidtha Hansongnern, Chaveng Pakawatchai, Saowanit Saithong, Yuthana Tantirungrotechai, Nararak Leesakul Spectrochim Acta A Mol Biomol Spectrosc. 2012 Feb;86:538-46.doi: 10.1016/j.saa.2011.11.007.Epub 2011 Nov 18.

4-(2-Pyridylazo)-N,N-dimethylaniline and 4-(2-pyridylazo)-N,N-diethylaniline, two photoactive azoimine dyes, were prepared from the reaction of 2-aminopyridine with N,N-dialkyl-1,4-nitrosoaniline at room temperature. Structural characterizations of these dyes using single crystal X-ray diffraction, (1)H NMR, elemental analysis, mass spectroscopy and IR spectroscopy have been carried out. The X-ray structure indicates a trans configuration around the azo group. The photochemical behavior of these compounds differs from that of 2-phenylazopyridine, the non-dialkylamino substituent compound. The synthesized compounds show emission spectra at room temperature while 2-phenylazopyridine does not. The excitation spectra of these compounds differ from their absorption spectra which can be explained on the basis of the trans to cis photoisomerization which is supported by the TD-PBE0/6-31G(d,p) calculations. Both oxidation of the dialkylamino substituents (-NR(2); R=-CH(3) and -C(2)H(5)) and reduction of -N=N-/-N=N-(-) and -N=N-(-)/-N=N-(2-) were observed in the cyclic voltammogram indicating a π-acidity of both dyes.

3. 1,3,4-Thiadiazole-Containing Azo Dyes: Synthesis, Spectroscopic Properties and Molecular Structure

Agnieszka Kudelko, Monika Olesiejuk, Marcin Luczynski, Marcin Swiatkowski, Tomasz Sieranski, Rafal Kruszynski Molecules. 2020 Jun 18;25(12):2822.doi: 10.3390/molecules25122822.

Three series of azo dyes derived from 2-amino-5-aryl-1,3,4-thiadiazoles and aniline, N,N-dimethylaniline and phenol were synthesized in high yields by a conventional diazotization-coupling sequence. The chemical structures of the prepared compounds were confirmed by 1H-NMR, 13C-NMR, IR, UV-Vis spectroscopy, mass spectrometry and elemental analysis. In addition, the X-ray single crystal structure of a representative azo dye was presented. For explicit determination of the influence of a substituent on radiation absorption in UV-Vis range, time-dependent density functional theory calculations were performed.

This azo-benzothiazole compound is a conjugated dye-like scaffold with limited direct linker-ready functionality. It should be used in PROTAC-style design only after target-binding relevance and a suitable exit vector are established.

Structure: This compound is an azo-linked benzothiazole anilino dye-like scaffold containing a 6-methoxybenzothiazole ring, an azo bridge, and a dimethylamino aniline ring. The conjugated N=N system and electron-donating dimethylamino/methoxy groups dominate its electronic structure.

Reactivity: The structure contains no obvious free acid, amine, alkyne, halide, or alcohol handle for direct PROTAC coupling. If used as a target-binding or reporter-derived ligand, linker installation would require analog synthesis on the dimethylamino aryl ring, methoxy aryl region, or benzothiazole periphery while preserving the azo chromophore if it is functionally relevant. Pairing with CRBN, VHL, or IAP ligands should use alkyl or PEG linkers only after confirming the scaffold has a validated protein-binding target.

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It is commonly abbreviated as: C₁V₁ = C₂V₂