Name: China Supplier High Quality Wholesale Price Emeramide (BDTH2) CAS 351994-94-0
Brand: Wuhan Fortuna Chemical Co., Ltd.

N,N'-Bis(2-Mercaptoethyl)isophthalamide is a synthetic organic compound belonging to the class of dithiol chelators and aryl dialkyl thiols. Its systematic name describes a precise molecular architecture designed for specific supramolecular interactions.

Core Scaffold: The central unit is an isophthaloyl dichloride derivative, specifically an *m*-phenylene diamine where the amine groups have been acylated. This provides a rigid, aromatic isophthalamide core that dictates the molecule's geometry and serves as a structural platform.
Linker/Spacer: Extending from each amide nitrogen is a short, flexible alkanethiol precursor chain: a two-carbon ethylene spacer (-CH₂-CH₂-). This spacer provides conformational freedom, allowing the terminal functional groups to adopt optimal positions for binding.
Functional Groups: The critical moieties are the terminal thiol groups (-SH), also known as mercapto groups. These are soft Lewis bases with a high affinity for soft Lewis acids, particularly heavy metals and metal surfaces.

Chemical Properties and Reactivity

The molecule's functionality arises from the synergy of its components:

Chelation and Coordination Chemistry: The molecule acts as a bidentate ligand. The two thiol groups can simultaneously coordinate to a single metal ion (e.g., Cd²⁺, Hg²⁺, Pb²⁺) to form a stable, often five-membered chelate ring involving the -S-M-S- entity and the ethylene spacers. This chelate effect greatly enhances complex stability compared to monodentate thiols.
Surface Chemistry and Self-Assembly: This is its most prominent application. The thiol groups undergo spontaneous, exothermic chemisorption onto the surface of noble metals, most notably gold (Au(111)). The S-Au bond is highly stable (~40-50 kcal/mol). The meta substitution of the central ring prevents the molecule from lying flat, encouraging the formation of a standing-up phase. This leads to the formation of highly ordered Self-Assembled Monolayers (SAMs). The amide groups within the SAM can participate in intermolecular hydrogen bonding (N-H···O=C), significantly enhancing the thermal and structural stability of the monolayer.
Redox Activity: The thiol groups are redox-active, capable of being oxidized to disulfides (R-S-S-R). This property can be exploited for creating dynamic covalent systems or cross-linked polymer networks.

Primary Chemical Applications

Surface Functionalization: Used to create robust, thin organic films on gold electrodes for biosensors and electrochemical platforms. The amide group provides a convenient handle for further covalent attachment of biomolecules like proteins or DNA.
Heavy Metal Sequestration: Its high binding constant for soft heavy metals makes it a potential chelator for environmental remediation or detoxification processes.
Nanomaterial Capping Agent: Can be used to stabilize metal nanoparticles by forming a protective monolayer on their surface, preventing aggregation.

In summary, N,N'-Bis(2-Mercaptoethyl)isophthalamide is a sophisticated ligand engineered for strong, bidentate surface adhesion and metal chelation, with its chemical behavior defined by the cooperative action of its rigid aromatic core, flexible linkers, and highly reactive thiol termini.