2-[[(2,6-Difluorophenyl)methyl](ethoxycarbonyl)amino]-4-[(dimethylamino)methyl]-5-(4-nitrophenyl)-3-Thiophenecarboxylic acid
[CAS# 1589503-95-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Thiophene compound
• Name: 2-[[(2,6-Difluorophenyl)methyl](ethoxycarbonyl)amino]-4-[(dimethylamino)methyl]-5-(4-nitrophenyl)-3-Thiophenecarboxylic acid
• Molecular Formula: C₂₄H₂₃F₂N₃O₆S
• Molecular Weight: 519.52
• CAS Registry Number: 1589503-95-6
• EC Number: 854-550-9
• SMILES: CCOC(=O)N(CC1=C(C=CC=C1F)F)C2=C(C(=C(S2)C3=CC=C(C=C3)[N+](=O)[O-])CN(C)C)C(=O)O

Properties

• Solubility: Sparingly Soluble (7.3E^-3 g/L) (25 °C), Calc.^*
• Density: 1.408±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 653.5±55.0 °C 760 mmHg (Calc.)^*
• Flash point: 349.1±31.5 °C (Calc.)^*
• Index of refraction: 1.625 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H302-H315-H319-H335-H351
• Safety Statements: P203-P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Carcinogenicity	Carc.	2	H351
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

2-[[(2,6-Difluorophenyl)methyl](ethoxycarbonyl)amino]-4-[(dimethylamino)methyl]-5-(4-nitrophenyl)-3-Thiophenecarboxylic acid is a synthetic heteroaromatic compound that contains a substituted thiophene ring with multiple functional groups and aromatic substituents. The molecular formula is C₂₀H₂₁F₂N₃O₆S, and the structure is characterized by a thiophene-3-carboxylic acid core that is heavily modified at the 2, 4, and 5 positions.

At the 2-position of the thiophene ring, the compound bears a substituted urea-like moiety formed by the attachment of a (2,6-difluorophenyl)methyl group and an ethoxycarbonyl group through an amino linker. This portion contributes both hydrophobic character and potential hydrogen bonding capacity due to the presence of fluorine atoms and carbonyl oxygen.

The 4-position is substituted with a (dimethylamino)methyl group, a basic aliphatic amine that can impart water solubility and influence ionization under physiological conditions. This group is often seen in biologically active molecules due to its capacity to interact with polar residues or facilitate membrane permeability.

The 5-position is functionalized with a 4-nitrophenyl group, which is an electron-withdrawing aromatic substituent known for its participation in π-stacking interactions and electron transfer processes. The presence of the nitro group further enhances the electron-deficient nature of the molecule, potentially affecting binding affinities and chemical reactivity.

The carboxylic acid group at the 3-position of the thiophene ring is a polar and reactive functional group that plays a role in solubility, ionization, and possible coordination with biological or synthetic targets. It also provides a synthetic handle for further derivatization or conjugation.

The overall structure is amphiphilic, combining both hydrophilic and hydrophobic regions, and features multiple functional groups capable of hydrogen bonding, acid-base interaction, and electronic modulation. These characteristics make the compound a strong candidate for use in medicinal chemistry, particularly in the design of receptor modulators, enzyme inhibitors, or antimicrobial agents.

While this specific compound is not among the most widely studied derivatives of thiophene, its structural elements are common in medicinal chemistry, including difluorobenzyl, nitrophenyl, and substituted amino groups. Such moieties are found in marketed drugs and investigational agents where fine-tuning of physicochemical and pharmacokinetic properties is required.

In terms of physicochemical properties, the compound is expected to be a solid at room temperature. It is likely soluble in polar organic solvents such as dimethyl sulfoxide and methanol, and its ionizable groups suggest some solubility in aqueous buffers at pH values supporting the deprotonated carboxylic acid form.

From a synthetic perspective, preparation of this compound may involve multistep coupling strategies, including thiophene ring functionalization, amide or carbamate formation, and aromatic substitution reactions. Each functional group must be introduced with attention to reactivity and compatibility with others already present.

In summary, 2-[[(2,6-Difluorophenyl)methyl](ethoxycarbonyl)amino]-4-[(dimethylamino)methyl]-5-(4-nitrophenyl)-3-Thiophenecarboxylic acid is a functionally rich thiophene derivative that integrates fluorinated aromatics, polar amines, electron-withdrawing nitro groups, and carboxylic acid chemistry into one molecular framework. Its potential applications lie in drug design, receptor targeting, and molecular probe development.

References

none