1,3,5-Benzenetricarboxylic acid chloride

• CAS: 4422-95-1
• Catalog Number: ACM4422951
• Category: Main Products
• Molecular Weight: 265.48
• Molecular Formula: C₉H₃Cl₃O₃
• Synonyms: 1,3,5-BENZENETRICARBOXYLIC CHLORIDE;1,3,5-BENZENETRICARBOXYLIC ACID CHLORIDE;1,3,5-BENZENETRICARBONYL CHLORIDE;1,3,5-BENZENETRICARBONYL TRICHLORIDE;BENZENETRICARBONYL CHLORIDE;BENZENE-1,3,5-TRICARBONYL CHLORIDE;BENZENE-1,3,5-TRICARBOXYLIC ACID TRICHLORIDE
• IUPAC Name: benzene-1,3,5-tricarbonylchloride
• SMILES: C1=C(C=C(C=C1C(=O)Cl)C(=O)Cl)C(=O)Cl
• InChI Key: UWCPYKQBIPYOLX-UHFFFAOYSA-N
• Boiling Point: 180ºC (16 mmHg)
• Melting Point: 34.5-36ºC
• Flash Point: >230 °F
• Density: 1.487 g/mL at 25ºC(lit.)
• Appearance: light yellow crystalline
• EC Number: 224-594-8
• Exact Mass: 263.91500
• Hazard Statements: C:Corrosive
• Packing Group: II
• Safety Description: S24/25
• Stability: Stable under normal temperatures and pressures.
• WGK Germany: 3

Case Study

1,3,5-Benzenetricarbonyl Trichloride as a Key Building Block for Supramolecular Anion Sensors

Matmin, J. U. A. N., et al. Advanced Materials Research 925 (2014): 228-232.

Supramolecular chemistry utilizing hydrogen bonding interactions offers a powerful platform for selective sensing of environmentally hazardous anions such as nitrate and nitrite. In this study, 1,3,5-benzenetricarbonyl trichloride was employed as a trifunctional acylating agent for the synthesis of a benzene-1,3,5-tricarboxamide derivative bearing hydrophobic aminododecane side chains, designed for nitrate anion sensing.
The target compound was synthesized via Schotten-Baumann amidation of 1,3,5-benzenetricarbonyl trichloride with 1-aminododecane in the presence of N,N-diisopropyl ethylamine. The reaction proceeded under inert conditions in dichloromethane at room temperature for 18 h, followed by purification by silica gel chromatography.
Key Results:
· The desired benzene-1,3,5-tricarboxamide (1) was obtained in 93% yield as a white powder solid. FT-IR analysis revealed characteristic hydrogen bonding interactions: N-H stretching at 3233 cm-1 and C=O stretching at 1638 cm-1, indicating self-assembly via intermolecular hydrogen bonds. SEM showed that compound 1 self-assembles into tape-like morphologies with helical one-dimensional organization, attributed to J-aggregation through side-by-side hydrogen bonding.
· Upon exposure to nitrate anions (1 mM, 15 min stirring), the hydrogen-bonded network underwent deformation. SEM imaging confirmed the loss of ordered tape-like structures, showing random aggregate distribution after nitrate interaction, demonstrating the potential of this supramolecular system for nitrate sensing via hydrogen bonding disruption.

1,3,5-Benzenetricarbonyl Trichloride as a Versatile Building Block for Liquid Crystalline Benzene-1,3,5-tricarboxamides

Lintang, H. O., et al. Journal of Physics: Conference Series. Vol. 1282. No. 1. IOP Publishing, 2019.

Liquid crystalline materials with room-temperature mesophases are highly sought after for display technologies and optoelectronic devices. In this study, 1,3,5-benzenetricarbonyl trichloride (BTC) was employed as a trifunctional core for the synthesis of a series of benzene-1,3,5-tricarboxamides (BTAs) bearing hydrophobic alkyl side chains of varying lengths (C10-C18), enabling systematic investigation of structure-liquid crystalline property relationships.
BTAs were synthesized via Schotten-Baumann amidation of BTC with primary alkyl amines (decylamine to octadecylamine) in the presence of N,N-diisopropyl ethylamine. The reactions proceeded in dichloromethane at room temperature for 18 h, affording the target compounds in high yields (71-93%) after purification by column chromatography.
Key Results:
· Successful synthesis of five BTAs was confirmed by MALDI-TOF MS, ¹H/¹³C NMR, and FT-IR.
· DSC revealed that all BTAs form wide-range mesophases, with phase transition temperatures strongly dependent on alkyl chain length: BTA_C10 (decylamine): crystalline → mesophase at 21.8 °C, mesophase → isotropic at 196.3 °C (room-temperature mesophase); BTA_C12: 41.9-212.4 °C; BTA_C14: 57.9-203.7 °C; BTA_C16: 76.1-207.7 °C; BTA_C18: 80.5-200.1 °C.
· The increasing crystallization temperature with chain length reflects higher energy requirements for alkyl chain melting, while mesophase-to-isotropic transitions remain relatively constant (≤10 °C variation), indicating that columnar assembly via intermolecular hydrogen bonding is the dominant stabilizing interaction.
· BTA_C10 uniquely exhibits liquid crystalline behavior spanning room temperature, attributed to reduced van der Waals interactions with shorter alkyl chains.