217655-36-2

Usage

Structure

Dimethyl ester of 1,3-benzenedicarboxylic acid with a phenylethynyl group at the 5-position

Functional groups

Aromatic ring, carboxylic acid ester, and alkyne

Organic synthesis

Building block for various organic compounds

Materials science

Potential use in the development of new materials

Optical and electronic devices

Exhibits photoresponsive behavior

Pharmaceutical industry

Potential applications in drug development

Physical properties

Unknown, but likely solid at room temperature due to its molecular size and complexity

Solubility

Likely soluble in organic solvents such as ethanol, methanol, and acetone, but insoluble in water due to the presence of the ester and aromatic groups

Stability

Stable under normal conditions, but may be sensitive to heat, light, or strong acids and bases

Reactivity

May undergo reactions such as ester hydrolysis, alkyne hydrogenation, and electrophilic aromatic substitution

Synthesis

Can be synthesized through the reaction of 1,3-benzenedicarboxylic acid with a suitable phenylethynyl compound and a methylating agent

Safety

Potential hazards include skin and eye irritation, and should be handled with care in a well-ventilated area or under a fume hood. Appropriate personal protective equipment (PPE) should be used.

Upstream product

• 51760-21-5 dimethyl 5-bromoisophthalate 
• 536-74-3 phenylacetylene 
• 7681-65-4 copper(I) iodide 
• 168619-21-4 3,5-bis(methoxycarbonyl)phenyl trifluoromethanesulfonate 

Downstream Products

• 432025-99-5 5-phenylethynylisophthalic acid 
• 393543-14-1 5-(2-phenylethynyl)isophthalic acid chloride 

Relevant academic research and scientific papers

UV–vis and fluorescence detection by receptors based on an isophthalamide bearing a phenylethynyl group

We have successfully prepared 5-(2-phenylethynyl)isophathalilc acid as a signaling unit and the corresponding derivatives for an anion receptor 2 and a barbiturate receptor 4. Receptor 2 showed characteristic UV–vis changes and dramatic fluorescence quenc

AROMATIC CARBOXYLIC ACIDS, ACID HALIDES THEREOF AND PROCESSES FOR PREPARING BOTH

A novel aromatic carboxylic acid useful as a material for macromolecular compounds and, in particular, for polycondensed macromolecular compounds exhibiting excellent heat resistance, an acid halide derivative thereof and a process for producing these compounds are disclosed. The aromatic carboxylic acid and the acid halide derivative thereof have structures represented general formulae (1) and (2), respectively, and can be efficiently produced from a dialkyl ester derivative of isophthalic acid and an acetylene derivative in accordance with the disclosed process comprising specific steps. In the above formulae, A represents:- C≡C-R1 or (R1 represents hydrogen atom, an alkyl group or an aromatic group, R2 represents an alkyl group or an aromatic group) and X represents a halogen atom.

Efficient Palladium-Catalyzed Coupling of Aryl Chlorides and Tosylates with Terminal Alkynes: Use of a Copper Cocatalyst Inhibits the Reaction

Less catalyst, lower temperature, and greater generality are the advantages of the new general protocol over those previously described for the palladium-catalyzed coupling of aryl chlorides and alkynes (see scheme). Better results are obtained without a copper cocatalyst, which has been found to inhibit product formation in the coupling reaction of aryl chlorides with terminal alkynes.

Preparation of functionalised aryl alkynes as precursors to extended cyclophanes

The preparation of 2,6-substituted arylhalides and triflates is described. These compounds are suitable precursors for cyclophane formation. (C) 2000 Elsevier Science Ltd.

Palladium-catalysed coupling of terminal alkynes with aryl halides aided by catalytic zinc

The palladium-catalysed coupling of aryl halides with terminal alkynes can be performed using base, zinc chloride and sodium iodide. This protocol represents a convenient method for the generation of nucleophilic acetylides in situ.