3753-81-9

Basic information

• Product Name: 1 3-BIS(P-CARBOXYPHENOXY)PROPANE
• Synonyms: benzoicacid,4,4’-[1,2-propanediylbis(oxy)]bis-;4,4-propanediyldioxydibenzoic acid;4-[3-(4-carboxyphenoxy)propoxy]benzoic acid;1 3-BIS(P-CARBOXYPHENOXY)PROPANE;4,4’-[1,2-propanediylbis(oxy)]bis(benzoicacid)
• CAS NO: 3753-81-9
• Molecular Formula: C₁₇H₁₆O₆
• Molecular Weight: 316.30534
• Product Categories: C13 to C42+;Carbonyl Compounds;Carboxylic Acids;Building Blocks;C13 to C42+;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 3753-81-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 310 °C(lit.)
• Boiling Point: 533.5°C at 760 mmHg
• Flash Point: 196.7°C
• Appearance: /
• Density: 1.318g/cm³
• Vapor Pressure: 3.26E-12mmHg at 25°C
• Refractive Index: 1.602
• PKA: 4.15±0.10(Predicted)
• CAS DataBase Reference: 1 3-BIS(P-CARBOXYPHENOXY)PROPANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1 3-BIS(P-CARBOXYPHENOXY)PROPANE(3753-81-9)
• EPA Substance Registry System: 1 3-BIS(P-CARBOXYPHENOXY)PROPANE(3753-81-9)

Safety Data

• Hazard Codes: Xi,N
• Statements: 43-50/53
• Safety Statements: 36/37-60-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 3753-81-9(Hazardous Substances Data)

Usage

Description

1,3-Bis(p-carboxyphenoxy)propane, also known as trimesic acid, is an organic compound that serves as a versatile building block for the synthesis of various polymers and materials. It is characterized by its three phenolic hydroxyl groups, which can be easily modified to create a range of applications in different industries.

Uses

Used in Pharmaceutical Industry:
1,3-Bis(p-carboxyphenoxy)propane is used as a building block for polyanhydrides, a class of bioerodible polymers, for drug delivery applications. These polymers are advantageous due to their biodegradability, tunable degradation rates, and ability to encapsulate a wide range of therapeutic agents, making them suitable for controlled drug release and targeted delivery systems.
Used in Polymer Industry:
1,3-Bis(p-carboxyphenoxy)propane is used as a monomer in the synthesis of various polymers, such as polyimides and polyesters, which find applications in the electronics, aerospace, and automotive industries. These polymers exhibit excellent thermal stability, mechanical properties, and chemical resistance, making them ideal for high-performance applications.
Used in Biomedical Applications:
1,3-Bis(p-carboxyphenoxy)propane can be used as a component in the development of biomaterials for tissue engineering and regenerative medicine. Its ability to form hydrogels and other biocompatible materials can be exploited for the design of scaffolds and drug delivery systems that promote cell growth, tissue repair, and controlled release of therapeutic agents.

InChI:InChI=1/C17H16O6/c18-16(19)12-2-6-14(7-3-12)22-10-1-11-23-15-8-4-13(5-9-15)17(20)21/h2-9H,1,10-11H2,(H,18,19)(H,20,21)

Upstream product

• 142-28-9 1,3-Dichloropropane 
• 99-96-7 4-hydroxy-benzoic acid 
• 120-47-8 Ethyl 4-hydroxybenzoate 
• 109-64-8 1,3-dibromo-propane 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 50685-36-4 C₁₉H₂₀O₆ 
• 69703-27-1 diethyl 1,3-propylidenebis(4-oxybenzoate) 
• 3722-80-3 1,3-bis(4-formylphenoxy)propane 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 7476-06-4 1,3-bis(4-cyanophenoxy)propane 
• 13401-77-9 C₂₁H₂₀O₈ 
• 69703-37-3 C₁₇H₁₄Cl₂O₄ 

Relevant articles and documents

Biological evaluation of bisbenzaldehydes against four Mycobacterium species

A series of bisbenzaldehydes and structurally related analogs, conveniently synthesized via microwave-assisted reactions, were evaluated in vitro against drug susceptible and multi-drug resistant Mycobacterium tuberculosis, against virulent Mycobacterium bovis, against Mycobacterium ulcerans and against two Mycobacterium avium subspecies. Among the 33 substances that were tested, compound 12, i.e. 4,4′-[1,12-dodecanediyl(oxy)]bisbenzaldehyde, emerged as the most promising hit. Its activity was further confirmed in an intracellular growth inhibition assay of M. tb in murine J774 A.1 macrophages. None of the compounds showed significant cytotoxicity on human C3A hepatocytes in a neutral red dye uptake assay and no genotoxicity or mutagenicity was observed as demonstrated by a VITOTOX test and confirmed with a comet assay.

New polyamides based on 1,3-bis(4-carboxy phenoxy) propane and hydantoin derivatives: Synthesis and properties

Six new polyamides 5a-f containing flexible trimethylene segments in the main chain were synthesized through the direct polycondensation reaction of 1,3-bis(4-carboxy phenoxy) propane 3 with six derivatives of hydantoins 4a-f in a medium consisting of N-methyl-2-pyrrolidone, triphenyl phosphite, calcium chloride and pyridine. The polycondensation reaction produced a series of novel polyamides in high yield with inherent viscosities between 0.30-0.47 dL/g. The resulted polymers were fully characterized by means of FT-IR, 1H-NMR spectroscopy, elemental analyses, inherent viscosity, solubility tests and gel permeation chromatography (GPC). Thermal properties of these polymers were investigated by using thermal gravimetric analysis (TGA) and differential thermal gravimetry (DTG). The glass-transition temperatures of these polyamides were recorded between 130 and 155 °C by differential scanning catorimetry (DSC), and the 5% weight loss temperatures were ranging from 325 to 415 °C under nitrogen. 1,3-bis(4-Carboxy phenoxy) propane 3 was prepared from the reaction of 4-hydroxy benzoic acid 1 with 1,3-dibromo propane 2 in the presence of NaOH solution.

FROM CONVENTIONAL TO LIQUID CRYSTALLINE POLYESTERS

To obtain liquid crystalline copolyesters with improved thermal behavior, p-acetoxybenzoyloxy-benzoic acid and a variety of dicarboxylic acids derived from p-hydroxybenzoic acid in combination with acetylated hydroquinone derivatives have been used as poly(ethylene terephthalate) (PETP) modifiers.The influence of the modifier structure on thermotropic properties of the copolyesters and results of dynamic mechanical measurements are discussed.