27550-59-0

Basic information

• Product Name: 4-HYDROXYPHTHALIC ANHYDRIDE
• Synonyms: 4-HYDROXYPHTHALIC ANHYDRIDE;5-hydroxyisobenzofuran-1,3-dione;5-hydroxy-2-benzofuran-1,3-dione
• CAS NO: 27550-59-0
• Molecular Formula: C₈H₄O₄
• Molecular Weight: 164.11
• Mol File: 27550-59-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 171-173 °C(Solv: acetic acid (64-19-7))
• Boiling Point: 407.8 °C at 760 mmHg
• Flash Point: 179.4 °C
• Appearance: /
• Density: 1.625 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 6.52±0.20(Predicted)
• CAS DataBase Reference: 4-HYDROXYPHTHALIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXYPHTHALIC ANHYDRIDE(27550-59-0)
• EPA Substance Registry System: 4-HYDROXYPHTHALIC ANHYDRIDE(27550-59-0)

Safety Data

• Hazardous Substances Data: 27550-59-0(Hazardous Substances Data)

Usage

General Description

4-Hydroxyphthalic anhydride, also known as 4-HPA, is a chemical compound with the molecular formula C8H4O5. It is a white to off-white solid that is soluble in organic solvents. 4-HPA is primarily used as a building block in the manufacture of high-performance polymers, including polyester resins and polyimides. It is also utilized as a chemical intermediate in the production of dyes, pigments, and pharmaceuticals. The compound is classified as an irritant and can cause irritation to the skin, eyes, and respiratory system upon exposure. Additionally, 4-Hydroxyphthalic anhydride is considered to be a potential environmental hazard and special care should be taken in its handling and disposal.

Upstream product

• 4707-32-8 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione 
• 30757-50-7 4-hydroxy-1,2-benzenedicarbonitrile 
• 31643-49-9 4-Nitrophthalonitrile 
• 5434-21-9 4-aminophthalic acid 
• 89-08-7 4-sulfophthalic acid 
• 22572-84-5 diethyl 4-aminophthalate 
• 64139-21-5 Diethyl 4-hydroxyphthalate 
• 610-35-5 4-hydroxyphthalic acid 

Downstream Products

• 28281-76-7 5-methoxyisobenzofuran-1,3-dione 
• 860597-60-0 4-hydroxy-2-(4-methoxy-benzoyl)-benzoic acid 
• 859943-28-5 5-hydroxy-2-(4-methoxy-benzoyl)-benzoic acid 
• 111796-36-2 6-hydroxy-2,3-diphenyl-2,3-dihydro-phthalazine-1,4-dione 
• 3913-46-0 5-hydroxy-2-(1-propyl)isoindole-1,3-dione 
• 109803-76-1 2-(1-hexyl)-5-hydroxyisoindole-1,3-dione 
• 103416-94-0 5-Hydroxy-2-(4-hydroxy-butyl)-isoindole-1,3-dione 
• 3975-51-7 2-cyclohexyl-5-hydroxyisoindoline-1,3-dione 
• 3913-45-9 2-ethyl-5-hydroxy-isoindoline-1,3-dione 
• 109803-75-0 5-Hydroxy-2-pentyl-isoindole-1,3-dione 
• 4112-60-1 2-butyl-5-hydroxyisoindoline-1,3-dione 
• 109803-71-6 2-cyclopentyl-5-hydroxyisoindoline-1,3-dione 
• 4112-65-6 5-hydroxy-2-methylisoindoline-1,3-dione 
• 103416-93-9 5-Hydroxy-2-(3-hydroxy-propyl)-isoindole-1,3-dione 

Relevant articles and documents

Naphthalimide/benzimide-based excited-state intramolecular proton transfer active luminogens: Aggregation-induced enhanced emission and potential for chemical modification

Fluorescent organic particles are important in a number of areas, including medical imaging; hence, the development of organic materials that exhibit aggregation-induced emissions is an important objective. To that end, we report the synthesis of naphthalimide- and benzimide-based 2-(2-hydroxyphenyl)benzothiazole (HBT) derivatives (HNIBT and HPIBT, respectively) that exhibit aggregation-induced emission enhancement (AIEE), in contrast to most naphthalimide- or benzimide-based derivatives that are prone to aggregation-induced quenching. Experimental studies like single-crystal X-ray diffraction analysis and theoretical calculations demonstrate that the ability to undergo excited-state intramolecular proton transfer is pivotal for AIEE. Further studies revealed that a terminal alkynyl chain at the N-imide site of HPIBT has little impact on the emission behavior of the resultant compound (HPIBT-yl). HPIBT-Pe, an amphiphilic molecule obtained through the click reaction of HPIBT-yl and a tetraethylene-glycol-derived azide, self-assembled to form highly photostable particles that have long-term fluorescence imaging potential in cellular environments.

Preparation method of 4-hydroxyl phthalic anhydride

The invention provides a preparation method of 4-hydroxyl phthalic anhydride. The preparation method comprises the following steps: carrying out diazotization and hydrolysis reaction by adopting sodium nitrite and sulfuric acid so as to prepare 4-hydroxyl phthalic acid from 4-amino phthalic acid in one step; finally, sublimating the 4-hydroxyl phthalic acid in vacuum to obtain the 4-hydroxyl phthalic anhydride, wherein the total yield of the reaction reaches 82 percent or more. The method provided by the invention has high 4-hydroxyl phthalic acid yield; a hydrolysis process is more stable anda few of byproducts are produced; the subsequent purification difficulty and cost are reduced. In a whole preparation flow, raw materials are easy to obtain; meanwhile, a reaction process is simple,and complicated reaction equipment and strict reaction conditions are not needed.

Dental materials with improved hydrolysis stability based on phthalic acid monomers

Dental material which contains a polymerizable phthalic acid derivative of the general Formula I: with R1=H, methyl or a C1-C5 alkyl residue; R2=H, a phenyl, benzyl or C1-C8 alkyl residue; Q1=is absent or is a C1-C15 alkylene residue, wherein the carbon chain can be interrupted by O or S; Q2=is absent or a (n+1)-valent aliphatic C1-C20 residue, wherein the carbon chain can be interrupted by O or S and wherein Q1 and Q2 cannot be absent simultaneously; X=is absent, is O, S or (—CO—NR4—)—, wherein R4 is H, CH3 or C2H5; Y=is absent, is O, S or (—CO—NR5—)—, wherein R5 is H, CH3 or C2H5; n, m=independently of one another in each case mean 1, 2 or 3; R3=H, CH3, C2H5, Cl, Br or OCH3, and wherein the two carboxyl groups of the benzene ring can together form an anhydride group.