51674-11-4

Basic information

• Product Name: 3,6-dihydroxyphthalimide
• Synonyms: 3,6-dihydroxyphthalimide;4,7-Dihydroxy-1H-isoindole-1,3(2H)-dione;Einecs 257-344-1;Phthalimide, 3,6-dihydroxy-;Nsc 229301
• CAS NO: 51674-11-4
• Molecular Formula: C₈H₅NO₄
• Molecular Weight: 179.1296
• EINECS: 257-344-1
• Product Categories: Fluorescent
• Mol File: 51674-11-4.mol

Chemical Properties

• Melting Point: >250°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: White/Solid
• Density: 1.715g/cm³
• Refractive Index: 1.718
• Solubility: Solubility Insoluble in water; soluble in ethanol, methanol
• PKA: 1.65, 6.97(at 25℃)
• CAS DataBase Reference: 3,6-dihydroxyphthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-dihydroxyphthalimide(51674-11-4)
• EPA Substance Registry System: 3,6-dihydroxyphthalimide(51674-11-4)

Safety Data

• Hazardous Substances Data: 51674-11-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3,6-dihydroxyphthalimide is utilized as a precursor in the synthesis of pharmaceuticals, playing a crucial role in the development of new drugs. Its unique structural features and functional groups contribute to its potential applications in medicinal chemistry and drug discovery.
Used in Dye Production:
3,6-dihydroxyphthalimide is also employed as a precursor in the production of dyes, where its chemical properties are harnessed to create a range of colorants for various applications.
Used in Organic Synthesis:
3,6-dihydroxyphthalimide serves as a reagent in organic synthesis, facilitating the creation of a variety of organic compounds through chemical reactions.
Used in Heterocyclic Compound Preparation:
It is used as a building block for the preparation of various heterocyclic compounds, which are important in the fields of pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
Due to its structural features and functional groups, 3,6-dihydroxyphthalimide is valuable in research and development for exploring new chemical reactions and applications.
Safety Considerations:
It is important to handle 3,6-dihydroxyphthalimide with care, as it may be harmful if ingested or inhaled, and can cause irritation to the skin and eyes. Proper safety measures should be taken during its use to minimize potential health risks.

InChI:InChI=1/C8H5NO4/c10-3-1-2-4(11)6-5(3)7(12)9-8(6)13/h1-2,10-11H,(H,9,12,13)

Upstream product

• 603-62-3 4-nitro-1H-isoindole-1,3(2H)-dione 
• 106-51-4 p-benzoquinone 
• 124511-82-6 3,6-diacethoxyphthalic anhydride 
• 490-79-9 2,5-dihydroxybenzoic acid. 
• 3958-79-0 methyl 3,6-dioxocyclohexa-1,4-diene-1-carboxylate 
• 2150-46-1 Methyl 2,5-dihydroxybenzoate 
• 4733-50-0 2,3-dicyano-1,4-hydroquinone 

Downstream Products

• 490-79-9 2,5-dihydroxybenzoic acid. 

Relevant articles and documents

Unusual nucleophilic substitution in the nitrophthalimide series

The reactions of 3-and 4-nitrophthalimides with hydroxylamine in aqueous alcohol media were studied. A mixture of 3-amino-4-nitro-and 4-amino-5-nitrophthalimides is formed in the case of 4-nitrosubstituted derivative, whereas 3,6-dihydroxyphthalimide is unexpectedly found to be the main product of the reaction of 4-nitrosubstituted derivative. A possible mechanism of the transformation was suggested.

Method for preparing 3,6-dihydroxyphthalimide

The invention discloses a method for preparing 3,6-dihydroxyphthalimide. According to the method disclosed by the invention, the 3,6-dihydroxyphthalimide is obtained by taking 3,6-dihydroxyphthalonitrile, acetic anhydride and urea as main raw materials through three steps of reaction. The method provided by the invention has the advantages that a process is simple, convenient and stable to operate; a product of each step is easy to separate, has high yield and is environmentally friendly and the comprehensive yield is 85 percent or more; the raw materials are cheap and easy to obtain and the production cost is greatly reduced so that industrial large-scale production is facilitated.

Biscatenanes and a Bisrotaxane-Model Compounds for Polymers with Mechanically Interlocked Components

The self-assembly of three biscatenanes and a bisrotaxane, by two complementary strategies, is reported.A synthetic route to derivatives of bis-para-phenylenecrown-10 (BPP34C10) and 1,5-naphtho-para-phenylene-crown-10 (1/5NPP36C10) containing a fused five-membered ring with a secondary amine function is described.These intermediate N-allylimido macrocyclic polyethers undergo template-directed reactions with 1,1'-bis-4,4'-bipyridinium bis-(hexafluorophosphate) and 1,4-bis(bromo-methyl)benzene to produce catenanes containing an N-allyl functionality.The allylimido macrocyclic polyethers have also beeen reduced and deprotected to afford macrocycles possessing a free NH group, which are then linked through a 4,4'-biphenyldicarbonyl spacer to produce bis(crown ether)s, in which each crown ether moiety has two recognition sites.These ditopic BPP34C10 and 1/5NPP36C10 derivatives are capable of sustaining self-assembly reactions at both recognition sites to yield biscatenanes.The self-assembly of a complementary biscatenane, in which two tetracationic cyclophanes are linked together with a flexible hexyl chain, has also been achieved by treating 1,1'-bis-4,4'-bipyridinum bis-(hexafluorophosphate) with a compound containing two linked 1,4-bis(bromomethyl)benzene units in the presence of BPP34C10.Replacing BPP34C10 with a dumbbell-shaped compound containing a linear polyether unit intercepted by a naphthalene residue and terminated by two bulky adamantoyl groups has led to the self-assembly of a bisrotaxane.The X-ray crystal structures of one of the catenanes and its associated crown ether component are reported, together with solution state dynamic 1H NMR spectroscopic studies, showing that there is substantial degree of order characterizing the molecular structure of the catenanes. - Keywords: catenanes, polycatenanes, polyrotaxanes, rotaxanes, self-assembly.