MELLITIC ACID

Base Information

• Chemical Name: MELLITIC ACID
• CAS No.: 517-60-2
• Molecular Formula: C12H6O12
• Molecular Weight: 342.172
• Hs Code.: 29173990
• European Community (EC) Number: 208-243-6
• NSC Number: 229358
• UNII: P80QSP14DM
• DSSTox Substance ID: DTXSID50199650
• Nikkaji Number: J6.578A
• Wikipedia: Mellitic_acid
• Wikidata: Q734078
• Metabolomics Workbench ID: 56404
• ChEMBL ID: CHEMBL1231329
• Mol file: 517-60-2.mol

Synonyms:Benzenehexacarboxylicacid (8CI,9CI);Mellitic acid (6CI);Hexacarboxybenzene;Mellic acid;NSC229358;

Chemical Property of MELLITIC ACID

Chemical Property:

• Vapor Pressure: 3.92E-19mmHg at 25°C
• Melting Point: 287 °C
• Refractive Index: 1.761
• Boiling Point: 674.845 °C at 760 mmHg
• PKA: pK1: 0.68;pK2: 2.21;pK3: 3.52;pK4: 5.09;pK5: 6.32; pK6: 7.49 (25°C)
• Flash Point: 375.911 °C
• PSA: 223.80000
• Density: 2.078 g/cm³
• LogP: -0.12420
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Completely soluble in water
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 6
• Exact Mass: 341.98592562
• Heavy Atom Count: 24
• Complexity: 470

Purity/Quality:

97% ^*data from raw suppliers

Mellitic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1(=C(C(=C(C(=C1C(=O)O)C(=O)O)C(=O)O)C(=O)O)C(=O)O)C(=O)O
• General Description: Mellitic acid, also known as benzenehexacarboxylic acid, is a highly symmetric organic compound with six carboxyl groups attached to a benzene ring. It serves as a versatile precursor for the synthesis of mellitic triimides, which are valuable as C3-symmetric electron acceptors and supramolecular building blocks due to their planar structure and strong electron-withdrawing properties. The acid can be readily converted into triimides through a solid-state reaction with primary amines, enabling the introduction of diverse substituents while maintaining stereochemical integrity. This synthetic approach simplifies the production of these functionalized derivatives, overcoming previous challenges in yield and purification.

Technology Process of MELLITIC ACID

There total 40 articles about MELLITIC ACID which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 54.0%

1,2,3,4,5,6-cyclohexanehexacarboxylic acid (2216-84-4) → benzenehexacarboxylic acid (517-60-2)

Guidance literature:

1,2,3,4,5,6-cyclohexanehexacarboxylic acid; With phosphorus pentachloride; In neat (no solvent); at 130 ℃; for 1h;

With water; In neat (no solvent); at 130 ℃; for 4h;

DOI:10.1021/jo5005185

Reference yield: 49.0%

Hexamethylbenzene (87-85-4) → benzenehexacarboxylic acid (517-60-2)

Guidance literature:

With cerium(III) chloride; 1,1,1-trichloroethanol; oxygen; In acetonitrile; at 60 ℃; Irradiation;

DOI:10.1007/s11426-021-1032-7

Reference yield:

→ benzenehexacarboxylic acid (517-60-2)

Guidance literature:

With nitric acid; vanadia;

upstream raw materials:

maleic anhydride

Tetrakis-hydroxymethyl-furan

triphenylene

Hexamethylbenzene

Downstream raw materials:

hexamethyl benzenehexacarboxylate

benzene-1,2,3,4,5,6-hexacarboxylic acid hexaethyl ester

1,2,4,5-benzenetetracarboxylic acid

benzene-1,3,5-tricarboxylic acid

Refernces

An expedient synthesis of mellitic triimides

10.1021/jo800185v

The study presents a straightforward and versatile method for synthesizing mellitic triimides. The researchers discovered that heating solid ammonium salts, obtained by treating mellitic acid with three equivalents of a primary amine, yields trisubstituted mellitic triimides through dehydration and imide ring closure. This method allows for the incorporation of various substituents such as alkyl, aryl, and amino acid ester groups, significantly expanding the range of C3-symmetric organic electron acceptors. The study highlights the potential of these compounds as supramolecular building blocks due to their unique planar 3-fold symmetric structure and strong electron-accepting ability. The new synthetic approach overcomes limitations of previous methods, such as low yields and complex purification processes, by using solid-state chemistry, which simplifies the synthesis and isolation of the desired triimides. The study also explores the stereochemical integrity of the synthesized compounds, confirming that the substituents retain their stereochemistry during the synthesis.