4253-24-1

Basic information

• Product Name: MELLITIC TRIANHYDRIDE
• Synonyms: Benzenehexacarboxylic trianhydride;Benzenehexacarboxylic 1,2:3,4:5,6-trianhydride;Benzenehexacarboxylic acid-1,2:3,4:5,6-trianhydride;Benzo[1,2-c:3,4-c':5,6-c'']trifuran-1,3,4,6,7,9-hexaone;Mellitic anhydride;Nsc80679;Benzo[1,2-c:3,4-c':5,6-c'']trifuran-1,3,4,6,7,9-hexone
• CAS NO: 4253-24-1
• Molecular Formula: C₁₂O₉
• Molecular Weight: 288.12
• Mol File: 4253-24-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 756.7°Cat760mmHg
• Flash Point: 339.1°C
• Appearance: /
• Density: 2.236g/cm³
• CAS DataBase Reference: MELLITIC TRIANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: MELLITIC TRIANHYDRIDE(4253-24-1)
• EPA Substance Registry System: MELLITIC TRIANHYDRIDE(4253-24-1)

Safety Data

• Hazardous Substances Data: 4253-24-1(Hazardous Substances Data)

Usage

General Description

Mellitic trianhydride, also known as benzenehexacarboxylic acid, is a chemical compound with the molecular formula C12H6O9. It is a white crystalline powder that is insoluble in water and organic solvents. It is used in the synthesis of various organic compounds and polymers, and has applications in the manufacture of dyes, pharmaceuticals, and agrochemicals. Mellitic trianhydride is also used as a catalyst in certain chemical reactions and as a corrosion inhibitor in metal finishing processes. It is important to handle this compound with care, as prolonged exposure to it can cause irritation to the skin, eyes, and respiratory system.

Synthetic route

benzenehexacarboxylic acid (517-60-2) → benzene-1,2:3,4:5,6-hexacarboxylic trianhyride (4253-24-1)

Conditions	Yield
With acetyl chloride at 160℃; im Rohr;
With benzoyl chloride
With acetic anhydride
With acetic anhydride for 16h; Heating; Yield given;

benzenehexacarboxylic acid (517-60-2) + acetic anhydride (108-24-7) → benzene-1,2:3,4:5,6-hexacarboxylic trianhyride (4253-24-1)

Conditions	Yield
3-stdg. Erhitzen;

4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE (36768-62-4) + benzene-1,2:3,4:5,6-hexacarboxylic trianhyride (4253-24-1) → C39H54N6O6

Conditions	Yield
With pyridine; acetic anhydride In tetrahydrofuran at 58℃; Solvent; Cooling with ice;	93.3%

benzene-1,2:3,4:5,6-hexacarboxylic trianhyride (4253-24-1) + cobalt(II) chloride (7646-79-9) → cobalt phthalocyanine-1,2:3,4:8,9:10,11:15,16:17,18:22,23:24,15-octakis(dicarboximide) (128096-81-1)

Conditions

Yield

With ammonium molybdate; urea In nitrobenzene mixing hexacarboxylic acid trianhydride, CoCl2, urea, and ammoniummolybdate, adding mixt. to nitrobenzene, heating (2 h, 200°C), adding further urea, heating (2 h); washing (3x, HCl, boiling H2O, MeOH), adding product to concd. H2SO4, shaking (5 h, room temp.), filtering, adding filtrate to ice, standing (several h), centrifuging, decanting, collecting pptn., washing (H2O, EtOH), drying (vac., P2O5); elem. anal.;

83.5%

benzene-1,2:3,4:5,6-hexacarboxylic trianhyride (4253-24-1) + iron(II) chloride → iron phthalocyanine-1,2:3,4:8,9:10,11:15,16:17,18:22,23:24,15-octakis(dicarboximide) (128096-82-2)

Conditions

Yield

With ammonium molybdate; urea In nitrobenzene mixing hexacarboxylic acid trianhydride, FeCl2, urea, and ammoniummolybdate, adding mixt. to nitrobenzene, heating (2 h, 200°C), adding further urea, heating (2 h); washing (3x, HCl, boiling H2O, MeOH), adding product to concd. H2SO4, shaking (5 h, room temp.), filtering, adding filtrate to ice, standing (several h), centrifuging, decanting, collecting pptn., washing (H2O, EtOH), drying (vac., P2O5); elem. anal.;

37.1%

benzene-1,2:3,4:5,6-hexacarboxylic trianhyride (4253-24-1) → tribenzoyl-benzene-1,3,5-tricarboxylic acid

Conditions	Yield
With aluminium trichloride; benzene

benzene-1,2:3,4:5,6-hexacarboxylic trianhyride (4253-24-1) → pentacarbon dioxide (51799-36-1) + Hepta-1,2,3,4,5,6-hexaene-1,7-dione (63615-05-4)

Conditions	Yield
at 900 - 1000℃; Irradiation;

methanol (67-56-1) + benzene-1,2:3,4:5,6-hexacarboxylic trianhyride (4253-24-1) → mellitic acid tetramethyl ester

Conditions	Yield
at 100℃; im Rohr;

benzene-1,2:3,4:5,6-hexacarboxylic trianhyride (4253-24-1) → fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0)

Conditions	Yield
In diphenylether org. compd. suspn. refluxing for 24 h under Ar, cooling;
In neat (no solvent) org. compd. heating in evac. quartz tube;

Upstream product

• 517-60-2 benzenehexacarboxylic acid 
• 108-24-7 acetic anhydride 

Relevant articles and documents

Towards the total synthesis of cyclo[n] carbons and the generation of cyclo[6]carbon

We describe efforts towards the synthesis of some allotropes of carbon, the cyclo[n]carbons where n = 18, 24 and 30. The key intermediate 11 is hexa-1,3,5-triyne with the central triple bond masked as a 1-amino-1,2,3-triazole derivative. Cyclo-oligomerisation of this by oxidative coupling gives macrocyclic precursors of C18, C24 and C30. C30 is a proposed intermediate in the formation of C60 and we also describe some attempts at the synthesis of C60 via the chemical generation of benzotriyne, cyclo[6]carbon.