31996-10-8

Basic information

• Product Name: Tetramethyl 1,4,5,8-naphthalenetetracarboxylate
• Synonyms: TETRAMETHYL 1,4,5,8-NAPHTHALENETETRACARBOXYLATE;1,4,5,8-Naphthalenetetracarboxylic acid tetramethyl ester;tetramethyl naphthalene-1,4,5,8-tetracarboxylate
• CAS NO: 31996-10-8
• Molecular Formula: C18H16O8
• Molecular Weight: 360.31
• Mol File: 31996-10-8.mol

Chemical Properties

• Melting Point: 200-203 °C
• Boiling Point: 508.9 °C at 760 mmHg
• Flash Point: 224.5 °C
• Appearance: /
• Density: 1.309
• Vapor Pressure: 1.78E-10mmHg at 25°C
• Refractive Index: 1.577
• CAS DataBase Reference: Tetramethyl 1,4,5,8-naphthalenetetracarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Tetramethyl 1,4,5,8-naphthalenetetracarboxylate(31996-10-8)
• EPA Substance Registry System: Tetramethyl 1,4,5,8-naphthalenetetracarboxylate(31996-10-8)

Safety Data

• Hazardous Substances Data: 31996-10-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Tetramethyl 1,4,5,8-naphthalenetetracarboxylate is used as a precursor in the synthesis of various organic materials for its versatile reactivity and structural properties.
Used in Dye and Pigment Production:
It is used as a key intermediate in the production of dyes and pigments, contributing to the color and stability of these compounds.
Used in Pharmaceutical Industry:
Tetramethyl 1,4,5,8-naphthalenetetracarboxylate is used as a reagent in pharmaceutical chemistry, aiding in the development of new drugs due to its unique chemical characteristics.
Used as a Flame Retardant:
Due to its high thermal stability, Tetramethyl 1,4,5,8-naphthalenetetracarboxylate is used as a flame retardant in certain applications, enhancing the safety of materials.
Used in Organic Electronics and Photovoltaics:
It is utilized in the field of organic electronics and photovoltaics as an electron-accepting material, contributing to the efficiency and performance of devices due to its good film-forming ability.

InChI:InChI=1/C18H16O8/c1-23-15(19)9-5-6-11(17(21)25-3)14-12(18(22)26-4)8-7-10(13(9)14)16(20)24-2/h5-8H,1-4H3

Upstream product

• 128-97-2 naphthalene-1,4,5,8-tetracarboxylic acid 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 37686-24-1 naphthalene-1,4,5,8-tetracarbonyl tetrachloride 
• 81-30-1 1,4,5,8-naphthalenetetracarboxylic dianhydride 

Downstream Products

• 80293-92-1 tetraethyl 1,3,6,8-tetrahydropyrene-2,2,7,7-tetracarboxylate 

Relevant articles and documents

Molecular design using electrostatic interactions. Part 4: Synthesis and properties of flexible tetrapodand tetracations derived from naphthalene. Role of structured water in the electrostatic binding of polyanion guests: A model for interactions in biological systems

The 1,4,5,8-tetracations 5 and 11 have been prepared from 1,4,5,8-tetrakis(bromomethyl)naphthalene and 1,4,5,8-tetrakis(bromomethyl)-2,3,6,7-tetramethylnaphthalene, respectively by treatment with DABCO in acetonitrile. Their interactions with the benzene-1,2,4,5-tetracarboxylate and naphthalene-1,4,5,8-tetracarboxylate tetraanions in water were investigated by 1H NMR titration and both tetracations were found to have greater binding affinity to the benzene tetracarboxylate. Both also gave precipitates with ferricyanide but only the naphthalene tetracation 5 gave a precipitate with ferrocyanide. The X-ray structure of the crystalline ferricyanide tetracation 14 from tetramethylnaphthalene showed the methylDABCO cationic arms to be alternately above and below the naphthalene ring, which was itself distorted from the plane. The bound water in the non-charge-matched complex 14 appears to have a more intimate role in the crystal structure than does the bound water in the charge-matched ferricyanide 15 derived from 2,4,6-tris(DABCO-N-methyl)mesitylene tribromide which we reported previously. An analogy with interactions in biological receptors is made.

EPR Studies on Carboxylic Esters. Part 15. Spin Density Distribution in the Radical Anions of Naphthalenecarboxylic Esters

Persistent radical anions of naphthalene mono-, di-, and tetracarboxylic esters are generated by in situ electroreduction.The spin density distribution is determined from the proton hfs coupling constants as measured by EPR spectroscopy and is discussed in terms of semi-empirical MO calculations.

A New Synthesis of 1,4,5,8-Tetramethylnaphthalene

A convenient four-step preparation of 1,4,5,8-tetramethylnaphthalene from commercially available 1,4,5,8-naphthalenetetracarboxylic acid is presented.

Preparation and Oxidation of the Bis(tetra-n-butylammonium) Salt of 2,2'-(2,7-Pyrenediyl)bis Dianion

2,2'-(2,7-Pyrenediyl)bis (2) is synthesized in 12 steps from 1,4,5,8-naphthalenetetracarboxylic dianhydride in 7percent overall yield.Upon oxidation with a variety of reagents an insoluble purple solid is formed whose infrared spectrum and elemental analysis imply it not to be 11,11,12,12-tetracyanopyreno-2,7-quinodimethane (TCNP) and whose insolubility suggests it to be polymeric.Upon oxidation at a platinum or vitreous carbon electrode the bis(tetra-n-butylammonium) salt (15) of the conjugate base of 2 (in 0.1 M tetra-n-butylammonium perchlorate inacetonitrile) undergoes a reversible one-electron oxidation pa1 = 0.075 V relative to Ag/AgCl(s)> and an irreversible second oxidation (Epa2 = 0.340 V).At low temperatures (-20 deg C, 0.9 mM) the product of the first oxidation, the radical anion of TCNP, dimerizes.