36063-07-7

Basic information

• Product Name: 1,2,3,4-Naphthalenetetracarboxylic acid, tetramethyl ester
• Synonyms: tetramethyl naphtalene-1,2,3,4-tetracarboxylate;Tetramethylnaphthalin-1,2,3,4-tetracarboxylat;1,2,3,4-Tetramethoxycarbonylnaphthalin;1,2,3,4-Naphthalenetetracarboxylic acid,tetramethyl ester
• CAS NO: 36063-07-7
• Molecular Formula: C18H16O8
• Molecular Weight: 360.32
• Mol File: 36063-07-7.mol

Chemical Properties

• Melting Point: 147 °C
• Boiling Point: 428.2±40.0 °C(Predicted)
• Density: 1.309±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 1,2,3,4-Naphthalenetetracarboxylic acid, tetramethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-Naphthalenetetracarboxylic acid, tetramethyl ester(36063-07-7)
• EPA Substance Registry System: 1,2,3,4-Naphthalenetetracarboxylic acid, tetramethyl ester(36063-07-7)

Safety Data

• Hazardous Substances Data: 36063-07-7(Hazardous Substances Data)

Upstream product

• 2789-89-1 1,2-bis(4-bromophenyl)acetylene 
• 873-55-2 sodium benzenesulfonate 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 85-44-9 phthalic anhydride 
• 16882-08-9 bis(4-(methoxycarbonyl)phenyl)acetylene 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 623-08-5 N-methyl-p-toluidine 
• 71-43-2 benzene 
• 591-50-4 iodobenzene 

Relevant articles and documents

Rhodium-catalyzed desulfination of sodium arenesulfinates and oxidative annulation with alkynes

Polycyclic aromatic compounds are widely used in materials science, so it is highly desirable to develop an efficient and practical approach to them. In this paper, a novel, efficient and practical method for the rhodium(III)-catalyzed desulfination of sodium arenesulfinates and oxidative annulation with alkynes has been developed, and the corresponding polycyclic aromatic compounds with multiple substituents were prepared in moderate to good yields. The reactions proceeded through sequential rhodium(III)-catalyzed desulfination, intermolecular addition of aryl-Rh(III) complexes to dialkyl but-2-ynedioates and diarylalkynes, and intramolecular oxidative annulation via C-H activation. The present method is the first example of the oxidative annulation of arene derivatives with two different alkynes. Therefore, it should afford a useful strategy for the synthesis of polycyclic aromatic compounds.

Three-bond breaking of cyclic anhydrides: Easy access to polyfunctionalized naphthalenes and phenanthrenes

Benzannulation of phthalic anhydrides with alkynes to polyfunctionalized naphthalenes and phenanthrenes was confirmed to be straightforward using a palladium catalytic system. Sequential liberation of CO2 and CO occurred via oxidative decomposition of anhydride. In the case of 1,8-naphthalenedicarboxylic anhydrides, both aryls were encompassed in the annulation reaction to afford acenaphthylenes.

Reaction cascades initiated by nucleophilic attack of heteropentalene mesomeric betaine and nitrogen-rich mesoionic tetrazolium-5-amides on electron-deficient unsaturated compounds. Synthesis of novel heterocyclic systems.

The reactions of heteropentalene mesomeric betaine 1 and nitrogen-rich mesoionic tetrazolium-5-amides 4, 11 and 16-18 with electron-deficient unsaturated compounds have been studied. Novel heterocyclic systems, tetrazolo[4,5-a][1,7]benzodiazonine inner sa

Selective palladium-catalyzed cocyclotrimerization of arynes with dimethyl acetylenedicarboxylate: A versatile method for the synthesis of polycyclic aromatic hydrocarbons

Benzyne (1a) and the substituted derivatives 4,5-difluorobenzyne (1b) and 3-methoxybenzyne (2) undergo chemoselective palladium-catalyzed [2 + 2 + 2]-cocyclotrimerization with dimethyl acetylenedicarboxylate (DMAD) to afford the corresponding phenanthrenes s and/or naphthalenes. The major products are phenanthrenes if Pd(PPh3)4 is used as the catalyst, naphthalenes if Pd2(dba)3 is used. When the method is applied to polycyclic arynes 3-6, which are generated from the corresponding o-trimethylsilylaryl triflates, the same reactivity pattern is observed: the reaction can be selectively directed either toward the cocyclization of one molecule of aryne and two molecules of alkyne or to the reaction of two molecules of aryne with one molecule of alkyne, by appropriate choice of the palladium catalyst. The synthesis of polycyclic aromatic compounds 33-39 using this methodology is reported.

PALLADIUM-PROMOTED AROMATIC ANNELATION WITH ACETYLENE DICARBOXYLATES

Benzene rings of N-alkyltoluidine and benzene (or iodobenzene) in acetic acid were annelated with acetylenedicarboxylates by palladium(II) acetate to give N-alkylindole-2,3-dicarboxylate and naphthalene-1,2,3,4-tetracarboxylate.The formation of the products are explained in terms of toluidine radical cation intermediates.