15810-16-9

Basic information

• Product Name: DIMETHYL 9,10-PHENANTHRENEDICARBOXYLATE
• Synonyms: DIMETHYL 9,10-PHENANTHRENEDICARBOXYLATE
• CAS NO: 15810-16-9
• Molecular Formula: C₁₈H₁₄O₄
• Molecular Weight: 294.3
• Mol File: 15810-16-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 130 °C
• Boiling Point: 438.4±18.0 °C(Predicted)
• Appearance: /
• Density: 1.260±0.06 g/cm3(Predicted)
• CAS DataBase Reference: DIMETHYL 9,10-PHENANTHRENEDICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL 9,10-PHENANTHRENEDICARBOXYLATE(15810-16-9)
• EPA Substance Registry System: DIMETHYL 9,10-PHENANTHRENEDICARBOXYLATE(15810-16-9)

Safety Data

• Hazardous Substances Data: 15810-16-9(Hazardous Substances Data)

Upstream product

• 762-42-5 dimethyl acetylenedicarboxylate 
• 98-80-6 phenylboronic acid 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 85-44-9 phthalic anhydride 
• 16882-08-9 bis(4-(methoxycarbonyl)phenyl)acetylene 
• 13029-09-9 2,2'-dibromobiphenyl 
• 592-41-6 1-hexene 
• 124-38-9 carbon dioxide 
• 71-43-2 benzene 

Relevant articles and documents

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.

Microwave-induced covalent functionalization of few-layer graphene with arynes under solvent-free conditions

A non-conventional modification of exfoliated few-layer graphene (FLG) with different arynes under microwave (MW) irradiation and solvent-free conditions is reported. The described approach allows reaching fast, efficient and mild covalent functionalization of FLG.

Chromium-mediated synthesis of polycyclic aromatic compounds from halobiaryls

(Chemical Equation Presented) Reaction of 2,2′-dihalobiphenyl with butyllithium followed by the addition of chromium(III) chloride and alkynes afforded the corresponding phenanthrene derivatives via formal [4 + 2] cycloaddition. A variety of alkynes could be used for this reaction, such as alkyl, aryl, silyl, and alkoxycarbonyl alkynes. Repetitive process of the reaction gave more extended polycyclic compounds such as benzo[g]chrysene and azacyclopentaphenalene derivatives.