751-38-2

Basic information

• Product Name: 1,2,3,4-TETRAPHENYLNAPHTHALENE
• Synonyms: 1,2,3,4-TETRAPHENYLNAPHTHALENE;1,2,3,4-Tetraphenylnaphtalene;1,2,3,4-Tetraphenylnaphthalene 97%
• CAS NO: 751-38-2
• Molecular Formula: C₃₄H₂₄
• Molecular Weight: 432.55
• Product Categories: Arenes;Building Blocks;Organic Building Blocks
• Mol File: 751-38-2.mol
• Article Data: 71

Chemical Properties

• Melting Point: 199-201 °C(lit.)
• Boiling Point: 486.1 °C at 760 mmHg
• Flash Point: 250.2 °C
• Appearance: /
• Density: 1.124 g/cm³
• Vapor Pressure: 3.96E-09mmHg at 25°C
• Refractive Index: 1.662
• CAS DataBase Reference: 1,2,3,4-TETRAPHENYLNAPHTHALENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,4-TETRAPHENYLNAPHTHALENE(751-38-2)
• EPA Substance Registry System: 1,2,3,4-TETRAPHENYLNAPHTHALENE(751-38-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 751-38-2(Hazardous Substances Data)

Usage

Uses

The triplet excited-state of 1,2,3,4-tetraphenylnaphthalene is a primary intermediate of the photochemical transformation of 7,7′-dimethylgerma-1,4,5,6-tetraphenyl-2,3-benzo-norbornadiene (GNB) in hexane solution.

Purification Methods

Crystallise the naphthalene from MeOH or EtOH. [Fieser & Haddadin Org Synth 46 107 1966, Beilstein 5 IV 2918.]

InChI:InChI=1/C34H24/c1-5-15-25(16-6-1)31-29-23-13-14-24-30(29)32(26-17-7-2-8-18-26)34(28-21-11-4-12-22-28)33(31)27-19-9-3-10-20-27/h1-24H

Upstream product

• 479-33-4 2,3,4,5-tetraphenylcyclopenta-2,4-dienone 
• 118-92-3 anthranilic acid 
• 4151-77-3 dibromo(phenyl)borane 
• 501-65-5 diphenyl acetylene 
• 1614-12-6 1H-1,2,3-benzotriazol-1-amine 
• 615-42-9 1,2-Diiodobenzene 
• 67-56-1 methanol 
• 84213-49-0 11-Cyclopropyl-1,8,9,10,11-pentaphenyl-11-sila-tricyclo[6.2.1.0^2,7]undeca-2,4,6,9-tetraene 
• 119-61-9 benzophenone 
• 120-12-7 anthracene 
• 102649-09-2 11,11'-Dimethyl-1,8,9,10,1',8',9',10'-octaphenyl-[11,11']bi[11-sila-tricyclo[6.2.1.0^2,7]undecyl]-2⁽⁷⁾,3,5,9,2'(7'),3',5',9'-octaene 
• 1059-75-2 2,3,4,5-tetraphenylthiophene 1,1-dioxide 
• 4661-46-5 2-carboxybenzene diazonium chloride 
• 100-39-0 benzyl bromide 

Downstream Products

• 313-63-3 dibenzo[fg,ij]naphtho[1,2,3,4-rst]pentaphene 

Relevant articles and documents

SELF-REACTION OF PENTAMETHYLDISILYL RADICALS: IS DIMETHYLSILYLENE A PRODUCT?

The self-reaction of the pentamethyldisilyl radical was investigated, in solution, at 298 deg K.Products due to the disproportionation and combination of these radicals were detected in a ratio /=0.48.However, there was no evidence for silylene formation.These results suggest that silylenes, which are formed during polysilane photolysis, are not produced from the self-reaction of polysilyl radicals but must be photo-extruded from the polysilane itself.

Iodide [(η5-indenyl)IrI2]n: an effective precursor to (indenyl)iridium sandwich complexes

The reactions of [(η5-indenyl)IrI2]η with CpTl or arenes in the presence of AgBF4 afford [(η5-indenyl)IrCp]+ or [(η5-indenyl)Ir(arene)]2+ cations (arene = benzene, mes

Synthesis of tetrasubstituted naphthalenes by palladium-catalyzed reaction of aryl iodides with internal alkynes

The 1:2 coupling of aryl iodides with acetylene-dicarboxylate esters and diphenylacetylene efficiently proceeds in the presence of a palladium catalyst with use of silver carbonate as base to produce the corresponding tetrasubstituted naphthalenes.

Formation of a Naphthalene Framework by Rhodium(III)-Catalyzed Double C-H Functionalization of Arenes with Alkynes: Impact of a Supporting Ligand and an Acid Additive

An efficient protocol has been developed for the synthesis of larger condensed arenes from aromatic hydrocarbons and internal alkynes. This protocol uses readily available [CpRhI2]nas a catalyst and Cu(OAc)2as an oxidant and proceeds smoothly through undirected double C-H activation. The addition of trifluoroacetic acid has a crucial positive impact on the reaction selectivity and the yields of the target products. In contrast to the previously reported catalytic systems, the new conditions allow the use of both dialkyl- and diarylacetylenes with the same high efficiency.

Synthesis of Overloaded Cyclopentadienyl Rhodium(III) Complexes via Cyclotetramerization of tert-Butylacetylene

Herein we describe the synthesis and reactivity of rhodium catalysts with the very bulky cyclopentadienyl ligand C8H3tBu4 (designated as tBu4Cp). The reaction of [Rh(cod)Cl]2 with tert-butylacetylene in the presence of Et3N gives the complex (tBu4Cp)Rh(cod) (60-65% yield), in which the cyclopentadienyl ligand tBu4Cp is assembled from four alkyne molecules. The oxidation of (tBu4Cp)Rh(cod) with chlorine or bromine gives the corresponding halide complexes (tBu4Cp)RhX2 (X = Cl (85%), Br (95%)), which have unusual 16-electron monomeric structures due to the steric shielding provided by tBu groups. A similar reaction with iodine gives the ionic dinuclear complex [(tBu4Cp)RhI3Rh(tBu4Cp)]I (99%) with halide bridges. The bromide complex (tBu4Cp)RhBr2 reacts with phosphorus ligands such as P(OMe)3, P(OPh)3, PMe2Ph, and PMePh2 to give the 18-electron adducts (tBu4Cp)RhBr2(PR3), but no reaction occurs with larger phosphines such as PPh3. The racemic chloride (tBu4Cp)RhCl2 can be separated into enantiomers by preparative TLC of its diastereomeric adducts with (R)-phenylglycinol. The complex (tBu4Cp)RhBr2 catalyzes C-H activation and annulation of O-pivaloyl-hydroxamate as well as insertion of phenyldiazoacetate into E-H bonds, although the reaction rates and the substrate scope are limited by the bulky tBu4Cp ligand.

Trimethylammonium-containing rhodacarborane [(9-NMe3-7,8-C2B9H10)RhCl2]2 as a catalyst for the annulation of arylcarboxylic acids with alkynes

Rhodacarborane [(9-NMe3-7,8-C2B9H10)RhCl2]2 exhibited moderate catalytic activity in the reaction of annulation of arylcarboxylic acids with alkynes, giving naphthalenes as the major produc