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

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

Used in Photochemical Research:
1,2,3,4-Tetraphenylnaphthalene is used as a primary intermediate for the photochemical transformation of 7,7′-dimethylgerma-1,4,5,6-tetraphenyl-2,3-benzo-norbornadiene (GNB) in hexane solution. Its triplet excited-state plays a crucial role in understanding the underlying mechanisms and reactions involved in this process, contributing to the advancement of photochemical research and the development of new materials and applications.
While the provided materials do not explicitly mention other industries or applications for 1,2,3,4-Tetraphenylnaphthalene, its unique photochemical properties may potentially be utilized in various fields such as materials science, pharmaceuticals, or chemical engineering. Further research and development could reveal additional uses and applications for this compound.

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 
• 28312-69-8 C₄₁H₃₀O 
• 109-99-9 tetrahydrofuran 
• 16797-75-4 di-tert-butylthioketene 

Downstream Products

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

Relevant articles and documents

CIDNP 1H study of the photolysis of 7-sila- and 7-germa-norbornadienes

The photochemical decomposition of 7-sila- and 7-germa-norbornadienes (1a,b) was studied by the CIDNP 1H technique.The reactions proceeds by a two-step mechanism via the reversible formation of singlet biradicals, II.The triplet biradical (II), formed as a result of S-T conversion of (II)(S), irreversibly decomposes giving Me2E (E = Si, Ge).The insertion of Me2E into the C-Br bond of PhCH2Br and the Sn-Cl bond of Me3SnCl occurs via a radical mechanism, as deduced from the CIDNP effects observed in these reactions.

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.

Paramagnetic intermediates in the photolysis of 7-silanorbornadiene studied by means of spin chemistry method

The influence of an external magnetic field on the yield of photo-decomposition products of 7,7′-dimethyl-7-silanorbornadiene derivative has been detected in laser pulse photolysis experiments. The observations of magnetic field effects alterations in the presence of scavengers, O2 and PPh3, in combination with 1H-CIDNP data form the basis for the identification of the structure of paramagnetic intermediates involved in the process. It has been shown that magnetic field effects originate in biradical intermediates. These species result from both endocyclic Si-C bond cleavage in the initial compound and the reaction of dimethylsilylene (in a singlet or a triplet excited state) with starting 7-silanorbornadiene. To explain the influence of O2 upon the magnetic field effects, the reversible formation of oxygen complex with biradical species has been suggested.

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

Iridium-catalyzed reaction of aroyl chlorides with internal alkynes to produce substituted naphthalenes and anthracenes

Benzoyl chlorides efficiently react with 2 equiv of dialkylacetylenes as well as diphenylacetylene in the presence of an iridium catalyst accompanied by decarbonylation to produce 1,2,3,4-tetrasubstituted naphthalenes in good yields. Use of 2-naphthoyl ch

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.

Attempts to observe spin catalysis by paramagnetic particles in the photolysis of 7-silanorbonadiene in solution

Addition of the stable radical, 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl (4-OH-TEMPO), to the reaction mixture in the photolysis of 7-silanorbornadiene in solution results in the decrease of the magnetic field effect detected for the yield of stable

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 Benzo-Fused Cyclic Compounds via Rhodium-Catalyzed Decarboxylative Coupling of Aromatic Carboxylic Acids with Alkynes

The decarboxylative coupling of diversely substituted benzoic acids with internal alkynes proceeds smoothly in the presence of a [RhCl(cod)] 2/1,2,3,4-tetraphenyl-1,3-cyclopentadiene catalyst system to selectively produce highly substituted nap

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.