2432-11-3

Basic information

• Product Name: 2,6-Diphenylphenol
• Synonyms: 1,1':3',1''-Terbenzen-2'-ol;2,6-Diphenylphenol,97%;2,6-Diphenylphenol, 97% 25GR;2,6-Diphenylphenol, 97% 5GR;2,6-Diphenylphenol 98%;2'-HYDROXY-M-TERPHENYL;2,6-DIPHENYLPHENOL;[1,1':3',1''-Terphenyl]-2'-ol
• CAS NO: 2432-11-3
• Molecular Formula: C₁₈H₁₄O
• Molecular Weight: 246.3
• EINECS: 219-401-9
• Product Categories: Organic Building Blocks;Oxygen Compounds;Phenols;Building Blocks;C9 to C20+;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 2432-11-3.mol
• Article Data: 25

Chemical Properties

• Melting Point: 101-103 °C(lit.)
• Boiling Point: 349.31°C (rough estimate)
• Flash Point: 183.2 °C
• Appearance: White to off-white/Crystals or Powder
• Density: 1.0572 (rough estimate)
• Refractive Index: 1.4700 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.02±0.10(Predicted)
• BRN: 2051224
• CAS DataBase Reference: 2,6-Diphenylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Diphenylphenol(2432-11-3)
• EPA Substance Registry System: 2,6-Diphenylphenol(2432-11-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 2432-11-3(Hazardous Substances Data)

Usage

Description

2,6-Diphenylphenol is an organic compound characterized by its white to off-white crystalline or powdery appearance. It is known for its reactivity with various metals, such as (n)BuLi, NaH, KH, Rb, or Cs, in benzene, resulting in the formation of solvent-free complexes [M(OAr)]x. 2,6-Diphenylphenol is widely utilized in the synthesis of specific chemical systems and derivatives, making it a valuable component in the field of chemistry.

Uses

Used in Chemical Synthesis:
2,6-Diphenylphenol is used as a ligand during the synthesis of reduced coordination (less than 6), unchelated manganese oxygen cluster systems. Its role in this process is crucial for the formation of these complex systems, which have potential applications in various industrial and research settings.
Used in Pharmaceutical and Chemical Industries:
In the preparation of derivatives of pyrazine-2,3-dicarbonitrile, 2,6-Diphenylphenol serves as a precursor required for the synthesis of octaazaphthalocyanine (AzaPc) derivatives. These AzaPc derivatives have potential applications in the pharmaceutical industry, particularly in the development of new drugs and therapeutic agents.
Used in Coordination Chemistry:
2,6-Diphenylphenol is utilized as a building block in the creation of various coordination compounds. Its ability to form complexes with different metals contributes to the development of new materials with unique properties and potential applications in areas such as catalysis, sensing, and energy storage.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 2784, 1986 DOI: 10.1021/jo00364a031

Upstream product

• 101-84-8 diphenylether 
• 1623-99-0 phenyl sodium 
• 71-43-2 benzene 
• 10368-54-4 2,6-diphenyl-1,4-benzoquinone diazide 
• 20834-02-0 cis-2,6-diphenylcyclohexanone 
• 507233-69-4 triphenyl bismuth ⁽²⁺⁾; dichloride 
• 90-43-7 2-Phenylphenol 
• 67-63-0 isopropyl alcohol 
• 75-65-0 tert-butyl alcohol 
• 108-95-2 phenol 
• 1746-13-0 allyl phenyl ether 
• 108-86-1 bromobenzene 
• 87-65-0 2,6-Dichlorophenol 
• 780-69-8 triethoxyphenylsilane 

Downstream Products

• 135505-61-2 1,3-Diphenyl-2-(phenylmethoxy)benzene 
• 185543-61-7 6-chloro-4-phenyl-(6H)-dibenz<1,2>oxaphosphorin 
• 20104-41-0 2,6-diphenyl-4-(2,6-diphenylphenoxy)anisole 
• 20104-42-1 2,6-diphenyl-4-(2,6-diphenylphenoxy)phenol 
• 103230-41-7 cis-WCl₄(2,6-diphenylphenoxide) 
• 149856-23-5 (2,6-Ph₂PhO)V(py)3 

Relevant articles and documents

The effect of topologically controlled coulombic interactions on the regioselectivity of the reductive cleavage of alkyl phenyl ethers

The importance of electrostatic effects in the chemical evolution of charged intermediates of the radical anion type is demonstrated. Thus, the regioselectivity of the electron transfer-induced reductive cleavage of alkyl 2,6-diphenylphenyl ethers and alkyl 2,6-dimethoxyphenyl ethers is completely reversed when a positive charge is placed in a controlled manner near the alkyl ether bond.

Through-Space Polar-π Interactions in 2,6-Diarylthiophenols

Molecular recognition between polar groups and aromatic molecules is fundamentally important to rational drug design. Although it has been well established that many polar functionalities interact with electron-rich aromatic residues through energetically favorable polar-π interactions, there is a limited understanding of the association between thiols and aromatic systems. Herein we report physical-organic chemistry studies on 2,6-diarylthiophenols that possess the central thiophenol ring and two flanking aromatic rings with tunable electronic properties caused by substituents at distant para position. Hammett analysis revealed that pKa values and proton affinities correlate well with Hammett sigma values of substituents. Additional energy decomposition analysis supported the conclusion that both through-space SH-π interactions and S?-π interactions contribute to intramolecular stabilization of 2,6-diarylthiophenols.

Palladium-Catalyzed Reductive [5+1] Cycloaddition of 3-Acetoxy-1,4-enynes with CO: Access to Phenols Enabled by Hydrosilanes

A new palladium-catalyzed reductive [5+1] cycloaddition of 3-acetoxy-1,4-enynes with CO, enabled by hydrosilanes, has been developed for delivering valuable functionalized phenols. This methodology employs hydrosilanes as the external reagent to facilitate the [5+1] carbonylative benzannulation. The reaction is a conceptually and mechanistically novel carbonylative cycloaddition route for the construction of substituted phenols, through the formation of four new chemical bonds, with excellent functional-group tolerance.