5189-40-2

Basic information

• Product Name: 4,4'-Cyclohexylidenemethylenediphenol
• Synonyms: 4-[cyclohexylidene(4-hydroxyphenyl)methyl]phenol;4,4'-DIHYDROXY BENZHYDRYLIDENE CYCLOHEXANE;F 6060;Cyclofenildiphenol, 4,4-Cyclohexylidenemethylenediphenol;4,4'-(Cyclohexylidenemethylene)bisphenol;4-[Cyclohexylidene(p-hydroxyphenyl)methyl]phenol;4,4'-Cyclohexylidenemethylenediphenol
• CAS NO: 5189-40-2
• Molecular Formula: C19H20O2
• Molecular Weight: 280.36
• EINECS: 225-972-5
• Mol File: 5189-40-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 235-236 °C(Solv: ethanol (64-17-5); ligroine (8032-32-4))
• Boiling Point: 462.8 °C at 760 mmHg
• Flash Point: 217 °C
• Appearance: White powder,
• Density: 1.18 g/cm³
• Vapor Pressure: 3.46E-09mmHg at 25°C
• Refractive Index: 1.635
• Storage Temp.: 2-8°C
• PKA: 9.83±0.30(Predicted)
• CAS DataBase Reference: 4,4'-Cyclohexylidenemethylenediphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Cyclohexylidenemethylenediphenol(5189-40-2)
• EPA Substance Registry System: 4,4'-Cyclohexylidenemethylenediphenol(5189-40-2)

Safety Data

• Hazardous Substances Data: 5189-40-2(Hazardous Substances Data)

Usage

General Description

4,4'-Cyclohexylidenemethylenediphenol, also known as bisphenol CM, is a chemical compound used as a heat-resistant and transparent material in the manufacturing of electronic components, optical lenses, and protective coatings. It is a member of the bisphenol family and is derived from the reaction of acetone and phenol. Bisphenol CM is known for its high thermal stability and resistance to chemicals, making it a valuable ingredient in the production of durable and long-lasting materials. However, concerns have been raised about its potential health risks, as it is a type of bisphenol that has been linked to endocrine disruption and reproductive issues. As a result, there is a growing interest in finding alternative chemicals with similar properties but without the associated health concerns.

InChI:InChI=1/C19H20O2/c20-17-10-6-15(7-11-17)19(14-4-2-1-3-5-14)16-8-12-18(21)13-9-16/h6-13,20-21H,1-5H2

Upstream product

• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 10218-57-2 1,1'-(cyclohexylidenemethylene)bis(4-methoxy)benzene 
• 2624-43-3 cyclofenil 
• 611-99-4 4,4'-Dihydroxybenzophenone 
• 108-94-1 cyclohexanone 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 17878-44-3 (4-bromophenoxy)trimethylsilane 
• 3289-28-9 ethyl cyclohexanecarboxylate 

Downstream Products

• 1242078-07-4 (4-(2-fluoroethoxy)phenyl)-(4-hydroxyphenyl)methylenecyclohexane 
• 1224593-67-2 C₃₅H₃₉N₃O₂ 
• 1224593-62-7 C₂₃H₂₇BrO₂ 
• 110024-82-3 4-((4-(2-(dimethylamino)ethoxy)phenyl)(cyclohexylidene)methyl)-phenol 
• 1246852-95-8 4-((4-((4-(2-(dimethylamino)ethoxy)phenyl)(cyclohexylidene)methyl)phenoxy)methyl)-6-bromo-7-hydroxycoumarin 
• 1246852-94-7 2-(4-((4-(4,5-dimethoxy-2-nitrobenzyloxy)phenyl)(cyclohexylidene)methyl)phenoxy)-N,N-dimethylethanamine 
• 1220520-44-4 (4-(tert-butyldimethylsilyloxy)phenyl)(4-hydroxyphenyl)methylenecyclohexane 
• 1220520-47-7 ethyl 6-[4-[cyclohexylidene(4-hydroxyphenyl)methyl]phenoxy]hexanoate 
• 918803-14-2 4-((4-(2-aminoethoxy)phenyl)(cyclohexylidene)methyl)phenol 
• 2624-43-3 cyclofenil 

Relevant articles and documents

Optical control of protein activity and gene expression by photoactivation of caged cyclofen

The use of light to control the expression of genes and the activity of proteins is a rapidly expanding field. While many of these approaches use a fusion between a light activatable protein and the protein of interest to control the activity of the latter, it is also possible to control the activity of a protein by uncaging a specific ligand. In that context, controlling the activation of a protein fused to the modified estrogen receptor (ERT) by uncaging its ligand cyclofen-OH has emerged as a generic and versatile method to control the activation of proteins quantitatively, quickly and locally in a live organism. Here, we present the experimental details behind this approach.

Synthesis and evaluation of fluoroethyl cyclofenil analogs: Models for potential estrogen receptor imaging agent

Cyclofenil analogs (2a-2f) and their fluorine-containing derivatives (3a-3f) were synthesized and evaluated as candidate ligands for positron emission tomography (PET) imaging of estrogen receptors. Most of them show relatively high binding affinities comparable with estradiol (E2). (4-Fluoroethoxyphenyl)-(4-hydroxyphenyl) methylenecyclopentane (3a) showed both the highest binding affinity for ERs (88.6 for ERβ, 13.8 for ERα) and highest β/α ratio (β/α for 6.4-fold). The radioactive compound [18F]3a was prepared via displacement of the corresponding mesylate precursor 4 with [18F]fluoride (18F: β+; 96.7%, T1/2 = 109.8 min). The biodistribution studies in immature female SD rats demonstrated that the uptake in the uterus and ovaries were 1.358 ± 0.089% ID/g, 1.439 ± 0.214% ID/g, respectively, both of the ratios of uterus/blood and ovaries/blood was less than 2:1. Micro-PET imaging of immature female SD rats has also been reported.

Practical synthesis of FEt-penta-cyclofenil and its derivatives for potential PET imaging

Generally, FEt-penta-cyclofenil and its derivatives have greater relative binding affinity to estradiol receptors than estradiol. (4-Fluoroethoxyphenyl)- (4'-hydroxyphenyl) methylenecyclopentane and its derivatives were synthesized for potential radioactive image agents, and their structures were characterized by ultraviolet, infrared, 1H NMR, 19F NMR, and high-resolution mass spectrometry. Copyright