379-55-5

Basic information

• Product Name: BIS-(4-FLUORO-PHENYL)-PHENYL-METHANOL
• Synonyms: BIS-(4-FLUORO-PHENYL)-PHENYL-METHANOL;BenzeneMethanol, 4-fluoro-a-(4-fluorophenyl)-a-phenyl-
• CAS NO: 379-55-5
• Molecular Formula: C₁₉H₁₄F₂O
• Molecular Weight: 296.31
• Mol File: 379-55-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 100 °C
• Boiling Point: 410.605°C at 760 mmHg
• Flash Point: 202.127°C
• Appearance: /
• Density: 1.241g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: 2-8°C
• PKA: 12.60±0.29(Predicted)
• CAS DataBase Reference: BIS-(4-FLUORO-PHENYL)-PHENYL-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: BIS-(4-FLUORO-PHENYL)-PHENYL-METHANOL(379-55-5)
• EPA Substance Registry System: BIS-(4-FLUORO-PHENYL)-PHENYL-METHANOL(379-55-5)

Safety Data

• Hazardous Substances Data: 379-55-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H14F2O/c20-17-10-6-15(7-11-17)19(22,14-4-2-1-3-5-14)16-8-12-18(21)13-9-16/h1-13,22H

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 352-13-6 4-flourophenylmagnesium bromide 
• 345-92-6 4,4'-Difluorobenzophenone 
• 100-58-3 phenylmagnesium bromide 
• 462-06-6 fluorobenzene 
• 98-08-8 α,α,α-trifluorotoluene 

Downstream Products

• 386-95-8 bis-(4-fluoro-phenyl)-phenyl-methane 
• 379-54-4 bis(4-fluorophenyl)phenylchloromethane 
• 52449-13-5 4-fluorophenyl-4-hydroxyphenyl(phenyl)methane 
• 103193-96-0 CDD₃₅₄₃ 
• 289656-82-2 bis(4-fluorophenyl)phenylacetonitrile 
• 289656-45-7 Senicapoc 
• 1391151-86-2 C₂₀H₁₄F₂O₂ 

Relevant articles and documents

Process development and optimization for production of a potassium ion channel blocker, ICA-17043

A scalable process for the manufacture of a potassium ion channel blocker was developed and optimized. Key features of the process include an optimized Grignard reaction, a direct cyanation of the intermediate trityl alcohol derivative, and an improved nitrile hydrolysis protocol, relative to the original acidic hydrolysis conditions, to generate the crude active pharmaceutical ingredient (API) with >95% HPLC purity. The Grignard and the cyanation reactions could be telescoped, resulting in an improved throughput compared to the original four-step process. An effective recrystallization of the API was also developed and the process scaled up to manufacture multiple batches at the pilot scale.

Novel inhibitors of the gardos channel for the treatment of sickle cell disease

Sickle cell disease (SCD) is a hereditary condition characterized by deformation of red blood cells (RBCs). This phenomenon is due to the presence of abnormal hemoglobin that polymerizes upon deoxygenation. This effect is exacerbated when dehydrated RBCs experience a loss of both water and potassium salts. One critical pathway for the regulation of potassium efflux from RBCs is the Gardos channel, a calcium-activated potassium channel. This paper describes the synthesis and biological evaluation of a series of potent inhibitors of the Gardos channel. The goal was to identify compounds that were potent and selective inhibitors of the channel but had improved pharmacokinetic properties compared to 1, Clotrimazole. Several triarylamides such as 10 and 21 were potent inhibitors of the Gardos channel (IC50 of 10 nM) and active in a mouse model of SCD. Compound 21 (ICA-17043) was advanced into phase 3 clinical trials for SCD.

GARDOS CHANNEL ANTAGONISTS

Novel inhibitors of potassium flux are disclosed. The inhibitors show surprising resistance to degradation in biological media and enhanced in vivo half-lives relative to non-fluorine substituted homologues. Methods for the use of these compounds include