216701-21-2

Basic information

• Product Name: (2-fluoro-[1,1’-biphenyl]-4-yl)methanol
• Synonyms: (2-fluoro-[1,1’-biphenyl]-4-yl)methanol
• CAS NO: 216701-21-2
• Molecular Weight: 202.228
• Mol File: 216701-21-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2-fluoro-[1,1’-biphenyl]-4-yl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2-fluoro-[1,1’-biphenyl]-4-yl)methanol(216701-21-2)
• EPA Substance Registry System: (2-fluoro-[1,1’-biphenyl]-4-yl)methanol(216701-21-2)

Safety Data

• Hazardous Substances Data: 216701-21-2(Hazardous Substances Data)

Usage

Description

(2-fluoro-[1,1’-biphenyl]-4-yl)methanol is a chemical compound with the formula C13H11FO. It is a derivative of biphenyl with a fluorine atom attached to the 2-position and a hydroxyl group at the 4-position of one of the phenyl rings. This unique structure and properties make it a valuable building block in organic synthesis, particularly for the introduction of fluorine into organic molecules.

Uses

Used in Pharmaceutical Industry:
(2-fluoro-[1,1’-biphenyl]-4-yl)methanol is used as a building block in the synthesis of pharmaceutical compounds. Its unique structure allows for the introduction of fluorine into organic molecules, which can improve the pharmacokinetic and pharmacodynamic properties of the resulting drugs.
Used in Agrochemical Industry:
(2-fluoro-[1,1’-biphenyl]-4-yl)methanol is used as a starting material for the synthesis of various agrochemicals. The incorporation of fluorine into these compounds can enhance their stability, selectivity, and effectiveness in agricultural applications.
Used in Materials Science:
(2-fluoro-[1,1’-biphenyl]-4-yl)methanol is used as a precursor in the development of new materials with specific properties. Its unique structure and ability to introduce fluorine into organic molecules can lead to the creation of materials with improved performance characteristics.
Used in Organic Synthesis:
(2-fluoro-[1,1’-biphenyl]-4-yl)methanol is used as a starting material for the synthesis of various fluorinated organic compounds. Its unique structure allows for the introduction of fluorine into organic molecules, which can lead to the development of new compounds with diverse applications in various industries.

Upstream product

• 153556-42-4 4-bromo-3-fluorobenzoic acid 
• 222978-01-0 4-bromo-3-fluorobenzyl alcohol 
• 98-80-6 phenylboronic acid 
• 137045-30-8 2-fluoro-4-biphenylacetic acid 
• 57592-43-5 2-fluoro-1,1'-biphenyl-4-carbaldehyde 
• 352-70-5 m-Fluorotoluene 
• 108-86-1 bromobenzene 
• 69168-29-2 2-fluoro-4-methyl-1,1'-biphenyl 

Downstream Products

• 5001-96-7 2-(2-fluoro-[1,1'-biphenyl]-4-yl)acetic acid 

Relevant articles and documents

Identification and development of biphenyl substituted iminosugars as improved dual glucosylceramide synthase/neutral glucosylceramidase inhibitors

This work details the evaluation of a number of N-alkylated deoxynojirimycin derivatives on their merits as dual glucosylceramide synthase/neutral glucosylceramidase inhibitors. Building on our previous work, we synthesized a series of d-gluco and l-ido-configured iminosugars N-modified with a variety of hydrophobic functional groups. We found that iminosugars featuring N-pentyloxymethylaryl substituents are considerably more potent inhibitors of glucosylceramide synthase than their aliphatic counterparts. In a next optimization round, we explored a series of biphenyl-substituted iminosugars of both configurations (d-gluco and l-ido) with the aim to introduce structural features known to confer metabolic stability to drug-like molecules. From these series, two sets of molecules emerge as lead series for further profiling. Biphenyl-substituted l-ido-configured deoxynojirimycin derivatives are selective for glucosylceramidase and the nonlysosomal glucosylceramidase, and we consider these as leads for the treatment of neuropathological lysosomal storage disorders. Their d-gluco-counterparts are also potent inhibitors of intestinal glycosidases, and because of this characteristic, we regard these as the prime candidates for type 2 diabetes therapeutics.

New flurbiprofen derivatives: Synthesis, membrane affinity and evaluation of in vitro effect on β-amyloid levels

Alzheimer′s disease (AD) is characterized by irreversible and progressive loss of memory and cognition and profound neuronal loss. Current therapeutic strategies for the treatment of AD have been directed to a variety of targets with the aim of reversing or preventing the disease but, unfortunately, the available treatments often produce no significant clinical benefits. During the last decades compounds that inhibit or modulate γ-secretase, reducing β amyloid (Aβ) levels, have been considered as potential therapeutics for AD. Among these the (R)-enantiomer of flurbiprofen (FLU) seems to be very promising, but it shows low brain penetration. In this study, in order to improve the properties of FLU against Alzheimer′s pathogenesis we synthesized some novel FLU lipophilic analogues. Lipophilicity of the new molecules has been characterized in terms of clogP, log KC18/W and log K IAM/W values. Permeability has been determined in both gastrointestinal PAMPA (PAMPA-GI) at different pH values and in brain blood barrier PAMPA (PAMPA-BBB) models. They were also tested for their ability to inhibit in vitro γ-secretase activity using rat CTXTNA2 astrocytes. Interestingly, the investigated molecules demonstrated to reduce Aβ 42 levels without affecting the amyloid precursor protein APP level in a clear concentrations-dependent manner.

The superbase approach to flurbiprofen: An exercise in optionally site-selective metalation

A superior route to the analgesic flurbiprofen has been devised. Key steps are the selective deprotonation of 3-fluorotoluene with tert-butyllithium in the presence of potassium tert-butoxide (LIT-KOR) at the 4-position and the selective deprotonation of the 4-methyl-2-fluorobiphenyl with lithium diisopropylamide in the presence of potassium tert-butoxide (LIDA-KOR) at the benzylic position. Depending on the reagent and the substituent pattern, the 3- and 5-positions of 2-fluorobiphenyls can also be specifically attacked.