186590-23-8

Basic information

• Product Name: 6-Bromo-2,3-difluorophenol
• Synonyms: 6-Bromo-2,3-difluorophenol
• CAS NO: 186590-23-8
• Molecular Formula: C₆H₃BrF₂O
• Molecular Weight: 208.9882264
• EINECS: 604-604-1
• Mol File: 186590-23-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 6-Bromo-2,3-difluorophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromo-2,3-difluorophenol(186590-23-8)
• EPA Substance Registry System: 6-Bromo-2,3-difluorophenol(186590-23-8)

Safety Data

• Hazardous Substances Data: 186590-23-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Bromo-2,3-difluorophenol is used as a reagent for the synthesis of macrocyclic ghrelin receptor antagonists and inverse agonists. These compounds have potential applications in the development of drugs targeting ghrelin receptors, which play a role in regulating appetite and body weight. By modulating the activity of these receptors, macrocyclic ghrelin receptor antagonists and inverse agonists may help in the treatment of obesity and related metabolic disorders.

Upstream product

• 6418-38-8 2,3-difluorophenol 

Downstream Products

• 950852-75-2 (S)-2-(6-bromo-2,3-difluorophenoxy)-1-methylethylamine 
• 1185454-25-4 C₁₄H₁₈BrF₂NO₃ 
• 888318-22-7 1-bromo-3,4-difluoro-2-methoxy-benzene 
• 1376334-92-7 4-(3,4-difluoro-2-methoxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 1376334-86-9 4-(3,4-difluoro-2-methoxy-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 1376334-44-9 8-chloro-3-(cyclopropylmethyl)-7-[4-(3,4-difluoro-2-methoxyphenyl)-1-piperidinyl]-1,2,4-triazolo[4,3-a]pyridine 
• 1376334-98-3 4-(3,4-difluoro-2-methoxy-phenyl)-piperidine 
• 1047664-01-6 C₁₄H₂₁BrF₂O₂Si 

Relevant articles and documents

Discovery and Optimization of DNA Gyrase and Topoisomerase IV Inhibitors with Potent Activity against Fluoroquinolone-Resistant Gram-Positive Bacteria

Herein, we describe the discovery and optimization of a novel series that inhibits bacterial DNA gyrase and topoisomerase IV via binding to, and stabilization of, DNA cleavage complexes. Optimization of this series led to the identification of compound 25

Synthesis of Nonracemic 1,4-Benzoxazines via Ring Opening/Cyclization of Activated Aziridines with 2-Halophenols: Formal Synthesis of Levofloxacin

Novel 3,4-dihydro-1,4-benzoxazine derivatives have been synthesized by an efficient and simple method in excellent enantio- and diastereospecificity (ee > 99%, de > 99%). The reaction proceeds via Lewis acid-catalyzed SN2-type ring opening of activated aziridines with 2-halophenols followed by Cu(I)-catalyzed intramolecular C-N cyclization in a stepwise fashion under one-pot conditions to furnish the 3,4-dihydro-1,4-benzoxazine derivatives in excellent yields (up to 95%). The strategy offers a short and efficient synthesis to (S)-3-methyl-1,4-benzoxazine (S)-3v, a late stage intermediate in the synthesis of levofloxacin.

Stereoselective Access to 1-[2-Bromo(het)aryloxy]propan-2-amines Using Transaminases and Lipases; Development of a Chemoenzymatic Strategy Toward a Levofloxacin Precursor

Two independent enzymatic strategies have been developed toward the synthesis of enantioenriched 1-[2-bromo(het)aryloxy]propan-2-amines. With that purpose a series of racemic amines and prochiral ketones have been synthesized from commercially available 2-bromophenols or brominated pyridine derivatives bearing different pattern substitutions in the aromatic ring. Biotransamination experiments have been studied using ketones as starting materials, yielding both the (R)- and (S)-amine enantiomers with high selectivity (91-99% ee) depending on the transaminase source. In a complementary approach, the classical kinetic resolutions of the racemic amines have been investigated using Candida antarctica lipase type B as biocatalyst. Ethyl methoxyacetate was found as a suitable acyl donor leading to the corresponding (S)-amines (90-99% ee) and (R)-amides (88-99% ee) with high selectivity in most of the cases. A preparative biotransamination process has been developed for the synthesis of (2S)-1-(6-bromo-2,3-difluorophenoxy)propan-2-amine in 61% isolated yield after 24 h, a valuable precursor of the antimicrobial agent Levofloxacin.

NOVEL TETRAHYDROPYRIDOPYRIMIDINES AND TETRAHYDROPYRIDOPYRIDINES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION

The invention provides novel compounds having the general formula (I): wherein R1, R2, R3, Q, U,W, Z, X and Y are as described herein, compositions including the compounds and methods of using the compounds. These compounds are HbsAg inhibitors and are useful as medicaments for the treatment or prophylaxis of HBV infection.

RADIOLABELLED mGluR2 PET LIGANDS

The present invention relates to novel, selective, radiolabelled mGluR2 ligands which are useful for imaging and quantifying the metabotropic glutamate receptor mGluR2 in tissues, using positron-emission tomography (PET). The invention is also directed to compositions comprising such compounds, to processes for preparing such compounds and compositions, to the use of such compounds and compositions for imaging a tissue, cells or a host, in vitro or in vivo and to precursors of said compounds.

RADIOLABELLED mGLuR2 PET LIGANDS

The present invention relates to novel, selective, radiolabelled mGluR2 ligands which are useful for imaging and quantifying the metabotropic glutamate receptor mGluR2 in tissues, using positron-emission tomography (PET). The invention is also directed to compositions comprising such compounds, to processes for preparing such compounds and compositions, to the use of such compounds and compositions for imaging a tissue, cells or a host, in vitro or in vivo and to precursors of said compounds.

Synthesis, evaluation, and radiolabeling of new potent positive allosteric modulators of the metabotropic glutamate receptor 2 as potential tracers for positron emission tomography imaging

The synthesis and in vitro and in vivo evaluation of a new series of 7-(phenylpiperidinyl)-1,2,4-triazolo[4,3-a]pyridines, which were conveniently radiolabeled with carbon-11, as potential positron emission tomography (PET) radiotracers for in vivo imagin

MACROCYCLIC GHRELIN RECEPTOR MODULATORS AND METHODS OF USING THE SAME

The present invention provides novel conformationally-defined macrocyclic compounds that can function as selective modulators of the ghrelin receptor (growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, gastrointestinal disorders, cardiovascular disorders, obesity and obesity-associated disorders, central nervous system disorders, bone disorders, genetic disorders, hyperproliferative disorders and inflammatory disorders.

Enantiopure 1,4-benzoxazines via 1,2-cyclic sulfamidates. Synthesis of levofloxacin

1,2-Cyclic sulfamidates undergo efficient and regiospecific nucleophilic cleavage with 2-bromophenols (and related anilines and thiophenols), followed by Pd(0)mediated amination to provide an entry to substituted and enantiomerically pure 1,4-benzoxazines (and quinoxalines and 1,4-benzothiazines). This chemistry provides a short and efficient entry to (3S)-3-methyl-1,4-benzoxazine 19, a late stage intermediate in the synthesis of levofloxacin.

CALCILYTIC COMPOUNDS

Novel calcilytic compounds and methods of using them are provided.