27475-14-5

Basic information

• Product Name: 5-BROMOACETYL-2-BENSYLOXYBENZOIC ACID METHYL ESTER
• Synonyms: 5-BROMOACETYL-2-BENSYLOXYBENZOIC ACID METHYL ESTER;Methyl 2-(benzyloxy)-5-(2-broMoacetyl)benzoate;Methyl-5-(2-broMoacetyl)-2-benzyloxy benzoate
• CAS NO: 27475-14-5
• Molecular Formula: C₁₇H₁₅BrO₄
• Molecular Weight: 363.2
• Mol File: 27475-14-5.mol

Chemical Properties

• Boiling Point: 501.7°C at 760 mmHg
• Flash Point: 257.2°C
• Appearance: /
• Density: 1.414g/cm³
• Vapor Pressure: 3.38E-10mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: 5-BROMOACETYL-2-BENSYLOXYBENZOIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMOACETYL-2-BENSYLOXYBENZOIC ACID METHYL ESTER(27475-14-5)
• EPA Substance Registry System: 5-BROMOACETYL-2-BENSYLOXYBENZOIC ACID METHYL ESTER(27475-14-5)

Safety Data

• Hazardous Substances Data: 27475-14-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-BROMOACETYL-2-BENSYLOXYBENZOIC ACID METHYL ESTER is used as a building block for the synthesis of other organic molecules, leveraging its functional groups to facilitate the formation of complex structures.
Used in Medicinal Chemistry:
5-BROMOACETYL-2-BENSYLOXYBENZOIC ACID METHYL ESTER is used as a precursor for the preparation of pharmaceutical compounds, with its reactivity and synthetic pathways determining its specific applications in the development of new drugs.
Used in Research and Development:
In the research industry, 5-BROMOACETYL-2-BENSYLOXYBENZOIC ACID METHYL ESTER is used as a starting material for exploring novel synthetic pathways and discovering its potential in creating biologically active molecules, which could lead to advancements in various therapeutic areas.

InChI:InChI=1/C17H15BrO4/c1-21-17(20)14-9-13(15(19)10-18)7-8-16(14)22-11-12-5-3-2-4-6-12/h2-9H,10-11H2,1H3

Upstream product

• 27475-09-8 5-acetyl-2-benzyloxybenzoic acid methyl ester 
• 16475-90-4 estere metilico dell'acido 5-acetilsalicilico 
• 100-44-7 benzyl chloride 
• 7789-45-9 copper(II)bromide 
• 100-39-0 benzyl bromide 

Downstream Products

• 74068-80-7 5-(2-{Benzyl-[1-(4-cyclohexyl-phenyl)-ethyl]-amino}-acetyl)-2-benzyloxy-benzoic acid methyl ester 
• 160889-18-9 2-benzyloxy-5-(2-bromo-1(R)-hydroxyethyl)benzoic acid methyl ester 
• 74068-64-7 1-(4-Benzyloxy-3-hydroxymethyl-phenyl)-2-pyrrolidin-1-yl-ethanol 
• 74068-68-1 1-(4-Benzyloxy-3-hydroxymethyl-phenyl)-2-(4-phenyl-piperidin-1-yl)-ethanol 
• 74068-82-9 2-{Benzyl-[2-(4-cyclohexyl-phenyl)-1-methyl-ethyl]-amino}-1-(4-benzyloxy-3-hydroxymethyl-phenyl)-ethanol 
• 74068-77-2 1-(4-Benzyloxy-3-hydroxymethyl-phenyl)-2-[benzyl-(4-phenyl-cyclohexylmethyl)-amino]-ethanol 
• 74083-47-9 2-{Benzyl-[1-(4-cyclohexyl-phenyl)-ethyl]-amino}-1-(4-benzyloxy-3-hydroxymethyl-phenyl)-ethanol 
• 74083-46-8 1-(4-Benzyloxy-3-hydroxymethyl-phenyl)-2-(4-methyl-piperazin-1-yl)-ethanol 

Relevant articles and documents

Conformational control enabled by the fluorine gauche effect in a model of the β2-AR agonist salbutamol (Ventolin)

The bronchodilator salbutamol adopts a characteristic gauche conformation about the ?O-C-C-N torsion angle. This topology is predicated on stabilizing stereoelectronic interactions of the type σ → σC-X*. X-ray crystallographic analysis of salbutamol also indicates that an intramolecular hydrogen bond reinforces this intuitive conformation (?O-C-C-N ≈ 60°). In this study, we demonstrate that single site OH → F substitution in model salbutamol systems preserves the gauche conformational preference by virtue of reinforcing hyperconjugative interactions of the type σC-H → σC-F* and σC-C → σC-N*. Since the amine remains fully protected throughout this conformational analysis, intramolecular hydrogen bonding can be discounted. Conformational mimesis is confirmed by NMR spectroscopy in solution, and also in the solid state.

PROCESS FOR THE PREPARATION OF SALMETEROL AND ITS INTERMEDIATES

The present invention discloses a process for the preparation of methyl 2-(benzyloxy)- 5-(2-bromoacetyl)benzoate (V), comprising: (d) benzylating methyl-5-acetyl-2-hydroxybenzoate (VIII) with benzyl chloride in the presence of a base and a catalyst in a suitable polar solvent to obtain 5-acetyl-2- benzyloxy benzoate (VII); (e) brominating methyl 5-acetyl-2-(benzyloxy)benzoate (VII) with a suitable brominating agent in one or more suitable' solvents in the presence of an acid catalyst to obtain methyl 2-(benzyloxy)-5-(2-bromoacetyl)benzoate V; (c) optionally, purifying the methyl 2-(benzyloxy)-5-(2-bromoacetyl)benzoate (V) in a suitable solvent; and (f) isolating the methyl 2-(benzyloxy)-5-(2-bromoacetyl)benzoate (V).

A multivalent approach to the discovery of long-acting β2- adrenoceptor agonists for the treatment of asthma and COPD

A multivalent approach was applied to the design of long-acting inhaled β2-adrenoceptor agonists. A series of dimeric arylethanolamines based on the short acting β2-adrenoceptor agonist albuterol were prepared, varying the nature and length of the linker between the basic nitrogens. None of the C2-symmetric dimers demonstrated increased potency, however dimer 5j, derived from 4-phenethylamine, was found to have increased binding potency in vitro relative to the parent monomer. Optimization of this structure led to the identification of 22 (milveterol) which demonstrates high potency in vitro and long duration of action in a guinea pig model of bronchoprotection.

PHENYL SUBSTITUTED PYRAZINOYLGUANIDINE SODIUM CHANNEL BLOCKERS POSSESSING BETA AGONIST ACTIVITY

The present invention relates to sodium channel blockers. The present invention also includes a variety of methods of treatment using these inventive sodium channel blockers.

Compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity

The invention is directed to compounds of formula I: wherein R1, R2, R3, R4, R5, R6, R7a, R7b, W, G1, G2, a, b, c, d and m are as defined in the specification, or a pharmaceutically acceptable salt or solvate or stereoisomer thereof. The invention is also directed to pharmaceutical compositions comprising such compounds; methods of using such compounds; and process and intermediates for preparing such compounds.

Biphenyl derivatives

This invention provides biphenyl derivatives of formula I: wherein R1, R2, R3, R4, R5, R6, R7, W, a, b and c are as defined in the specification, or a pharmaceutically acceptable salt or solvate or stereoisomer thereof. The biphenyl derivatives of this invention possess both β2 adrenergic receptor agonist and muscarinic receptor antagonist activity and therefore, such biphenyl derivatives are useful for treating pulmonary disorders, such as chronic obstructive pulmonary disease and asthma.

ALKOXY ARYL β2 ADRENERGIC RECEPTOR AGONISTS

The invention provides novel β2 adrenergic receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated β2 adrenergic receptor activity, and processes and intermediates useful for preparing such compounds.

Tricyclic compounds and drug compositions containing the same

Compounds having a β-3 adrenaline receptor agonist and are useful as drugs for the treatment and prevention of diabetes, obesity, hyperlipemia, etc., represented by a general formula (I) and salts thereof, and a process for producing these, and their intermediates, wherein R represents hydrogen or methyl; R1 represents hydrogen, halogen, hydroxy, benzyloxy, amino, or hydroxymethyl; R2 represents hydrogen, hydroxymethyl, NHR3, SO2 NR4 R4', or nitro; R6 represents hydrogen or lower alkyl; and X represents nitrogen, R9 represents hydrogen, one of R7 and R8 represent hydrogen, and the other thereof represents hydrogen, amino, acetylamino, or hydroxy.

SINTESI E STUDIO FARMACOLOGICO DI DERIVATI DELL'ORCIPRENALINA E DEL SALBUTAMOLO

The effect of replacing the basic aliphatic residue of orciprenaline and salbutamol with: a) a heterocyclic amine; b) a basic residue containing a phenylcyclohexane radical has been studied.The synthesis of the compounds is outlined.They were tested in vitro for relaxation of histamine-induced spasm of tracheal chains and on the isolated Langendorff heart, and in vivo according to the Konzett and Roessler technique and for their action on the cardiovascular system.In all tests the new derivatives were less active than the reference substances; the only exception was (A) where R = 4-phenylpiperidine (M.G.6604), which was almost as active as orciprenaline in the Konzett and Roessler test, had one third of its activity on isolated trachea and showed absolutely no influence on heart rate in vitro or in vivo.Its effect was not inhibited by β-blocking agents; it therefore showed as antihistaminic profile.