177034-57-0

Basic information

• Product Name: 4-Isopropoxyethoxymethylphenol
• Synonyms: 4-[[2-Isopropyloxyethoxy]Methyl]phenol;Bisoprolol EP Impurity M;4-ISOPROPOXYETHOXYMETHYL-1-HYDROXYBENZENE;4-Isopropoxyethoxymethylphenol;PHENOL, 4-[[2-(1-METHYLETHOXY)ETHOXY]METHYL]-;4-Isopropoxyethoxymethyphenol(ForBisoprolol);4-ISOPROPOXYETHOXYMETHYL-1-HYDROXYBENZENE(FOR BISOPROLOL);4-Isopropoxyethoxymethylphenol (Bisoprolol)
• CAS NO: 177034-57-0
• Molecular Formula: C₁₂H₁₈O₃
• Molecular Weight: 210.27
• EINECS: 1308068-626-2
• Product Categories: Intermediates;APIs Intermediate;Aromatics Compounds;Aromatics
• Mol File: 177034-57-0.mol

Chemical Properties

• Boiling Point: 308.742 °C at 760 mmHg
• Flash Point: 140.523 °C
• Appearance: pale yellow oil
• Density: 1.052 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.509
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 9.66±0.15(Predicted)
• CAS DataBase Reference: 4-Isopropoxyethoxymethylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Isopropoxyethoxymethylphenol(177034-57-0)
• EPA Substance Registry System: 4-Isopropoxyethoxymethylphenol(177034-57-0)

Safety Data

• Hazardous Substances Data: 177034-57-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Isopropoxyethoxymethylphenol is used as an intermediate for the synthesis of Bisoprolol, a selective β1-adrenergic receptor blocker used in the treatment of hypertension, angina pectoris, and other cardiovascular conditions. Its role in the synthesis process is crucial for the development of this widely prescribed medication.
As a chemical intermediate, 4-Isopropoxyethoxymethylphenol plays a significant role in the production of various pharmaceutical compounds, contributing to the advancement of medical treatments and therapies. Its chemical properties, such as being a pale yellow oil, make it suitable for use in the synthesis of complex organic molecules.

InChI:InChI=1/C12H18O3/c1-10(2)15-8-7-14-9-11-3-5-12(13)6-4-11/h3-6,10,13H,7-9H2,1-2H3

Upstream product

• 109-59-1 2-(1-methylethoxy)-ethanol 
• 623-05-2 (4-hydroxyphenyl)methanol 

Downstream Products

• 111051-40-2 bisoprolol 
• 208523-18-6 (R)-(+)-bisoprolol hemifumarate 
• 111051-40-2 (+)-Bisoprolol 
• 99103-03-4 (-)-Bisoprolol 
• 208523-18-6 (S)-(-)-bisoprolol hemifumarate 
• 66722-57-4 2-((4-((2-isopropoxyethoxy)methyl)phenoxy)methyl)oxirane 

Relevant articles and documents

Bisoprolol-based 18F-PET tracer: Synthesis and preliminary in vivo validation of β1-blocker selectivity for β1-adrenergic receptors in the heart

The selectivity of a drug toward various isoforms of the target protein family is important in terms of toxicology. Typically, drug or candidate selectivity is assessed by in vitro assays, but in vivo investigations are currently lacking. Positron emission tomography (PET) allows the non-invasive determination of the in vivo distribution of a radiolabeled drug, which can provide in vivo data regarding drug selectivity. Since the discovery of propranolol, a non-selective β-blocker inhibiting both β1- and β2-adrenoreceptors (β-ARs), various selective β1-blockers, including bisoprolol, have been developed to overcome disadvantages associated with β2-AR inhibition. As a proof of concept, we performed an in vivo PET study to understand the selectivity and efficacy of bisoprolol as a selective β-blocker toward β1-AR, as the heart and peripheral smooth muscles demonstrate distinct populations of β1- and β2-ARs. Biodistribution of 18F-labeled bisoprolol (1, [18F]bisoprolol) showed the retention of its uptake in the heart compared with other β-AR-rich organs at late time points post-injection. The competitive blocking assay using unlabeled bisoprolol exhibited no inhibition of [18F]bisoprolol uptake in any organ but exhibited significantly rapid loss of radioactivity between two different time points in β1-AR-rich organs such as the heart and brain. Furthermore, the organ-to-blood ratio revealed the slow excretion and better accumulation of [18F]bisoprolol inside the heart. Collectively, the ex vivo biodistribution and blocking study presented insightful evidence to better comprehend the in vivo distribution pattern of bisoprolol as a selective inhibitor targeting β1-ARs in the heart and provided the possibility of PET as an in vivo technique for evaluating drug selectivity.

NOVEL AROMATIC COMPOUND AND USE THEREOF

Provided is a compound showing a bone formation promoting action (and/or bone resorption suppressive action). A compound of the formula (I) or a pharmacologically acceptable salt: [wherein each substituent is as defined in the DESCRIPTION], has low toxicity, shows good pharmacokinetics, has an action to promote bone formation, and is useful for the prophylaxis or To treatment of metabolic bone diseases (osteoporosis, fibrous osteitis (hyperparathyroidism), osteomalacia, Paget's disease that influences the systemic bone metabolism parameter etc.) associated with a decrease in the bone formation ability as compared to the bone resorption capacity.

A simple and an efficient indium trichloride catalyzed benzyl etherification

An efficient method has been developed for the synthesis of benzyl ethers of alkyl, allyl and propargyl alchols by simple, direct coupling of alcohols in the presence of catalytic amount of L1C13 under solvent-free condition.

A NOVEL PROCESS FOR THE SYNTHESIS OF BISODPROLOL AND ITS INTERMEDIATE

This invention relates to a manufacturing process for the preparation of bisoprolol and its pharmaceutically acceptable salt as well as its intermediates. The intermediate 4-[(2-isopropoxyethoxy)methyl]phenol is prepared by reaction of 4-hydroxybenzyl alcohol with 2-isopropoxy ethanol in presence of Amberlyst 15 in high yield with high purity.

Rare earth metal trifluoromethanesulfonates catalyzed benzyl-etherification.

Rare earth metal trifluoromethanesulfonates [rare earth metal triflate, RE(OTf)3] were found to be efficient catalyst for benzyl-etherification. In the presence of a catalytic amount of RE(OTf)3, condensation of benzyl alcohols and aliphatic alcohols proceeded smoothly to afford the benzyl ethers. The condensation between benzyl alcohols and thiols also proceeded, and thio ethers were obtained in good yield. In these reactions, RE(OTf)3 could be recovered easily after the reactions were completed and could be reused without loss of activity.