1847-63-8

Basic information

• Product Name: Nafoxidine
• Synonyms: NSC-70735;U-11100A;Nafoxiden;1-[2-[4-(3,4-dihydro-6-Methoxy-2-phenyl-1-naphthalenyl)phenoxy]ethyl]pyrrolidine Hydrochloride;1-[2-[p-(3,4-dihydro-6-Methoxy-2-phenyl-1-naphthyl)phenoxy]ethyl]pyrrolidine Hydrochloride;11100A;CP-56;U 11100
• CAS NO: 1847-63-8
• Molecular Formula: C₂₉H₃₁NO₂*ClH
• Molecular Weight: 462.02288
• Mol File: 1847-63-8.mol

Chemical Properties

• Melting Point: 165-168℃
• Boiling Point: 574.5°Cat760mmHg
• Flash Point: 176.7°C
• Appearance: white to tan/
• Density: 1.137g/cm³
• Vapor Pressure: 3.33E-13mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: room temp
• Solubility: H2O: ≥8mg/mL
• CAS DataBase Reference: Nafoxidine(CAS DataBase Reference)
• NIST Chemistry Reference: Nafoxidine(1847-63-8)
• EPA Substance Registry System: Nafoxidine(1847-63-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36
• RIDADR: 2811
• WGK Germany: 3
• RTECS: UY0880000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 1847-63-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Nafoxidine is used as an estrogen receptor antagonist for its anti-proliferative properties. It is particularly useful in the treatment of conditions that are influenced by estrogen levels, such as certain types of cancer.
Used in Cancer Treatment:
Nafoxidine is used as an anti-cancer agent, particularly in the treatment of hormone receptor-positive breast cancer. It works by blocking the action of estrogen, which can help to slow down or stop the growth of cancer cells.
Used in Research:
Nafoxidine is also used in scientific research as a tool to study the role of estrogen in various biological processes. Its ability to block estrogen receptors makes it a valuable compound for investigating the effects of estrogen on cell growth and proliferation.
Chemical Properties:
Nafoxidine is an off-white solid, which means it is a solid substance with a pale, off-white color. This property is important for its stability and handling in pharmaceutical formulations and research applications.

InChI:InChI=1/C29H31NO2/c1-31-26-14-16-28-24(21-26)11-15-27(22-7-3-2-4-8-22)29(28)23-9-12-25(13-10-23)32-20-19-30-17-5-6-18-30/h2-4,7-10,12-14,16,21H,5-6,11,15,17-20H2,1H3

Upstream product

• 1081-73-8 1-[2-(4-bromophenoxy)ethyl]pyrrolidine 
• 1769-84-2 6-methoxy-2-phenyl-1-tetralone 
• 123-75-1 pyrrolidine 
• 1449689-98-8 4-[4-(2-chloro-ethoxy)-phenyl]-7-methoxy-3-phenyl-1,2-dihydro-naphthalene 
• 1078-19-9 6-methoxy-3,4-dihydro-1(2H)-naphthalenone 
• 108-86-1 bromobenzene 
• 1845-11-0 nafoxidine 
• 180915-95-1 1-{2-[4-(2-Bromo-6-methoxy-3,4-dihydronaphthalen-1-yl)phenoxy] ethyl}pyrrolidine 
• 497-19-8 sodium carbonate 
• 98-80-6 phenylboronic acid 

Downstream Products

• 917591-23-2 1-{2-[4-(6-methoxy-2-phenyl-naphthalen-1-yl)-phenoxy]-ethyl}-pyrrolidine hydrochloride 
• 22845-53-0 cis-6-phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-2-methoxy-5,6,7,8-tetrahydronaphthalene hydrochloride 
• 5879-98-1 1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-phenoxy]-ethyl}-pyrrolidine 
• 180915-78-0 (5S,6R)-6-Phenyl-5-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-5,6,7,8-tetrahydro-naphthalen-2-ol 

Relevant articles and documents

Development of concise two-step catalytic approach towards lasofoxifene precursor nafoxidine

We have elaborated a two-step catalytic approach to nafoxidine, a key precursor to lasofoxifene. Firstly, an efficient α-arylation of 6-methoxy-3,4-dihydronaphthalen-1(2H)-one with chlorobenzene was developed, which operates at low 0.1 mol% Pd-132 catalyst loading in the presence of 1.9 equivalents of sodium tert-butoxide at 60 °C in 1,4-dioxane and provides 6-methoxy-2-phenyl-3,4-dihydronaphthalen-1(2H)-one in 90% yield. Secondly, we have demonstrated that 6-methoxy-2-phenyl-3,4-dihydronaphthalen-1(2H)-one can be converted to nafoxidine in 61% yield via CeCl3 promoted reaction with (4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)lithium, which is formed in-situ from the corresponding arylbromide precursor and n-butyllithium. Altogether, the shortest two-step approach to nafoxidine from simple tetralone commodity starting material has been developed with overall 55% yield. The developed synthetic approach to nafoxidine has several beneficial aspects over the one used in the synthetic route primarily developed for the preparation of lasofoxifene.

Total synthesis of lasofoxifene and nafoxidine

An intramolecular reductive coupling process of diketone with low-valent titanium species to form a dihydronapthalene skeleton was an important step in the synthesis of nafoxidine (1) and lasofoxifene (2). Diketone 6 was prepared in a convenient, three-st

A new process for the synthesis of nafoxidene as a key intermediate of lasofoxifene

Abstract A novel brief process for the synthesis of nafoxidene has been developed. The epoxidation of 6-methoxy-1-{4-[2-(pyrrolin-1-yl)ethoxy)]phenyl}-3,4-dihydronaphthalene by m-CPBA directly gave the ketone 6-methoxy-1-[4-(2-(pyrrolidin-1-yl)ethoxy)phenyl]-3,4-dihydronaphthalen-2(1H)-one, which was subject to phenyl magnesium bromide/cerium chloride and subsequently treated with an acid to yield nafoxidene. In addition, the preparation of the starting naphthalene was also optimized by replacing the aromatic lithium at low temperature with its Grignard reagent at refluxing THF. This mild process, without the use of toxic or noble metals, was more cost-efficient and easily worked up.

A PROCESS FOR THE PREPARATION OF LASOFOXIFENE TARTRATE

The present invention relates to solid state chemistry of 1-(2-[4-(6-methoxy-3,4-dihydronaphthalene-1-yl) phenoxy]ethyl)pyrrolidine, a process for its preparation and its use as an intermediate in the synthesis of lasofoxifene.

Pharmaceutical composition and methods comprising combinations of 2-alkylidene-19-nor-vitamin D derivatives and an estrogen agonist/antagonist

The present invention relates to pharmaceutical compositions and methods of treatment comprising administering to a patient in need thereof a combination of a 2-alkylidene-19-nor-vitamin D derivative and an estrogen agonistlantagonist or a pharmaceuticall

Estrogen agonists/antagonists

Compounds of this formula are useful for treating or preventing, obesity, breast cancer, osteoporosis, endometriosis, cardiovascular disease and prostatic disease.