1081-73-8

Basic information

• Product Name: N-[2-(4-Bromophenoxy)ethyl]pyrrolidine
• Synonyms: LABOTEST-BB LT00452768;4-[2-PYRROLIDINOETHOXY]PHENYL BROMIDE;4-[2-N,N-PYRROLIDINOETHOXY]PHENYL BROMIDE;1-[2-(4-BROMOPHENOXY)ETHYL]PYRROLIDINE;N-[2-(4-BROMOPHENOXY)ETHYL]PYRROLIDINE;N-(2-(p-bromophenoxy)ethyl)pyrrolidine;1-[2-(p-Bromophenoxy)ethyl]pyrrolidine;(S)-1-Pyrrolidin-2-isopropyl-2-N-allyl-amino-ethanedihydrochlorid
• CAS NO: 1081-73-8
• Molecular Formula: C₁₂H₁₆BrNO
• Molecular Weight: 270.17
• EINECS: 214-100-9
• Product Categories: Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrrolidines;PyrrolidinesHeterocyclic Building Blocks
• Mol File: 1081-73-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 138-140 °C1.2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: colorless or light yellow liquid
• Density: 1.304 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00772mmHg at 25°C
• Refractive Index: n20/D 1.557(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.54±0.20(Predicted)
• CAS DataBase Reference: N-[2-(4-Bromophenoxy)ethyl]pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-[2-(4-Bromophenoxy)ethyl]pyrrolidine(1081-73-8)
• EPA Substance Registry System: N-[2-(4-Bromophenoxy)ethyl]pyrrolidine(1081-73-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 1081-73-8(Hazardous Substances Data)

Usage

Uses

1-[2-(4-Bromophenoxy)ethyl]pyrrolidine was used in the synthesis of 4-OCH2CH2 -pyrrolidine.

InChI:InChI=1/C11H7ClF3N/c1-6-5-9(12)7-3-2-4-8(10(7)16-6)11(13,14)15/h2-5H,1H3

Upstream product

• 34743-88-9 2-(4-bromophenoxy)ethanol 
• 123-75-1 pyrrolidine 
• 55162-34-0 1-bromo-4-(2-chloroethoxy)benzene 
• 106-41-2 4-bromo-phenol 
• 7250-67-1 1-(2-chloroethyl)pyrrolidine hydrochloride 

Downstream Products

• 190791-29-8 Lasofoxifene tartrate 
• 180916-16-9 lasofoxifene 
• 1847-63-8 1-{2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine hydrochloride 
• 180915-94-0 6-methoxy-1-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-3,4-dihydronaphthalene 
• 50609-01-3 4-(2-pyrrolidinoethoxy)aniline 

Relevant articles and documents

N2-substituted alkoxy aromatic cyclo-2-aminopyrimidine derivative and application thereof

The invention provides an N2-substituted alkoxy aromatic cyclo-2-aminopyrimidine derivative and application thereof. The N2-substituted alkoxy aromatic cyclo-2-aminopyrimidine derivative comprises anoptical isomer and pharmaceutically acceptable salt thereof. Preliminary pharmacodynamic indication shows that the compound disclosed by the invention has FLT3 inhibitory activity, wherein the proliferation inhibition activity is realized on various leukemia cell strains; moreover, the derivative is effective for multiple mutations of AML, such as internal tandem repeat mutation of a near-membranestructural domain and D835 point mutation of an activated ring in a kinase structural domain and almost has no inhibition effect on c-KIT. The derivative can overcome drug resistance brought by clinical point mutation, can reduce toxic and side effects of bone marrow inhibition, and can be applied to preparation of antitumor drugs. The general structural formula of the derivative is shown in thespecification.

Development of an efficient and stereoselective manufacturing route to idoxifene

A literature route to 1-(2-{4-[(E)-1-(4-iodophenyl)-2-phenyl-but-1-enyl]phenoxy}ethyl)pyrrolidine (idoxifene) has been modified to tackle various scale-up issues and provide initial supplies. A new highly efficient, robust, and stereoselective manufacturing route is described in detail. This route involves diastereoselective synthesis of tertiary alcohol (1RS,2SR)-1-(4-iodophenyl)-2-phenyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]butan- 1-ol by Grignard addition to the ketone 1-(4-iodophenyl)-2-phenyl-1-butanone followed by derivatisation and stereoselective syn elimination to provide idoxifene in excellent yield and geometric purity. Evaluation of a more direct route to idoxifene using a McMurry low-valent titanium coupling reaction is also described.