2474-07-9

Basic information

• Product Name: 2-(4-Bromophenoxy)-N,N-dimethylethylamine
• Synonyms: 2-(4-BROMOPHENOXY)-N,N-DIMETHYLETHYLAMINE;[2-(4-BROMO-PHENOXY)-ETHYL]-DIMETHYL-AMINE;4-(2-DIMETHYLAMINOETHOXY)BROMOBENZENE;4-[2-N,N-DIMETHYLETHOXY]PHENYLBROMIDE;4-[2-N,N-DIMETHYLAMINOETHOXY]BROMOBENZENE;2-(4-Bromophenoxy)-N,N-dimethylethylamine 97%;4-[2-N,N-DIMETHYLAMINOETHOXY]PHENYLBROMIDE;2-(N,N-Dimethylamino)ethyl 4-bromophenyl ether
• CAS NO: 2474-07-9
• Molecular Formula: C₁₀H₁₄BrNO
• Molecular Weight: 244.13
• Product Categories: Amines;Aromatics;Intermediates
• Mol File: 2474-07-9.mol

Chemical Properties

• Boiling Point: 286.7 °C at 760 mmHg
• Flash Point: 127.2 °C
• Appearance: /
• Density: 1.309 g/cm³
• Vapor Pressure: 0.0026mmHg at 25°C
• Refractive Index: 1.537
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in chloroform, dichloromethane.
• PKA: 8.59±0.28(Predicted)
• CAS DataBase Reference: 2-(4-Bromophenoxy)-N,N-dimethylethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Bromophenoxy)-N,N-dimethylethylamine(2474-07-9)
• EPA Substance Registry System: 2-(4-Bromophenoxy)-N,N-dimethylethylamine(2474-07-9)

Safety Data

• Hazard Codes: C
• Statements: 36/37/38-34
• Safety Statements: 26-36/37/39-45-23
• HazardClass: 8
• Hazardous Substances Data: 2474-07-9(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Oil

Uses

An intermediate for the synthesis of Tamoxifen.

InChI:InChI=1/C10H14BrNO/c1-12(2)7-8-13-10-5-3-9(11)4-6-10/h3-6H,7-8H2,1-2H3

Upstream product

• 106-41-2 4-bromo-phenol 
• 107-99-3 2-(dimethylamino)ethyl chloride 
• 591-20-8 3-Bromophenol 
• 4584-46-7 (2-chloroethyl)dimethylamine hydrochloride 

Downstream Products

• 98346-38-4 [2-(4-Bromo-phenoxy)-ethyl]-dimethyl-(4-nitro-benzyl)-ammonium; chloride 
• 98692-89-8 <4-Chlor-benzyl>-<2-(4-brom-phenoxy)-aethyl>-dimethyl-ammoniumchlorid 
• 98692-88-7 [2-(4-Bromo-phenoxy)-ethyl]-(2-chloro-benzyl)-dimethyl-ammonium; chloride 
• 131558-76-4 Dimethyl-[2-(4-phenylethynyl-phenoxy)-ethyl]-amine 
• 13002-65-8 (E)-tamoxifen 
• 97151-11-6 trans-(Z)-1-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethylene 
• 97151-10-5 cis-1,2-diphenyl-1-<4-(2-dimethylaminoethoxy)phenyl>ethylene 
• 131558-78-6 [2-(4-Hex-1-ynyl-phenoxy)-ethyl]-dimethyl-amine 
• 2474-10-4 C₃₀H₄₈Br₂N₂O₂⁽²⁺⁾*2Br^(1-) 
• 194594-60-0 (4-(2-(dimethylamino)ethoxy)phenyl)boronic acid 
• 96474-35-0 2-Methyl-4-hydroxytamoxifen 
• 97135-09-6 (Z)-4-hydroxy-2-methyltamoxifen 
• 119716-81-3 cis-1-<4-<2-(dimethylamino)ethoxy>phenyl>-1-(4-hydroxy-2,3,5-trimethylphenyl)-2-phenyl-(Z)-but-1-ene 
• 119716-80-2 4-hydroxy-2,3,5-trimethyltamoxifen 

Relevant articles and documents

COMPOUNDS HAVING PRESERVATIVE, ANTIMICROBIAL AND ANTISEPTIC ACTIVITY

The present invention relates to domiphen bromide derivatives of formula (I), which are useful as preservatives and antimicrobials and as antiseptics.

An atom efficient synthesis of tamoxifen

The direct carbolithiation of diphenylacetylenes and their cross-coupling procedure taking advantage of the intermediate alkenyllithium reagents are presented. By employing our recently discovered highly active palladium nanoparticle based catalyst, we were able to couple an alkenyllithium reagent with a high (Z/E) selectivity (10:1) and good yield to give the breast cancer drug tamoxifen in just 2 steps from commercially available starting materials and with excellent atom economy and reaction mass efficiency.

HISTONE METHYLTRANSFERASE EZH2 INHIBITOR, PREPARATION METHOD AND PHARMACEUTICAL USE THEREOF

The invention relates to a histone methyltransferase EZH2 inhibitor, a preparation method and pharmaceutical use thereof. In particular, the invention relates to a compound represented by the general formula (I), a preparation method thereof, a pharmaceut

Pd(OAc)2-Catalyzed Desulfinative Cross-Coupling of Sodium Sulfinates with β-Bromostyrenes: Synthesis of Tamoxifen

A Pd(OAc)2-catalyzed desulfinative cross-coupling of (Z)-β-halostyrenes with sodium sulfinates in the presence of PPh3 and Na2CO3 at reflux in good yields is reported. The stereocontrolled cross-coupling process provides a series of sulfonylmethyl (Z)-stilbenes. A synthesis of tamoxifen was studied.

Transition-Metal-Free α-Arylation of Enolizable Aryl Ketones and Mechanistic Evidence for a Radical Process

The α-arylation of enolizable aryl ketones can be carried out with aryl halides under transition-metal-free conditions using KOtBu in DMF. The α-aryl ketones thus obtained can be used for step- and cost-economic syntheses of fused heterocycles and Tamoxifen. Mechanistic studies demonstrate the synergetic role of base and solvent for the initiation of the radical process.

ESTROGEN RECEPTOR IMAGING AGENTS

Compounds useful for molecular imaging of cells expressing estrogen receptors are provided. Also provided are intermediates for making the compounds and methods of making the compounds using a modular convergent strategy. Further, methods of making the intermediates are described, as well as methods of diagnosing disease in a subject by using the compounds as imaging agents.

Continuous flow-processing of organometallic reagents using an advanced peristaltic pumping system and the telescoped flow synthesis of (E/Z)-tamoxifen

A new enabling technology for the pumping of organometallic reagents such as n-butyllithium, Grignard reagents, and DIBAL-H is reported, which utilises a newly developed, chemically resistant, peristaltic pumping system. Several representative examples of its use in common transformations using these reagents, including metal-halogen exchange, addition, addition-elimination, conjugate addition, and partial reduction, are reported along with examples of telescoping of the anionic reaction products. This platform allows for truly continuous pumping of these highly reactive substances (and examples are demonstrated over periods of several hours) to generate multigram quantities of products. This work culminates in an approach to the telescoped synthesis of (E/Z)-tamoxifen using continuous-flow organometallic reagent-mediated transformations.

Glycol methyl ether and glycol amine substituted titanocenes as antitumor agents

6-[4-(2-Methoxyethoxy)phenyl]fulvene (3a) and 6-{4-[2-(dimethylamino) ethoxy]phenyl}fulvene (3b) were prepared as the starting materials for the synthesis of three different classes of titanocenes, which are ansa-titanocenes, diarylmethyl-substituted titanocenes and benzyl-substituted titanocenes. Because the synthetic possibilities seem to be limited, only ansa-titanocene {1,2-bis(cyclopentadienyl)-1,2-bis[4-(2-methoxyethoxy)phenyl]ethanediyl} titanium dichloride (4a) and benzyl-substituted titanocene bis-{[4-(2- methoxyethoxy)benzyl]cyclopentadienyl}titanium(IV) dichloride (6a) were obtained and characterised. The change in the substitution pattern of the phenyl moiety from an oxygen atom to a nitrogen atom had such a big influence on the reaction that not one compound of the three titanocene classes could be synthesised, and it was also not possible to obtain diarylmethyl-substituted titanocenes with the use of either of the fulvenes. When benzyl-substituted titanocene 6a was tested against pig kidney cells (LLC-PK), an antiproliferative effect that results in an IC50 value of 43 μM, was observed. This IC50 value is in the lower range of the cytotoxicities evaluated for titanocenes up to now. ansa-Titanocene 4a surprisingly showed, when tested on the same cell line, a proliferative effect together with a fast rate of hydrolysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Regio- and stereoselective route to tetrasubstituted olefins by the palladium-catalyzed three-component coupling of aryl iodides, internal alkynes, and arylboronic acids

The Pd-catalyzed three-component coupling of readily available aryl iodides, internal alkynes, and arylboronic acids provides a convenient, one-step, regio- and stereoselective route to tetrasubstituted olefins in good to excellent yields, although electron-poor aryl iodides and dialkylalkynes normally afford only low yields under our standard reaction conditions. The proper combination of substrates and reaction conditions is important for high yields. The presence of water generally substantially increases the yields of the desired tetrasubstituted olefins. The reaction involves cis-addition of the aryl group from the aryl iodide to the less hindered or more electron-rich end of the alkyne, while the aryl group from the arylboronic acid adds to the other end. A modified, room-temperature procedure has also been successfully developed, which works very well for some substrates. Tamoxifen and its derivatives are synthesized in a concise, regio- and stereoselective manner by applying our synthetic protocol.