trans-(E)-1-Bromo-2-[4-[2-(dimethylamino)ethoxy]phenyl]-1,2-diphenylethene

Base Information

• Chemical Name: trans-(E)-1-Bromo-2-[4-[2-(dimethylamino)ethoxy]phenyl]-1,2-diphenylethene
• CAS No.: 19118-19-5
• Molecular Formula: C24H24 Br N O
• Molecular Weight: 422.365
• Hs Code.: 2922299090
• Mol file: 19118-19-5.mol

Synonyms:19118-19-5;TRANS-(E)-1-BROMO-2-[4-[2-(DIMETHYLAMINO)ETHOXY]PHENYL]-1,2-DIPHENYLETHENE;2-[4-[(E)-2-bromo-1,2-diphenylethenyl]phenoxy]-N,N-dimethylethanamine;(E,Z)-1-Bromo-2-[4-[2-(dimethylamino)ethoxy]phenyl]-1,2-diphenylethene;(E)-2-(4-(2-Bromo-1,2-diphenylethenyl)phenoxy)-N,N-dimethylethanamine;Ethanamine, 2-(4-(2-bromo-1,2-diphenylethenyl)phenoxy)-N,N-dimethyl-, (E)-;Ethanamine, 2-[4-[(1E)-2-bromo-1,2-diphenylethenyl]phenoxy]-N,N-dimethyl-;19076-79-0;C24H24BrNO;C24-H24-Br-N-O;1-Bromo-2-[4-[2-(dimethylamino)ethoxy]phenyl]-1,2-diphenylethene

Chemical Property of trans-(E)-1-Bromo-2-[4-[2-(dimethylamino)ethoxy]phenyl]-1,2-diphenylethene

Chemical Property:

• Vapor Pressure: 5.22E-10mmHg at 25°C
• Melting Point: 105-107°C
• Boiling Point: 496.8°Cat760mmHg
• Flash Point: 254.3°C
• PSA: 12.47000
• Density: 1.255g/cm³
• LogP: 5.93850
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 421.10413
• Heavy Atom Count: 27
• Complexity: 455

Purity/Quality:

97% ^*data from raw suppliers

trans-(E)-1-Bromo-2-[4-[2-(dimethylamino)ethoxy]phenyl]-1,2-diphenylethene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCOC1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Br)C3=CC=CC=C3
• Isomeric SMILES: CN(C)CCOC1=CC=C(C=C1)/C(=C(\C2=CC=CC=C2)/Br)/C3=CC=CC=C3
• Uses: An analogue of tamoxifen with anti-estrogenic properties

Technology Process of trans-(E)-1-Bromo-2-[4-[2-(dimethylamino)ethoxy]phenyl]-1,2-diphenylethene

There total 4 articles about trans-(E)-1-Bromo-2-[4-[2-(dimethylamino)ethoxy]phenyl]-1,2-diphenylethene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

E,Z-1-bromo-1,2-diphenyl-2-(4-hydroxyphenyl)ethene (61923-53-3,97151-00-3) + (2-chloroethyl)dimethylamine hydrochloride (4584-46-7) → trans-(E)-1-bromo-2-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene (19118-19-5) + cis-(Z)-1-bromo-2-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene (97151-01-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 60 ℃; for 0.25h; Yield given. Yields of byproduct given;

DOI:10.1021/jm00148a020

Reference yield:

cis-1,2-diphenyl-1-<4-(2-dimethylaminoethoxy)phenyl>ethylene (97151-10-5) → trans-(E)-1-bromo-2-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene (19118-19-5) + cis-(Z)-1-bromo-2-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene (97151-01-4)

Guidance literature:

With bromine; triethylamine; In dichloromethane; at 25 ℃; optical yield given as %de;

DOI:10.1055/s-0029-1217600

Reference yield:

bromobenzene (108-86-1,52753-63-6) → trans-(E)-1-bromo-2-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene (19118-19-5) + cis-(Z)-1-bromo-2-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene (97151-01-4)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(I) bromide; N,N,N,N,-tetramethylethylenediamine; palladium(II) acetylacetonate / 16 h / 140 °C / Inert atmosphere

2: bromine; triethylamine / dichloromethane / Inert atmosphere; Darkness

With palladium(II) acetylacetonate; N,N,N,N,-tetramethylethylenediamine; bromine; triethylamine; copper(I) bromide; In dichloromethane;

DOI:10.1039/c4cc03752a

upstream raw materials:

E,Z-1-bromo-1,2-diphenyl-2-(4-hydroxyphenyl)ethene

(2-chloroethyl)dimethylamine hydrochloride

cis-1,2-diphenyl-1-<4-(2-dimethylaminoethoxy)phenyl>ethylene

bromobenzene

Downstream raw materials:

tamoxifen

E,Z-1-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene

(E)-(+/-)-alpha-Hydroxytamoxifen

(Z)-(+/-)-alpha-Hydroxytamoxifen

Refernces

• 1、 Nunes, Carolina M.,Limberger, Jones,Poersch, Silvia,Seferin, Marcus,Monteiro, Adriano L.. "Trans-stilbene as a starting material for the synthesis of tamoxifen based on palladium-catalyzed cross-coupling reactions". experimental part. p. 2761 - 2765. Retrieved 2010/01/21.