(E)-4-Hydroxytoremifene

Base Information

• Chemical Name: (E)-4-Hydroxytoremifene
• CAS No.: 177748-22-0
• Molecular Formula: C₂₆H₂₈ClNO₂
• Molecular Weight: 421.967
• DSSTox Substance ID: DTXSID00443271
• Wikidata: Q82261011
• Mol file: 177748-22-0.mol

Synonyms:177748-22-0;(E)-4-Hydroxytoremifene;(E)-4-Hydroxy Toremifene;4-[(E)-4-chloro-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol;(E)-4-Hydroxy Toremifene (~5per cent Z-isomer);(E)-4-Hydroxy Toremifene (~5% Z-isomer);SCHEMBL906309;DTXSID00443271

Chemical Property of (E)-4-Hydroxytoremifene

Chemical Property:

• PSA: 32.70000
• LogP: 5.92060
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 421.1808568
• Heavy Atom Count: 30
• Complexity: 513

Purity/Quality:

95%+ or 98%+ ^*data from raw suppliers

(E)-4-HydroxyToremifene(~5%Z-isomer) ^*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(CCCl)C2=CC=CC=C2)C3=CC=C(C=C3)O
• Isomeric SMILES: CN(C)CCOC1=CC=C(C=C1)/C(=C(\CCCl)/C2=CC=CC=C2)/C3=CC=C(C=C3)O
• Uses: Labelled (E)-4-Hydroxytoremifene. (E)-4-Hydroxytoremifene is the inactive (E)-isomer of 4-Hydroxy Toremifene

Technology Process of (E)-4-Hydroxytoremifene

There total 20 articles about (E)-4-Hydroxytoremifene 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: 75.0%

2,2-Dimethyl-propionic acid 4-{(E)-4-chloro-1-[4-(2-dimethylamino-ethoxy)-phenyl]-2-phenyl-but-1-enyl}-phenyl ester (177748-20-8) → (Z)-4-Hydroxytoremifene (110503-62-3,177748-22-0)

Guidance literature:

With methyllithium; In tetrahydrofuran; diethyl ether; at -78 ℃; for 2h;

DOI:10.1021/jo952279l

Reference yield:

2,2-Dimethyl-propionic acid 4-{(E)-4-chloro-1-[4-(2-dimethylamino-ethoxy)-phenyl]-2-phenyl-but-1-enyl}-phenyl ester (177748-20-8) → 4-hydroxytoremifene (177748-22-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; Heating;

DOI:10.1016/j.bmcl.2005.11.030

Reference yield:

C24H21ClO3 + dimethyl amine (124-40-3) → 4-hydroxytoremifene (177748-22-0)

Guidance literature:

C₂₄H₂₁ClO₃; dimethyl amine; With magnesium sulfate; In tetrahydrofuran; at 20 ℃; for 16h;

With sodium tetrahydroborate; ethanol; at 0 - 20 ℃; for 1h;

upstream raw materials:

3-chloropropiophenone

4-<2-(N,N-dimethylamino)ethoxy>-4'-hydroxybenzophenone

2,2-Dimethyl-propionic acid 4-{(E)-4-chloro-1-[4-(2-dimethylamino-ethoxy)-phenyl]-2-phenyl-but-1-enyl}-phenyl ester

4,4'-Dihydroxybenzophenone