Idoxifene

Base Information

• Chemical Name: Idoxifene
• CAS No.: 116057-75-1
• Molecular Formula: C28H30INO
• Molecular Weight: 523.457
• Hs Code.: 2933990090
• UNII: 456UXE9867
• DSSTox Substance ID: DTXSID5043926
• Nikkaji Number: J1.178.231K,J254.116E,J2.063.573H
• Wikipedia: Idoxifene
• Wikidata: Q5989541
• NCI Thesaurus Code: C1406
• ChEMBL ID: CHEMBL6318
• Mol file: 116057-75-1.mol

Synonyms:1-(4-iodophenyl)-1-(4-(2-pyrrolidinoethoxy)phenyl)-2-phenyl-1-butene;4-iodopyrrolidinotamoxifen;idoxifene;Pyr-I-Tam;pyrrolidino-4-iodotamoxifen

Chemical Property of Idoxifene

Chemical Property:

• Vapor Pressure: 3.72E-13mmHg at 25°C
• Melting Point: 108-109° (McCague et al.)
• Refractive Index: 1.622
• Boiling Point: 573.447 °C at 760 mmHg
• PKA: 9.61±0.20(Predicted)
• Flash Point: 300.61 °C
• PSA: 12.47000
• Density: 1.329 g/cm³
• LogP: 7.07280
• Storage Temp.: 2-8°C
• XLogP3: 8.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 8
• Exact Mass: 523.13721
• Heavy Atom Count: 31
• Complexity: 547

Purity/Quality:

99% ^*data from raw suppliers

Idoxifene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=C(C1=CC=C(C=C1)OCCN2CCCC2)C3=CC=C(C=C3)I)C4=CC=CC=C4
• Isomeric SMILES: CC/C(=C(/C1=CC=C(C=C1)OCCN2CCCC2)\C3=CC=C(C=C3)I)/C4=CC=CC=C4
• Uses: SERM for treatment of urogenital atrophy weak estrogen and antiestrogen in uterus Idoxifene is a non-steroidal estrogen antagonist. It is structurally analogous to tamoxifen (T006000).

Technology Process of Idoxifene

There total 33 articles about Idoxifene 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: 97.0%

pyrrolidine (123-75-1) + (E)-1-<4-(2-chloroethoxy)phenyl>-1-(4-iodophenyl)-2-phenyl-1-butene (116057-73-9) → idoxifene (116057-75-1)

Guidance literature:

In ethanol; at 100 ℃; for 4h; under 1034.3 Torr;

Reference yield: 35.0%

pyrrolidine (123-75-1) + para-diiodobenzene (624-38-4,1032416-46-8) + 1--2-phenyl-butan-1-one (103628-22-4) → idoxifene (116057-75-1)

Guidance literature:

para-diiodobenzene; 1--2-phenyl-butan-1-one; With n-butyllithium; In hexane; toluene; at -67 - -54 ℃; for 0.883333h; Large scale;

With hydrogenchloride; In ethanol; water; at 78 ℃; Large scale;

pyrrolidine; In ethanol; water; at 40 - 83 ℃; for 16h; Large scale;

DOI:10.1021/op0100394

Reference yield: 21.0%

pyrrolidine (123-75-1) + 1-[4-(2-chloroethoxy)phenyl]-1-(4-iodophenyl)methanone (370563-63-6) + 1-phenyl-propan-1-one (93-55-0) → idoxifene (116057-75-1)

Guidance literature:

1-[4-(2-chloroethoxy)phenyl]-1-(4-iodophenyl)methanone; 1-phenyl-propan-1-one; With titanium tetrachloride; 1,2-bis-(diphenylphosphino)ethane; zinc; In 1,4-dioxane; at 20 ℃; for 2.5h; Inert atmosphere; Reflux;

pyrrolidine; In ethanol; for 18h; Reflux; Inert atmosphere;

DOI:10.1021/op0100394

upstream raw materials:

pyrrolidine

(E)-1-<4-(2-chloroethoxy)phenyl>-1-(4-iodophenyl)-2-phenyl-1-butene

2-Phenoxyethanol

1--2-phenyl-butan-1-one

Refernces

• 1、 McCague, Raymond,Potter, Gerard A.,Jarman, Michael. "AN EFFICIENT, LARGE-SCALE SYNTHESIS OF IDOXIFENE PHENYL>-1-(4-IODOPHENYL)-2-PHENYL-1-BUTENE". . p. 343 - 346. Retrieved 2007/10/02.