(E)-Tamoxifen

Base Information

• Chemical Name: (E)-Tamoxifen
• CAS No.: 13002-65-8
• Molecular Formula: C26H29 N O
• Molecular Weight: 371.522
• Hs Code.: 2922299090
• European Community (EC) Number: 682-560-1
• UNII: 56SY0DIL6N
• DSSTox Substance ID: DTXSID701317495
• Wikidata: Q27261431
• ChEMBL ID: CHEMBL300460
• Mol file: 13002-65-8.mol

Synonyms:(E)-TAMOXIFEN;13002-65-8;Tamoxifen (E);cis-Tamoxifen;Tamoxifen, (E)-;{2-[4-(1,2-diphenylbut-1-en-1-yl)phenoxy]ethyl}dimethylamine;UNII-56SY0DIL6N;2-[4-[(E)-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine;BRN 2062021;56SY0DIL6N;2-[4-[(E)-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethyl-ethanamine;Ethanamine, 2-(4-(1,2-diphenyl-1-butenyl)phenoxy)-N,N-dimethyl-, (E)-;(2-{4-[(1E)-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine;Ethanamine, 2-[4-(1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethyl-;Ethylamine, N,N-dimethyl-2-(p-(1,2-diphenyl-1-butenyl)phenoxy)-, (E)-;7728-73-6;Novadex;(2-[4-(1,2-Diphenylbut-1-en-1-yl)phenoxy]ethyl)dimethylamine;UPCMLD-DP027:001;Nolgen (Salt/Mix);Noltam (Salt/Mix);TMX (Salt/Mix);Apo-Tamox (Salt/Mix);SCHEMBL4085;ICI 46474;(Z)-Tamoxifen (Citrate);trans-Tamoxifen (Citrate);Tamoxifen citrate (Salt/Mix);CHEMBL300460;SCHEMBL1056785;Ethanamine, 2-[4-(1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethyl-,(E)-;Ethylamine, 2-[p-(1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethyl-,(E)-;CHEBI:92766;NKANXQFJJICGDU-OCEACIFDSA-N;DTXSID701317495;TAMOXIFEN (E)-FORM [MI];AKOS015895172;FS-3812;NCGC00161604-01;LS-68100;CS-0368327;EN300-119496;TAMOXIFEN CITRATE IMPURITY A [EP IMPURITY];J-005739;BRD-K43744935-048-01-6;Q27261431;(Z)-2-(p-(1,2-Diphenyl-1-butenyl)-phenoxy)-N,N-dimethylethylamine;(Z)-2-[p-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethanamine;2-(4-(1,2-Diphenylbut-1-en-1-yl)phenoxy)-N,N-dimethylethanamine;cis-N,N-Dimethyl-2-(p-(1,2-diphenyl-1-butenyl)phenoxy)ethylamine;(E)-2-(4-(1,2-diphenylbut-1-en-1-yl)phenoxy)-N,N-dimethylethan-1-amine;cis-1-(p-(2-(N,N-Dimethylamino)ethoxy)phenyl)-1,2-diphenylbut-1-ene;N-(2-(4-[(1E)-1,2-Diphenyl-1-butenyl]phenoxy)ethyl)-N,N-dimethylamine #;ETHANAMINE, 2-(4-((1E)-1,2-DIPHENYL-1-BUTEN-1-YL)PHENOXY)-N,N-DIMETHYL-;ETHANAMINE, 2-(4-((1E)-1,2-DIPHENYL-1-BUTENYL)PHENOXY)-N,N-DIMETHYL-;ETHYLAMINE, 2-(P-(1,2-DIPHENYL-1-BUTENYL)PHENOXY)-N,N-DIMETHYL-, (E)-

Chemical Property of (E)-Tamoxifen

Chemical Property:

• Melting Point: 72-74° from methanol
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 501.18°C (rough estimate)
• PSA: 12.47000
• Density: 1.0630 (rough estimate)
• LogP: 5.99610
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 7.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 8
• Exact Mass: 371.224914549
• Heavy Atom Count: 28
• Complexity: 463

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=C(C1=CC=CC=C1)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3
• Isomeric SMILES: CC/C(=C(/C1=CC=CC=C1)\C2=CC=C(C=C2)OCCN(C)C)/C3=CC=CC=C3
• Uses: (E)-Tamoxifen is an antineoplastic. Antineoplastic.

Technology Process of (E)-Tamoxifen

There total 81 articles about (E)-Tamoxifen 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: 65.0%

(E)-1,2-diphenyl-1-butene boronic acid (918793-63-2) + [2-(4-bromophenoxy)ethyl]dimethylamine (2474-07-9) → 1,2-diphenyl-butan-1-one (16282-16-9) + tamoxifen (10540-29-1,7728-73-6) + (E)-tamoxifen (13002-65-8,7728-73-6)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; water; Heating;

DOI:10.1021/jo061949s

Reference yield: 51.0%

2-(dimethylamino)ethyl chloride (107-99-3) + 1-(4-hydroxyphenyl)-1,2-diphenylbut-1-ene (68684-63-9) → tamoxifen (10540-29-1,7728-73-6) + (E)-tamoxifen (13002-65-8,7728-73-6)

Guidance literature:

In N,N-dimethyl-formamide; at 50 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2003.11.119

Reference yield: 39.0%

4-(4-[2-dimethylaminoethoxy]phenyl)-3,4-diphenylbut-1-ene → tamoxifen (10540-29-1,7728-73-6) + (E)-tamoxifen (13002-65-8,7728-73-6)

Guidance literature:

With potassium tert-butylate; In dimethyl sulfoxide; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2007.09.008

upstream raw materials:

tamoxifen

ICI 77949

(2-chloroethyl)dimethylamine hydrochloride

(1S,2R)-1-[4-(2-Dimethylamino-ethoxy)-phenyl]-1,2-diphenyl-butan-1-ol

Downstream raw materials:

tamoxifen

rel-(1R,2S)-1-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylbutane

{2-[4-((E)-1,2-Diphenyl-but-1-enyl)-phenoxy]-ethyl}-methyl-amine

Refernces

• 1、 Zell, Daniel,Kingston, Cian,Jermaks, Janis,Smith, Sleight R.,Seeger, Natalie,Wassmer, Jana,Sirois, Lauren E.,Han, Chong,Zhang, Haiming,Sigman, Matthew S.,Gosselin, Francis. "Stereoconvergent and -divergent synthesis of tetrasubstituted alkenes by nickel-catalyzed cross-couplings". supporting information. p. 19078 - 19090. Retrieved 2021/11/22.
• 2、 Heijnen, Dorus,Van Zuijlen, Milan,Tosi, Filippo,Feringa, Ben L.. "An atom efficient synthesis of tamoxifen". supporting information. p. 2315 - 2320. Retrieved 2019/03/06.