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Basic Information
CAS No.: 13002-65-8
Name: 2-[4-[(E)-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethyl-ethanamine
Molecular Structure:
Molecular Structure of 13002-65-8 (2-[4-[(E)-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethyl-ethanamine)
Formula: C26H29 N O
Molecular Weight: 371.522
Synonyms: Ethanamine,2-[4-(1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethyl-, (E)-; Ethanamine, 2-[4-[(1E)-1,2-diphenyl-1-butenyl]phenoxy]-N,N-dimethyl-(9CI); Ethylamine, 2-[p-(1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethyl-, (E)-(8CI); (E)-Tamoxifen; cis-Tamoxifen
Density: 1.0630 (rough estimate)
Melting Point: 72-74° from methanol
Boiling Point: 501.18°C (rough estimate)
Safety: Experimental reproductive effects. Human systemic effects: nausea or vomiting. When heated to decomposition it emits acrid smoke and irritating vapors.
PSA: 12.47000
LogP: 5.99610
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Synthetic route
69967-79-9

ICI 77949

4584-46-7

(2-chloroethyl)dimethylamine hydrochloride

13002-65-8

(E)-tamoxifen

Conditions
ConditionsYield
With potassium carbonate In ethanol; toluene at 80 - 85℃; for 3h; Inert atmosphere;97%
With sodium ethanolate In ethanol for 24h; Heating;62%
With sodium hydride 1.) DMF, 2.) 60 deg C, 30 min; Yield given. Multistep reaction;
93790-54-6

[2-(4-iodophenoxy)ethyl]dimethylamine

624731-39-1

(Z)-2-(1,2-diphenylbut-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

13002-65-8

(E)-tamoxifen

Conditions
ConditionsYield
With sodium hydroxide; bis(tri-t-butylphosphine)palladium(0) In tetrahydrofuran at 60℃; for 24h; Suzuki-Miyaura coupling;95%
With sodium hydroxide; bis(tri-t-butylphosphine)palladium(0) In tetrahydrofuran at 60℃; for 24h; Suzuki-Miyaura coupling;95%
591-50-4

iodobenzene

865999-31-1

(Z)-1-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-1-[4''-(2'''-dimethylaminoethoxy)phenyl]-2-phenyl-1-butene

13002-65-8

(E)-tamoxifen

Conditions
ConditionsYield
With sodium hydroxide; bis(tri-t-butylphosphine)palladium(0) In tetrahydrofuran at 60℃; for 24h;75%

(E)-1,2-diphenylbut-1-en-1-yl dimethylcarbamate

35258-27-6

(4-(2-(dimethylamino)ethoxy)phenyl)magnesium bromide

13002-65-8

(E)-tamoxifen

Conditions
ConditionsYield
With N,N'-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene hydrochloride; palladium diacetate In tetrahydrofuran at 50℃; for 18h; Schlenk technique; Inert atmosphere; Sealed tube; stereoselective reaction;70%
918793-63-2

(E)-1,2-diphenyl-1-butene boronic acid

2474-07-9

[2-(4-bromophenoxy)ethyl]dimethylamine

A

16282-16-9

1,2-diphenyl-butan-1-one

B

10540-29-1

tamoxifen

C

13002-65-8

(E)-tamoxifen

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water Suzuki-Miyaura cross-coupling; Heating;A n/a
B 65%
C n/a
...Expand
873078-93-4

N,N-dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethanamine

(2R,3R)-2-ethyl-2,3-diphenyloxirane

13002-65-8

(E)-tamoxifen

Conditions
ConditionsYield
Stage #1: (2R,3R)-2-ethyl-2,3-diphenyloxirane With N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium In diethyl ether; pentane at -78℃; for 0.25h;
Stage #2: N,N-dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethanamine In diethyl ether at 20 - 38℃;		63%
107-99-3

2-(dimethylamino)ethyl chloride

68684-63-9

(E,Z)-4-(1,2-diphenylbut-1-en-1-yl)phenol

A

10540-29-1

tamoxifen

B

13002-65-8

(E)-tamoxifen

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 50℃; for 0.5h;A 51%
B 44%
With sodium hydride In N,N-dimethyl-formamide at 50℃; for 0.5h;
...Expand

4-(4-[2-dimethylaminoethoxy]phenyl)-3,4-diphenylbut-1-ene

A

10540-29-1

tamoxifen

B

13002-65-8

(E)-tamoxifen

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 1h;A 39%
B 37%
872254-52-9

(1-phenylpropyl)phosphonic acid di-o-tolyl ester

51777-15-2

(4-(2-(dimethylamino)ethoxy)phenyl)(phenyl)methanone

A

10540-29-1

tamoxifen

B

13002-65-8

(E)-tamoxifen

Conditions
ConditionsYield
Stage #1: (1-phenylpropyl)phosphonic acid di-o-tolyl ester With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: (4-(2-(dimethylamino)ethoxy)phenyl)(phenyl)methanone In tetrahydrofuran; hexane at -78℃; for 48h; Horner reaction;		A 28%
B 12%
...Expand
10540-29-1

tamoxifen

13002-65-8

(E)-tamoxifen

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 4h; Heating;
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Chemistry

IUPAC Name:2-[4-[(E)-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine
Molecular Formula:C26H29NO
Molecular Weight:371.51456
Synonyms of (E)-TAMOXIFEN (13002-65-8):2-[4-[(E)-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethyl-ethanamine;CIS-TAMOXIFEN;(E)-1,2-Diphenyl-1-[4-[2-(dimethylamino)ethoxy]phenyl]-1-butene;(E)-α-[4-[2-(Dimethylamino)ethoxy]phenyl]-β-ethylstilbene;2-[4-[(E)-1,2-Diphenyl-1-butenyl]phenoxy]-N,N-dimethylethaneamine;N,N-Dimethyl-2-[4-[(E)-1,2-diphenyl-1-butenyl]phenoxy]ethanamine;N,N-Dimethyl-2-[p-[(E)-1,2-diphenyl-1-butenyl]phenoxy]ethanamine

Uses

(E)-TAMOXIFEN (13002-65-8) now is used in the therapy  for breast cancer.

Toxicity Data With Reference

1.   

orl-wmn TDLo:4 mg/kg/5D-I:GIT

   BJCPAT    British Journal of Clinical Practice. 44 (1990),716.

Safety Profile

Experimental reproductive effects. Human systemic effects: nausea or vomiting. When heated to decomposition it emits acrid smoke and irritating vapors.

Specification

(E)-TAMOXIFEN (13002-65-8) acts as an anti-estrogen  in the mammary tissue, but as an estrogen in cholesterol metabolism, bone density, and cell proliferation in the endometrium.