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Cas Database

Name	(E)-TAMOXIFEN	EINECS	N/A
CAS No.	13002-65-8	Density	1.0630 (rough estimate)
PSA	12.47000	LogP	5.99610
Solubility	N/A	Melting Point	72-74° from methanol
Formula	C26H29 N O	Boiling Point	501.18°C (rough estimate)
Molecular Weight	371.522	Flash Point	N/A
Transport Information	N/A	Appearance	N/A
Safety	Experimental reproductive effects. Human systemic effects: nausea or vomiting. When heated to decomposition it emits acrid smoke and irritating vapors.	Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
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	Article Data	31

(E)-TAMOXIFEN Synthetic route

: 69967-79-9
ICI 77949

: 4584-46-7
(2-chloroethyl)dimethylamine hydrochloride

: 13002-65-8
(E)-tamoxifen

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

: 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

Conditions	Yield
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

Conditions	Yield
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;

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

A: 10540-29-1
tamoxifen

B: 13002-65-8
(E)-tamoxifen

Conditions

Conditions	Yield
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

Conditions	Yield
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%

: 10540-29-1
tamoxifen

: 13002-65-8
(E)-tamoxifen

Conditions

Conditions	Yield
With hydrogenchloride In ethanol for 4h; Heating;

(E)-TAMOXIFEN Chemical Properties

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

(E)-TAMOXIFEN Uses

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

(E)-TAMOXIFEN Toxicity Data With Reference

orl-wmn TDLo:4 mg/kg/5D-I:GIT

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

(E)-TAMOXIFEN Safety Profile

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

(E)-TAMOXIFEN 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.

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