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10540-29-1

Basic Information
CAS No.: 10540-29-1
Name: Ethanamine,2-[4-[(1Z)-1,2-diphenyl-1-buten-1-yl]phenoxy]-N,N-dimethyl-
Molecular Structure:
Molecular Structure of 10540-29-1 (Ethanamine,2-[4-[(1Z)-1,2-diphenyl-1-buten-1-yl]phenoxy]-N,N-dimethyl-)
Formula: C26H29NO
Molecular Weight: 371.51
Synonyms: Ethanamine,2-[4-(1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethyl-, (Z)-;Ethanamine, 2-[4-[(1Z)-1,2-diphenyl-1-butenyl]phenoxy]-N,N-dimethyl-(9CI);Ethylamine, 2-[p-(1,2-diphenyl-1-butenyl)phenoxy]-N,N-dimethyl-, (Z)-(8CI);(Z)-2-[4-(1,2-Diphenyl-1-butenyl)phenoxy]-N,N-dimethylethanamine;ICI47699;Mammaton;Novaldex;Z-Tamoxifen;trans-Tamoxifen;? Tamoxifen;
EINECS: 234-118-0
Density: 1.042 g/cm3
Melting Point: 97-98 °C(lit.)
Boiling Point: 482.3 °C at 760 mmHg
Flash Point: 140 °C
Solubility: Insoluble in water. Soluble in methanol, ethanol, propanol or propylene glycol.Soluble in dimethyl sulfoxide, dichloromethane and ethanol. Insoluble in water.
Appearance: White crystalline solid
Hazard Symbols: ToxicT, IrritantXi
Risk Codes: 45-60-61-64-36/37/38
Safety: 53-45-36-26
Transport Information:
PSA: 12.47000
LogP: 5.99610
Synthetic route
97818-83-2

(Z)-1-<4-(2-chloroethoxy)phenyl>-1,2-diphenyl-1-butene

124-40-3

dimethyl amine

10540-29-1

tamoxifen

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 65℃; for 12h; Inert atmosphere;99%
In ethanol at 80℃; for 16h;93%
In ethanol at 75℃; for 72h;85 mg
108-01-0

2-(N,N-dimethylamino)ethanol

(Z)-(1-(4-iodophenyl)but-1-ene-1,2-diyl)dibenzene

10540-29-1

tamoxifen

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate at 110℃; for 53h; Inert atmosphere;96%
69967-80-2

1-phenyl-1-(p-hydroxyphenyl)-2-phenylbut-1-ene

4584-46-7

(2-chloroethyl)dimethylamine hydrochloride

10540-29-1

tamoxifen

Conditions
ConditionsYield
With potassium carbonate In ethanol; toluene at 80 - 85℃; for 3h; Inert atmosphere;93%
With sodium ethanolate In ethanol for 24h; Heating;60%
With sodium hydride 1.) DMF, 2.) 50 deg C; Yield given. Multistep reaction;
591-50-4

iodobenzene

1421712-14-2

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

10540-29-1

tamoxifen

Conditions
ConditionsYield
With tri-tert-butyl phosphine; potassium hydroxide; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; water at 60℃; for 24h; Suzuki-Miyaura Coupling; regioselective reaction;93%

(Z)-N-((8-cyano-7-hydroxyquinolin-2-yl)methyl)-2-(4-(1,2-diphenylbut-1-en-1-yl)phenoxy)-N,N-dimethylethan-1-aminium methanesulfonate

A

10540-29-1

tamoxifen

B

C11H7N2O2(1-)

Conditions
ConditionsYield
In ethanol pH=7.2; UV-irradiation;A 91%
B n/a
604010-60-8

(Z)-2-(4-(1,2-diphenylbuta-1,3-dien-1-yl)phenoxy)-N,N-dimethylethanamine

10540-29-1

tamoxifen

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate for 2h; atmospheric pressure;85%
With hydrogen; palladium on activated charcoal

2-(4-(1,2-diphenylbuta-1,3-dien-1-yl)phenoxy)-N,N-dimethylethanamine

10540-29-1

tamoxifen

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In ethyl acetate at 22℃; for 2h;85%
918793-63-2

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

93790-54-6

[2-(4-iodophenoxy)ethyl]dimethylamine

A

16282-16-9

1,2-diphenyl-butan-1-one

B

10540-29-1

tamoxifen

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water for 18h; Suzuki-Miyaura cross-coupling; Heating;A n/a
B 73%
113619-15-1

(Z)-1-iodo-1,2-diphenyl-1-butene

194594-60-0

(4-(2-(dimethylamino)ethoxy)phenyl)boronic acid

10540-29-1

tamoxifen

Conditions
ConditionsYield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water Suzuki-Miyaura cross-coupling; Heating;73%
1148025-82-4

(E)-1-(4-dimethylaminoethoxyphenyl)-1,2-diphenyl-2-(4-tolyl)thioethene

2386-64-3

ethylmagnesium chloride

10540-29-1

tamoxifen

Conditions
ConditionsYield
With Ni(1,2-bis(diphenylphosphino)ethane)Cl2 In diethyl ether for 15h; Inert atmosphere; Reflux;73%
19118-19-5

trans-(E)-1-bromo-2-<4-<2-(dimethylamino)ethoxy>phenyl>-1,2-diphenylethene

811-49-4

ethyllithium

10540-29-1

tamoxifen

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at -78 - 20℃; for 6h;72%
865999-25-3

(E)-1-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-1,2-diphenyl-1-butene

93790-54-6

[2-(4-iodophenoxy)ethyl]dimethylamine

10540-29-1

tamoxifen

Conditions
ConditionsYield
With sodium hydroxide; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; hexane at 60℃; for 48h;70%
With sodium hydroxide; bis(tri-t-butylphosphine)palladium(0) In tetrahydrofuran at 60℃; for 24h;59%
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

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

93790-54-6

[2-(4-iodophenoxy)ethyl]dimethylamine

10540-29-1

tamoxifen

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); sodium hydroxide In tetrahydrofuran at 60℃; for 24h; Schlenk technique; Inert atmosphere; stereoselective reaction;65%
2474-07-9

[2-(4-bromophenoxy)ethyl]dimethylamine

20218-41-1

(E)-but-1-ene-1,2-diyldibenzene

10540-29-1

tamoxifen

Conditions
ConditionsYield
Stage #1: (E)-but-1-ene-1,2-diyldibenzene With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane at 25℃; for 0.166667h; Heck Reaction;
Stage #2: [2-(4-bromophenoxy)ethyl]dimethylamine In 1,2-dimethoxyethane for 5h; Heck Reaction; Reflux;
65%

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

35258-27-6

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

10540-29-1

tamoxifen

Conditions
ConditionsYield
With N,N'-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene hydrochloride; palladium diacetate In tetrahydrofuran at 50℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube; stereoselective reaction;62%
93790-54-6

[2-(4-iodophenoxy)ethyl]dimethylamine

1-trimethylstannyl-1,2-diphenylbutene

10540-29-1

tamoxifen

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; tris-(dibenzylideneacetone)dipalladium(0); copper(l) iodide; triphenyl-arsane; lithium chloride at 45℃; for 48h;52%
13002-65-8

(E)-tamoxifen

10540-29-1

tamoxifen

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane at 0℃; for 3h;51%
With trifluorormethanesulfonic acid In dichloromethane at 0℃; for 3h;51%
With pyridine; bromine In diethyl ether; dichloromethane for 2h; Ambient temperature; Irradiation; Yield given;
107-99-3

2-(dimethylamino)ethyl chloride

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;

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%
124-38-9

carbon dioxide

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

10540-29-1

tamoxifen

Conditions
ConditionsYield
With lithium aluminium tetrahydride 1.) THF, -45 deg C - 60 deg C, 2.) 60 deg C, 10 min; Yield given. Multistep reaction;
69967-79-9

ICI 77949

4584-46-7

(2-chloroethyl)dimethylamine hydrochloride

A

10540-29-1

tamoxifen

B

13002-65-8

(E)-tamoxifen

Conditions
ConditionsYield
With sodium methylate; hydrogen cation Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
748-97-0, 77542-06-4, 77542-07-5, 81992-83-8, 111914-74-0

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

A

10540-29-1

tamoxifen

B

13002-65-8

(E)-tamoxifen

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 0.333333h; Heating; Yield given;
116057-69-3

trans-4-Bromotamoxifen

10540-29-1

tamoxifen

Conditions
ConditionsYield
With water; tert.-butyl lithium 1) THF, -75 deg C; Multistep reaction;
748-97-0

1-(4-(2-(dimethylamino)ethoxy)phenyl)-1,2-diphenylbutan-1-ol

10540-29-1

tamoxifen

Conditions
ConditionsYield
With sulfuric acid at 50℃; for 16h; Yield given;
113619-15-1

(Z)-1-iodo-1,2-diphenyl-1-butene

C10H14BrNOZn

10540-29-1

tamoxifen

Conditions
ConditionsYield
With triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 55℃; for 10h; Yield given;
74-96-4

ethyl bromide

10540-29-1

tamoxifen

Tamoxifen ethyl bromide

Conditions
ConditionsYield
at 20℃; for 5h;99.1%
In acetone Heating;
10540-29-1

tamoxifen

75504-34-6

[14C]-Tamoxifen N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide In methanol; water at 20℃; for 10h; Darkness;97%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 1h;79%
With dihydrogen peroxide In methanol at 50 - 60℃; for 3h;43%
With dihydrogen peroxide In methanol at 20℃; for 48h;
In aq. phosphate buffer at 25℃; pH=7.4; Kinetics; Catalytic behavior; Concentration; Electrochemical reaction;
10540-29-1

tamoxifen

(Z)-N-desmethyltamoxifen hydrochloride

Conditions
ConditionsYield
Stage #1: tamoxifen With carbonochloridic acid 1-chloro-ethyl ester In dichloromethane at 0 - 50℃; for 24h;
Stage #2: With methanol In toluene at 70℃; for 3h;
95%
With carbonochloridic acid 1-chloro-ethyl ester In dichloromethane at 0℃; Inert atmosphere; Reflux;91%
Stage #1: tamoxifen With carbonochloridic acid 1-chloro-ethyl ester In toluene at 0℃; for 0.25h;
Stage #2: In toluene for 19h; Reflux;
50%
With Vinyl chloroformate
10540-29-1

tamoxifen

74-88-4

methyl iodide

107256-99-5

Tamoxifen methiodide

Conditions
ConditionsYield
at 0℃; for 0.166667h;94.9%
In acetone at 50℃; for 48h; Inert atmosphere;87%
109-65-9

1-bromo-butane

10540-29-1

tamoxifen

Tamoxifen butyl bromide

Conditions
ConditionsYield
at 20℃; for 5h;94.8%
In acetone Heating;
10540-29-1

tamoxifen

31750-47-7, 31750-48-8

N-demethyltamoxifen

Conditions
ConditionsYield
With carbonochloridic acid 1-chloro-ethyl ester In 1,2-dichloro-ethane for 27.15h; Reflux;91%
Stage #1: tamoxifen With 2-Chloroethyl chloroformate In 1,2-dichloro-ethane at 0℃; for 24h; Reflux;
Stage #2: In methanol for 3h; Reflux;
91%
With carbonochloridic acid 1-chloro-ethyl ester In 1,2-dichloro-ethane at 0 - 70℃;91%
10540-29-1

tamoxifen

106-94-5

propyl bromide

1245538-92-4

Br(1-)*C29H36NO(1+)

Conditions
ConditionsYield
at 20℃; for 5h;90.1%
10540-29-1

tamoxifen

(8-cyano-7-hydroxyquinolin-2-yl)methyl methanesulfonate

(Z)-N-((8-cyano-7-hydroxyquinolin-2-yl)methyl)-2-(4-(1,2-diphenylbut-1-en-1-yl)phenoxy)-N,N-dimethylethan-1-aminium methanesulfonate

Conditions
ConditionsYield
In acetonitrile for 5h; Reflux;70%
4224-70-8

6-bromohexanoic acid

10540-29-1

tamoxifen

(Z)-6-((2-(4-(1,2-diphenylbut-1-en-1-yl)phenoxy)ethyl)dimethylammonio)hexanoic acid

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 77℃; for 72h;70%
10540-29-1

tamoxifen

2-(chloromethyl)-7-hydroxyquinoline-8-carbonitrile

(Z)-N-((8-cyano-7-hydroxyquinolin-2-yl)methyl)-2-(4-(1,2-diphenylbut-1-en-1-yl)phenoxy)-N,N-dimethylethanaminium chloride

Conditions
ConditionsYield
In acetonitrile for 5h; Reflux;65%
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Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 1 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 66 ,1996,p. 253.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 66 ,1996,p. 253.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) (Benefits outweigh risk for breast cancer patients. 22 Feb, 1997). EPA Genetic Toxicology Program.

Specification

The Novadex is an organic compound with the formula C26H29NO. The IUPAC name of this chemical is 2-[4-[(Z)-1,2-diphenylbut-1-enyl]phenoxy]-N,N-dimethylethanamine. With the CAS registry number 10540-29-1, it is also named as 1-p-b-Dimethylaminoethoxyphenyl-trans-1,2-diphenylbut-1-ene. The product's categories are Active Pharmaceutical Ingredients; Protein Kinase Inhibitors and Activators; Intermediates & Fine Chemicals; Pharmaceuticals; Isotope Labeled Compounds. Besides, it is a white crystalline solid, which should be stored in a closed cool and dry place at temperature of 2 - 8 °C. It acts as an anti-estrogen (inhibiting agent) in the mammary tissue, but as an estrogen (stimulating agent) in cholesterol metabolism. Also, it is a nonsteroidal estrogen antagonist of interest in the treatment of some forms of breast cancer and it is a Protein Kinase C inhibitor, and induces apoptosis in human malignant glioma cell lines.

Physical properties about Novadex are: (1)ACD/LogP: 7.88; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.04; (4)ACD/LogD (pH 7.4): 6.58; (5)ACD/BCF (pH 5.5): 827.41; (6)ACD/BCF (pH 7.4): 28455.67; (7)ACD/KOC (pH 5.5): 664.18; (8)ACD/KOC (pH 7.4): 22842.23; (9)#H bond acceptors: 2; (10)#Freely Rotating Bonds: 8; (11)Polar Surface Area: 12.47 Å2; (12)Index of Refraction: 1.582; (13)Molar Refractivity: 118.89 cm3; (14)Molar Volume: 356.2 cm3; (15)Polarizability: 47.13×10-24cm3; (16)Surface Tension: 40.4 dyne/cm; (17)Density: 1.042 g/cm3; (18)Flash Point: 140 °C; (19)Enthalpy of Vaporization: 74.72 kJ/mol; (20)Boiling Point: 482.3 °C at 760 mmHg; (21)Vapour Pressure: 1.85E-09 mmHg at 25°C.

Preparation: this chemical can be prepared by (E,Z)-2-(4-bromophenyl)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-1-phenyl-1-butene hydrochloride. This reaction will need reagent H2, catalyst 5 percent Pd on C and solvent dimethylformamide. The reaction time is 60 min. The yield is about 92%.

When you are using this chemical, please be cautious about it as the following:
It may cause cancer and may impair fertility. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. It may cause harm to the unborn child and breast-fed babies. When you are using it, wear suitable protective clothing. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O(c1ccc(cc1)/C(c2ccccc2)=C(\c3ccccc3)CC)CCN(C)C
(2)InChI: InChI=1/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-
(3)InChIKey: NKANXQFJJICGDU-QPLCGJKRBF
(4)Std. InChI: InChI=1S/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-
(5)Std. InChIKey: NKANXQFJJICGDU-QPLCGJKRSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 575mg/kg (575mg/kg)   Journal of Antibiotics. Vol. 43, Pg. 1533, 1990.
mouse LD50 oral 2150mg/kg (2150mg/kg)   Drugs of the Future. Vol. 9, Pg. 186, 1984.
rat LD50 intraperitoneal 700mg/kg (700mg/kg)   Drugs of the Future. Vol. 9, Pg. 186, 1984.
rat LD50 oral 4100mg/kg (4100mg/kg)   Drugs of the Future. Vol. 9, Pg. 186, 1984.
women TDLo oral 5600ug/kg/1W- (5.6mg/kg) SKIN AND APPENDAGES (SKIN): BREAST: OTHER British Medical Journal. Vol. 291, Pg. 1172, 1985.
women TDLo unreported 200ug/kg/D (0.2mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BLOOD: LEUKOPENIA

BLOOD: THROMBOCYTOPENIA
Cancer Treatment Reports. Vol. 60, Pg. 1431, 1976.
women TDLo unreported 5600ug/kg/2W- (5.6mg/kg) BLOOD: NORMOCYTIC ANEMIA

MUSCULOSKELETAL: JOINTS
British Journal of Rheumatology. Vol. 33, Pg. 583, 1994.