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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-
Article Data: 69
Cas Database
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: 371.522
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: N/A
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%
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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.