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Cas Database

10540-29-1

10540-29-1

Identification

  • Product Name:Tamoxifen

  • CAS Number: 10540-29-1

  • EINECS:234-118-0

  • Molecular Weight:371.522

  • Molecular Formula: C26H29NO

  • HS Code:29221990

  • Mol File:10540-29-1.mol

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;

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Safety information and MSDS view more

  • Pictogram(s):ToxicT, IrritantXi

  • Hazard Codes:T,Xi

  • Signal Word:Danger

  • Hazard Statement:H302 Harmful if swallowedH350 May cause cancer H360 May damage fertility or the unborn child H362 May cause harm to breast-fed children

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price view more

  • Manufacture/Brand
  • Product Description
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  • Manufacture/Brand:Usbiological
  • Product Description:Tamoxifen
  • Packaging:2.5g
  • Price:$ 418
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  • Manufacture/Brand:TRC
  • Product Description:Tamoxifen
  • Packaging:25g
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  • Product Description:Tamoxifen ≥99%(HPLC)
  • Packaging:100
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Tamoxifen analytical standard
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Tamoxifen certified reference material, TraceCERT
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Tamoxifensolution 1?mg/mLinmethanol,certifiedreferencematerial,ampuleof1?mL,Cerilliant?
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Tamoxifen ≥99%
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Relevant articles and documentsAll total 66 Articles be found

Iridium-catalyzed diborylation of benzylic C-H bonds directed by a hydrosilyl group: Synthesis of 1,1-benzyldiboronate esters

Cho, Seung Hwan,Hartwig, John F.

, p. 694 - 698 (2014)

We describe a regioselective diborylation of primary benzylic C-H bonds catalyzed by [Ir(COD)OMe]2 and 4,4′-di-tert-butyl-2,2′- bipyridine (dtbpy). The hydrosilyl group acts as a traceless directing group, providing access to a range of 1,1-benzyldiboronate esters in good yields. Transformations of the 1,1-benzyldiboronate ester products include chemoselective Suzuki-Miyaura cross-couplings and synthesis of tetrasubstituted alkenyl boronate esters.

Opportune gem-Silylborylation of Carbonyl Compounds: A Modular and Stereocontrolled Entry to Tetrasubstituted Olefins

La Cascia, Enrico,Cuenca, Ana B.,Fernández, Elena

, p. 18737 - 18741 (2016)

An easy access to highly versatile gem-silylboronate synthons is achieved by means of a new olefination reagent, HC(Bpin)2(SiMe3). Subsequent silicon or boron-based selective functionalization allows for the modular and stereocontrolled synthesis of all-carbon tetrasubstituted alkenes. A particular attraction of this approach is the iododesilylation reaction, which becomes a pivotal tool for C?Si functionalization.

An atom efficient synthesis of tamoxifen

Heijnen, Dorus,Van Zuijlen, Milan,Tosi, Filippo,Feringa, Ben L.

, p. 2315 - 2320 (2019)

The direct carbolithiation of diphenylacetylenes and their cross-coupling procedure taking advantage of the intermediate alkenyllithium reagents are presented. By employing our recently discovered highly active palladium nanoparticle based catalyst, we were able to couple an alkenyllithium reagent with a high (Z/E) selectivity (10:1) and good yield to give the breast cancer drug tamoxifen in just 2 steps from commercially available starting materials and with excellent atom economy and reaction mass efficiency.

Stereoselective synthesis of trisubstituted alkenylboranes by palladium-catalysed reaction of alkynyltriarylborates with aryl halides

Ishida, Naoki,Miura, Tomoya,Murakami, Masahiro

, p. 4381 - 4383 (2007)

The palladium-catalysed reaction of alkynyltriarylborates with aryl halides afforded trisubstituted alkenylboranes, in which two different aryl groups were installed across the carbon-carbon double bond in a cis arrangement. The Royal Society of Chemistry.

Stereoconvergent and -divergent synthesis of tetrasubstituted alkenes by nickel-catalyzed cross-couplings

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

supporting information, p. 19078 - 19090 (2021/11/22)

We report the development of a method to diastereoselectively access tetrasubstituted alkenes via nickel-catalyzed Suzuki-Miyaura cross-couplings of enol tosylates and boronic acid esters. Either diastereomeric product was selectively accessed from a mixture of enol tosylate starting material diastereomers in a convergent reaction by judicious choice of the ligand and reaction conditions. A similar protocol also enabled a divergent synthesis of each product isomer from diastereomerically pure enol tosylates. Notably, high-throughput optimization of the monophosphine ligands was guided by chemical space analysis of the kraken library to ensure a diverse selection of ligands was examined. Stereoelectronic analysis of the results provided insight into the requirements for reactive and selective ligands in this transformation. The synthetic utility of the optimized catalytic system was then probed in the stereoselective synthesis of various tetrasubstituted alkenes, with yields up to 94% and diastereomeric ratios up to 99:1 Z/E and 93:7 E/Z observed. Moreover, a detailed computational analysis and experimental mechanistic studies provided key insights into the nature of the underlying isomerization process impacting selectivity in the cross-coupling.

NOVEL TRIBORYLALKENE, PRODUCTION METHOD THEREOF, AND PRODUCTION METHOD OF MULTISUBSTITUTED ALKENE

-

Paragraph 0206, (2020/03/10)

PROBLEM TO BE SOLVED: To provide a compound as a synthetic intermediate for a tetraarylalkene useful as medicaments and electronic materials. SOLUTION: The invention provides a triborylalkene represented by the general formula (I) in the figure, where Ra represents an optionally substituted aryl group. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Process route upstream and downstream products

Process route

(E)-1-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)-1,2-diphenyl-1-butene
865999-25-3

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

[2-(4-iodophenoxy)ethyl]dimethylamine
93790-54-6

[2-(4-iodophenoxy)ethyl]dimethylamine

Conditions
Conditions Yield
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%
[2-(4-bromophenoxy)ethyl]dimethylamine
2474-07-9

[2-(4-bromophenoxy)ethyl]dimethylamine

(E)-but-1-ene-1,2-diyldibenzene
20218-41-1

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

Conditions
Conditions Yield
(E)-but-1-ene-1,2-diyldibenzene; With palladium diacetate; sodium carbonate; triphenylphosphine; In 1,2-dimethoxyethane; at 25 ℃; for 0.166667h;
[2-(4-bromophenoxy)ethyl]dimethylamine; In 1,2-dimethoxyethane; for 5h; Reflux;
65%
(Z)-2-(4-(1,2-diphenylbuta-1,3-dien-1-yl)phenoxy)-N,N-dimethylethanamine
604010-60-8

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

Conditions
Conditions Yield
With hydrogen; palladium on activated charcoal; In ethyl acetate; for 2h; atmospheric pressure;
85%
With hydrogen; palladium on activated charcoal;
1-phenyl-1-(p-hydroxyphenyl)-2-phenylbut-1-ene
69967-80-2

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

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

(2-chloroethyl)dimethylamine hydrochloride

Conditions
Conditions Yield
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; Yield given. Multistep reaction; 1.) DMF, 2.) 50 deg C;
iodobenzene
591-50-4

iodobenzene

1-phenyl-1-butyne
622-76-4,83585-27-7

1-phenyl-1-butyne

(4-(2-(dimethylamino)ethoxy)phenyl)boronic acid
194594-60-0

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

2-(biphenyl-4'-yloxy)-N,N-dimethylethylamine
52402-78-5

2-(biphenyl-4'-yloxy)-N,N-dimethylethylamine

Conditions
Conditions Yield
With potassium carbonate; bis(benzonitrile)palladium(II) dichloride; In water; N,N-dimethyl-formamide; at 45 ℃; for 24h;
68%
Conditions
Conditions Yield
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; Yield given; Ambient temperature; Irradiation;
(Z)-(1-bromobut-1-ene-1,2-diyl)dibenzene
96212-86-1

(Z)-(1-bromobut-1-ene-1,2-diyl)dibenzene

(4-(2-(dimethylamino)ethoxy)phenyl)boronic acid
194594-60-0

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

Conditions
Conditions Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; Heating;
67%
(Z)-1-iodo-1,2-diphenyl-1-butene
113619-15-1

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

(4-(2-(dimethylamino)ethoxy)phenyl)boronic acid
194594-60-0

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

Conditions
Conditions Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; Heating;
73%
(Z)-1-<4-(2-chloroethoxy)phenyl>-1,2-diphenyl-1-butene
97818-83-2

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

dimethyl amine
124-40-3

dimethyl amine

Conditions
Conditions Yield
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
(E)-1,2-diphenyl-1-butene boronic acid
918793-63-2

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

[2-(4-iodophenoxy)ethyl]dimethylamine
93790-54-6

[2-(4-iodophenoxy)ethyl]dimethylamine

1,2-diphenyl-butan-1-one
16282-16-9

1,2-diphenyl-butan-1-one

Conditions
Conditions Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 18h; Heating;
73%

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