68684-63-9

Basic information

• Product Name: 1-(4-hydroxyphenyl)-1,2-diphenyl-1-butene
• Synonyms: 1-(4-hydroxyphenyl)-1,2-diphenyl-1-butene;TAMOXIFENMETABOLITEE;4-(1,2-Diphenylbut-1-enyl)phenol;ICI 77949
• CAS NO: 68684-63-9
• Molecular Formula: C₂₂H₂₀O
• Molecular Weight: 300.3936
• Mol File: 68684-63-9.mol

Chemical Properties

• Melting Point: 104-105℃
• Boiling Point: 420.6°Cat760mmHg
• Flash Point: 197.2°C
• Appearance: /
• Density: 1.096g/cm³
• Vapor Pressure: 1.13E-07mmHg at 25°C
• Refractive Index: 1.622
• PKA: 9.37±0.15(Predicted)
• CAS DataBase Reference: 1-(4-hydroxyphenyl)-1,2-diphenyl-1-butene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-hydroxyphenyl)-1,2-diphenyl-1-butene(68684-63-9)
• EPA Substance Registry System: 1-(4-hydroxyphenyl)-1,2-diphenyl-1-butene(68684-63-9)

Safety Data

• Hazardous Substances Data: 68684-63-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-hydroxyphenyl)-1,2-diphenyl-1-butene is used as a pharmaceutical compound for its potential therapeutic applications. Its unique structure may allow it to interact with specific biological targets, potentially leading to the development of new drugs or therapies.
Used in Dye Industry:
In the dye industry, 1-(4-hydroxyphenyl)-1,2-diphenyl-1-butene is used as a chemical intermediate for the synthesis of various dyes. Its distinct chemical properties may contribute to the creation of novel dyes with specific color characteristics or improved stability.
Used in Materials Science:
1-(4-hydroxyphenyl)-1,2-diphenyl-1-butene is utilized as a component in the development of advanced materials. Its incorporation into materials may enhance their properties, such as optical, electronic, or mechanical characteristics, for use in various applications, including electronics, sensors, or coatings.

InChI:InChI=1/C22H20O/c1-2-21(17-9-5-3-6-10-17)22(18-11-7-4-8-12-18)19-13-15-20(23)16-14-19/h3-16,23H,2H2,1H3/b22-21+

Upstream product

• 69967-78-8 (1-(4-methoxyphenyl)but-1-ene-1,2-diyl)dibenzene 
• 100-66-3 methoxybenzene 
• 10540-29-1 tamoxifen 
• 451-40-1 phenyl benzyl ketone 
• 540-38-5 p-Iodophenol 
• 5543-98-6 2-(4-hydroxyphenyl)-1,2-diphenyl-ethan-1-one 
• 93-55-0 1-phenyl-propan-1-one 
• 1137-42-4 4-Hydroxybenzophenone 
• 93-54-9 1-Phenyl-1-propanol 
• 650624-48-9 4-(4-methoxyphenyl)-3,4-diphenylbut-1-ene 
• 857085-82-6 1-((Z)-1,2-Diphenyl-buta-1,3-dienyl)-4-methoxy-benzene 

Downstream Products

• 10540-29-1 tamoxifen 
• 749-16-6 3-[4-(1,2-diphenylbut-1-en-1-yl)phenoxy]-N,N-dimethylpropan-1-amine 
• 97818-87-6 Z-1,2-diphenyl-1-<4-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>phenyl>-1-butene 
• 97818-88-7 E-1,2-diphenyl-1-<4-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>phenyl>-1-butene 
• 10540-29-1 tamoxifen 
• 13002-65-8 (E)-tamoxifen 

Relevant articles and documents

Peroxidase-mediated dealkylation of tamoxifen, detected by electrospray ionization-mass spectrometry, and activation to form DNA adducts

Tamoxifen (TAM) is extensively used for the treatment and prevention of breast cancer. Associated with TAM treatment is a two- to eightfold increase in risk of endometrial cancer. To understand the mechanisms associated with this increased risk several pa

Rational design of ERα targeting hypoxia turn-on fluorescent probes with antiproliferative activity for breast cancer

The overexpression of estrogen receptor (ER) α is not only closely related to the development of ER+ breast cancer, but is also an important biomarker for clinical diagnosis and treatment. Herein, we report several ERα targeting hypoxia turn-on fluorescent probes with antitumor activity for breast cancer cells. Among them, probes 3 and 5 displayed good ERα targeting ability and favorable hypoxia turn-on response in MCF-7 cells. Moreover, the probes 3 and 5 exhibited good antiproliferative activity towards MCF-7 cells (IC50 = 8.5 μM, 10.3 μM) and a much lower cytotoxicity to normal cells compared with the positive control. It is expected that these novel fluorescent probes may provide useful tools for the theranostics of ER+ breast cancer.

Design and synthesis of norendoxifen analogues with dual aromatase inhibitory and estrogen receptor modulatory activities

Both selective estrogen receptor modulators and aromatase inhibitors are widely used for the treatment of breast cancer. Compounds with both aromatase inhibitory and estrogen receptor modulatory activities could have special advantages for treatment of br

Efficient synthesis of polysubstituted olefins using stable palladium nanocatalyst: Applications in synthesis of tamoxifen and isocombretastatin A4

A phosphine-free stable palladium nanocatalyst was used for an efficient synthesis of polysubstituted olefins from N-tosylhydrazones and aryl iodides. This methodology was successfully utilized in the synthesis of biologically important tamoxifen and isocombretastatin A4. The nanocatalyst was easily recovered and reused without any apparent loss in size and catalytic activity.

Direct copper-catalyzed α-arylation of benzyl phenyl ketones with aryl iodides: Route towards tamoxifen

No activation needed: The first efficient method for direct α-arylation of non-activated or non-protected family of enolizable ketones with simple aryl iodides employs a catalytic copper system. The method shows potential for the easy and step-economical synthesis of tamoxifen, the most commonly administrated drug for the management of breast cancer. R, R′, R′′ = electron-donating or electron-withdrawing groups. Copyright

An expeditious synthesis of tamoxifen, a representative SERM (selective estrogen receptor modulator), via the three-component coupling reaction among aromatic aldehyde, cinnamyltrimethylsilane, and β-chlorophenetole

Two new synthetic pathways to the anti-cancer agent tamoxifen and its derivatives were developed. The first route involved the aldol reaction of benzyl phenyl ketone with acetaldehyde followed by Friedel-Crafts substitution with anisole in the presence of Cl2Si(OTf)2 to produce 1,1,2-triaryl-3-acetoxybutane, a precursor of the tamoxifen derivatives. The second one utilized the novel three-component coupling reaction among aromatic aldehydes, cinnamyltrimethylsilane, and aromatic nucleophiles using HfCl4 as a Lewis acid catalyst to produce 3,4,4-triarylbutene, that is also a valuable intermediate of the tamoxifen derivatives. The former strategy requires a total of 10 steps from the aldol formation to the final conversion to tamoxifen, whereas the latter needs only three or four steps to produce tamoxifen and droloxifene including the installation of the side-chain moiety and the base-induced double-bond migration to form the tetra-substituted olefin structure. This synthetic strategy seems to serve as a new and practical pathway to prepare not only the tamoxifen derivatives but also the other SERMs (selective estrogen receptor modulators) including estrogen-dependent breast cancer and osteoporosis agents.

Facile synthesis of multisubstituted buta-1,3-dienes via Suzuki-Miyaura and Kumada cross-coupling strategy of 2,4-diiodo-buta-1-enes with arylboronic acids and Grignard reagents

One-pot Suzuki-Miyaura-type and Kumada-type cross-coupling reactions of 2,4-diiodo-buta-l-enes with arylboronic acids and alkyl/aryl magnesium bromides were carried out in the presence of accessibly simple catalysts under mild conditions. As a result, some 1,1,2-trisubstituted buta-1,3-dienes were obtained including the Tamoxifen-type, which have potential adjuvant therapy in women who have suffered from breast cancer and cyclooxygenase-2-type (COX-2-type) inhibitors, some of which have been proved to elicit efficient anti-inflammatory analgesic activities and less adverse gastrointestinal side effects and to be very useful in the prophylactic treatment of a wide variety of cancers and neurodegenerative disorders. The Royal Society of Chemistry 2005.

Short-step synthesis of tamoxifen and its derivatives via the three-component coupling reaction and migration of the double bond

The anti-tumor agent, tamoxifen, is easily synthesized by the successive allylation of benzaldehyde and the Friedel-Crafts alkylation reaction of anisole with the intermediary homoallyl silyl ethers, followed by the migration of the double bond to form the desired tetra-substituted ethylenes. Several derivatives of tamoxifen are also produced according to a similar synthetic strategy.