76425-88-2

Basic information

• Product Name: trans-3-HYDROXYSTILBENE
• Synonyms: 3-[(E)-2-phenylvinyl]phenol;phenol, 3-[(E)-2-phenylethenyl]-
• CAS NO: 76425-88-2
• Molecular Formula: C₁₄H₁₂O
• Molecular Weight: 196.25
• Product Categories: Stilbenes (substituted)
• Mol File: 76425-88-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 355.8°C at 760 mmHg
• Flash Point: 171.4°C
• Appearance: /
• Density: 1.147g/cm³
• Vapor Pressure: 1.49E-05mmHg at 25°C
• Refractive Index: 1.691
• CAS DataBase Reference: trans-3-HYDROXYSTILBENE(CAS DataBase Reference)
• NIST Chemistry Reference: trans-3-HYDROXYSTILBENE(76425-88-2)
• EPA Substance Registry System: trans-3-HYDROXYSTILBENE(76425-88-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 76425-88-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H12O/c15-14-8-4-7-13(11-14)10-9-12-5-2-1-3-6-12/h1-11,15H/b10-9+

Upstream product

• 626-20-0 3-methoxystyrene 
• 591-50-4 iodobenzene 
• 100-52-7 benzaldehyde 
• 100885-83-4 C₁₄H₁₄O 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 100-83-4 meta-hydroxybenzaldehyde 
• 14064-41-6 1-methoxy-3-styrylbenzene 
• 100-39-0 benzyl bromide 
• 100-42-5 styrene 
• 591-20-8 3-Bromophenol 

Downstream Products

• 33675-75-1 3-hydroxybibenzyl 

Relevant articles and documents

Catalytic Arene meta-C-H Functionalization Exploiting a Quinoline-Based Template

Strong σ-coordination by a heteroatom containing directing group (DG) is one of the effective strategies for performing site-selective C-H functionalization. Despite tremendous progress in directed ortho-C-H functionalization, selective meta-C-H functionalization using strong σ-coordination remains extremely challenging. Herein, we introduce the 8-nitroquinoline-based DG to ensure the formation of a stable palladacycle which enables selective meta-alkenylation and acetoxylation of arenes. Kinetic experiments, ESI-MS, NMR, and DFT studies provided important information regarding the mechanism of the reaction. The scalability as well as diversification of the products have been examined and are expected to be beneficial in pharmaceutical and material sciences.

Convenient Access to meta-Substituted Phenols by Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling and Oxidation

We report a new approach to the synthesis of meta-substituted phenols in which a single palladium catalyst accomplishes a Suzuki–Miyaura cross-coupling between a β-chlorocyclohexenone and an arylboronic acid, and oxidation of the resulting cyclohexenone to the corresponding phenol upon introduction of a terminal oxidant and electron transfer mediator. Notably, this method also allows ready access to ortho, meta-disubstituted phenols, sterically congested biaryl phenols, and more highly substituted phenols.

TRPA1 channels as targets for resveratrol and related stilbenoids

A series of twenty resveratrol analogues was synthesized and tested on TRPA1 and TRPV1 channels. None was able to significantly modulate TRPV1 channels. Conversely, most of them exhibited remarkably higher TRPA1 modulating activity than resveratrol. Optimal potency was observed with ortho monoxygenated stilbenes 6 and 17.