895-37-4

Basic information

• Product Name: 4,4'-Dimethoxy-α,β-dimethylstilbene
• Synonyms: 1,1'-(1,2-Dimethyl-1,2-ethenediyl)bis(4-methoxybenzene);2,3-Bis(4-methoxyphenyl)-2-butene;4,4'-Dimethoxy-α,β-dimethylstilbene
• CAS NO: 895-37-4
• Molecular Formula: C₁₈H₂₀O₂
• Molecular Weight: 268.35
• Mol File: 895-37-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4,4'-Dimethoxy-α,β-dimethylstilbene(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Dimethoxy-α,β-dimethylstilbene(895-37-4)
• EPA Substance Registry System: 4,4'-Dimethoxy-α,β-dimethylstilbene(895-37-4)

Safety Data

• Hazardous Substances Data: 895-37-4(Hazardous Substances Data)

Upstream product

• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 119-61-9 benzophenone 
• 98-86-2 acetophenone 
• 108-94-1 cyclohexanone 
• 41159-07-3 2-(4-methoxyphenyl)-2-methyl-1,3-dithiolane 
• 6310-14-1 4'-methoxyacetophenone hydrazone 

Relevant articles and documents

SnCl4-Zn: A novel reductive system for deoxygenative coupling of aliphatic, aromatic, chalcone epoxide, and indanone carbonyl compounds to olefins

SnCl4-Zn complex provided a novel reductive system in the deoxygenative cross-coupling of aliphatic, aromatic, chalcone epoxide and indanone carbonyl compounds to olefins in high yield (55-86%) at reflux temperature in THF. The advantage of this reagent is inexpensive, short reaction time, and high yield compared to the reagents used in the McMurry cross-coupling reaction.

Insights into the general and efficient cross McMurry reactions between ketones

The selective cross McMurry couplings of diaryl or aryl ketones with various substituted ketones were achieved in 53-94% isolated yields. It is believed that the strong affinity of the substituents to the low-valent titanium surface plays an important role in regards to moderating selectivity. Through the introduction of such substituents followed by their removal post McMurry coupling, structurally similar ketones can be effectively cross-coupled.

New desulfurdimerization of dithioketals induced by a 2,2'-bipyridine ligated nickel(0) complex

Desulfurdimerization of various aromatic dithioketals is efficiently induced by a 2,2'-bipyridine ligated nickel(0) complex under mild conditions.

Influence of external ligands and auxiliaries on the reactivity of low-valent titanium in McMurry reaction: Selectivity and mechanistic profile

Influence of various external ligands/auxiliaries on the reductive carbonyl coupling reactions mediated by low-valent titanium (LVT) reagents (McMurry coupling) has been explored. The LVT species generated from Tyrlik's TiCl3-Mg-THF system has been selected for the reactivity-tuning trials. Our studies show that incorporation of about 10 equiv of pyridine (a π-acceptor ligand) with respect to TiCl3 to the THF solvated LVT reagent could arrest the reductive dimerization of acetophenone at the intermediate pinacol stage. Modulation of the LVT-species by covalently-binding monohydroxy, 1,2- and 1,3-dihydroxy auxiliaries also resisted deoxygenation completely to give the pinacols in higher yields and better diastereoselectivity, as compared to pyridine-modified LVT system. Amongst these modified reagents, the LVT-catechol (1:1) system was found to be the most efficient combination for total pinacolization of aromatic carbonyl compounds, even under refluxing conditions. The actual titanium reagent responsible for this transformation is proposed to be a Ti(II) complex formed in situ. Further enhancement of stereoselectivity (threo-selectivity) of the pinacols has been achieved by carrying out the reactions with LVT-complexes modified by a variety of covalently-linking auxiliaries at low temperatures. The results demonstrate that by the judicious incorporation of various ligands/auxiliaries into LVT reagents it is possible to widen the scope and applicability of the classical McMurry reaction.

Unprecedented Reductive Dealkoxylation of Aryl Alkyl Ethers and Intramolecular C-C Coupling of 2,2'-Dialkoxystilbenes with Low Valent Titanium: One-pot Synthesis of Phenanthrenes

Facile dealkoxylation of aryl alkyl ethers has been carried out using TiCl3-Li-THF (tetrahydrofuran), a novel one-pot synthesis of phenanthrenes from ortho-alkoxyaromatic aldehydes/ketones is described.