70610-09-2

Basic information

• Product Name: Benzene, 1-methoxy-3-(2-phenylethyl)-
• CAS NO: 70610-09-2
• Molecular Formula: C15H16O
• Molecular Weight: 212.291
• Mol File: 70610-09-2.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1-methoxy-3-(2-phenylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-methoxy-3-(2-phenylethyl)-(70610-09-2)
• EPA Substance Registry System: Benzene, 1-methoxy-3-(2-phenylethyl)-(70610-09-2)

Safety Data

• Hazardous Substances Data: 70610-09-2(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 14064-41-6 (E)-3-methoxystilbene 
• 1041479-70-2 tri(phenylethanyl)indium 
• 108-88-3 toluene 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 766-85-8 3-methoxy-1-iodobenzene 
• 103-63-9 1-phenyl-2-bromoethane 
• 874-98-6 1-bromomethyl-3-methoxybenzene 
• 6921-34-2 benzylmagnesium chloride 
• 37696-01-8 1-methoxy-3-(phenylethynyl)benzene 
• 100-39-0 benzyl bromide 
• 603-35-0 triphenylphosphine 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 2398-37-0 3-methoxyphenyl bromide 

Downstream Products

• 10366-19-5 4'-hydroxy-3'-methoxy-1,2-diphenylethane 
• 195300-59-5 2-methoxy-6-(2-phenylethyl)phenol 

Relevant articles and documents

Enantioselective Synthesis of Indolines, Benzodihydrothiophenes, and Indanes by C?H Insertion of Donor/Donor Carbenes

We employ a single catalyst/oxidant system to enable the asymmetric syntheses of indolines, benzodihydrothiophenes, and indanes by C?H insertion of donor/donor carbenes. This methodology enables the rapid construction of densely substituted five-membered rings that form the core of many drug targets and natural products. Furthermore, oxidation of hydrazones to the corresponding diazo compounds proceeds in situ, enabling a relatively facile one- or two-pot protocol in which isolation of potentially explosive diazo alkanes is avoided. Regioselectivity studies were performed to determine the impact of sterics and electronics in donor/donor metal carbene C?H insertions to form indolines. This methodology was applied to a variety of substrates in high yield, diastereomeric, and enantiomeric ratios and to the synthesis of a patented indane estrogen receptor agonist with anti-cancer activity.

Catalytic Chemoselective and Stereoselective Semihydrogenation of Alkynes to E-Alkenes Using the Combination of Pd Catalyst and ZnI2

An efficient E-selective semihydrogenation of internal alkynes was developed under low dihydrogen pressure and low reaction temperature from commercially available reagents: Cl2Pd(PPh3)2, Zn0, and ZnI2. Kinetic studies and control experiments underline the significant role of ZnI2 in this process under H2 atmosphere, establishing that the transformation involves syn-hydrogenation followed by isomerization. This simple and easy-to-handle system provides a route to E-alkenes under mild conditions.

Mechanism and Applications of the Photoredox Catalytic Coupling of Benzyl Bromides

The photoredox catalytic coupling of halomethyl arenes to bibenzyl derivatives has been demonstrated. The catalytic protocol employed the Hantzsch ester, potassium phosphate, and a photoactive cyclometalated IrIIIcomplex catalyst. A photochemical quantum yield as high as 20 % was obtained. The catalytic mechanism was investigated in detail by performing photophysical and electrochemical measurements, as well as by quantum chemical calculations. The results suggest that two-electron mediation might be responsible for the improved photon economy. The reaction protocol was compatible with halomethyl arenes that contain a variety of functional groups. Finally, the synthetic utility of our protocol was demonstrated by the preparation of a natural dihydrostilbenoid, brittonin A.

General Ambient Temperature Benzylic Metalations Using Mixed-Metal Li/K-TMP Amide

Highly regioselective benzylic metalations in hydrocarbon solvent have been achieved at rt and 0 °C using a mixed-metal Li/K-TMP amide comprised of KOtBu, BuLi, and 2,2,6,6,-tetramethylpiperidine (TMP(H)). Mixing of KOtBu, BuLi, and TMP(H) in heptane gave a solution of the base mixture which when used in deuterium labeling experiments confirmed the requirement of the three reagent components for both reactivity and selectivity. The reaction protocol is operationally straightforward and found to be applicable to a broad range of substrates. Upon generation of the metalated products, they are reacted in heptane at ambient temperature in a variety of synthetically useful ways. Illustrated examples include generation of the benzyltrimethylsilanes and α,α-bis(trimethylsilyl)toluenes reagents, which are bench-stable surrogates of benzyl anions and α-silyl carbanions utilized for nucleophilic addition and Peterson olefination reactions. Direct C-C couplings mediated by 1,2-dibromoethane provided entries into bibenzyls and [2.2]metacyclophanes. Comparison of reaction outcomes with the same reactions carried out in THF at -78 °C showed no negative effects for conducting the reactions under these milder more user-friendly conditions.

Two dimensional inorganic electride-promoted electron transfer efficiency in transfer hydrogenation of alkynes and alkenes

A simple and highly efficient transfer hydrogenation of alkynes and alkenes by using a two-dimensional electride, dicalcium nitride ([Ca2N]+·e-), as an electron transfer agent is disclosed. Excellent yields in the transformation are attributed to the remarkable electron transfer efficiency in the electride-mediated reactions. It is clarified that an effective discharge of electrons from the [Ca2N]+·e- electride in alcoholic solvents is achieved by the decomposition of the electride via alcoholysis and the generation of ammonia and Ca(OiPr)2. We found that the choice of solvent was crucial for enhancing the electron transfer efficiency, and a maximum efficiency of 80% was achieved by using a DMF mixed isopropanol co-solvent system. This is the highest value reported to date among single electron transfer agents in the reduction of C-C multiple bonds. The observed reactivity and efficiency establish that electrides with a high density of anionic electrons can readily participate in the reduction of organic functional groups.

TMEDA in iron-catalyzed Kumada coupling: Amine adduct versus homoleptic "ate" complex formation

The reactions of iron chlorides with mesityl Grignard reagents and tetramethylethylenediamine (TMEDA) under catalytically relevant conditions tend to yield the homoleptic "ate" complex [Fe(mes)3] - (mes=mesityl) rather than adducts of the diamine, and it is this ate complex that accounts for the catalytic activity. Both [Fe(mes) 3]- and the related complex [Fe(Bn)3] - (Bn=benzyl) react faster with representative electrophiles than the equivalent neutral [FeR2(TMEDA)] complexes. FeI species are observed under catalytically relevant conditions with both benzyl and smaller aryl Grignard reagents. The X-ray structures of [Fe(Bn) 3]- and [Fe(Bn)4]- were determined; [Fe(Bn)4]- is the first homoleptic σ-hydrocarbyl FeIII complex that has been structurally characterized. Casting iron in catalytic roles: Chelating diamine ligands such as TMEDA are routinely used in iron-catalyzed cross-coupling reactions of aryl Grignard reagents. However, it was found that under catalytically relevant conditions, there is little evidence for their coordination to iron centers; homoleptic anionic organoiron species are produced instead. Copyright

Homo- and hetero-oxidative coupling of benzyl anions

The regioselective benzylic metalation of substituted toluenes using BuLi/KO-t-Bu/TMP(H) (LiNK metalation conditions) with subsequent in situ oxidative C-C coupling has been developed for the facile generation of 1,2-diarylethanes. A range of oxidants can be used for the oxidative coupling step, with 1,2-dibromoethane proving optimal. Heterocouplings can be achieved starting from a mixture of two different toluenes with a bias toward cross coupling achievable by using a 2-fold excess of one toluene starting material. The utility of this approach is illustrated by the synthesis of several biologically active natural products. A distinct advantage is that the synthetic steps typically required to preactivate the coupling substrates are eliminated and no transition metal is required to facilitate the C-C bond formation.

Nickel-mediated inter- and intramolecular reductive cross-coupling of unactivated alkyl bromides and aryl iodides at room temperature

A nickel-mediated intermolecular reductive cross-coupling reaction of unactivated alkyl bromides and aryl iodides at room temperature has been developed and successfully extended to less explored intramolecular versions and tandem cyclization-intermolecular cross-coupling. Highly stereoselective (or stereospecific) synthesis of linear-fused perhydrofuro[2,3-b]furan (pyran) and spiroketal skeletons allows rapid access to these useful building blocks, which would be potentially valuable in the synthesis of relevant natural products. A rational explanation for the formation of contiguous stereogenic centers is given. Copyright

Highly selective palladium-catalyzed oxidative Csp2-Csp 3 cross-coupling of arylzinc and alkylindium reagents through double transmetallation

Using desyl chloride (2-chloro-1,2-diphenylethanone) as the oxidant, the palladium-catalyzed reaction of arylzinc with alkylindium reagents occurred smoothly in a highly selective manner to afford the products in 57-90% yields. Preliminary kinetic data in

The photochemical addition of 2,2,2-trifluoroethanol to methoxy-substituted stilbenes

The excited-state lifetime of the trans-stilbene chromophore in acetonitrile is prolonged by methoxy substituents in the meta positions. The long-lived singlet excited state of trans-3,5-dimethoxystilbene (trans-2d) is quenched upon the addition of 2,2,2-trifluoroethanol (TFE), and the Markovnikov ether is observed as the major product from steady-state irradiations. The results indicate that the reaction pathway proceeds through a carbocation intermediate.