14064-67-6

Basic information

• Product Name: Benzene, 1-chloro-3-(2-phenylethenyl)-, (Z)-
• CAS NO: 14064-67-6
• Molecular Formula: C14H11Cl
• Molecular Weight: 214.694
• Mol File: 14064-67-6.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1-chloro-3-(2-phenylethenyl)-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-chloro-3-(2-phenylethenyl)-, (Z)-(14064-67-6)
• EPA Substance Registry System: Benzene, 1-chloro-3-(2-phenylethenyl)-, (Z)-(14064-67-6)

Safety Data

• Hazardous Substances Data: 14064-67-6(Hazardous Substances Data)

Upstream product

• 587-04-2 m-Chlorobenzaldehyde 
• 88652-80-6 (1RS,2SR)-1,2-diphenyl-2-diphenylphosphinoylmethan-1-ol 
• 102-04-5 1,3-Diphenylpropanone 
• 98-87-3 benzylidene dichloride 
• 536-74-3 phenylacetylene 
• 100-42-5 styrene 
• 625-99-0 3-iodochlorobenzene 
• 10271-57-5 1-chloro-2-(2-phenylethynyl)benzene 
• 51624-34-1 1-chloro-3-(2-phenylethynyl)benzene 
• 1100-88-5 benzyltriphenylphosphonium chloride 

Downstream Products

• 14064-43-8 (E)-3-chlorostilbene 

Relevant articles and documents

Electrochemical Proton Reduction over Nickel Foam for Z-Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes

Selective reduction strategies based on abundant-metal catalysts are very important in the production of chemicals. In this paper, a method for the electrochemical semihydrogenation and semideuteration of alkynes to form Z-alkenes was developed, using a simple nickel foam as catalyst and H3O+ or D3O+ as sources of hydrogen or deuterium. Good yields and excellent stereoselectivities (Z/E up to 20 : 1) were obtained under very mild reaction conditions. The reaction proceeded with terminal and nonterminal alkynes, and also with alkynes containing easily reducible functional groups, such as carbonyl groups, as well as aryl chlorides, bromides, and even iodides. The nickel-foam electrocatalyst could be recycled up to 14 times without any change in its catalytic properties.

Copper(0) nanoparticle catalyzed Z-Selective Transfer Semihydrogenation of Internal Alkynes

The use of copper(0) nanoparticles in the transfer semihydrogenation of alkynes has been investigated as a lead-free alternative to Lindlar catalysts. A stereo-selective methodology for the hydrogenation of internal alkynes to the corresponding (Z)-alkenes in high isolated yields (86% average) has been developed. This green and sustainable transfer hydrogenation protocol relies on non-noble copper nanoparticles for reduction of both electron-rich and electron-deficient, aliphatic-substituted and aromatic- substituted internal alkynes. Polyols, such as ethylene glycol and glycerol, have been proven to act as hydrogen sources, and excellent stereo- and chemoselectivity have been observed. Enabling technologies, such as microwave and ultrasound irradiation are shown to enhance heat and mass transfer, whether used alone or in combination, resulting in a decrease in reaction time from hours to minutes. (Figure presented.).

Efficient photocatalytic chemoselective and stereoselective C-C bond formation over AuPd@N-rich carbon nitride

Heterogeneous chemoselective or stereoselective C-C coupling reactions remain extremely challenging in traditional organic synthesis. Here, we constructed a AuPd@N-rich carbon nitride (NRCN) photocatalyst through simple ammonia solution heat treatment of carbon nitride and then AuPd NP loading. AuPd@NRCN exhibited extraordinary light color promoted catalytic performance in C-C bond formation under visible light in air. Surprisingly, both high chemoselectivity to unsymmetrical Ullmann biaryl products and satisfactory stereoselectivity to Z-type Heck reaction products could be achieved by changing the light source color. Various substrates exhibited great potential for the economical synthesis of unsymmetrical biaryl products and Z-type olefins. Efficient visible light promoted C-I bond activation accompanied with improved photocatalytic coupling reaction efficiency over AuPd@NRCN was verified firstly by in situ DRIFTS. Considering that the Ullmann cross-coupling reaction is a multi-photon reaction, the improved photocatalytic performance in the Ullmann cross-coupling reaction using a combination of light sources with different colors might be due to the activation of different substrates and/or steps requiring different energies, and the combination of the two energy sources was beneficial for improving the activation efficiency of different substrates and/or steps. The activation of iodobenzene and styrene in the Heck reaction with light was also beneficial to the formation of the stilbene product. The light color promoted chemoselectivity and stereoselectivity are expected to have profound impact on organic synthetic methodology improvement. This journal is

cis-Selective Transfer Semihydrogenation of Alkynes by Merging Visible-Light Catalysis with Cobalt Catalysis

Herein, the first example of visible-light-driven, cobalt-catalyzed transfer semihydrogenation of alkynes to alkenes is reported. It is carried out by using Ir[dF(CF3)ppy]2(dtbbpy)]PF6 as photosensitizer, CoBr2/n-Bu3P as proton-reducing catalyst, and i-Pr2NEt/AcOH as the hydrogen source. Under the established catalytic system, the semihydrogenation proceeds with Z as the major selectivity and with inhibition of over-reduction. Under mild reaction conditions, both internal and terminal alkynes, as well as reducible functional groups such as halogen, cyano, and ester, are tolerated. Preliminary mechanistic studies revealed the dual role of the photosensitizer in initiating the reaction via a single-electron transfer process and controlling the stereoselectivity via an energy transfer process. (Figure presented.).

Methanol as the Hydrogen Source in the Selective Transfer Hydrogenation of Alkynes Enabled by a Manganese Pincer Complex

The first base metal-catalyzed transfer hydrogenation of alkynes with methanol is described. An air and moisture stable manganese pincer complex catalyzes the reduction of a variety of different alkynes to the corresponding (Z)-olefins in high yields. The

Ligand-controlled iridium-catalyzed semihydrogenation of alkynes with ethanol: highly stereoselective synthesis of E- and Z-alkenes

A ligand-controlled iridium-catalyzed semihydrogenation of alkynes to E- and Z-alkenes with ethanol was developed. Effective selectivity control was achieved by ligand regulation. The use of 1,2-bis(diphenylphosphino)ethane (DPPE) and 1,5-cyclooctadiene (COD) was critical for the stereoselective semihydrogenation of alkynes. The general applicability of this procedure was highlighted by the synthesis of more than 40 alkenes, with good stereoselectivities. The value of our approach in practical applications was investigated by studying the effects of pinosylvin and 4,4′-dihydroxystilbene (DHS) on zebrafish as a vertebrate model.

Diboron-Assisted Copper-Catalyzed Z-Selective Semihydrogenation of Alkynes Using Ethanol as a Hydrogen Donor

We herein describe a B2Pin2-assisted copper-catalyzed semihydrogenation of alkynes. A variety of alkenes were obtained in good to excellent yields with Z-selectivity under mild reaction conditions. Mechanistic studies indicated that a transfer hydrogenation process was involved and ethanol acted as both a solvent and a hydrogen donor in this reaction. The present protocol enabled convenient synthesis of deuterium-substituted Z-alkenes such as Z-Combretastain A4-d2 in a high deuteration ratio by using readily available ethanol-d1 as the deuterium source.

Highly Chemo- and Stereoselective Transfer Semihydrogenation of Alkynes Catalyzed by a Stable, Well-Defined Manganese(II) Complex

Herein we report unprecedented manganese-catalyzed semihydrogenation of internal alkynes to (Z)-alkenes using ammonia borane as a hydrogen donor. The reaction is catalyzed by a pincer complex of the earth-abundant manganese(II) salt in the absence of any

COBALT COMPLEXES, PROCESS FOR PREPARATION AND USE THEREOF

The present invention discloses a cobalt compound of formula (I), a process for the preparation and use thereof. The present invention further relates to a pharmaceutical composition and a method inhibition of Tau Aggregation in a subject in need thereof using compound of formula (I).

Phosphine-free cobalt pincer complex catalyzed: Z -selective semi-hydrogenation of unbiased alkynes

Herein, we report a novel, molecularly defined NNN-type cobalt pincer complex catalyzed transfer semi-hydrogenation of unbiased alkynes to Z-selective alkenes. This unified process is highly stereo- and chemo-selective and exhibits a broad scope as well as wide functional group tolerance. Ammonia-borane (AB), a bench-stable substrate with high gravimetric hydrogen capacity, was used as a safe and practical transfer hydrogenating source.