64123-83-7

Basic information

• Product Name: methyl 2-(3-chlorophenyl)acrylate
• Synonyms: methyl 2-(3-chlorophenyl)acrylate
• CAS NO: 64123-83-7
• Molecular Weight: 196.633
• Mol File: 64123-83-7.mol

Chemical Properties

• Boiling Point: 297.3±33.0 °C(Predicted)
• Density: 1.176±0.06 g/cm3(Predicted)
• CAS DataBase Reference: methyl 2-(3-chlorophenyl)acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-(3-chlorophenyl)acrylate(64123-83-7)
• EPA Substance Registry System: methyl 2-(3-chlorophenyl)acrylate(64123-83-7)

Safety Data

• Hazardous Substances Data: 64123-83-7(Hazardous Substances Data)

Upstream product

• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 34757-14-7 methyl 2-diazopropanoate 
• 108-37-2 1-bromo-3-chlorobenzene 
• 1878-65-5 3-chlorophenylacetic acid 
• 50-00-0 formaldehyd 
• 53088-68-9 methyl 3-chlorophenylacetate 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 766-83-6 m-chlorophenylacetylene 
• 108-24-7 acetic anhydride 

Downstream Products

• 103040-42-2 (S)-methyl 2-(3-chlorophenyl)propanoate 
• 1174749-44-0 (S)-3-(3-chlorophenyl)-1,3-dimethylindolin-2-one 
• 41904-39-6 3-chloro-benzeneacetyl chloride 
• 27662-65-3 pyrazolinone 
• 64124-05-6 1,4-bis-(3-chlorophenyl)-2-ethyl-3-pyrazolin-5-one 
• 64124-06-7 4-(3-chlorophenyl)-1-(α,α,α-trifluoro-3-tolyl)-3-pyrazolin-5-one 

Relevant articles and documents

Multiple-Functional Diphosphines: Synthesis, Characterization, and Application to Pd-Catalyzed Alkoxycarbonylation of Alkynes

A series of diphosphine ligands (L1-L5) containing bis-phosphino fragments and bis-amido groups as well as intensive electron-withdrawing F atoms were synthesized and fully characterized. The structures of the prepared complex of Pd-L5 demonstrate that as for L5, the incorporated two phosphino fragments participate in the chelation to the Pd center inversely along with two Cl-ligands to present a typical square-planar configuration, whereas the two amido groups simultaneously develop a hydrogen-bond interaction with Cl-ligands to facilitate the timely dissociation of Cl-ligands from the Pd center. It was found that L5 enabled the Pd complex to be more active in the alkoxycarbonylation of alkynes with MeOH for the synthesis of branched/linear α,β-unsaturated carboxylic esters with general yields of 60-89%. In L5, the incorporated diphosphino fragments, diamino groups, and F atoms conferred a catalytic effect to the Pd complex synergetic toward the reaction.

Room-temperature Pd-catalyzed methoxycarbonylation of terminal alkynes with high branched selectivity enabled by bisphosphine-picolinamide ligand

We report the room-temperature Pd-catalyzed methoxy-carbonylation with high branched selectivity using a new class of bisphosphine-picolinamide ligands. Systematic optimization of ligand structures and reaction conditions revealed the significance of both

Synthesis of Cyclopentenones through Rhodium-Catalyzed C-H Annulation of Acrylic Acids with Formaldehyde and Malonates

An efficient rhodium-catalyzed protocol for the synthesis of cyclopentenones based on a three-component reaction of acrylic acids, formaldehyde, and malonates via vinylic C-H activation is reported. Exploratory studies showed that 5-alkylation of as-prepared cyclopentenones could be realized smoothly by the treatment of a variety of alkyl halides with a Na2CO3/MeOH solution. Excess formaldehyde and malonate led to a multicomponent reaction that afforded the multisubstituted cyclopentenones through a Michael addition.

Cobalt-Catalyzed Vinylic C-H Addition to Formaldehyde: Synthesis of Butenolides from Acrylic Acids and HCHO

A carboxyl-assisted C-H functionalization of acrylic acids with formaldehyde to give butenolides is described. It is the first time that the addition of an inert vinylic C-H bond to formaldehyde has been achieved via cobalt-catalyzed C-H activation. The unique reactivity of the cobalt species was observed when compared with related Rh or Ir catalysts. γ-Hydroxymethylated butenolides were produced by the treatment of Na2CO3 after the catalytic reaction in one pot.

Palladium-catalyzed intermolecular C-H silylation initiated by aminopalladation

A Pd(ii)-catalyzed intermolecular C-H silylation reaction initiated by aminopalladation has been developed. The C-H bonds were activated by an alkyl Pd(ii) species generated through aminopalladation and then disilylated with hexamethyldisilane to form disilylated indolines as the final products. The reaction provides a new method for the introduction of silyl groups into complex organic molecules.

Enantioselective Construction of Quaternary All-Carbon Centers via Copper-Catalyzed Arylation of Tertiary Carbon-Centered Radicals

An enantioselective copper-catalyzed arylation of tertiary carbon-centered radicals, leading to quaternary all-carbon stereocenters, has been developed herein. The tertiary carbon-centered radicals, including both benzylic and nonbenzylic radicals, were produced by the addition of trifluoromethyl radical to α-substituted acrylamides, and subsequently captured by chiral aryl copper(II) species to give C-Ar bonds with excellent enantioselectivity. Importantly, an acylamidyl (CONHAr) group adjacent to the tertiary carbon radical is essential for the asymmetric radical coupling. The reaction itself features broad substrate scope, excellent functional group compatibility and mild conditions.

Selective Palladium-Catalyzed Carbonylation of Alkynes: An Atom-Economic Synthesis of 1,4-Dicarboxylic Acid Diesters

A class of novel diphosphine ligands bearing pyridine substituents was designed and synthesized for the first time. The resulting palladium complexes of L1 allow for chemo- and regioselective dialkoxycarbonylation of various aromatic and aliphatic alkynes affording a wide range of 1,4-dicarboxylic acid diesters in high yields and selectivities. Kinetic studies suggest the generation of 1,4-dicarboxylic acid diesters via cascade hydroesterification of the corresponding alkynes. Based on these investigations, the chemo- and regioselectivities of alkyne carbonylations can be controlled as shown by switching the ligand from L1 to L3 or L9 to give α,β-unsaturated esters.

Water as a Hydride Source in Palladium-Catalyzed Enantioselective Reductive Heck Reactions

Pd-catalyzed intramolecular asymmetric carbopalladation of N-aryl acrylamides followed by reduction of C(sp3)-Pd intermediate using diboron–water as a hydride source afforded enantioenriched 3,3-disubstituted oxindoles in high yields and enantioselectivities. When heavy water was used as a deuterium donor in combination with bis(catecholato)diboron (Cat2B2), deuterium was incorporated into the products with high synthetic efficiency. The ligand determined both the enantioselectivity of the reaction and the reaction pathways, thereby affording either hydroarylation (reductive Heck) or carboborylation products.

PREPARATION OF CHIRAL 1-METHYL-2,3,4,5-1H-BENZODIAZEPINES VIA ASYMMETRIC REDUCTION OF ALPHA-SUBSTITUTED STYRENES

The present invention provides an asymmetric and economic synthesis of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1 H-benzo[d]azepine via novel intermediates applying an asymmetric enzymatic, biomimetic or catalytic reduction. The present invention also provides a novel green asymmetric catalytic reduction adapted for an aqueous medium to be applied in the synthesis of 8-chloro-1-methyl-2,3,4,5-tetrahydro-1 H-benzo[d]azepine or novel intermediates.

Palladium-catalyzed coupling reaction of -diazocarbonyl compounds with aromatic boronic acids or halides

Efficient palladium-catalyzed cross-coupling reactions of -diazocarbonyl compounds and arylboronic acids or aryl halides have been developed. The reaction proceeds smoothly for a range of diazo compounds, boronic acids, and halides. The coupling reaction conditions tolerate various substituents on the aromatic rings of the substrates, such as chloro, fluoro, acyl, oxo, ester, and nitro groups. This coupling reaction constitutes a novel access to -aryl-substituted ,-unsaturated carbonyl compounds. Mechanistically, palladium-carbene is supposed to be the key intermediate; its formation is followed by migratory insertion of an aryl group to the carbenic carbon of the palladium-carbene complex and subsequent -hydride elimination. Kinetic isotope effect (KIE) data measured for intra- and intermolecular competition experiments suggest that -hydride elimination is not involved in the rate-determining step