1879-52-3

Basic information

• Product Name: Benzene, 1-chloro-4-(1-propenyl)-, (Z)-
• Synonyms: (Z)-1-(4-chlorophenyl)-1-propene;Z-1-(p-chlor-phenyl)-propen;(Z)-1-(4-chlorophenyl)propene;(Z)-1-(p-chlorophenyl)-1-propene;1-Chloro-4-((Z)-propenyl)-benzene;cis-4-chloro-β-methylstyrene;(Z)-1-chloro-4-propenylbenzene
• CAS NO: 1879-52-3
• Molecular Formula: C9H9Cl
• Molecular Weight: 152.623
• Mol File: 1879-52-3.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 72 °C (8 mmHg)
• CAS DataBase Reference: Benzene, 1-chloro-4-(1-propenyl)-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-chloro-4-(1-propenyl)-, (Z)-(1879-52-3)
• EPA Substance Registry System: Benzene, 1-chloro-4-(1-propenyl)-, (Z)-(1879-52-3)

Safety Data

• Hazardous Substances Data: 1879-52-3(Hazardous Substances Data)

Upstream product

• 599-70-2 ethyl phenyl sulfone 
• 873-76-7 para-Chlorobenzyl alcohol 
• 873-73-4 4-n-chlorophenylacetylene 
• 104-88-1 4-chlorobenzaldehyde 
• 896-33-3 ethyltriphenylphosphonium chloride 
• 1135820-79-9 C₂₁H₂₂OP⁽¹⁺⁾*I^(1-) 
• 1135821-12-3 ethyl-(2-methoxy-phenyl)-diphenyl-phosphonium; iodide 
• 1202-60-4 -2-methyl-3-(4-chlorophenyl)prop-2-enoic acid 
• 1884-95-3 4-(4'-chlorophenyl)-3-methyl-3-buten-2-one 
• 4736-60-1 ethyltriphenylphosphonium iodide 
• 100-52-7 benzaldehyde 
• 1754-88-7 ethylenetriphenylphosphorane 
• 1745-18-2 1-allyl-4-chlorobenzene 
• 1202-60-4 3-(4-chlorophenyl)-3-methyl-2-acrylic acid 

Downstream Products

• 135682-94-9 cis-4-chloro-β-methylstyrene oxide 
• 1879-53-4 E-1-(4-chlorophenyl)-1-propene 
• 1404433-42-6 (1R,2R,3S)-2,6-dimethylphenyl 2-(4-chlorophenyl)-3-methylcyclopropanecarboxylate 
• 1886-50-6 (+/-)-cis-1-(4-Chlorphenyl)-2-methyl-ethylenoxid 
• 50337-50-3 2-(4'-chlorophenyl)-3-methyloxirane 

Relevant articles and documents

Cis Selectivity of "Salt-Free" Wittig Reactions: A "Leeward Approach" of the Aldehyde at the Origin?

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Cobalt-Catalyzed Z to e Isomerization of Alkenes: An Approach to (E)-β-Substituted Styrenes

An efficient cobalt-catalyzed Z to E isomerization of β-substituted styrenes using the amido-diphosphine ligand was developed, delivering the (E)-isomers with good functional tolerance and high stereoselectivity. The reaction could be scaled up to gram-scale with a catalyst loading of 0.1 mol %, using a mixture of (Z)- and (E)-alkene as the starting material. Preliminary mechanistic studies indicated that cobalt(I)-hydride and a benzylic-cobalt species were probably involved in the reaction, as supported by experiments and DFT calculations.

Direct Olefination of Alcohols with Sulfones by Using Heterogeneous Platinum Catalysts

Carbon-supported Pt nanoparticles (Pt/C) were found to be effective heterogeneous catalysts for the direct Julia olefination of alcohols in the presence of sulfones and KOtBu under oxidant-free conditions. Primary alcohols, including aryl, aliphatic, allyl, and heterocyclic alcohols, underwent olefination with dimethyl sulfone and aryl alkyl sulfones to give terminal and internal olefins, respectively. Secondary alcohols underwent methylenation with dimethyl sulfone. Under 2.5 bar H2, the same reaction system was effective for the transformation of alcohol OH groups to alkyl groups. Structural and mechanistic studies of the terminal olefination system suggested that Pt0 sites on the Pt metal particles are responsible for the rate-limiting dehydrogenation of alcohols and that KOtBu may deprotonate the sulfone reagent. The Pt/C catalyst was reusable after the olefination, and this method showed a higher turnover number (TON) and a wider substrate scope than previously reported methods, which demonstrates the high catalytic efficiency of the present method. Olefination of alcohols: The first heterogeneous catalytic terminal and internal olefination of primary alcohols and methylenation of secondary alcohols with sulfones, a reusable carbon-supported Pt catalyst, and KOtBu is reported (see scheme).

Nickel-Catalyzed Allylic C(sp2)–H Activation: Stereoselective Allyl Isomerization and Regiospecific Allyl Arylation of Allylarenes

Stereoselective allyl isomerization and regiospecific allyl arylation reactions of allylarenes with a catalytic system comprising nickel(II) with an aryl Grignard reagent were studied. Both reactions are triggered by allylic internal C(sp2)–H activation by in-situ-formed Ni0, which is inserted into the C–H bond at the 2-position of the allyl moiety without a directing group. The isomerization of allylarene to 1-propenylarene favors the E isomer and proceeds with quantitative conversion. The arylation takes place through oxidative cross-coupling of allylarenes with excess Grignard reagent. It occurs regiospecifically at the position of C(sp2)–H activation and represents a new method for the synthesis of 1,1-disubstituted olefins. The results of deuterium labeling experiments reveal an alkenyl/alkyl mechanism involving allylic internal C(sp2)–H activation and multiple intermolecular 1,2-, 1,3-, and 2,3-hydride shifts. These methods represent new approaches to the functionalization of olefins, and the mechanistic investigations could be helpful for the discovery and design of new strategies for olefin functionalization.