68522-49-6

Basic information

• Product Name: Benzene, 1-chloro-4-(1-methyl-1-propenyl)-
• CAS NO: 68522-49-6
• Molecular Formula: C10H11Cl
• Molecular Weight: 166.65
• Mol File: 68522-49-6.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Benzene, 1-chloro-4-(1-methyl-1-propenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-chloro-4-(1-methyl-1-propenyl)-(68522-49-6)
• EPA Substance Registry System: Benzene, 1-chloro-4-(1-methyl-1-propenyl)-(68522-49-6)

Safety Data

• Hazardous Substances Data: 68522-49-6(Hazardous Substances Data)

Upstream product

• 1073-67-2 4-vinylbenzyl chloride 
• 74-85-1 ethene 
• 1064000-89-0 1-chloro-4-(2,2-dibromo-1-methylcyclopropyl)benzene 
• 1712-70-5 1-chloro-4-(1-methylethenyl)-benzene 
• 99-91-2 para-chloroacetophenone 
• 21758-20-3 1-(but-1-en-2-yl)-4-chlorobenzene 
• 6285-05-8 4'-chloropropiophenone 
• 4518-65-4 (1-methoxyprop-1-en-1-yl)benzene 
• 1530-32-1 ethyltriphenylphosphonium bromide 

Downstream Products

• 344832-12-8 (Z)-3-(4'-chlorophenyl)-2-nitro-2-butene 

Relevant articles and documents

Cobalt(II)-Catalyzed Stereoselective Olefin Isomerization: Facile Access to Acyclic Trisubstituted Alkenes

Stereoselective synthesis of trisubstituted alkenes is a long-standing challenge in organic chemistry, due to the small energy differences between E and Z isomers of trisubstituted alkenes (compared with 1,2-disubstituted alkenes). Transition metal-catalyzed isomerization of 1,1-disubstituted alkenes can serve as an alternative approach to trisubstituted alkenes, but it remains underdeveloped owing to issues relating to reaction efficiency and stereoselectivity. Here we show that a novel cobalt catalyst can overcome these challenges to provide an efficient and stereoselective access to a broad range of trisubstituted alkenes. This protocol is compatible with both mono- and dienes and exhibits a good functional group tolerance and scalability. Moreover, it has proven to be a useful tool to construct organic luminophores and a deuterated trisubstituted alkene. A preliminary study of the mechanism suggests that a cobalt-hydride pathway is involved in the reaction. The high stereoselectivity of the reaction is attributed to both a π-πstacking effect and the steric hindrance between substrate and catalyst.

Intermolecular Carbonyl–olefin Metathesis with Vinyl Ethers Catalyzed by Homogeneous and Solid Acids in Flow

The carbonyl–olefin metathesis reaction has experienced significant advances in the last seven years with new catalysts and reaction protocols. However, most of these procedures involve soluble catalysts for intramolecular reactions in batch. Herein, we show that recoverable, inexpensive, easy to handle, non-toxic, and widely available simple solid acids, such as the aluminosilicate montmorillonite, can catalyze the intermolecular carbonyl–olefin metathesis of aromatic ketones and aldehydes with vinyl ethers in-flow, to give alkenes with complete trans stereoselectivity on multi-gram scale and high yields. Experimental and computational data support a mechanism based on a carbocation-induced Grob fragmentation. These results open the way for the industrial implementation of carbonyl–olefin metathesis over solid catalysts in continuous mode, which is still the origin and main application of the parent alkene–alkene cross-metathesis.

Bioinspired Metal-Free Formal Decarbonylation of α-Branched Aliphatic Aldehydes at Ambient Temperature

A sequence of a Baeyer–Villiger oxidation and a Lewis acid-promoted reduction of the resulting formate with Et3SiH enabled the metal-free formal decarbonylation of tertiary and secondary aliphatic aldehydes. The new methodology mimics the biosynthetic decarbonylation pathway through oxidative C?C bond cleavage rather than the C(O)?H bond activation known from conventional Tsuji–Wilkinson-type reactions. The substrate scope is complementary to existing transition-metal-catalyzed protocols.