40028-03-3

Basic information

• Product Name: Benzene, 1,1'-(1-chloro-1,3-propanediyl)bis-
• CAS NO: 40028-03-3
• Molecular Formula: C15H15Cl
• Molecular Weight: 230.737
• Mol File: 40028-03-3.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-(1-chloro-1,3-propanediyl)bis-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-(1-chloro-1,3-propanediyl)bis-(40028-03-3)
• EPA Substance Registry System: Benzene, 1,1'-(1-chloro-1,3-propanediyl)bis-(40028-03-3)

Safety Data

• Hazardous Substances Data: 40028-03-3(Hazardous Substances Data)

Upstream product

• 14097-24-6 1,3-diphenylpropan-1-ol 
• 110-82-7 cyclohexane 
• 180847-73-8 1,3-Dichloro-1,3-diphenylpropane 
• 100-42-5 styrene 
• 960-16-7 tributylphenylstannane 
• 300-57-2 allylbenzene 
• 104-53-0 3-phenyl-propionaldehyde 
• 591-51-5 phenyllithium 

Downstream Products

• 7448-85-3 4-(1,3-diphenyl-propyl)-morpholine 

Relevant articles and documents

Nickel-Catalyzed Multicomponent Coupling: Synthesis of α-Chiral Ketones by Reductive Hydrocarbonylation of Alkenes

A nickel-catalyzed, multicomponent regio- and enantioselective coupling via sequential hydroformylation and carbonylation from readily available starting materials has been developed. This modular multicomponent hydrofunctionalization strategy enables the straightforward reductive hydrocarbonylation of a broad range of unactivated alkenes to produce a wide variety of unsymmetrical dialkyl ketones bearing a functionalized α-stereocenter, including enantioenriched chiral α-aryl ketones and α-amino ketones. It uses chiral bisoxazoline as a ligand, silane as a reductant, chloroformate as a safe CO source, and a racemic secondary benzyl chloride or an N-hydroxyphthalimide (NHP) ester of a protected α-amino acid as the alkylation reagent. The benign nature of this process renders this method suitable for late-stage functionalization of complex molecules.

Development of a catalytic platform for nucleophilic substitution: Cyclopropenone-catalyzed chlorodehydration of alcohols

Cyclopropenone makes the switch: 2,3-Bis-(p-methoxyphenyl)cyclopropenone is a highly efficient catalyst for the chlorodehydration of 20 diverse alcohol substrates (see scheme; X=Cl). With oxalyl chloride as catalytic activator, this nucleophilic substitution proceeded through cyclopropenium-activated intermediates and resulted in complete stereochemical inversion in substrates with chiral centers.

Palladium-catalyzed oxidative arylhalogenation of alkenes: Synthetic scope and mechanistic insights

This article describes the development of a Pd-catalyzed reaction for the arylhalogenation (halogen = Cl or Br) of diverse α-olefins by oxidatively intercepting Mizoroki-Heck intermediates. These transformations afford synthetically useful 1,2- and 1,1-arylhalogenated products in good yields with good to excellent selectivities that can be modulated by changing the nature of the halogenating reagent and/or the reaction conditions. The selectivity of these reactions can be rationally tuned by (i) controlling the relative rates of oxidative functionalization versus β-hydride elimination from equilibrating PdII-alkyl species and (ii) stabilization of organometallic PdII intermediates through the formation of π-benzyl adducts. These arylhalogenations exhibit modest to excellent levels of stereoselectivity, and the key carbon-halogen bond-forming step proceeds with predominant retention of stereochemistry at carbon.

Oxidatively intercepting heck intermediates: Pd-catalyzed 1,2- and 1,1-arylhalogenation of alkenes

This communication describes the development of two Pd-catalyzed reactions for the arylchlorination of diverse α-olefins by oxidatively intercepting Heck intermediates. Depending on the nature of the oxidant and the reaction conditions, these transformati

Laser Flash, Laser-Drop, and Lamp Photolysis of 1,3-Dichloro-1,3-diphenylpropane. One- versus Two-Photon Reaction Pathways

Low intensity irradiation of 1,3-dichloro-1,3-diphenylpropane (1) in cyclohexane leads to the formation of 3-chloro-1,3-diphenylpropyl radical (2) through homolytic C-Cl bond cleavage. Radical 2 gives rise to final products typical of free radical reactions. Neither 1,2-diphenylcyclopropanes (6) nor 3-cyclohexyl-1,3-diphenylpropene (20) are obtained under these conditions. Nevertheless, high intensity laser irradiation of the initially formed monoradical 2 leads to the 1,3-diphenylpropenyl radical (3) detected with nanosecond techniques. This intermediate is completely trapped by the cyclohexyl radicals generated in the medium to yield 20. Photolysis of 1 with the laser-drop technique leads to the cyclopropanes 6 as major photoproducts.

Lamp versus laser photolysis of 1,3-dichloro-1,3-diphenylpropane in cyclohexane. Direct observation of 1,3-diphenylpropenyl radical

Laser photolysis of the title compound leads to two-photon processes indicating the involvement of the 1,3-diphenylpropanediyl biradical (12) and the 1,3-diphenylallyl radical (10).