42432-30-4

Basic information

• Product Name: Benzene, 1-(3-bromo-1-propenyl)-4-chloro-
• CAS NO: 42432-30-4
• Molecular Formula: C9H8BrCl
• Molecular Weight: 231.52
• Mol File: 42432-30-4.mol
• Article Data: 25

Chemical Properties

• CAS DataBase Reference: Benzene, 1-(3-bromo-1-propenyl)-4-chloro-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-(3-bromo-1-propenyl)-4-chloro-(42432-30-4)
• EPA Substance Registry System: Benzene, 1-(3-bromo-1-propenyl)-4-chloro-(42432-30-4)

Safety Data

• Hazardous Substances Data: 42432-30-4(Hazardous Substances Data)

Upstream product

• 24583-70-8 3-(4-chlorophenyl)-2-propene-1-ol 
• 58824-54-7 p-chlorophenylvinylcarbinol 
• 637-87-6 1-Chloro-4-iodobenzene 
• 1075-77-0 (E)-4-chlorocinnamic aldehyde 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 104-88-1 4-chlorobenzaldehyde 
• 24393-52-0 ethyl (E)-3-(4-chlorophenyl)prop-2-enoate 
• 24583-70-8 (E)-3-(p-chlorophenyl)prop-2-en-1-ol 
• 7560-44-3 methyl 4-chlorocinnamate 
• 20754-21-6 methyl 3-(4-chlorophenyl)propenoate 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 1075-77-0 4-chlorocinnamaldehyde 
• 1826-67-1 vinyl magnesium bromide 
• 2749-98-6 4-chlorophenylallene 

Downstream Products

• 949568-27-8 (-)-(S)-1-chloro-4-(1-phenylallyl)benzene 
• 949568-50-7 (+)-(R)-1-chloro-4-(1-phenylallyl)benzene 
• 20442-76-6 1-(4-chloro-phenyl)-3-phenyl-propene 
• 1147357-09-2 C₁₆H₁₅Cl 
• 101282-51-3 C₁₆H₁₅ClO 

Relevant articles and documents

Synthesis of Enantioenriched 3,4-Disubstituted Chromans through Lewis Base Catalyzed Carbosulfenylation

A method for the catalytic, enantioselective, carbosulfenylation of alkenes to construct 3,4-disubstituted chromans is described. Alkene activation proceeds through the intermediacy of enantioenriched, configurationally stable thiiranium ions generated from catalytic, Lewis base activation of an electrophilic sulfenylating agent. The transformation affords difficult-to-generate, enantioenriched, 3,4-disubstituted chromans in moderate to high yields and excellent enantioselectivities. A variety of substituents are compatible including electronically diverse functional groups as well as several functional handles such as aryl halides, esters, anilines, and phenols. The resulting thioether moiety is amenable to a number of functional group manipulations and transformations. Notably, the pendant sulfide was successfully cleaved to furnish a free thiol which readily provides access to most sulfur-containing functional groups which are present in natural products and pharmaceuticals.

Enantioselective Allenoate-Claisen Rearrangement Using Chiral Phosphate Catalysts

Herein we report the first highly enantioselective allenoate-Claisen rearrangement using doubly axially chiral phosphate sodium salts as catalysts. This synthetic method provides access to β-amino acid derivatives with vicinal stereocenters in up to 95percent ee. We also investigated the mechanism of enantioinduction by transition state (TS) computations with DFT as well as statistical modeling of the relationship between selectivity and the molecular features of both the catalyst and substrate. The mutual interactions of charge-separated regions in both the zwitterionic intermediate generated by reaction of an amine to the allenoate and the Na+-salt of the chiral phosphate leads to an orientation of the TS in the catalytic pocket that maximizes favorable noncovalent interactions. Crucial arene-arene interactions at the periphery of the catalyst lead to a differentiation of the TS diastereomers. These interactions were interrogated using DFT calculations and validated through statistical modeling of parameters describing noncovalent interactions.

Olefin Oxyamination with Unfunctionalized N-Alkylanilines

N-Alkylanilines have rarely been used in oxyamination reactions, due to the normally necessary pre-functionalization of the N-atom. Also, the formation of aminium radical cations (ARCs) of anilines bearing alkyl substituents is plagued by the ARC's tendency to instantaneously convert to α-amino radicals or iminium ions. We present a readily available reagent combination that addresses both challenges, and thus allows for an oxyamination with N-alkylanilines via ARCs as the crucial reactive intermediates and excellent diastereoselectivity. (Figure presented.).