1037048-15-9

Basic information

• Product Name: 1-(buta-2,3-dien-2-yl)-4-chlorobenzene
• Synonyms: 1-(buta-2,3-dien-2-yl)-4-chlorobenzene
• CAS NO: 1037048-15-9
• Molecular Weight: 164.634
• Mol File: 1037048-15-9.mol

Chemical Properties

• CAS DataBase Reference: 1-(buta-2,3-dien-2-yl)-4-chlorobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(buta-2,3-dien-2-yl)-4-chlorobenzene(1037048-15-9)
• EPA Substance Registry System: 1-(buta-2,3-dien-2-yl)-4-chlorobenzene(1037048-15-9)

Safety Data

• Hazardous Substances Data: 1037048-15-9(Hazardous Substances Data)

Upstream product

• 925-90-6 ethylmagnesium bromide 
• 1064000-89-0 1-chloro-4-(2,2-dibromo-1-methylcyclopropyl)benzene 
• 99-91-2 para-chloroacetophenone 
• 1712-70-5 1-chloro-4-(1-methylethenyl)-benzene 

Downstream Products

• 1037048-23-9 2-(4-chlorophenyl)-2-methylbut-3-en-1-ol 
• 1808-99-7 1-chloro-4-(3-chlorobuta-1,3-dien-2-yl)benzene 
• 1453803-92-3 C₁₂H₁₁Cl 
• 1453803-93-4 C₁₂H₁₁Cl 
• 1453803-52-5 C₂₁H₃₁ClSi 
• 1453803-62-7 C₂₁H₃₁ClSi 
• 1235590-56-3 C₁₉H₂₁ClO₆ 

Relevant articles and documents

Silylium-Ion-Promoted Hydrosilylation of Aryl-Substituted Allenes: Interception by Cyclization of the Allyl-Cation Intermediate

A trityl-cation-initiated, silylium-ion-promoted hydrosilylation of aryl-substituted allenes is reported. Depending on the hydrosilane-to-initiator ratio, the hydrosilylation can be intercepted by an intramolecular electrophilic aromatic substitution or a Nazarov electrocyclization of an allyl-cation intermediate in the form of its endo isomer. By this, the selective formation of either the conventional 1,2-hydrosilylation product (vinylsilane) or a cyclized product (silylated indane) can be controlled.

Construction of All-Carbon Chiral Quaternary Centers through CuI-Catalyzed Enantioselective Reductive Hydroxymethylation of 1,1-Disubstituted Allenes with CO2

A catalytic enantioselective construction of all-carbon chiral quaternary centers through reductive hydroxymethylation of 1,1-disubstituted allenes with CO2 has been developed. In the presence of a copper/Mandyphos catalyst, CO2 is t

Regioselective Diboron-Mediated Semireduction of Terminal Allenes

A method for the regioselective reduction of the terminal double bond of 1,1-disubstituted allenes has been developed. In the presence of a palladium catalyst, tetrahydroxydiboron and stoichiometric water, allene semireduction proceeds in high yield to afford Z-alkenes selectively.

A convenient access to allylic triflones with allenes and triflyl chloride in the presence of (EtO)2P(O)H

A simple method for the preparation of allylic triflones from allenes and triflyl chloride in the presence of (EtO)2P(O)H has been developed. The features of this reaction are catalyst-free and simple starting substrates. This method tolerates diverse functional groups and substituted allylic triflones are obtained in moderate to good yields.

Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: Synthesis of vicinal-dichlorides and chlorodienes

Allyl and vinyl chlorides represent important structural motifs in organic chemistry. Herein is described the chemoselective and regioselective reaction of aryl- and α-substituted phenylallenes with the hypervalent iodine (HVI) reagent 1-chloro-1,2-benz-iodoxol-3-one. The reaction typically results in vicinal dichlorides, except with proton-containing α-alkyl substituents, which instead give chlorinated dienes as the major product. Experimental evidence suggests that a radical mechanism is involved.

Fluorinative Rearrangements of Substituted Phenylallenes Mediated by (Difluoroiodo)toluene: Synthesis of α-(Difluoromethyl)styrenes

Phenylallenes undergo fluorinative rearrangement upon the action of (difluoroiodo)toluene in the presence of 20 mol % BF3?OEt2 to yield α-difluoromethyl styrenes. This unprecedented reaction was entirely chemoselective for the internal allene π bond, and showed remarkable regioselectivity during the fluorination event. Substituted phenylallenes, phenylallenes possessing both phenyl- and α-allenyl substituents, and diphenylallenes were investigated, and good functional-group compatibility was observed throughout. The ease with which allenes can be prepared on a large scale, and the operational simplicity of this reaction allowed us to rapidly access fluorine-containing building blocks that have not been accessed by conventional deoxyfluorination strategies.

Iodothiocyanation/Nitration of Allenes with Potassium Thiocyanate/Silver Nitrite and Iodine

Direct strategies for the iodothiocyanation and iodonitration of allenes have been developed. In this process, potassium thiocyanate/silver nitrite and molecular iodine are used as the source of SCN, ONO2and iodine to provide the desired products in moderate to good yields with high stereoselectivity. (Figure presented.).

Cobalt-catalyzed asymmetric addition of silylacetylenes to 1,1-disubstituted allenes

The asymmetric addition of silylacetylenes to 1,1-disubstituted allenes proceeded in the presence of a cobalt/chiral bisphosphine ligand to give the corresponding enynes with high enantioselectivity. The results of deuterium-labeling experiments indicated

Lewis acid promoted reactions of ethenetricarboxylates with allenes: Synthesis of indenes and γ-lactones via conjugate addition/cyclization reaction

(Figure presented) Indenes are important core structures in organic chemistry. Few simple arylallenes have been used to construct indene skeletons by Friedel-Crafts reaction. Lewis acid catalyzed reaction of ethenetricarboxylates 1 and arylallenes has been examined in this study. The reaction of arylallenes and ethenetricarboxylate triesters with SnCl4 gave indene derivatives efficiently, via a conjugate addition/Friedel-Crafts cyclization reaction. On the other hand, the reactions of 1,1-diethyl 2-hydrogen ethenetricarboxylate and arylallenes or alkylallenes with SnCl4 at -78 °C or room temperature and subsequent treatment with Et3N gave γ-lactones. The reactions of triethyl ethenetricarboxylate and 1,1-dialkylallenes with SnCl4 at room temperature also gave γ-lactones.

Ruthenium catalyzed C-C bond formation via transfer hydrogenation: Branch-selective reductive coupling of allenes to paraformaldehyde and higher aldehydes

(Chemical Equation Presented) Under the conditions of ruthenium-catalyzed transfer hydrogenation employing 2-propanol as the terminal reductant, 1,1-disubstituted allenes 1a-h engage in reductive coupling to paraformaldehyde to furnish homoallylic alcohol