3047-24-3

Usage

Uses

Used in Pharmaceutical Industry:
4-P-Chlorophenyl-1-butene is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its aromatic and unsaturated structure makes it a valuable component in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical industry, 4-P-Chlorophenyl-1-butene is utilized as an intermediate in the production of herbicides and insecticides, contributing to the development of effective crop protection agents.
Used in Specialty Chemicals Production:
4-P-Chlorophenyl-1-butene is employed as a building block in the synthesis of specialty chemical products, leveraging its unique chemical properties to create innovative and high-value compounds for various applications.

InChI:InChI=1/C10H11Cl/c1-2-3-4-9-5-7-10(11)8-6-9/h2,5-8H,1,3-4H2

Upstream product

• 107323-82-0 4-chlorobenzylmagnesium bromide 
• 106-95-6 allyl bromide 
• 5162-44-7 1-bromo-4-butene 
• 106-46-7 para-dichlorobenzene 
• 622-95-7 4-chlorobenzyl bromide 
• 1730-25-2 allylmagnesium bromide 
• 104-88-1 4-chlorobenzaldehyde 
• 346713-20-0 allylsamarium bromide 
• 107-05-1 3-chloroprop-1-ene 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 75677-02-0 3-(4-chlorophenyl)propionaldehyde 
• 6282-88-8 3-(p-chlorophenyl)propanol 
• 2019-34-3 3-(4-chlorophenyl)propanoic acid 
• 591-87-7 Allyl acetate 

Downstream Products

• 15451-35-1 4-(but-3-en-1-yl)benzoic acid 
• 59363-17-6 1,2-Epoxy-4-(4-chlorophenyl)butane 
• 53332-81-3 4-(4-Chlormethylphenyl)-1-buten 
• 49853-97-6 -<4-(4-chlormethylphenyl)butyl>dimethylsilan 
• 53332-82-4 -<4-(4-chlormethylphenyl)butyl>methylsilan 
• 1010685-85-4 C₁₆H₁₆Cl₂ 
• 1010685-84-3 C₁₆H₁₆Cl₂ 
• 161725-12-8 5-(4-chlorophenyl)pentanoic acid 
• 1351520-86-9 1-(4-chlorophenyl)-4-deuteriobutane 
• 160341-87-7 1-(4-chlorophenyl)-4-iodobutane 
• 1351520-90-5 5-(4-chlorophenyl)-1-phenylpentan-1-ol 
• 1074764-88-7 trans-1-(but-2-en-1-yl)-4-chlorobenzene 
• 18654-73-4 1-[(E)-(but-1-en-1-yl)]-4-chlorobenzene 
• 19967-22-7 4-(p-chlorophenyl)-1-butanol 

Relevant academic research and scientific papers

Ni-Catalyzed Carboxylation of Aziridines en Route to β-Amino Acids

A Ni-catalyzed reductive carboxylation of N-substituted aziridines with CO2 at atmospheric pressure is disclosed. The protocol is characterized by its mild conditions, experimental ease, and exquisite chemo- and regioselectivity pattern, thus unlocking a new catalytic blueprint to access β-amino acids, important building blocks with considerable potential as peptidomimetics.

Enantioselective Intermolecular C-H Amination Directed by a Chiral Cation

The enantioselective amination of C(sp3)-H bonds is a powerful synthetic transformation yet highly challenging to achieve in an intermolecular sense. We have developed a family of anionic variants of the best-in-class catalyst for Rh-catalyzed C-H amination, Rh2(esp)2, with which we have associated chiral cations derived from quaternized cinchona alkaloids. These ion-paired catalysts enable high levels of enantioselectivity to be achieved in the benzylic C-H amination of substrates bearing pendant hydroxyl groups. Additionally, the quinoline of the chiral cation appears to engage in axial ligation to the rhodium complex, providing improved yields of product versus Rh2(esp)2 and highlighting the dual role that the cation is playing. These results underline the potential of using chiral cations to control enantioselectivity in challenging transition-metal-catalyzed transformations.

Access to Trisubstituted Fluoroalkenes by Ruthenium-Catalyzed Cross-Metathesis

Although the olefin metathesis reaction is a well-known and powerful strategy to get alkenes, this reaction remained highly challenging with fluororalkenes, especially the Cross-Metathesis (CM) process. Our thought was to find an easy accessible, convenient, reactive and post-functionalizable source of fluoroalkene, that we found as the methyl 2-fluoroacrylate. We reported herein the efficient ruthenium-catalyzed CM reaction of various terminal and internal alkenes with methyl 2-fluoroacrylate giving access, for the first time, to trisubstituted fluoroalkenes stereoselectively. Unprecedent TON for CM involving fluoroalkene, up to 175, have been obtained and the reaction proved to be tolerant and effective with a large range of olefin partners giving fair to high yields in metathesis products. (Figure presented.).

Controllable Isomerization of Alkenes by Dual Visible-Light-Cobalt Catalysis

We report herein that thermodynamic and kinetic isomerization of alkenes can be accomplished by the combination of visible light with Co catalysis. Utilizing Xantphos as the ligand, the most stable isomers are obtained, while isomerizing terminal alkenes over one position can be selectively controlled by using DPEphos as the ligand. The presence of the donor–acceptor dye 4CzIPN accelerates the reaction further. Transformation of exocyclic alkenes into the corresponding endocyclic products could be efficiently realized by using 4CzIPN and Co(acac)2 in the absence of any additional ligands. Spectroscopic and spectroelectrochemical investigations indicate CoI being involved in the generation of a Co hydride, which subsequently adds to alkenes initiating the isomerization.

Umpolung of Carbonyl Groups as Alkyl Organometallic Reagent Surrogates for Palladium-Catalyzed Allylic Alkylation

Palladium-catalyzed allylic alkylation of nonstabilized carbon nucleophiles is difficult and remains a major challenge. Reported here is a highly chemo- and regioselective direct palladium-catalyzed C-allylation of hydrazones, generated from carbonyls, as a source of umpolung unstabilized alkyl carbanions and surrogates of alkyl organometallic reagents. Contrary to classical allylation techniques, this umpolung reaction utilizes hydrazones prepared not only from aryl aldehydes but also from alkyl aldehydes and ketones as renewable feedstocks. This strategy complements the palladium-catalyzed coupling of unstabilized nucleophiles with allylic electrophiles by providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.

Palladium-Catalyzed Electrochemical Allylic Alkylation between Alkyl and Allylic Halides in Aqueous Solution

A new route for the direct cross-coupling of alkyl and allylic halides using electrochemical technique has been developed in aqueous media under air. Catalyzed by Pd(OAc)2, the Zn-mediated allylic alkylations proceed smoothly between a full range of alkyl halides (primary, secondary, and tertiary) and substituted allylic halides. Protection-deprotection of acidic hydrogen in the substrates is avoided.

Monocarboxylation and intramolecular coupling of butenylated arenes via palladium-catalyzed C-H activation process

A novel and practical reaction for the direct intramolecular oxidative coupling of butenylated arenes is reported. With the catalysis of Pd(OAc)2, reactions of various butenylated arenes and carboxylic acids with Selectfluor reagent in CH3CN solution afforded the corresponding monocarboxylation/cyclization products in good yields under mild conditions. This research demonstrated an economic method with the synthesis of 2-tetralyl carboxylic esters, a valuable class of bioactive compounds.

Chemo-, regio-, and stereoselective iron-catalysed hydroboration of alkenes and alkynes

The highly chemo-, regio-, and stereoselective synthesis of alkyl- and vinyl boronic esters with good functional group tolerance has been developed using in situ activation of a bench-stable iron(ii) pre-catalyst and pinacolborane (16 examples, 45-95% yield, TOF up to 30000 mol h-1). The first iron-catalysed alkene hydrogermylation is also reported.

Dual role of allylsamarium bromide as a Grignard reagent and a single electron transfer reagent in the one-pot synthesis of terminal olefins

The utility of allylsamarium bromide, both as a nucleophilic reagent and a single-electron transfer reagent, in the reaction of carbonyl compounds with allylsamarium bromide in the presence of diethyl phosphate is reported in this communication. From a synthetic point of view, a simple one-pot method for the preparation of terminal olefins is developed.

Regioselective cross-coupling of allylindium reagents with activated benzylic bromides-a simple and efficient procedure for the synthesis of terminal alkenes

Allylindium reagents undergo facile and highly regioselective cross-coupling with benzylic and cinnamyl bromides in THF at room temperature without any catalyst producing terminal alkenes in high yields. The addition is highly regioselective and is found to provide γ-adducts in all reactions.