15499-27-1

Usage

Uses

Used in Chemical Synthesis:
4-N-Butylchlorobenzene is used as a chemical intermediate for the synthesis of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable component in the production of a wide array of chemicals.
Used in Solvent Applications:
Due to its ability to dissolve in organic solvents, 4-N-Butylchlorobenzene is utilized as a solvent in various industrial processes. Its solubility properties make it suitable for use in applications where a stable and effective solvent is required.
Used in Polymer Production:
4-N-Butylchlorobenzene is employed in the production of polymers, where it serves as a key component in the synthesis of polymeric materials. Its chemical properties contribute to the formation of polymers with specific characteristics, such as durability and resistance to certain environmental conditions.
Used in Pesticide Manufacturing:
In the agricultural industry, 4-N-Butylchlorobenzene is used as a chemical intermediate in the manufacturing of pesticides. Its involvement in the synthesis of these compounds helps to create effective pest control products that protect crops and contribute to increased agricultural yields.
Used in Pharmaceutical Production:
4-N-Butylchlorobenzene also plays a role in the pharmaceutical industry, where it is used as a chemical intermediate in the production of various medications. Its contribution to the synthesis of pharmaceutical compounds aids in the development of new and improved drugs for the treatment of various medical conditions.
Safety Precautions:
It is important to handle 4-N-Butylchlorobenzene with caution, as it is considered to be harmful if swallowed, inhaled, or exposed to the skin. Proper safety measures, such as wearing protective clothing and using appropriate containment and ventilation systems, should be implemented to minimize the risk of exposure and potential health hazards.

InChI:InChI=1/C10H13Cl/c1-2-3-4-9-5-7-10(11)8-6-9/h5-8H,2-4H2,1H3

Upstream product

• 4981-63-9 4-n-butanoylchlorobenzene 
• 104-51-8 1-butylbenzene 
• 7647-01-0 hydrogenchloride 
• 106-39-8 bromochlorobenzene 
• 693-04-9 butyl magnesium bromide 
• 29540-84-9 4-chlorophenyl trifluoromethanesulfonate 
• 42930-39-2 n-butylzinc chloride 
• 106-48-9 4-chloro-phenol 
• 28788-62-7 4-butylbenzoyl chloride 
• 625-99-0 3-iodochlorobenzene 
• 3047-24-3 4-(p-chlorophenyl)-1-butene 
• 109-72-8 n-butyllithium 
• 106-46-7 para-dichlorobenzene 
• 92273-73-9 n-butylzinc bromide 

Downstream Products

• 26206-42-8 1-butyl-4-vinylbenzene 
• 145240-28-4 4-butylphenylboronic acid 
• 78888-05-8 N-(4-n-butylphenyl)benzenamine 
• 644-08-6 4-Methylbiphenyl 
• 37909-95-8 4-butylbiphenyl 
• 959229-19-7 (4-butylphenyl)-4-morpholinylmethanone 
• 104-51-8 1-butylbenzene 
• 1200-14-2 4-(n-butyl)benzaldehyde 
• 625458-85-7 2-(4-butylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 944662-84-4 4-butyl-N-(4-nitrophenyl)aniline 
• 512178-32-4 N-(4-butylphenyl)-2-nitroaniline 
• 334988-37-3 2-(4-n-butylphenyl)pyridine 
• 137273-36-0 N-methyl-4-n-butylaniline 
• 20651-69-8 methyl 4-(n-butyl)benzoate 

Relevant academic research and scientific papers

Efficient Pd-Catalyzed Direct Coupling of Aryl Chlorides with Alkyllithium Reagents

Organolithium compounds are amongst the most important organometallic reagents and frequently used in difficult metallation reactions. However, their direct use in the formation of C?C bonds is less established. Although remarkable advances in the coupling of aryllithium compounds have been achieved, Csp2?Csp3 coupling reactions are very limited. Herein, we report the first general protocol for the coupling or aryl chlorides with alkyllithium reagents. Palladium catalysts based on ylide-substituted phosphines (YPhos) were found to be excellently suited for this transformation giving high selectivities at room temperature with a variety of aryl chlorides without the need for an additional transmetallation reagent. This is demonstrated in gram-scale synthesis including building blocks for materials chemistry and pharmaceutical industry. Furthermore, the direct coupling of aryllithiums as well as Grignard reagents with aryl chlorides was also easily accomplished at room temperature.

Gram-Scale, Cheap, and Eco-Friendly Iron-Catalyzed Cross-Coupling between Alkyl Grignard Reagents and Alkenyl or Aryl Halides

A new robust methodology for gram-scale iron-catalyzed cross-coupling between alkyl Grignard reagents and alkenyl or aryl halides is developed. This method does not require toxic additives such as NMP or expensive ligands. Its efficiency relies on the use of simple alkoxide magnesium salts as additives. On the basis of these results, a new procedure for one-pot synthesis of substituted benzamides from chloroesters is also proposed.

Water and Sodium Chloride: Essential Ingredients for Robust and Fast Pd-Catalysed Cross-Coupling Reactions between Organolithium Reagents and (Hetero)aryl Halides

Direct palladium-catalysed cross-couplings between organolithium reagents and (hetero)aryl halides (Br, Cl) proceed fast, cleanly and selectively at room temperature in air, with water as the only reaction medium and in the presence of NaCl as a cheap additive. Under optimised reaction conditions, a water-accelerated catalysis is responsible for furnishing C(sp3)–C(sp2), C(sp2)–C(sp2), and C(sp)–C(sp2) cross-coupled products, in competition with protonolysis, within a reaction time of 20 s, in yields of up to 99 %, and in the absence of undesired dehalogenated/homocoupling side products even when challenging secondary organolithiums serve as the starting material. It is worth noting that the proposed protocol is scalable and the catalyst and water can easily and successfully be recycled up to 10 times, with an E-factor as low as 7.35.

Murahashi Cross-Coupling at ?78 °C: A One-Pot Procedure for Sequential C?C/C?C, C?C/C?N, and C?C/C?S Cross-Coupling of Bromo-Chloro-Arenes

The coupling of organolithium reagents, including strongly hindered examples, at cryogenic temperatures (as low as ?78 °C) has been achieved with high-reactivity Pd-NHC catalysts. A temperature-dependent chemoselectivity trigger has been developed for the selective coupling of aryl bromides in the presence of chlorides. Building on this, a one-pot, sequential coupling strategy is presented for the rapid construction of advanced building blocks. Importantly, one-shot addition of alkyllithium compounds to Pd cross-coupling reactions has been achieved, eliminating the need for slow addition by syringe pump.

Modular Functionalization of Arenes in a Triply Selective Sequence: Rapid C(sp2) and C(sp3) Coupling of C?Br, C?OTf, and C?Cl Bonds Enabled by a Single Palladium(I) Dimer

Full control over multiple competing coupling sites would enable straightforward access to densely functionalized compound libraries. Historically, the site selection in Pd0-catalyzed functionalizations of poly(pseudo)halogenated arenes has been unpredictable, being dependent on the employed catalyst, the reaction conditions, and the substrate itself. Building on our previous report of C?Br-selective functionalization in the presence of C?OTf and C?Cl bonds, we herein complete the sequence and demonstrate the first general arylations and alkylations of C?OTf bonds (in I dimer. This allowed the realization of the first general and triply selective sequential C?C coupling (in 2D and 3D space) of C?Br followed by C?OTf and then C?Cl bonds.

Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides

This report describes a method for Pd-catalyzed decarbonylative cross-coupling that enables the conversion of carboxylic acid derivatives to biaryls, aryl amines, aryl ethers, aryl sulfides, aryl boronate esters, and trifluoromethylated arenes. The success of this transformation leverages the Pd0/Brettphos-catalyzed decarbonylative chlorination of aroyl chlorides, which can then participate in diverse cross-coupling reactions in situ using the same Pd catalyst.

Preparation of arylmagnesium/lithium from aryl bromides and their coupling and substitution reactions in tetrahydrofuran

One-pot synthesis of 2-aryltetrahydrofurans was achieved by a coupling reaction between arylmagnesium bromides prepared in situ and tetrahydrofuran under mild conditions. The reaction between ArBr and n-BuLi gave unexpected butylbenzene derivatives in mod

Amino acid-promoted C-H alkylation with alkylboronic acids using a removable directing group

Palladium-catalyzed C-H alkylation reaction with alkylboronic acids has successfully been developed using a removable pyridyldiisopropylsilyl directing group. The amino acid played a crucial role as a ligand in the reaction. The alkylation protocol is also applicable to the coupling of C(sp3)-H bonds with alkylboronic acids.

Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)3 and NaBH4

An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron(iii) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH4, in ethanol, under ambient conditions. This reaction has been applied to the reduction of terminal alkenes (22 examples, up to 95% yield) and nitro-groups (26 examples, up to 95% yield). Deuterium labelling studies indicate that this reaction proceeds via an ionic rather than radical mechanism.