65854-91-3

Usage

Uses

Used in Dye and Pigment Production:
4'-Chloropivaloanilide is used as a key intermediate in the synthesis of dyes and pigments, contributing to the development of colorants with specific properties for various applications.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 4'-Chloropivaloanilide is employed as a building block in the creation of new drugs, leveraging its chemical structure to enhance the therapeutic potential of medicinal compounds.
Used in Agrochemical Industry:
4'-Chloropivaloanilide is utilized in the formulation of agrochemicals, such as pesticides and herbicides, where its chemical properties can be harnessed to improve the effectiveness of these products in agricultural settings.
Used in Organic Synthesis:
As an intermediate in organic synthesis, 4'-Chloropivaloanilide is used to produce a range of organic compounds, expanding the scope of chemical research and development.

InChI:InChI=1/C11H14ClNO/c1-11(2,3)10(14)13-9-6-4-8(12)5-7-9/h4-7H,1-3H3,(H,13,14)

Upstream product

• 1634-04-4 tert-butyl methyl ether 
• 106-47-8 4-chloro-aniline 
• 3282-30-2 pivaloyl chloride 
• 100-00-5 4-chlorobenzonitrile 
• 26179-83-9 1-(1H-1,2,3-benzotriazol-1-yl)-2,2-dimethyl-1-propanone 
• 95-14-7 1,2,3-Benzotriazole 
• 75-98-9 Trimethylacetic acid 
• 75-84-3 2,2-dimethyl-propanol-1 
• 630-19-3 pivalaldehyde 
• 6625-74-7 N-pivaloylaniline 
• 1538-75-6 2,2-dimethylpropanoic anhydride 

Downstream Products

• 77422-76-5 C₁₈H₂₁ClN₄OS 
• 127472-35-9 N-(4-chloro-2-formylphenyl)-2,2-dimethylpropionamide 
• 1027078-04-1 2-(4'-chloro-N-t-butylcarbonyl)aniline-3-thienylmethanol 
• 80517-38-0 4-chloro-2-(3'-thienylcarbonyl)aniline 
• 91805-27-5 2-Bromo-N-[4-chloro-2-(thiophene-3-carbonyl)-phenyl]-acetamide 
• 1026556-46-6 4-chloro-2-(3'-thienylcarbonyl)-N-t-butylcarbonylaniline 
• 862646-44-4 N-[4-chloro-2-(4,4,4-trifluoro-3-methylbutyryl)-phenyl]-2,2-dimethylpropionamide 
• 185950-64-5 5-chloro-2-(pivaloylamino)benzeneboronic acid 
• 1262796-60-0 C₂₁H₂₀ClNO 
• 1007652-06-3 N-[4-chloro-2-(trifluoromethyl)phenyl]-2,2-dimethylpropanamide 
• 105192-42-5 (2-amino-5-chlorophenyl)(pyridin-4-yl)methanone 
• 907209-82-9 N-(4-chlorophenyl)-N-methyl pivalamide 
• 924708-78-1 2-(tert-butyl)-6-chlorobenzo[d]thiazole 
• 209414-27-7 (2S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol 

Relevant academic research and scientific papers

Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides

Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.

Equivalent Loading of Directed Arenes in Pd(II)-Catalyzed Oxidative Cross-Coupling of Aryl C-H Bonds at Room Temperature

The unsymmetrical biaryls (Ar1-Ar2) produced by the catalytic cross-couplings of aryl halides (Ar1-halo) with aryl metallics (Ar2-M) in the loading ratio of 1:1 are popular in chemical synthesis. In contrast, there has been less precedence on the same biaryls produced effectively from two normal aryl C-H bonds with equivalent loading. Here, we report that, in a palladium/oxidant/acid catalytic system at room temperature, one arene (Ar1-H, 1 equiv) can highly selectively couple with the other one (Ar2-H, 1 equiv) to afford the target Ar1-Ar2 just by controlling the directing groups and the substituted groups on their phenyl rings. The utility of this one-one cross-coupling is also demonstrated by synthesis of a few bioactive molecules.

Ligand Promoted Olefination of Anilides for Indirectly Introducing Fluorinated Functional Groups via Palladium Catalyst

We report a palladium-catalyzed, ligand promoted, C-H fluorine-containing olefination of anilides with 4-bromo-3,3,4,4-tetrafluorobutene as the fluorinated reagent, which has a potential transformation into other compounds due to its -CF2CF2Br functional group. -CF2CF2H was obtained by using the mild reducing agent sodium borohydride. Bioactive compounds such as aminoglutethimide derivative and propham were well-tolerated in this reaction, both of which highlight the synthetic importance of this method.

Benzylidene succinimides as 3C synthons for the asymmetric tandem Mannich reaction/transamidation of cyclic trifluoromethyl ketimines to obtain F3C-containing polycyclic dihydroquinazolinones

By taking advantage of benzylidene succinimides as a new class of 3C synthons, a highly diastereo- and enantioselective tandem Mannich reaction/transamidation has been established by reacting them with cyclic trifluoromethylN-acyl ketimines. Using aCinchonaalkaloid-derived squaramide as the catalyst, the tandem reaction proceeded smoothly under mild conditions and afforded a range of F3C-containing chiral polycyclic dihydroquinazolinones with excellent results (up to 99% yield, all cases >20?:?1 dr, up to 99% ee).

Meta Selective C-H Borylation of Sterically Biased and Unbiased Substrates Directed by Electrostatic Interaction

An electrostatically directed meta borylation of sterically biased and unbiased substrates is described. The borylation follows an electrostatic interaction between the partially positive and negative charges between the ligand and substrate. With this strategy, it has been demonstrated that a wide number of challenging substrates, especially 4-substituted substrates, can selectively be borylated at the meta position. Moreover, unsubstituted substrates also displayed excellent meta selectivity. The reaction employs a bench-stable ligand and proceeds at a milder temperature, precluding the need to synthesize a bulky and sophisticated ligand/template.

Room temperature clickable coupling electron deficient amines with sterically hindered carboxylic acids for the construction of amides

A method for the synthesis of difficult-to-access amides was developed through the coupling of sterically hindered carboxylic acids and electron deficient amines via SO2F2-mediated dehydration. The method feathers with broad substrate scope, mild conditions, excellent functional group compatibility and high yields.

Cu-Mediated Synthesis of Indolines and Dihydroisoquinolinones through Arylperfluoroalkylation of Unactivated Alkenes

The copper-mediated fluroalkylation/cyclization of N-allyl anilines has been described using fluoroalkyl iodides as fluoroalkylation reagents for the first time. The reaction provides an efficient and direct access to 3-fluoroalkyl indolines in moderate to good yields with unactivated double bonds as the radical acceptor. This protocol combines a simple experimental procedure with low-costing fluoroalkylated sources and excellent functional group tolerance.

Direct Amidation of Carboxylic Acids with Nitroarenes

N-Aryl amides are an important class of compounds in pharmaceutical and agrochemical chemistry. Rapid and low-cost synthesis of N-aryl amides remains in high demand. Herein, we disclose an operationally simple process to access N-aryl amides directly from readily available nitroarenes and carboxylic acids as coupling substrates. This method involves the in situ activation of carboxylic acids to acyloxyphosphonium salt for one-pot amidation, without the need for isolation of the corresponding synthetic intermediates. Furthermore, the ease of preparation and workup allow the quick and efficient synthesis of a wide range of N-aryl amides, including several amide-based druglike and agrochemical molecules.

Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer

Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.

General rhodium-catalyzed oxidative cross-coupling reactions between anilines: Synthesis of unsymmetrical 2,2′-diaminobiaryls

Described herein is a dual chelation-assisted RhCl3-catalyzed oxidative C-H/C-H cross-coupling reaction of aniline derivatives. The highlight of this methodology is the chemo- and regioselective cross-coupling between electronically similar substrates, which represents a highly challenging task in oxidative Ar-H/Ar-H cross-coupling reactions. Furthermore, this Cp?-free catalytic reaction tolerates a range of functional groups and requires only a low molar ratio of coupling partners. These features expedite the synthesis of unsymmetrical 2,2′-diaminobiaryls.