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Usage

Uses

Used in Pharmaceutical Synthesis:
N-(4-hydroxyphenyl)pivalamide is used as an intermediate in the pharmaceutical industry for the synthesis of various drugs. Its role as a protecting group for the phenolic hydroxyl group allows for the controlled modification of active pharmaceutical ingredients, enhancing the stability and efficacy of the final drug products.
Used in Dye Production:
In the dye industry, NHP is utilized as a key intermediate in the production of various dyes. Its chemical properties enable the creation of dyes with specific color characteristics and improved performance in different applications.
Used in Organic Synthesis:
N-(4-hydroxyphenyl)pivalamide is employed as a building block in organic synthesis across various chemical industries. Its versatility allows for the development of new organic compounds with diverse applications, including specialty chemicals, agrochemicals, and materials science.
As a Protecting Group in Chemical Reactions:
NHP serves as a protecting group for the phenolic hydroxyl group in various chemical reactions. This function is crucial in organic synthesis, as it allows chemists to temporarily mask the reactivity of the hydroxyl group, preventing unwanted side reactions and facilitating the synthesis of complex molecules with greater precision and control.

Upstream product

• 98-95-3 nitrobenzene 
• 3282-30-2 pivaloyl chloride 
• 100-65-2 N-Phenylhydroxylamine 
• 111750-22-2 N-phenyl-N-hydroxy-2,2-dimethylpropanamide 
• 123-30-8 4-amino-phenol 
• 75-98-9 Trimethylacetic acid 
• 6625-74-7 N-pivaloylaniline 
• 138459-91-3 3-pivaloyl-1,3-thiazolidine-2-thione 

Downstream Products

• 6625-74-7 N-pivaloylaniline 

Relevant academic research and scientific papers

Redox-Neutral Selenium-Catalysed Isomerisation of para-Hydroxamic Acids into para-Aminophenols

A selenium-catalysed para-hydroxylation of N-aryl-hydroxamic acids is reported. Mechanistically, the reaction comprises an N?O bond cleavage and consecutive selenium-induced [2,3]-rearrangement to deliver para-hydroxyaniline derivatives. The mechanism is studied through both 18O-crossover experiments as well as quantum chemical calculations. This redox-neutral transformation provides an unconventional synthetic approach to para-aminophenols.

Fenretinide derivatives act as disrupters of interactions of serum retinol binding protein (sRBP) with transthyretin and the sRBP receptor

Serum retinol binding protein (sRBP) is released from the liver as a complex with transthyretin (TTR), a process under the control of dietary retinol. Elevated levels of sRBP may be involved in inhibiting cellular responses to insulin and in generating first insulin resistance and then type 2 diabetes, offering a new target for therapeutic attack for these conditions. A series of retinoid analogues were synthesized and examined for their binding to sRBP and their ability to disrupt the sRBP-TTR and sRBP-sRBP receptor interactions. A number inhibit the sRBP-TTR and sRBP-sRBP receptor interactions as well as or better than Fenretinide (FEN), presenting a potential novel dual mechanism of action and perhaps offering a new therapeutic intervention against type 2 diabetes and its development. Shortening the chain length of the FEN derivative substantially abolished binding to sRBP, indicating that the strength of the interaction lies in the polyene chain region. Differences in potency against the sRBP-TTR and sRBP-sRBP receptor interactions suggest variant effects of the compounds on the two loops of sRBP guarding the entrance of the binding pocket that are responsible for these two protein-protein interactions.

Introduction of a hydroxy group at the para position and N-iodophenylation of N-arylamides using phenyliodine(III) bis(trifluoroacetate)

The reaction of anilides with phenyliodine(III) bis(trifluoroacetate) (PIFA) in trifluoroacetic acid (TFA), TFA-CHCl3, or hexafluoroisopropyl alcohol (HFIP) is described. When the acyl group of the anilide is highly electronegative, such as trifluoroacetyl, or the phenyl group is substituted with an electron-withdrawing group, the 4-iodophenyl group is transferred from PIFA to the amide nitrogen to afford acetyldiarylamines. On the other hand, when the acyl group contains an electron-donating function, such as 4-methoxyphenyl, or the phenyl group is substituted with an electron-donating group, a trifluoroacetoxy group is transferred to the para position of the anilide aromatic ring. This group is hydrolyzed during workup to produce the corresponding phenol.

Phosphorus in organic synthesis. Acyloxyphosphonium salts as chemoselective acylating reagents

Acyloxytriphenylphosphonium salts 1 prepared in situ react with a variety of aminophenols to give the corresponding amides in excellent yields. At -25°N-acylated products are formed exclusively, whereas 0°some O-acylated products are observed. 1 is also a

Highly chemoselective acylation of substituted aminophenols with 3-(trimethylacetyl)-1,3-thiazolidine-2-thione

A general procedure for chemoselective acylation of substituted aminophenols has been developed. The N-acetylated products 7 and 10a-h were prepared by treating the aminophenols with 3-(trimethylacetyl)-1,3-thiazolidine-2-thione (1) in refluxing THF in 70-100% yield. The esters 8 and 13d,b,j of 3- and 4-amino phenols could be obtained in 70-94% yield by treating with NaH and 1.

Herbicidal 2-[4-substituted carboxyamino-phenoxy (or phenyl mercapto)]-substituted pyrimidines

The novel substituted carboxylic acid anilides of the formula STR1 in which X represents oxygen or sulphur, R1 represents hydrogen, halogen, alkyl with 1 to 6 carbon atoms, trifluoromethyl, optionally substituted phenyl, alkoxy with 1 to 6 carb