4195-17-9

Basic information

• Product Name: 4-NITROPHENYL TRIMETHYLACETATE
• Synonyms: 4-NITROPHENYL PIVALATE;4-NITROPHENYL TRIMETHYLACETATE;p-nitrophenyl pivalate;4-Nitrophenyl trimethylacetate, 98+%;Propanoic acid, 2,2-dimethyl-, 4-nitrophenyl ester;4-Nitrophenylacetic acid trimethyl ester;2,2-Dimethylpropionic acid p-nitrophenyl;2,2-Dimethylpropionic acid p-nitrophenyl ester
• CAS NO: 4195-17-9
• Molecular Formula: C₁₁H₁₃NO₄
• Molecular Weight: 223.23
• EINECS: 224-076-1
• Product Categories: Acetics acid and esters;Building Blocks;C10 to C11;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks
• Mol File: 4195-17-9.mol

Chemical Properties

• Melting Point: 92-95 °C(lit.)
• Boiling Point: 364.51°C (rough estimate)
• Flash Point: 136.5 °C
• Appearance: light yellow crystalline powder
• Density: 1.2446 (rough estimate)
• Vapor Pressure: 0.000258mmHg at 25°C
• Refractive Index: 1.4960 (estimate)
• CAS DataBase Reference: 4-NITROPHENYL TRIMETHYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITROPHENYL TRIMETHYLACETATE(4195-17-9)
• EPA Substance Registry System: 4-NITROPHENYL TRIMETHYLACETATE(4195-17-9)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 24/25-36/37
• WGK Germany: 3
• Hazardous Substances Data: 4195-17-9(Hazardous Substances Data)

Usage

Uses

Used in Enzyme Research:
4-Nitrophenyl trimethylacetate is used as a sensitive probe for studying the catalytic activity of carboxypeptidase Y, an enzyme involved in various biological processes.
Used in Pharmaceutical Industry:
4-Nitrophenyl trimethylacetate serves as a valuable compound in the development of drug delivery systems and enzyme inhibitors, contributing to advancements in pharmaceutical research and drug design.
Used in Chemical Synthesis:
As a light yellow crystalline powder, 4-Nitrophenyl trimethylacetate can be utilized as an intermediate in the synthesis of various chemical compounds, particularly in the fields of organic chemistry and medicinal chemistry.

InChI:InChI=1/C11H13NO4/c1-11(2,3)10(13)16-9-6-4-8(5-7-9)12(14)15/h4-7H,1-3H3

Upstream product

• 100-02-7 4-nitro-phenol 
• 3282-30-2 pivaloyl chloride 
• 32707-03-2 thallium(I) 4-nitrophenoxide 
• 18997-19-8 Chloromethyl pivalate 
• 1014-66-0 trimethyl(4-nitrophenoxy)silane 
• 37170-49-3 trimethylsilyl 2,2-dimethylpropionate 
• 4920-92-7 pivalic acid phenyl ester 
• 69515-74-8 mitomycin-C 
• 159857-66-6 Carbonic acid 4-((S)-2-{(S)-2-[6-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-hexanoylamino]-3-phenyl-propionylamino}-6-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-hexanoylamino)-benzyl ester 4-nitro-phenyl ester 
• 75-98-9 Trimethylacetic acid 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 108-95-2 phenol 

Downstream Products

• 100-02-7 4-nitro-phenol 
• 14609-74-6 p-nitrophenolate 
• 75-98-9 Trimethylacetic acid 
• 14278-30-9 N-isopropyl-2,2-dimethylpropanamide 
• 686-96-4 N-tert-butyltrimethylacetamide 
• 27069-03-0 N-butyl-2,2-dimethylpropanamide 
• 120226-55-3 N-pivaloyl-p-chlorophenylmethylamine 
• 120226-49-5 N-(4-methoxybenzyl)pivalamide 
• 26209-45-0 N-benzyl-2,2-dimethylpropanamide 
• 14909-78-5 tert-butyl hydroperoxide 
• 34949-25-2 pivalate de methyle d3 
• 354116-64-6 C-methoxy-N-(4-trimethylacetyloxyphenyl)hydroxamic acid 
• 354116-65-7 C-methoxy-N-(4'-trimethylacetyloxyphenyl)-O-(2-phenylsulfanylpropanoyl)hydroxamic acid 
• 354116-69-1 5-(2,2-dimethyl-propionyloxy)-3-methyl-2-oxo-3-phenylsulfanyl-2,3-dihydro-indole-1-carboxylic acid methyl ester 

Relevant articles and documents

Efficient mitomycin C coupling with stable p-nitrophenyl-benzyl carbonates using N-hydroxybenzotriazole as a catalytic additive

Mitomycin C benzyl carbamates were prepared in high yield from stable p-nitrophenyl carbonates in the presence of catalytic amounts of 1-hydroxybenzotriazole/diisopropylethylamine in DMF.

Regioselective Ortho‐C–H sulfenylation of free phenols catalyzed by Co(II)-immobilized on silica-coated magnetic nanoparticles

Fe3O4?SiO2-UT?CoII is prepared by the silica-coated magnetic nanoparticles, urea-triazole, and CoCl2. This organic-inorganic hybride composite showed a good to excellent catalytic activity toward regioselective ortho-sulfenylation of free phenols and naphthols using pivalic anhydride as a directing group, also K2S2O8 and PPh3 were employed as oxidant and additive respectively. The newly synthesized catalyst was fully characterized by using different techniques such as FT-IR, TGA, DTG, TEM, SEM, EDS, ICP and VSM analyses. The competitive price, accessibility and lower toxicity of cobalt compared to expensive transition metals using for C–H bond activation and functionalization constitute precious advantages for this method. Moreover, this heterogeneous catalyst could be magnetically recovered and reused without significant loss of its catalytic activity after five cycles.

Enantioselective, Lewis Base-Catalyzed, Intermolecular Sulfenoamination of Alkenes

A method for the catalytic, enantioselective, intermolecular, 1,2-sulfenoamination of alkenes is described. Functionalization is achieved through the intermediacy of an enantioenriched, configurationally stable thiiranium ion generated by Lewis base activation of a readily available sulfur electrophile. A diverse set of anilines and benzylamines react with different styrenes to afford products in good yield and stereoselectivity. Downstream manipulation of the products is facilitated by deprotonation of the amines to enable carbon-sulfur bond cleavage.

4-(N,N -dimethylamino)pyridine hydrochloride as a recyclable catalyst for acylation of inert alcohols: Substrate scope and reaction mechanism

4-(N,N-Dimethylamino)pyridine hydrochloride (DMAP·HCl), a DMAP salt with the simplest structure, was used as a recyclable catalyst for the acylation of inert alcohols and phenols under base-free conditions. The reaction mechanism was investigated in detail for the first time; DMAP·HCl and the acylating reagent directly formed N-acyl-4-(N′,N′-dimethylamino) pyridine chloride, which was attacked by the nucleophilic substrate to form a transient intermediate that released the acylation product and regenerated the DMAP·HCl catalyst.

Erbium(III) chloride: A very active acylation catalyst

Erbium(iii) chloride is a powerful catalyst for the acylation of alcohols and phenols. The reaction works well for a large variety of simple and functionalized substrates by using different kinds of acidic anhydrides (Ac 2O, (EtCO)2O, (PriCO)2O, (Bu tCO)2O, and (CF3CO)2), without isomerization of chiral centres. Moreover, the catalyst can be easily recycled and reused without significant loss of activity. CSIRO 2007.

Magnesium bistrifluoromethanesulfonimide as a new and efficient acylation catalyst

Magnesium bistrifluoromethanesulfonimide catalyzed the acetylation of phenols, alcohols, and thiols under solvent-free conditions at room temperature and in short times. Electron-deficient and sterically hindered phenols provided excellent yields. The catalyst was found to be general for acylation with other anhydrides, such as propionic, isobutyric, pivalic, chloroacetic, and benzoic anhydrides. The rate of acylation was influenced by the electronic and steric factors associated with the anhydride. The reaction with less electrophilic anhydrides (e.g., chloroacetic and benzoic anhydrides) required higher temperature (～80 °C). Chemoselective acetylation, pivalation, and benzoylation took place with acid-sensitive alcohols without any competitive dehydration/rearrangement.

Erbium(III) triflate as an extremely active acylation catalyst

Erbium(III) triflate is a powerful catalyst for the acylation of alcohols and phenols. The reaction works well for a large variety of simple and functionalized substrates by using different kinds of acidic anhydrides {Ac 2O, (EtCO)2O, [(CH3)3CO] 2O, Bz2O, and (CF3CO)2O} without isomerisation of chiral centres. Moreover, the catalyst can be easily recycled and reused without significant loss of activity.

Fluoroboric acid adsorbed on silica gel as a new and efficient catalyst for acylation of phenols, thiols, alcohols, and amines

Fluoroboric acid supported on silica gel efficiently catalyzes acylation of structurally diverse phenols, alcohols, thiols, and amines under solvent free conditions. Acid-sensitive alcohols are smoothly acylated without competitive side reactions.

Kinetics and mechanism of aminolysis of phenyl acetates and phenyl trimethylacetates in dimethyl suldoxide

Kinetic studies have been carried out on the reactions of phenyl acetates and phenyl trimethylacetates in dimethyl sulfoxide.The rate ratios between the two acyl compounds, and the positive sign and large magnitude of the cross-interaction constants, ρXZ, between substituents X in the nucleophile and Z in the leaving group are considered to favour the rate-limiting expulsion of aryl oxide from the tetrahedral intermediate T+/-.The aprotic solvent used makes the proposed mechanism with a cyclic transition state more attractive especially in view of the greater charge dispersion and assistance to leaving group departure provided in such a structure.

Ozone-mediated Reaction of Anilides and Phenyl Esters with Nitrogen Dioxide: Enhanced Ortho-reactivity and Mechanistic Implications

In the presence of ozone, anilides 1 can be nitrated rapidly with nitrogen dioxide in chloroform at 0 deg C to give a high proportion of ortho-nitro derivatives (ortho:para = 1.2-4.4) in good yields.The phenyl esters 15 can be similarly nitrated on the aromatic ring without significant cleavage of the ester bond, giving a mixture of isomeric nitro derivatives in which the ortho-isomer predominantes (ortho:para = 1.1-1.5).The oridin of the enhanced ortho reactivity is discussed in terms of an electron-transfer process involving the nitrogen trioxide as initial electrophile.