17175-16-5

Usage

Uses

Used in Organic Synthesis:
Methyl-4-nitrophenylcarbonate is used as a reagent for the protection of amines in organic synthesis, providing a means to temporarily shield amines from unwanted reactions, thus facilitating the selective synthesis of complex organic compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, Me-4-NPC is utilized in the synthesis of various drugs, contributing to the development of new medicinal compounds and enhancing the range of available treatments.
Used in Agrochemical Production:
Methyl-4-nitrophenylcarbonate is employed in the production of agrochemicals, where it plays a role in the creation of pesticides and other agricultural chemicals that are essential for crop protection and yield enhancement.
Used in Dye Production:
In the dye industry, Me-4-NPC is used in the synthesis of dyes, contributing to the development of a diverse palette of colorants for various applications, including textiles, plastics, and printing inks.

InChI:InChI=1/C8H7NO5/c1-13-8(10)14-7-4-2-6(3-5-7)9(11)12/h2-5H,1H3

Upstream product

• 13509-27-8 methyl phenyl carbonate 
• 100-02-7 4-nitro-phenol 
• 79-22-1 methyl chloroformate 
• 67-56-1 methanol 
• 5070-13-3 bis-(p-nitrophenyl) carbonate 
• 14442-54-7 methyl-nitro-carbamic acid methyl ester 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 190664-22-3 2-methoxy-5,5-dimethyl-2-(4-nitrophenoxy)-Δ³-1,3,4-oxadiazoline 
• 7697-37-2 nitric acid 

Downstream Products

• 160350-17-4 (S)-1-Oxo-2-aza-spiro[4.5]deca-6,9-diene-2,3-dicarboxylic acid 3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl) ester 2-methyl ester 
• 100-17-4 para-methoxynitrobenzene 
• 1847-96-7 methyl 3-chlorophenyl carbonate 
• 1124-31-8 potassium 4-nitrophenolate 
• 36919-03-6 methyl pentafluorophenyl carbonate 
• 17175-18-7 methyl 4-cyanophenyl carbonate 
• 22159-41-7 methyl 4-methoxyphenyl carbonate 
• 1796-27-6 piperidine-1-carboxylic acid methyl ester 
• 14609-74-6 p-nitrophenolate 
• 6906-13-4 morpholine-4-carboxylic acid methyl ester 
• 50606-31-0 methyl piperazine-1-carboxylate 
• 100-02-7 4-nitro-phenol 
• 1284216-81-4 6,3',2'',5'',3''', 4'''-hexa-O-methoxycarbonyl-4',6'-benzylidene-per-N-Cbz-paromomycin 

Relevant academic research and scientific papers

Carbonic anhydrase catalyzed hydrolysis and decarboxylation. Kinetic studies of enzyme catalyzed decomposition of mono- and disubstituted derivatives of carbonic acid

The effect of bovine carbonic anhydrase on the stepwise hydrolysis of carbonate diesters is examined. While biphasic enzyme kinetics cannot be detected in the case of bis(4 nitrophenyl) carbonate, it is demonstrated that at pH 10.45 methyl 4 nitrophenyl carbonate is enzymatically hydrolyzed to produce an intermediate monoester, methyl carbonate, which does not undergo enzyme catalyzed decarboxylation. However, it is shown that at pH 7.27 methyl carbonate decarboxylation is accelerated by carbonic anhydrase. The enzymatic pH rate profile for methyl 4 nitrophenyl carbonate release of 4 nitrophenol rises with increasing pH, while the pH dependency for the enzyme catalyzed decarboxylation of methyl carbonate is such that it decreases with increasing pH. In this respect, the kinetic behavior of bovine carbonic anhydrase in regard to methyl 4 nitrophenyl carbonate hydrolysis appears to be similar to that observed in CO2 hydration; in both the rate varies as though dependent on the ionization of a group in the enzyme with pK near 7, only the basic form being active. On the other hand the enzyme catalyzed decarboxylation of methyl carbonate appears to be formally similar to that of bicarbonate; with these two anions the rate varies as though dependent on the ionization of a group in the enzyme of essentially the same pK(7) with only the acid form being active. Although at pH 7.27 the first order rate coefficient, k(buf), for methyl carbonate decomposition is 1.8 times larger than that for bicarbonate dehydration, the second order enzymatic rate coefficient, k(enz), for bicarbonate is three orders of magnitude greater than that for methyl carbonate. The large differences in these k(enz) values are discussed in terms of the role of the labile bicarbonate proton in the mechanism of carbonic anhydrase catalysis.

A mechanistic study of the [La2(OCH3) 2]4+-and [(1,5,9-triazacyclodo-decane):Zn:(OCH 3)]+-catalyzed methanolysis of carbonates: Possible application for the recycling of bisphenol A polycar

The kinetics of the methanolysis of seven methyl aryl carbonates (3) and two methyl alkyl carbonates (4) promoted by [12[ane]N3:Zn:(OCH 3)]+ and [La2(OCH3) 2]4+ catalysts (1 and 2, respecti

PROTEASE INHIBITORS HAVING ENHANCED FEATURES

Provided herein (among other things) are protease inhibitor compounds having enhanced features, along with methods for administering such compounds. For example, the subject compounds can be administered without concomitant administration of a CYP3A4 inhibitor, have increased therapeutic index and/or increased potency, and are low-resistance inducing in nature.

Indium-catalyzed reaction for the synthesis of carbamates and carbonates: selective protection of amino groups

We developed a simple, efficient, and selective method for preparing organic carbamates and carbonates using a catalytic amount of indium. A wide range of carbamates and carbonates were synthesized in high yields. The method is also applicable to the selective protection of amino groups under mild conditions.

Bisbenzamidines and bisbenzamidoximes for the treatment of human African trypanosomiasis

Disclosed are bisbenzamidine and bisbenzamidoxime compounds useful for treatment of treatment of trypanosomiasis. The compounds disclosed are useful for treating mammals infected with parasitic hemoflagellates, in particular Trypanosoma brucei gambiense and Trypanosoma brucei rhodesiense.

Novel prodrugs for antimicrobial amidines

A methods of treating an infection comprises administering a therapeutically effective amount of a compound described by the Formula (I): wherein: X may be O, S, or NR′ wherein R′ is H or loweralkyl; R1 and R2 may be independently selected from the group consisting of H, loweralkyl, oxyalkyl, alkoxyalkyl, cycloalkyl, aryl, hydroxyalkyl, aminoalkyl, and alkylaminoalkyl; R3 and R4 are each independently selected from the group consisting of H, loweralkyl, halogen, oxyalkyl, oxyaryl, and oxyarylalkyl; R5 is represented by a formula selected from the group consisting of: ?wherein: X1, X2, and X3 are independently selected from O and S; and R6 and R7 are independently selected from the group consisting of loweralkyl, aryl, alkylaryl, oxyaryl, an ester-containing substituent, and oxyalkyl; or a pharmaceutically acceptable salt thereof.

Prodrugs for amidines: Synthesis and anti-Pneumocystis carinii activity of carbamates of 2,5-bis(4-amidinophenyl)furan

Syntheses of several carbamate analogues of 2,5-bis(4- amidinophenyl)furan (1) under mild conditions and their evaluation as prodrugs against Pneumocystis carinii pneumonia (PCP) in an immunosuppressed rat model are described. Thus, nine new bis-carbamates: methoxycarbonyl (2), 2,2,2-trichloroethoxycarbonyl (3), ethylthiocarbonyl (4), benzyloxycarbonyl (5), (4-methyl-2-oxo-1,3-dioxol-4-en-5-yl)methoxycarbonyl (6), phenoxycarbonyl (7), 4-fluorophenoxycarbonyl (8), 4-methoxyphenoxycarbonyl (9), and (1-acetoxy)ethoxycarbonyl (10) and a biscarbonate ethoxycarbonyloxy (1) of the bis-amidine 1 have been synthesized and evaluated. The in vivo results show that the 4-fluorophenyl carbamate 8 and the 4-methoxyphenyl carbamate 9 in this series had the best anti-PCP activity by both intravenous and oral administration at a dosage level of 22 mol and 33 μmol/kg/day, respectively. Compounds 3-7 were also more active than the parent drug (1) on oral administration. The acute toxicity usually exhibited by the parent amidine 1 at a dosage level of 22 μmol/kg/day on intravenous administration has been significantly reduced by the prodrug modifications, with the exception of compound 10 which exhibited some toxicity. This report also describes the synthesis of several aryl-alkyl and aryl-aryl carbonates (12- 14, 16-23) as efficient reagents for the preparation of carbamate derivatives from bis-arylamidines.

Synthesis and evaluation of 2-amino-9-(3-acyloxymethyl-4-alkoxycarbonyloxybut-1-yl)purines and 2-Amino-9-(3-alkoxycarbonyloxymethyl-4-alkoxycarbonyloxybut-1-yl)purines as potential prodrugs of penciclovir

A series of 2-amino-9-(3-acyloxymethyl-4-alkoxycarbonyloxybut-1-yl)purines (1-8) and 2-amino-9-(3-alkoxycarbonyl- oxymethyl-4-alkoxycarbonyloxybut-1-yl)purines (9-12) were synthesized as potential prodrugs of penciclovir. Treatment of 6- deoxypenciclovir

Stoichiometric solvation effects. Part 3. Product-rate correlations for solvolyses of p-nitrophenyl chloroformate in alcohol-water mixtures

Rate constants for solvolyses of p-nitrophenyl chloroformate in water, D2O, CH3OD, 50% D2O-CH3OD, and in aqueous binary mixtures of acetone, acetonitrile, ethanol and methanol are reported at 25°C. Product selec

Ketene acetals from thermolysis of aryloxy methoxy oxadiazolines. Evidence for carbonyl ylide intermediates

Thermolysis of oxadiazolines (5) in benzene at 110°C leads to ketene acetals (11) as minor products. Carbonyl ylide intermediates (6), and oxiranes (7), presumably in equilibrium with those ylides, are implicated as unstable precursors of the ketene aceta