13683-89-1

Usage

Uses

Used in Pharmaceutical Industry:
METHYL (3-HYDROXYPHENYL)CARBAMATE is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
METHYL (3-HYDROXYPHENYL)CARBAMATE is used as an active ingredient in pesticide formulations, providing insecticidal and fungicidal properties to protect crops and enhance agricultural productivity.
Used in Neurological Treatments:
METHYL (3-HYDROXYPHENYL)CARBAMATE is being investigated for its potential use in the treatment of neurological disorders, offering a new avenue for research and development in the medical field.
Used as an Anticonvulsant:
METHYL (3-HYDROXYPHENYL)CARBAMATE is being explored for its potential as an anticonvulsant, which could be beneficial in managing conditions such as epilepsy and other seizure disorders.

InChI:InChI=1/C8H9NO3/c1-12-8(11)9-6-3-2-4-7(10)5-6/h2-5,10H,1H3,(H,9,11)

Upstream product

• 554-84-7 meta-nitrophenol 
• 79-22-1 methyl chloroformate 
• 591-27-5 m-Hydroxyaniline 
• 2603-10-3 N-phenyl methyl carbamate 

Downstream Products

• 23122-15-8 (2,4-Dimethoxy-phenyl)-carbamic acid 3-methoxycarbonylamino-phenyl ester 
• 23121-98-4 [3-(2-Chloro-2-methyl-propylcarbamoyloxy)-phenyl]-carbamic acid methyl ester 
• 23122-48-7 (3-Chloro-2-methyl-phenyl)-carbamic acid 3-methoxycarbonylamino-phenyl ester 
• 23122-16-9 (5-Chloro-2-methyl-phenyl)-carbamic acid 3-methoxycarbonylamino-phenyl ester 
• 23122-49-8 (2-Chloro-5-methyl-phenyl)-carbamic acid 3-methoxycarbonylamino-phenyl ester 
• 23122-20-5 (3,4-Dibromo-phenyl)-carbamic acid 3-methoxycarbonylamino-phenyl ester 
• 23121-87-1 (4-Chloro-2-methoxy-phenyl)-carbamic acid 3-methoxycarbonylamino-phenyl ester 
• 23191-83-5 (5-Chloro-2,4-dimethoxy-phenyl)-carbamic acid 3-methoxycarbonylamino-phenyl ester 
• 23191-82-4 (4-Chloro-2-methyl-phenyl)-carbamic acid 3-methoxycarbonylamino-phenyl ester 
• 23122-13-6 (4-Bromo-3-chloro-phenyl)-carbamic acid 3-methoxycarbonylamino-phenyl ester 
• 23122-51-2 (2-Chloro-4-nitro-phenyl)-carbamic acid 3-methoxycarbonylamino-phenyl ester 
• 23121-89-3 (2,5-Dimethoxy-phenyl)-carbamic acid 3-methoxycarbonylamino-phenyl ester 
• 23122-45-4 (2-Methyl-5-nitro-phenyl)-carbamic acid 3-methoxycarbonylamino-phenyl ester 
• 23122-33-0 C₁₈H₂₀N₂O₄ 

Relevant academic research and scientific papers

Pictet-Spengler condensations using 4-(2-aminoethyl)coumarins

Androgen-deprivation therapy (ADT) is only a palliative measure, and prostate cancer invariably recurs in a lethal, castration-resistant form (CRPC). Prostate cancer resists ADT by metabolizing weak, adrenal androgens to growth-promoting 5α-dihydrotestosterone (DHT), the preferred ligand for the androgen receptor (AR). Developing small-molecule inhibitors for the final steps in androgen metabolic pathways that utilize 17-oxidoreductases required probes that possess fluorescent groups at C-3 and intact, naturally occurring functionality at C-17. Application of the Pictet-Spengler condensation to substituted 4-(2-aminoethyl)coumarins and 5α-androstane-3-ones furnished spirocyclic, fluorescent androgens at the desired C-3 position. Condensations required the presence of activating C-7 amino or N,N-dialkylamino groups in the 4-(2-aminoethyl)coumarin component of these condensation reactions. Successful Pictet-Spengler condensation, for example, of DHT with 9-(2-aminoethyl)-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one led to a spirocyclic androgen, (3R,5S,10S,13S,17S)-17-hydroxy-10,13-dimethyl-1,2,2′,3′,4,5,6,7,8,8′,9,9′,10,11,12,12′,13,13′,14,15,16,17-docosahydro-7′H,11′H-spiro-[cyclopenta[a]phenanthrene-3,4′-pyrido[3,2,1-ij]pyrido[4′,3′:4,5]pyrano[2,3-f]quinolin]-5′(1′H)-one. Computational modeling supported the surrogacy of the C-3 fluorescent DHT analog as a tool to study 17-oxidoreductases for intracrine, androgen metabolism. This journal is

Synthesis and characterization of new inhibitors of cholinesterases based on N-phenylcarbamates: In vitro study of inhibitory effect, type of inhibition, lipophilicity and molecular docking

Based on current treatment of Alzheimer's disease, where the carbamate inhibitor Rivastigmine is used, two series of carbamate derivatives were prepared: (i) N-phenylcarbamates with additional carbamate group (1–12) and (ii) N-phenylcarbamates with monosaccharide moiety (13–24). All compounds were tested for the inhibitory effect on both of the cholinesterases, electric eel acetylcholinesterase (eeAChE) and butyrylcholinesterase from equine serum (eqBChE) and the inhibitory activity (expressed as IC50 values) was compared with that of the established drugs Galanthamine and Rivastigmine. The compounds with two carbamate groups 1–12 revealed higher inhibitory efficiency on both cholinesterases in compared with monosaccharide derived carbamates 13–24 and with Rivastigmine. The significant decrease of inhibitory efficiency on eqBChE (also for eeAChE but in less manner) was observed after deacetalization of monosaccharide. Moreover, the type of inhibitory mechanism of five chosen compounds was studied. It was found, that compounds with two carbamate groups act presumably via a mixed inhibitory mechanism and the compounds with monosaccharide moiety act as non-competitive inhibitors. The lipophilicity of tested compounds was determined using partition coefficient. Specific positions of the inhibitors in the binding sites of cholinesterases were determined using molecular modeling and the results indicate the importance of phenylcarbamate orientation in the catalytic gorges of both enzymes.

Coumarin-containing photo-responsive nanocomposites for NIR light-triggered controlled drug release via a two-photon process

A new multifunctional nanovehicle for tumor therapy and cell imaging was fabricated by coating NIR light-responsive polymers (HAMAFA-b-DDACMM) onto the surface of octadecyltrimethoxysilane (C18)-modified hollow mesoporous silica nanoparticles (HMS@C18) via self-assembly. First, the targeting NIR light-responsive block copolymer was synthesized by the RAFT living polymerization of [7-(didodecylamino) coumarin-4-yl] methyl methacrylate with hydroxyethylacrylate and N-(3-aminopropyl) methacrylamide hydrochloride and then grafted with folic acid (FA). The copolymers could be disrupted by excitation by a femtosecond NIR light laser (800 nm) via a two-photon absorption process due to the high two-photon absorption cross-section of the coumarin moiety. In order to enhance the drug loading capacity and biological stability of the nanovehicle, HMS nanoparticles modified by hydrophobic octadecyl chains were selected as the "core", which had a considerable drug loading efficiency of more than 70%. Then the core-shell nanocomposites (HMS@C18@HAMAFA-b-DDACMM) were obtained by coating the amphiphilic copolymers onto the core via self-assembly. Under excitation by NIR light at 800 nm, the pre-loaded drugs could be released from the nanocomposites due to the degradation of the light-responsive copolymers and the release efficiency was correlated with the irradiation time and light power. The in vitro experiments indicated that the nanocomposites were easily targeted into the tumor cells that over-expressed folic acid receptor (FR(+)) such as KB cells by endocytosis. Furthermore, the copolymer itself had strong fluorescence, which could be used to track the process of drug delivery.

Anion-accelerated palladium-mediated intramolecular cyclizations: Synthesis of benzofurans, indoles, and a benzopyran

Substituted benzo-fused heterocycles such as indoles, benzofurans, and a benzopyran were obtained using an intramolecular cross-coupling of vinyl halides with phenols. This transformation represents a new route to these heterocycles and is accomplished using a palladacyclic catalyst under anionic conditions.

CARBONYLATIVE REDUCTION OF NITROPHENOLS TO AMINOPHENOLS

Two- or three-component catalysts composed of (i) sulfur or sulfur compound (H2S, CS2, COS, Na2S), (ii) basic additive (triethylamine, CH3ONa, Na2S), and usually (iii) vanadium(V) compounds (e.g.NH4VO3) were found to catalyze efficiently the reaction of CO + H2O with isomeric nitrophenols to give the corresponding aminophenols.The reaction proceeds smoothly at 398 and 483 K and initial pressure of 7 MPa, and its rate increases from 2- to 4-nitrophenol.The selectivity to aminophenols exceeding 96 per cent was obtained at the water to nitrophenol molar ratio higher than 5.The solvents such as methanol and dioxane ensured better contact of the reactants, which was necessary for achievement of such a high selectivity.The effectiveness of the sulfur components (based on the S content) is expressed by the following sequence: S : CS2 : Na2S : H2S : COS = 1 : 1.2 : 2.5 : 10 : 11.The reaction takes place also under the reduced CO pressure to 0.1 - 0.35 MPa.Formation of side products and mechanism of the reaction are discussed.

IMPROVED METHOD FOR SYNTHESIS OF 7-AMINO-4-METHYLCOUMARIN

A new variant of the synthesis of 7-amino-4-methylcoumarin from m-aminophenol via a three-step scheme is proposed.Acylation of m-aminophenol with methoxycarbonyl chloride gave m-(N-methoxycarbonylamino)phenol, which was converted to 7-(N-methoxycarbonylamino)-4-methylcoumarin by condensation with acetoacetic ester in sulfuric acid.Heating of the coumarin with concentrated alkali leads to an intermediate, which, after acidification, is converted to 7-amino-4-methylcoumarin in high yield.

Process for the preparation of herbicidally active phenyl carbamates

Herbicidally active substituted phenyl carbamates I STR1 in which R1 represents a C1 -C6 alkyl group, a C3 -C6 cycloalkyl group or an aryl group, which aryl group may be substituted by a halogen atom and/or a C1 -C6 alkyl group and/or a trifluoromethyl group, and R2 represents a C1 -C6 alkyl, C2 -C6 alkenyl or C2 -C6 alkynyl group that may be substituted by a terminal halogen atom, are prepared by reacting N-hydroxyphenyl carbamates II STR2 with either isocyanates R1 --N=C=O or amino chlorides R1 --NH--COCl in an aqueous medium thus avoiding the use of organic solvents. The end product I may be extracted from the aqueous slurry into a water-immiscible solvent. The N-hydroxyphenyl carbamates II can be prepared by reacting 3-aminophenol with chloroformates in an aqueous medium, and the resulting product may be reacted in situ, without isolation, with isocyanates, in the same reaction vessel. Stabilized herbicidal compositions containing compounds I may be prepared by suspending the compounds I in a liquid phase comprising one or more oily components and one or more surfactants.

HYDROXYLATION DIRECTE D'ESTERS DE PHENYLE ET D'ANILIDES PAR LE PEROXYDE D'HYDROGENE EN MILIEU SUPERACIDE

In SbF5-HF, hydrogen peroxide reacts on the aromatic ring of esters 1a-5a and anilides 11a-15a to give monohydroxylated derivatives in good yields.With compounds 2a, 4a and 5a, meta or para isomers are by far the major products, whereas with formate 1a and benzoate 3a, the proportion of the ortho isomer is more important.With anilides, the reaction is less selective, the three isomers being obtained in comparable amounts.Thus, the relative proportions of ortho, meta and para-hydroxylated derivatives obtained using 70 percent H2O2 with acetate 2a and acetanilide 12a are 6/51/43 and 36.5/30/33.5, respectively.The important proportion of meta hydroxylation is the result of the reaction of protonated hydrogen peroxide H3O2+ on the protonated substrate.

Ester of (alkynyloxy)-, (alkenyloxy)-, and (cyanoalkoxy) carbanilic acids and their use as herbicides

The invention is novel esters of (alkynyloxy)-, (alkenyloxy)-, and (cyanoalkoxy) carbanilic acids and the thiono and dithio derivatives of the carbanilic acids, and their use for controlling broadleaf weeds and grasses.