18358-63-9

Basic information

• Product Name: METHYL 4-METHYLAMINOBENZOATE
• Synonyms: Benzoic acid, 4-(methylamino)-, methyl ester;p-Aminobenzoic acid di-methyl derivative;4-(METHYLAMINO)-BENZOIC ACID METHYL ESTER;METHYL 4-METHYLAMINOBENZOATE;METHYL 4-(N-METHYLAMINO)BENZOATE;METHYL 4-(AMINOMETHYL)-2-CHLOROBENZOATE;Methyl 4-methylaminobenzoate ,98%;Methyl-(4-MerthylaMino)benzoate
• CAS NO: 18358-63-9
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.19
• Product Categories: Aromatic Esters
• Mol File: 18358-63-9.mol

Chemical Properties

• Melting Point: 94-96°C
• Boiling Point: 277.5 °C at 760 mmHg
• Flash Point: 121.6 °C
• Appearance: /
• Density: 1.125 g/cm³
• Vapor Pressure: 0.00451mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 2.26±0.12(Predicted)
• Water Solubility: It is slightly soluble in water. (1.2 g/L) (25°C insoluble in hexane.
• BRN: 2803327
• CAS DataBase Reference: METHYL 4-METHYLAMINOBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-METHYLAMINOBENZOATE(18358-63-9)
• EPA Substance Registry System: METHYL 4-METHYLAMINOBENZOATE(18358-63-9)

Safety Data

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.
• HazardClass: IRRITANT
• Hazardous Substances Data: 18358-63-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 4-METHYLAMINOBENZOATE is used as a reagent for the synthesis of sulfonamide-containing N-hydroxyindole-2-carboxylates. These compounds serve as inhibitors of human lactate dehydrogenase-isoform 5 (hLDH-5), an enzyme that plays a crucial role in various metabolic processes. Inhibiting hLDH-5 can have therapeutic implications in treating certain diseases and conditions.
METHYL 4-METHYLAMINOBENZOATE is also used in the preparation of hyaluronic acid-methotrexate conjugates. These conjugates have potential applications as antiarthritic and anti-inflammatory agents. By combining the properties of hyaluronic acid, a naturally occurring polysaccharide in the human body, and methotrexate, an established anti-cancer and anti-inflammatory drug, these conjugates aim to improve the treatment of arthritis and other inflammatory conditions.
Used in Research:
METHYL 4-METHYLAMINOBENZOATE is suitable for lactate dehydrogenase (LDH) related research. LDH is an enzyme family involved in the conversion of lactate to pyruvate, a critical step in cellular respiration. By studying the interactions of METHYL 4-METHYLAMINOBENZOATE with LDH, researchers can gain insights into the enzyme's function, regulation, and potential as a therapeutic target for various diseases.

InChI:InChI=1/C9H11NO2/c1-10-8-5-3-7(4-6-8)9(11)12-2/h3-6,10H,1-2H3

Upstream product

• 67-56-1 methanol 
• 127903-03-1 N-methyl-N-(4-methoxycarbonylphenyl)sulfuric diamide 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 676-58-4 methylmagnesium chloride 
• 160852-85-7 2-[2-(2-methoxyethoxy)ethoxy]ethyl methyl carbonate 
• 619-45-4 4-methoxycarbonyl aniline 
• 124-38-9 carbon dioxide 
• 74-88-4 methyl iodide 
• 959698-63-6 methyl 3-[N-(2-iodo-4-methoxycarbonylphenyl)-N-methylamino]propionate 
• 5407-61-4 1-phenyl-2-(pyrrolidin-1-yl)ethanol 
• 20245-72-1 2-phenyl-2-pyrrolidin-1-yl-ethanol 
• 741275-29-6 methyl 4-[(tert-butoxycarbonyl)(methyl)amino]benzoate 
• 349398-11-4 methyl N-nosyl-p-aminobenzoate 
• 881005-27-2 methyl N-methyl-N-nosyl-p-aminobenzoate 

Downstream Products

• 51774-36-8 methyl 4-(N-benzoyl-N-methylamino)benzoate 
• 108191-10-2 4-methylamino-N-(1-phenylethyl)benzamide 
• 206434-79-9 4-[methyl-(2-piperidin-1-yl-ethyl)-amino]-benzoic acid methyl ester 
• 779355-83-8 4-[methyl(trimethylsilyl)amino]benzoic acid methyl ester 
• 167030-94-6 4-[(5-Cyano-6-methoxy-2-oxo-1,2,3,4-tetrahydro-pyridin-3-ylmethyl)-methyl-amino]-benzoic acid methyl ester 
• 213256-79-2 4-[(2,4-Diamino-7-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-methyl-amino]-benzoic acid 
• 213256-76-9 methyl 4-[N-(2,4-diamino-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-ylmethyl)-N-methylamino]benzoate 
• 213256-84-9 (S)-2-{4-[(2,4-Diamino-7-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanedioic acid dimethyl ester 
• 357400-74-9 methyl 4-[(4,4-dicyano-2-methoxycarbonylbutyl)methylamino]benzoate 
• 357400-66-9 dimethyl 2-cyano-4-{[(4-methoxycarbonylphenyl)methylamino]methyl}pentanedioate 
• 271253-84-0 methyl 4-[N-(2-amino-4,7-dioxo-3,4,5,6,7,8-hexahydropyrido[2,3-d]pyrimidin-6-ylmethyl)-N-methylamino]benzoate 
• 357400-63-6 4-[N-(2-amino-4,7-dioxo-3,4,5,6,7,8-hexahydropyrido[2,3-d]pyrimidin-6-ylmethyl)-N-methylamino]benzoic acid 
• 357400-60-3 dimethyl N-{4-[N-(2-amino-4,7-dioxo-3,4,5,6,7,8-hexahydropyrido[2,3-d]pyrimidin-6-ylmethyl)-N-methylamino]benzoyl}-L-glutamate 
• 135036-55-4 4-[(methyl)(methylsulfonyl)amino]benzoic acid methyl ester 

Relevant articles and documents

Additive-freeN-methylation of amines with methanol over supported iridium catalyst

An efficient and versatile zinc oxide-supported iridium (Ir/ZnO) catalyst was developed to catalyze the additive-freeN-methylation of amines with methanol. Mechanistic studies suggested that the high catalytic reactivity is rooted in the small sizes (1.4 nm) of Ir nanoparticles and the high ratio (93%) of oxidized iridium species (IrOx, Ir3+and Ir4+) on the catalyst. Moreover, the delicate cooperation between the IrOxand ZnO support also promoted its high reactivity. The selectivity of this catalyticN-methylation was controllable between dimethylation and monomethylation by carefully tuning the catalyst loading and reaction solvent. Specifically, neat methanol with high catalyst loading (2 mol% Ir) favored the formation ofN,N-dimethylated amine, while the mesitylene/methanol mixture with low catalyst loading (0.5 mol% Ir) was prone to producing mono-N-methylated amines. An environmentally benign continuous flow system with a recycled mode was also developed for the efficient production ofN-methylated amines. With optimal flow rates and amine concentrations, a variety ofN-methylamines were produced with good to excellent yields in this Ir/ZnO-based flow system, providing a starting point for the clean and efficient production ofN-methylamines with this cost-effective chemical process.

Biobased Spiroimides from Itaconic Acid and Formamides: Molecular Targets for a Novel Synthetic Application of Renewable Chemicals

Spiroimides exhibit a wide range of biological activities, such as anticonvulsant, antiarrhythmic, and antihyperglycemic activities. Herein, a novel synthetic application of renewable chemicals, itaconic acid and formamides, is described. Proper exploitation of the reactivity of itaconic acid and formamide allows for the development of an efficient synthetic approach for the production of several new biobased spiroimides, spiro[dihydroquinolin-2-one-succinimides] and spiro[indolin-2-one-glutarimides], in excellent overall yields (up to 98%).

CO2-tuned highly selective reduction of formamides to the corresponding methylamines

We herein describe an efficient, CO2-tuned and highly selective C-O bond cleavage of N-methylated formanilides. With easy-to-handle and commercially available NaBH4 as the reductant, a variety of formanilides could be turned into the desired tertiary amines in moderate to excellent yields. The role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments.

Recyclable covalent triazine framework-supported iridium catalyst for the N-methylation of amines with methanol in the presence of carbonate

An iridium complex Cp*Ir@CTF, which is synthesized by the coordinative immobilization of [Cp*IrCl2]2 on a functionalized covalent triazine framework (CTF), was found to be a general and highly efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate. Under environmentally benign conditions, a variety of desirable products were obtained in high yields with complete selectivities and functional group friendliness. Furthermore, the synthesized catalyst could be recycled by simple filtration without obvious loss of catalytic activity after sixth cycle. Notably, this research exhibited the potential of covalent triazine framework-supported transition metal catalysts for hydrogen autotransfer process.

N-Methylation of Amines with Methanol in the Presence of Carbonate Salt Catalyzed by a Metal-Ligand Bifunctional Ruthenium Catalyst [(p-cymene)Ru(2,2′-bpyO)(H2O)]

A ruthenium complex [(p-cymene)Ru(2,2′-bpyO)(H2O)] was found to be a general and efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate salt. Moreover, a series of sensitive substituents, such as nitro, ester, cyano, and vinyl groups, were tolerated under present conditions. It was confirmed that OH units in the ligand are crucial for the catalytic activity. Notably, this research exhibited the potential of metal-ligand bifunctional ruthenium catalysts for the hydrogen autotransfer process.

Discovery of a novel series of guanidinebenzoates as gut-restricted enteropeptidase and trypsin dual inhibitors for the treatment of metabolic syndrome

A novel series of guanidinebenzoate enteropeptidase and trypsin dual inhibitors has been discovered and SAR studies were conducted. Optimization was focused on improving properties for gut restriction, including increased aqueous solubility, lower cellular permeability, and reduced oral bioavailability. Lead compounds were identified with efficacy in a mouse fecal protein excretion study.

Photoinduced Hydroarylation and Cyclization of Alkenes with Luminescent Platinum(II) Complexes

Photoinduced hydroarylation of alkenes is an appealing synthetic strategy for arene functionalization. Herein, we demonstrated that aryl radicals generated from electron-deficient aryl chlorides/bromides could be trapped by an array of terminal/internal aryl alkenes in the presence of [Pt(O^N^C^N)] under visible-light (410 nm) irradiation, affording anti-Markovnikov hydroarylated compounds in up to 95 % yield. Besides, a protocol for [Pt(O^N^C^N)]-catalyzed intramolecular photocyclization of acrylanilides to give structurally diverse 3,4-dihydroquinolinones has been developed.

5,8-DISUBSTITUTED-[1,2,4]TRIAZOLO[1,5-A]PYRIDINYL AND 5,8-DISUBSTITUTED-IMIDAZO[1,2-A]PYRIDINE DERIVATIVES USEFUL AS INHIBITORS OF ENTEROPEPTIDASE

The present invention is directed to 5,8-disubstituted-[1,2,4]triazolo[1,5- a]pyridinyl and 5,8-disubstituted-imidazo[1,2-a]pyridine derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by the enteropeptidase enzyme.

Electrosynthesis of Dihydropyrano[4,3-b]indoles Based on a Double Oxidative [3+3] Cycloaddition

Oxidative [3+3] cycloadditions offer an efficient route for six-membered-ring formation. This approach has been realized based on an electrochemical oxidative coupling of indoles/enamines with active methylene compounds followed by tandem 6π-electrocyclization leading to the synthesis of dihydropyrano[4,3-b]indoles and 2,3-dihydrofurans. The radical–radical cross-coupling of the radical species generated by anodic oxidation combined with the cathodic generation of the base from O2 allows for mild reaction conditions for the synthesis of structurally complex heterocycles.

EffectiveN-methylation of nitroarenes with methanol catalyzed by a functionalized NHC-based iridium catalyst: a green approach toN-methyl amines

Compound [IrBr(CO)2(κC-tBuImCH2PyCH2OMe)] featuring a flexible pyridine/OMe functionalized NHC ligand κ1C coordinated efficiently catalyzes the selectiveN-monomethylation of nitroarenes using methanol as both the reducing agent and the C1 source. A range of functionalized nitroarenes including heterocyclic or sterically hindered derivatives have been efficiently converted to the correspondingN-monomethyl amines in good yields at low catalyst loadings using sub-stoichiometric amounts of Cs2CO3as a base. Mechanistic investigations support a borrowing-hydrogen mechanism in which methanol acts as the hydrogen source and methylating agent. Further, the hydrogen transfer reduction of nitrobenzene to aniline under optimized reaction conditions should proceed through a direct mechanism involving nitrosobenzene andN-phenylhydroxylamine intermediates.