72856-73-6

Basic information

• Product Name: 2-METHOXY-4-(METHYLTHIO)BENZOIC ACID, 96
• Synonyms: 2-METHOXY-4-(METHYLTHIO)BENZOIC ACID, 96;4-(methylthio)-o-anisic acid;2-Methoxy-4-methylsulfanyl-benzoic acid
• CAS NO: 72856-73-6
• Molecular Formula: C₉H₁₀O₃S
• Molecular Weight: 198.2389
• EINECS: 276-948-6
• Mol File: 72856-73-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 342.3 °C at 760 mmHg
• Flash Point: 160.8 °C
• Appearance: /
• Density: 1.29 g/cm³
• Vapor Pressure: 2.92E-05mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: 2-METHOXY-4-(METHYLTHIO)BENZOIC ACID, 96(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHOXY-4-(METHYLTHIO)BENZOIC ACID, 96(72856-73-6)
• EPA Substance Registry System: 2-METHOXY-4-(METHYLTHIO)BENZOIC ACID, 96(72856-73-6)

Safety Data

• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36:Wear suitable prot
• Hazardous Substances Data: 72856-73-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 28, p. 717, 1985 DOI: 10.1021/jm00383a006

InChI:InChI=1/C9H10O3S/c1-12-8-5-6(13-2)3-4-7(8)9(10)11/h3-5H,1-2H3,(H,10,11)

Upstream product

• 95420-72-7 4-mercapto-2-methoxybenzoic acid 
• 77-78-1 dimethyl sulfate 
• 74-83-9 methyl bromide 
• 74-93-1 methylthiol 
• 124-38-9 carbon dioxide 
• 2388-74-1 1-methoxy-3-methylsulfanyl-benzene 
• 79128-27-1 2-methoxy-4-methylthiobenzoic acid methyl ester 
• 28478-46-8 methyl 4-hydroxy-2-methoxybenzoate 
• 89-86-1 4-hydroxysalicylic acid 
• 2150-47-2 methyl 2,4-dihydroxybenzoate 
• 95420-30-7 4-<(dimethylamino)thioxomethoxy>-2-methoxybenzoic acid methyl ester 
• 136669-90-4 methyl 2-hydroxy-4-(trityloxy)benzoate 
• 2486-80-8 4-amino-2-methoxybenzoic acid 
• 4093-29-2 methyl 4-(acetylamino)-o-anisate 

Downstream Products

• 114086-41-8 4-methanesulfonyl-2-methoxybenzoic acid 
• 86315-69-7 2-<2-methoxy-4-(methylsulfenyl)phenyl>imidazo<4,5-c>pyridine hydrochloride 
• 99454-75-8 2-(2-methoxy-4-methylthiophenyl)-1H-imidazo<4,5-b>pyrazine 
• 77456-44-1 8-(2-methoxy-4-methylthiophenyl)purine 
• 95420-69-2 8-(2-Methoxy-4-methylsulfanyl-phenyl)-9H-purine; hydrochloride 
• 144563-52-0 2-<2-Methoxy-4-(methylthio)phenyl>-5-methylimidazo-1H-<4,5-b>pyridin 
• 127356-25-6 2-(2-Methoxy-4-methylsulfanyl-phenyl)-6-methyl-1H-imidazo[4,5-b]pyridine 
• 127356-24-5 6-Chloro-2-(2-methoxy-4-methylsulfanyl-phenyl)-1H-imidazo[4,5-b]pyridine 
• 129333-24-0 <<3-<<(diethylamino)thioxomethyl>thio>-4-pyridinyl>amino>oxo-<2-methoxy-4-(methylthio)>benzoic acid 
• 127356-46-1 2-(2-Methoxy-4-methylsulfanyl-phenyl)-1H-imidazo[4,5-c]pyridin-7-ylamine 
• 127356-18-7 5-Methoxy-2-(2-methoxy-4-methylsulfanyl-phenyl)-1H-imidazo[4,5-b]pyridine 
• 127356-30-3 6-Methoxy-2-(2-methoxy-4-methylsulfanyl-phenyl)-1H-imidazo[4,5-c]pyridine 
• 127356-31-4 7-Methoxy-2-(2-methoxy-4-methylsulfanyl-phenyl)-1H-imidazo[4,5-c]pyridine 
• 127356-20-1 7-Methoxy-2-(2-methoxy-4-methylsulfanyl-phenyl)-1H-imidazo[4,5-b]pyridine 

Relevant articles and documents

Synthesis of 2-Methoxy-4-(methylsulfanyl)benzoic Acid — An Intermediate Product in the Preparation of the Cardiotonic Drugs Sulmazole and Isomazole

Readily available 4-methyl-3-nitrobenzenesulfonic acid and 2-methyl-5-nitrophenol were used to develop two alternative approaches to the synthesis of 2-methoxy-4-(methylsulfanyl)benzoic acid in total yields of 17% and 37%, respectively. The synthesis starting from 2-methyl-5-nitrophenol is more process-oriented and can be used in the resynthesis of Sulmazole and Isomazole.

Synthesis and anti-inflammatory activity of antioxidants, 4-alkylthio-o-anisidine derivatives

In order to search for anti-inflammatory agents against autoimmune diseases, we synthesized 4-alkylthio-o-anisidine derivatives possessing antioxidant activity, and tested them for anti-inflammatory activity against the Arthus reaction in mice. Experimental inflammations, including the Arthus reaction, concanavalin A, phorhol ester and pyrophosphate-induced edemas in rats were inhibited by 4-propylthio-o-anisidine, which inhibited autoxidation of rat brain homogenate and suppressed the lipopolysaccharide-induced increase in the plasma malondialdehyde level in mice. An antioxidant may be an effective agent in immune complex type inflammation where active oxygen species play an important role.

Inotropic activity of heterocyclic analogues of isomazole

Aryl-substituted benzimidazole, imidazopyridine, imidazopyrazine, imidazopyridazine, oxazolopyridine, purine, pyrollopyridine and thiazolopyridine derivatives have been prepared and evaluated as inotropic agents.Purine 8 and the 1H-imidazo- and pyridazines 9 and 10 proved to be of most interest, having similar in vivo inotropic potencies to sulmazole.The pKa's, protonation sites and lipophilicities for most heterocycles were determined experimentally and some of their electronic properties calculated.For a subset of active heterocycles a correlation was observed between in vitro inotropism and the charge density of the imidazo nitrogen adjacent to the electrostatic potential minimum.Structure-activity relationships are discussed in some detail.