2840-04-2

Basic information

• Product Name: 5-Amino-2-methylbenzoic acid
• Synonyms: 2-METHYL-5-AMINOBENZOIC ACID;5-AMINO-2-METHYL-BENZOIC ACID;RARECHEM AL BO 1282;TIMTEC-BB SBB007566;METHYL 5-AMION-2-METHYLBENZOATE;Benzoic acid, 5-amino-2-methyl- (9CI);2-Methyl-5-Aminobenzoic;5-AMINO-2-METHYLBENZOIC ACID / 2-METHYL-5-AMINOBENZOIC ACID
• CAS NO: 2840-04-2
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• Product Categories: CARBOXYLICACID;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Carboxylic Acids;Phenyls & Phenyl-Het;Benzoic acid;Organic acids;Carboxylic Acids;Phenyls & Phenyl-Het
• Mol File: 2840-04-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 194-199 °C
• Boiling Point: 348.8 °C at 760 mmHg
• Flash Point: 164.7 °C
• Appearance: /
• Density: 1.254 g/cm³
• Vapor Pressure: 1.84E-05mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Ethyl acetate (Very Slightly, Heated)
• PKA: 2.95±0.25(Predicted)
• CAS DataBase Reference: 5-Amino-2-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-2-methylbenzoic acid(2840-04-2)
• EPA Substance Registry System: 5-Amino-2-methylbenzoic acid(2840-04-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 2840-04-2(Hazardous Substances Data)

Usage

Chemical Properties

Beige powder

Uses

5-Amino-2-methylbenzoic Acid is used as a reagent in synthesis of several organic compounds including that of dihydroxylphenyl amides which are Hsp90 inhibitors. Also used in synthesis of a series of 2,5-diaminopyrimidine inhibitors of bruton’s tyrosine kinase with potential for use in cancer drug development.

InChI:InChI=1/C8H9NO2/c1-5-2-3-6(9)4-7(5)8(10)11/h2-4H,9H2,1H3,(H,10,11)

Upstream product

• 57319-65-0 6-aminophthalide 
• 1975-52-6 5-nitro-o-toluic acid 
• 103204-70-2 5-acetylamino-2-methyl-benzoic acid 
• 50670-64-9 3-cyano-4-methylaniline 
• 10034-85-2 hydrogen iodide 
• 7647-01-0 hydrogenchloride 
• 118-90-1 ortho-methylbenzoic acid 
• 7745-93-9 2-bromo-4-nitrotoluene 
• 939-83-3 2-cyano-4-nitrotoluene 
• 77324-87-9 methyl 2-methyl-5-nitrobenzoate 

Downstream Products

• 111437-10-6 3-(hydroxymethyl)-4-methylaniline 
• 180136-18-9 5-(3-Cyclohexyl-propionylamino)-2-methyl-benzoic acid 
• 73502-03-1 methyl 5-methoxy-2-methyl-benzoate 
• 788081-99-2 methyl 2-(bromomethyl)-5-methoxy-benzoate 
• 896160-43-3 2-methyl-5-(3-(trifluoromethyl)benzamido)benzoic acid 
• 1431727-39-7 tert-butyl 3-(5-(2-methyl-5-(3-(trifluoromethyl)benzamido)benzamido)pyrimidin-2-ylamino)-phenylcarbamate 
• 1431727-20-6 N-(2-((3-aminophenyl)amino)pyrimidin-5-yl)-2-methyl-5-(3-(trifluoromethyl)benzamido)benzamide 
• 1431727-00-2 N-(2-(3-acrylamidophenylamino)pyrimidin-5-yl)-2-methyl-5-(3-(trifluoromethyl)benzamido)benzamide 
• 1431727-04-6 N-(2-(3-(2-acrylamidoacetamido)phenylamino)pyrimidin-5-yl)-2-methyl-5-(3-(trifluoromethyl)benzamido)benzamide 
• 914299-28-8 C₁₁H₁₄IN 
• 914299-27-7 C₁₁H₁₂IN 
• 1097201-36-9 methyl 4-methyl-3-pyrrolidin-2-ylbenzoate 
• 914299-26-6 C₁₄H₁₄INO₂ 
• 914299-29-9 C₁₆H₂₂INO₂ 

Relevant articles and documents

Gas-liquid flow hydrogenation of nitroarenes: Efficient access to a pharmaceutically relevant pyrrolobenzo[1,4]diazepine scaffold

Using a Tube-in-Tube device based on the amorphous Teflon AF-2400 fluoropolymer, a series of nitroarenes was hydrogenated to afford the corresponding aniline compounds. The system was then applied to the construction of a pyrrolobenzo[1,4]diazapene scaffold through a tandem hydrogenation-condensation-hydrogenation sequence.

Metabolically stable dibenzo[ b, e ]oxepin-11(6 H)-ones as highly selective p38 MAP kinase inhibitors: Optimizing anti-cytokine activity in human whole blood

Five series of metabolically stable disubstituted dibenzo[b,e]oxepin-11(6H) -ones were synthesized and tested in a p38α enzyme assay for their inhibition of tumor necrosis factor-α (TNF-α) release in human whole blood. Compared to the monosubstituted dibenzo[b,e]oxepin-11(6H)-one derivatives, it has been shown that the additional introduction of hydrophilic residues at position 9 leads to a substantial improvement of the inhibitory potency and metabolic stability. Using protein X-ray crystallography, the binding mode of the disubstituted dibenzoxepinones and the induction of a glyince flip in the hinge region were confirmed. The most potent compound of this series, 32e, shows an outstanding biological activity on isolated p38α, with an IC50 value of 1.6 nM, extraordinary selectivity (by a factor >1000, Kinase WholePanelProfiler), and low ATP competitiveness. The ability to inhibit the release of TNF-α from human whole blood was optimized down to an IC50 value of 125 nM. With the promising dibenzoxepinone inhibitor 3i, a pharmacokinetic study in mice was conducted.

FUSED HETEROCYCLIC COMPOUND

The present invention provides a fused heterocyclic compound having a tyrosine kinase inhibitory action, which is represented by the formula: wherein R1 is a hydrogen atom, a halogen atom, or an optionally substituted group bonded via a carbon atom, a nitrogen atom or an oxygen atom; R2 is a hydrogen atom, or an optionally substituted group bonded via a carbon atom or a sulfur atom, or R1 and R2, or R2 and R3 are optionally bonded to each other to form an optionally substituted ring structure; R3 is a hydrogen atom or an optionally substituted aliphatic hydrocarbon group, or R3 is optionally bonded to the carbon atom on ring A to form an optionally substituted ring structure; ring A is an optionally substituted benzene ring; and ring B is (i) an optionally substituted fused ring, or (ii) a pyridine ring having optionally substituted carbamoyl (the pyridine ring is optionally further substituted).