5006-44-0

Basic information

• Product Name: 6-METHYLCHROMONE-2-CARBOXYLIC ACID
• Synonyms: 6-METHYLCHROMONE-2-CARBOXYLIC ACID;6-METHYL-4-OXO-4H-CHROMENE-2-CARBOXYLIC ACID;AKOS GLO-BB-137;6-Methylchromone-2-carboxylic acid, 98+%
• CAS NO: 5006-44-0
• Molecular Formula: C₁₁H₈O₄
• Molecular Weight: 204.18
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzopyrans;Building Blocks;Heterocyclic Building Blocks;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 5006-44-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 267-270 °C(lit.)
• Boiling Point: 367.2 °C at 760 mmHg
• Flash Point: 148.4 °C
• Appearance: /
• Density: 1.421 g/cm³
• Vapor Pressure: 4.89E-06mmHg at 25°C
• PKA: 2.40±0.20(Predicted)
• CAS DataBase Reference: 6-METHYLCHROMONE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHYLCHROMONE-2-CARBOXYLIC ACID(5006-44-0)
• EPA Substance Registry System: 6-METHYLCHROMONE-2-CARBOXYLIC ACID(5006-44-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 5006-44-0(Hazardous Substances Data)

Usage

Chemical Properties

Almost white crystalline powder

General Description

6-Methylchromone-2-carboxylic acid is a chromone derivative. Chromones are cyclic compounds containing nine carbon atoms with sp2 hybridization. They are commonly referred as 1,4-benzapyranes or γ-benzopyrones. Its energy of combustion was measured by an isoperibolic micro-combustion calorimeter. Standard molar enthalpy of formation derived from the energy of combustion, for 6-methylchromone-2-carboxylic acid was reported to be -(656.2 ± 2.2)kJmol-1.

InChI:InChI=1/C11H8O4/c1-6-2-3-9-7(4-6)8(12)5-10(15-9)11(13)14/h2-5H,1H3,(H,13,14)/p-1

Upstream product

• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 95-92-1 oxalic acid diethyl ester 
• 38322-65-5 Ethyl 6-methyl-4-oxo-4H-1-benzopyran-2-carboxylate 
• 81501-70-4 C₁₉H₁₈N₂O₃ 
• 105591-57-9 6-Methyl-4-oxo-4H-1-benzopyran-2-carboxaldehyde oxime 
• 99851-63-5 6-methyl-4-oxo-4H-chromen-2-carbaldehyde 
• 33543-93-0 6-methylchromone-2-carbonitrile 

Downstream Products

• 88952-74-3 6-methyl-2-(p-tolyl)-4H-chromen-4-one 
• 29976-75-8 6-methylflavone 
• 33543-92-9 6-Methyl-4-oxo-4H-1-benzopyran-2-carboxamide 
• 60630-08-2 N,N'-bis-<1-(2-hydroxy-5-methylphenyl)ethylidene>ethylenediamine 
• 164171-53-3 5-(2-hydroxy-5-methylphenyl)-3-isoxazolecarboxylic acid 
• 90380-28-2 5-(2-hydroxy-5-methylphenyl)-2,3-dihydro-1,4-diazepine-7-carboxylic acid 

Relevant articles and documents

Chromene-containing aromatic sulfonamides with carbonic anhydrase inhibitory properties

Carbonic anhydrases (CAs, EC 4.2.1.1) catalyze the essential reaction of CO2 hydration in all living organisms, being actively involved in the regulation of a plethora of patho/physiological conditions. A series of chromene-based sulfonamides were synthesized and tested as possible CA inhibitors. Their inhibitory activity was assessed against the cytosolic human isoforms hCA I, hCA II and the transmembrane hCA IX and XII. Several of the investigated derivatives showed interesting inhibition activity towards the tumor associate isoforms hCA IX and hCA XII. Furthermore, computational procedures were used to investigate the binding mode of this class of compounds, within the active site of hCA IX.

Optimizing the synthetic route of chromone-2-carboxylic acids: A step forward to speed-up the discovery of chromone-based multitarget-directed ligands

6-Bromochromone-2-carboxylic acid (3) was synthesized by a microwave-assisted process. The optimization of the reaction was performed varying parameters, such as type of base/number of reagent equivalents, solvent, temperature and reaction time. The yield of the reaction was improved to 87%. The new synthetic route is versatile as several chromone-2-carboxylic acids (compounds 4B-10B) were obtained with good yields (54-93%). Only in the case of the nitro substituent (compound 11B), an ester was obtained instead of the desired carboxylic acid. Following this synthetic route chromone carboxylic acids can be attained with a high degree of purity, without the need of the tedious and expensive purification processes through column chromatography. The reaction is safe, cost-effective, fast and robust, and can be used in the development of concise and diversity-oriented libraries based on chromone scaffold. The overall study can be looked as a step forward to speed-up the discovery of chromone-based multitarget-directed ligands.

Synthesis and Reactions of Some 4-Oxo-4H-1-benzopyran-2-carboxaldehydes

Some new 4-oxo-4H-1-benzopyran-2-carboxaldehydes (III) have been prepared, and the conversion of the 2-carboxaldehyde group in III into 2-carbonitrile and 2-carboxylic acid groups has been discussed.Unlike the general behaviour of the 4-oxo-4H-1-benzopyrans towards some nucleophiles, where the reaction takes place with opening of the pyronering, the 6-methyl- and 6-chloro-4-oxo-4H-1-benzopyran-2-carboxaldehydes (IIIa and IIIb) have been found to react with different nucleophiles such as hydroxylamine hydrochloride, hydrazine, phenylhydrazine and primary aromatic amines to give the corresponding condensation products (IV, VII, VIII, X, XI) without the opening of pyrone ring.The only exception to this observation is the reaction of IIIa and IIIb with ethylene diamine where the opening of pyronering does not take place to give the expected 5,6-dihydropyrazine derivatives (XIIa and XIIb).The reactions of IIIa and IIIb with active methylene compounds, malonic acid, malonodinitrile, cyanoacetic acid, ethyl cyanoacetate, cyanoacetamide and hippuric acid have also been discussed.