5006-45-1

Basic information

• Product Name: 6-CHLOROCHROMONE-2-CARBOXYLIC ACID
• Synonyms: TIMTEC-BB SBB005445;6-chloro-4-oxo-4h-1-benzopyran-2-carboxylicaci;6-chloro-4-oxo-4h-1-benzopyran-2-carboxylicacid;OTAVA-BB BB7020410195;6-CHLOROCHROMONE-2-CARBOXYLIC ACID;6-CHLORO-4-OXO-4H-CHROMENE-2-CARBOXYLIC ACID
• CAS NO: 5006-45-1
• Molecular Formula: C₁₀H₅ClO₄
• Molecular Weight: 224.6
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 5006-45-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 254-256°C
• Boiling Point: 384.5 °C at 760 mmHg
• Flash Point: 186.4 °C
• Appearance: /
• Density: 1.612 g/cm³
• Vapor Pressure: 1.34E-06mmHg at 25°C
• PKA: 2.00±0.20(Predicted)
• CAS DataBase Reference: 6-CHLOROCHROMONE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLOROCHROMONE-2-CARBOXYLIC ACID(5006-45-1)
• EPA Substance Registry System: 6-CHLOROCHROMONE-2-CARBOXYLIC ACID(5006-45-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RTECS: DJ2260650
• HazardClass: IRRITANT
• Hazardous Substances Data: 5006-45-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 14, p. 758, 1971 DOI: 10.1021/jm00290a021

InChI:InChI=1/C10H5ClO4/c11-5-1-2-8-6(3-5)7(12)4-9(15-8)10(13)14/h1-4H,(H,13,14)/p-1

Upstream product

• 38322-69-9 6-chloro-4-oxo-4H-chromen-2-carboxylic acid ethyl ester 
• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 95-92-1 oxalic acid diethyl ester 
• 880142-59-6 diethyl (Z)-2-(4-chlorophenoxy)-2-butenedioate 
• 24355-83-7 2-(4-chlorophenoxy)fumaric acid 

Downstream Products

• 33544-16-0 6-chloro-4-oxo-4H-chromene-2-carboxylic acid amide 

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.

Diamine derivatives

A compound represented by the general formula (1): Q1-Q2-T0-N(R1)-Q3-N(R2)-T1-Q4??(1) wherein R1 and R2 are hydrogen atoms or the like; Q1 is a saturated or unsaturated, 5- or 6-membered cyclic hydrocarbon group which may be substituted, or the like; Q2 is a single bond or the like; Q3 is a group in which Q5 is an alkylene group having 1 to 8 carbon atoms, or the like; and T0 and T1 are carbonyl groups or the like; a salt thereof, a solvate thereof, or an N-oxide thereof. The compound is useful as an agent for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.