Coumarin-6-carboxylic acid

Name: Coumarin-6-carboxylic acid
Brand: Zhengzhou Whchem

CAS：7734-80-7 | Coumarin-6-carboxylic acid | Whchem

CAS: 7734-80-7

Other Names

Coumarin-6-carboxylic acid;2-oxo-2H-1-Benzopyran-6-carboxylic acid;2-oxo-1-benzopyran-6-carboxylic acid;2-oxochromene-6-carboxylic acid;2H-1-Benzopyran-6-carboxylicacid, 2-oxo-;2-oxo-1H-chromene-6-carboxylic acid;2-oxochromene-6-carboxylicaci;Coumarin-6-carboxylic acid ISO 9001：2015 REACH

Molecular Formula

Purity

>98%

Molecular Weight

190.15 g/mol

EINECS

1312995-182-4

Structure Available Verified Product

English Name	Coumarin-6-carboxylic acid
English Synonyms	Coumarin-6-carboxylic acid;2-oxo-2H-1-Benzopyran-6-carboxylic acid;2-oxo-1-benzopyran-6-carboxylic acid;2-oxochromene-6-carboxylic acid;2H-1-Benzopyran-6-carboxylicacid, 2-oxo-;2-oxo-1H-chromene-6-carboxylic acid;2-oxochromene-6-carboxylicaci;Coumarin-6-carboxylic acid ISO 9001：2015 REACH
CAS Number	7734-80-7
Molecular Formula	C10H6O4
Molecular Weight	190.15 g/mol
EINECS Number	1312995-182-4
Related Categories
Mol File	Download MOL File
Structure Image

Property	Value
Melting point	270-271 °C
Boiling point	440.0±40.0 °C (Predicted)
Density	1.466±0.06 g/cm³ (Predicted)
Storage condition	Sealed in dry, Room Temperature
Acidity Coefficient (pKa)	3.83±0.20 (Predicted)
Appearance	White to off-white solid
CAS Database Reference	7734-80-7

Coumarin-6-carboxylic acid (CAS 7734-80-7) is a high-purity fine chemical intermediate widely used in organic synthesis, pharmaceutical R&D, agrochemical manufacturing and specialty chemical applications.

As a professional supplier, Zhengzhou Whchem provides Coumarin-6-carboxylic acid with >98% purity, COA, structure confirmation and flexible packaging, available from research quantities to commercial scale with global shipping.

Category	Description (English Translation)
Uses & Synthesis Methods Coumarin derivative 6-carboxycoumarin is one of the carboxycoumarin derivatives. Depending on the exocyclic groups, coumarins have various derivatives: hydroxycoumarins, furanocoumarins, pyranocoumarins, dicoumarins, and dihydroisocoumarins, etc. Coumarin, also known as coumarin, is the lactone and derivative of cis-o-hydroxycinnamic acid. It is widely distributed in the plant kingdom in free form and as glycosides, particularly abundant in the families Apiaceae, Fabaceae, Rutaceae, and Oleaceae. Many coumarin compounds possess characteristic aromas and were formerly used primarily as fragrances. Later, many were found to have physiological activities, such as aesculin in ash bark, which has antibacterial effects; bergenin in Ardisia japonica, which has antitussive effects; daphnetin in Daphne giraldii, which has sedative and analgesic effects; and psoralen in Psoralea corylifolia, which is used to treat leukoderma, among others. The above information was edited by Yaoyao from Chemical Book (2015-10-10). Production Method: Starting Materials: 51690-26-7 (2-Oxo-2H-chromene-6-carboxaldehyde) 7734-80-7 (2-Oxo-2H-chromene-6-carboxylic acid) General procedure for the synthesis of 2-oxo-2H-chromene-6-carboxylic acid from 2-oxo-2H-chromene-6-carboxaldehyde: A mixture of 6-methylcoumarin (25 g, 0.156 mol) and chlorobenzene (25 mL) was slowly added dropwise to a solution of 62.5% sulfuric acid (152 mL, containing 35 g, 0.4026 mol), followed by dropwise addition of 62.5% sulfuric acid (20 mL). The reaction was carried out at 80-90°C for 1 hour. After completion, the reaction system was cooled to room temperature, and water (150 mL) was added. Under ice-bath cooling, 25% ammonia water (43 mL) was slowly added dropwise, followed by EtOAc (50 mL) and methyl ethyl ketone (100 mL). The mixture was extracted twice (20 mL each), and the combined organic layers were concentrated by steam to remove ketone solvents. DMSO (15 mL) and HCl (10 mL) were added to the system, and the residue was reintroduced into the reaction mixture. 25% sodium chlorite (55 mL) was slowly added dropwise at 15-40°C. The mixture was stirred at this temperature for 30 minutes, then at 74-80°C for 15 minutes. After completion, the mixture was cooled to room temperature, and the organic layer was separated. Water (125 mL) was added to the organic layer, and 25% ammonia water (20 mL) was added dropwise at 30-40°C until the pH reached 10. The aqueous layer was separated. DMSO (70 mL) was added to the aqueous layer, and HCl (16 mL) was added dropwise at 30-40°C, followed by raising the temperature to 65-75°C by dropwise addition of HCl (15 mL). The mixture was stirred at the same temperature for 30 minutes. Finally, 14.8 g of yellow solid product was obtained in 50% yield. References: [1] Patent: CN103183606, 2016, B. Location in patent: Paragraph 0039-0041

Category

Description (English Translation)

Uses & Synthesis Methods

Coumarin derivative 6-carboxycoumarin is one of the carboxycoumarin derivatives. Depending on the exocyclic groups, coumarins have various derivatives: hydroxycoumarins, furanocoumarins, pyranocoumarins, dicoumarins, and dihydroisocoumarins, etc.

Coumarin, also known as coumarin, is the lactone and derivative of cis-o-hydroxycinnamic acid. It is widely distributed in the plant kingdom in free form and as glycosides, particularly abundant in the families Apiaceae, Fabaceae, Rutaceae, and Oleaceae. Many coumarin compounds possess characteristic aromas and were formerly used primarily as fragrances. Later, many were found to have physiological activities, such as aesculin in ash bark, which has antibacterial effects; bergenin in Ardisia japonica, which has antitussive effects; daphnetin in Daphne giraldii, which has sedative and analgesic effects; and psoralen in Psoralea corylifolia, which is used to treat leukoderma, among others.

The above information was edited by Yaoyao from Chemical Book (2015-10-10).

Production Method:

Starting Materials:
51690-26-7 (2-Oxo-2H-chromene-6-carboxaldehyde)
7734-80-7 (2-Oxo-2H-chromene-6-carboxylic acid)

General procedure for the synthesis of 2-oxo-2H-chromene-6-carboxylic acid from 2-oxo-2H-chromene-6-carboxaldehyde: A mixture of 6-methylcoumarin (25 g, 0.156 mol) and chlorobenzene (25 mL) was slowly added dropwise to a solution of 62.5% sulfuric acid (152 mL, containing 35 g, 0.4026 mol), followed by dropwise addition of 62.5% sulfuric acid (20 mL). The reaction was carried out at 80-90°C for 1 hour. After completion, the reaction system was cooled to room temperature, and water (150 mL) was added. Under ice-bath cooling, 25% ammonia water (43 mL) was slowly added dropwise, followed by EtOAc (50 mL) and methyl ethyl ketone (100 mL). The mixture was extracted twice (20 mL each), and the combined organic layers were concentrated by steam to remove ketone solvents. DMSO (15 mL) and HCl (10 mL) were added to the system, and the residue was reintroduced into the reaction mixture. 25% sodium chlorite (55 mL) was slowly added dropwise at 15-40°C. The mixture was stirred at this temperature for 30 minutes, then at 74-80°C for 15 minutes. After completion, the mixture was cooled to room temperature, and the organic layer was separated. Water (125 mL) was added to the organic layer, and 25% ammonia water (20 mL) was added dropwise at 30-40°C until the pH reached 10. The aqueous layer was separated. DMSO (70 mL) was added to the aqueous layer, and HCl (16 mL) was added dropwise at 30-40°C, followed by raising the temperature to 65-75°C by dropwise addition of HCl (15 mL). The mixture was stirred at the same temperature for 30 minutes. Finally, 14.8 g of yellow solid product was obtained in 50% yield.

References:
[1] Patent: CN103183606, 2016, B. Location in patent: Paragraph 0039-0041

Category	Value
Hazard Class	IRRITANT
HS Code (Customs)	2932990090

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Coumarin-6-carboxylic acid

CAS：7734-80-7 | Coumarin-6-carboxylic acid | Whchem

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