Epoxy curing agent Knowledge Ethacrynic Acid Ethacrynic Acid

Ethacrynic Acid Ethacrynic Acid

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Ethacrylic acid structural formula

Structural formula

Business number 019H
Molecular formula C13H12Cl2O4
Molecular weight 303.14
label

2,3-Dichloro-4-(2-methylenebutyryl)phenoxyacetic acid,

(2,3-Dichloro-4-[2-methylenebutyryl]phenoxy)acetic acid

Numbering system

CAS number:58-54-8

MDL number:MFCD00056693

EINECS number:200-384-1

RTECS number:AG6600000

BRN number:None

PubChem number:24894577

Physical property data

1. Appearance: White crystalline powder

2. Density (g/mL, 25/4℃): Undetermined

3. Relative vapor density (g/mL , air=1): Undetermined

4. Melting point (ºC): 121~125

5. Boiling point (ºC, normal pressure): Undetermined

6. Boiling point (ºC, 5.2kPa): Undetermined

7. Refractive index: Undetermined

8. Flash point (ºC): Undetermined

9. Specific rotation (º): Undetermined

10. Autoignition point or ignition temperature (ºC): Undetermined

11. Vapor pressure (kPa, 25ºC): Undetermined

12. Saturated vapor pressure (kPa, 60ºC): Undetermined

13. Heat of combustion (KJ/mol): Undetermined

14. Critical temperature (ºC): Undetermined

15. Critical pressure (KPa): Undetermined

16. Log value of oil-water (octanol/water) partition coefficient: Undetermined

17. Explosion upper limit (%, V/V): Undetermined

18. Explosion lower limit (%, V/V): Undetermined

19. Solubility: Very soluble in ethanol, soluble in ether, chloroform or glacial acetic acid, insoluble in water.

Toxicological data

None

Ecological data

None

Molecular structure data

1. Molar refractive index: 72.41

2. Molar volume (cm3/mol): 224.4

3. Isotonic specific volume (90.2K ): 586.9

4. Surface tension (dyne/cm): 46.8

5. Polarizability (10-24cm3): 28.70

Compute chemical data

1. Reference value for hydrophobic parameter calculation (XlogP): 3.8

2. Number of hydrogen bond donors: 1

3. Number of hydrogen bond acceptors: 4

4. Number of rotatable chemical bonds: 6

5. Number of tautomers: none

6. Topological molecule polar surface area 63.6

7. Number of heavy atoms: 19

8. Surface charge: 0

9. Complexity: 370

10. Number of isotope atoms: 0

11. Determined number of atomic stereocenters: 0

12. Uncertain number of atomic stereocenters: 0

13.�The number of stereocenters of definite chemical bonds: 0

14. The number of stereocenters of uncertain chemical bonds: 0

15. The number of covalent bond units: 1

Properties and stability

None

Storage method

Keep in a sealed container away from light.

Synthesis method

2,3-Dichloroanisole is condensed with butyryl chloride and hydrolyzed into 2,3-dichloro-4-butyrylphenol, which is then condensed with ethyl bromoacetate, and then further condensed with formaldehyde and hydrolyzed into ethainide acid. 1.2. Preparation of 3-dichloro-4-butyrylphenol. Add butyryl chloride, dichlorobenzomethyl ether and aluminum trichloride to carbon disulfide in sequence, react at room temperature for 1 hour, and then recycle carbon disulfide after flowing for another 1 hour. After recovery is completed, add n-heptane, then add aluminum trichloride, and continue refluxing for 3 hours. Cool to 50°C, separate the n-heptane, cool, add dilute hydrochloric acid, raise the temperature to 86°C, immediately cool to 40°C, filter and wash to obtain crude 2,3-dichloro-4-butyrophenol. The crude product is refined by acid-base method and decolorized with activated carbon to obtain a fine product with a melting point of 108-111°C. The yield is 85%. 2. Preparation of ethacrynic acid: Heat 2,3-dichloro-4-butyrophenol, absolute ethanol and sodium acetate to reflux, add ethyl bromoacetate dropwise, and recover the ethanol after 3 hours of reaction. Cool, filter, wash, and recrystallize with ethanol to obtain ethyl 2,3-dichloro-4-butyrylphenoxyacetate. Then put it into a mixture of formaldehyde and ethanol, add a mixture of potassium carbonate, water and ethanol dropwise under reflux, and continue refluxing for 1.5 hours. Cool, add dilute hydrochloric acid to precipitate, filter, wash, dry, and finally undergo recrystallization and activated carbon decolorization to obtain ethacrynic acid. The yield is about 40%.

Purpose

This product is a strong diuretic. Acts quickly but short-lived. It has the effect of inhibiting the reabsorption of sodium and chloride ions by the renal tubules. It is a necessary drug for severe edema and is used for many types of edema. However, it is highly toxic and should be used sparingly in patients with chronic renal insufficiency.

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