Welcome to LookChem.com Sign In|Join Free

CAS

  • or

58-54-8

Post Buying Request

58-54-8 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

58-54-8 Usage

Description

Ethacrynic acid is a loop diuretic with anticancer activity., It inhibits the Na-K-2Cl (NKCC) cotransporter in duck erythrocytes (IC50 = 0.18 mM) and ATP-dependent chloride uptake in rat renal plasma membrane vesicles when used at a concentration of 0.3 mM., Ethacrynic acid also inhibits glutathione S-transferase P1-1 (GSTP1-1) and GSTA3-3 (IC50s = 4.9 and ~0.4 μM, respectively), and inhibits Wnt/β-catenin signaling in a cell-based reporter assay. It is cytotoxic to primary chronic lymphocytic leukemia cells (IC50 = 8.56 μM), as well as MCF-7, MDA-MB-231, and 4T1 cancer cells (IC50s = 45.53, 39.64, and 25.23 μM, respectively). Ethacrynic acid (250 μg per day) increases tumor growth reduction induced by the EGFR family inhibitors afatinib (Item Nos. 11492 | 21567) or neratinib in a 4T1 murine breast cancer model. Formulations containing ethacrynic acid have been used in the treatment of edema.

Chemical Properties

White Solid

Originator

Hydromedin,MSD,W. Germany,1966

Uses

Different sources of media describe the Uses of 58-54-8 differently. You can refer to the following data:
1. A diuretic used to treat high blood pressure and swelling caused by congestive heart failure, liver failure and kidney failure.
2. Ethacrynic acid is a powerful diuretic prescribed for edema associated with cardiac insufficiency, renal edema that does not respond to other diuretics, and edema of the brain and lungs.
3. Ethacrynic acid is used to inhibits symport of sodium, potassium, and chloride primarily in the ascending limb of Henle, but also in the proximal and distal tubules. This pharmacological action results in excretion of these ions, increased urinary output, and reduction in extracellular fluid. This compound has been classified as a loop or high ceiling diuretic.

Definition

ChEBI: An aromatic ether that is phenoxyacetic acid in which the phenyl ring is substituted by chlorines at positions 2 and 3, and by a 2-methylidenebutanoyl group at position 4. It is a loop diuretic used to treat high blood pressure resulting from diseases such as congestive heart failure, liver failure, and kidney failure. It is also a glutathione S-transferase (EC 2.5.1.18) inhibitor.

Manufacturing Process

Step A: Preparation of 2,3-Dichloro-4-Butyrylphenoxy Acid - The product is prepared using the following ingredients: 22.1 grams (0.1 mol) 2,3- dichlorophenoxyacetic acid; 21.3 grams (0.2 mol) n-butyryl chloride; and 53.3 grams (0.4 mol) powdered aluminum chloride.The 2,3-dichlorophenoxyacetic acid and n-butyryl chloride are placed in the reaction vessel and stirred while the aluminum chloride is added portionwise over a 45-minute period. The mixture then is heated on the steam bath for 3 hours and allowed to cool to room temperature. The gummy product obtained is added to a mixture of 300 ml of crushed ice and 30 ml concentrated hydrochloric acid. The resulting mixture is extracted with ether and the extract evaporated at reduced pressure. The residue is suspended in boiling water and dissolved by addition of a minimum quantity of 40% sodium hydroxide. After treatment with decolorizing charcoal and filtering, the hot filtrate is made acid to Congo red paper and chilled in ice.The oil that separates is extracted with ether, the extract dried over anhydrous sodium sulfate and then evaporated at reduced pressure. The residue is dissolved in boiling benzene (75 ml) treated with decolorizing charcoal, filtered, treated with boiling cyclohexane (275 milliliters) and cooled to give 22.3 grams of 2,3-dichloro-4-butyrylphenoxyacetic acid. After several recrystallizations from a mixture of benzene and cyclohexane, then from methyl cyclohexane, next from a mixture of acetic acid and water, and finally from methylcyclohexane, the product melts at 110° to 111°C (corr).Step B: Preparation of 2,3-Dichloro-4-[2-(Dimethylaminomethyl) Butyryl]Phenoxyacetic Acid Hydrochloride - In a 100 ml round flask equipped with an outlet tube suitable for application of intermittent suction, an intimate mixture of 5.20 grams (0.0179 mol) 2,3-dichloro-4-butyrylphenoxyacetic acid; 0.63 gram (0.0209 mol) paraformaldehyde; 1.59 grams (0.0195 mol) dry dimethylamine hydrochloride; and 4 drops acetic acid is heated on the steam bath for about 1.5 hours during which period suction is applied for about 1 minute intervals five or six times. Upon cooling, a solid is obtained, The crude reaction product is triturated with ether to give 5.8 grams (85%) of 2.3- dichloro-4-[2-dimethylaminomethyl)butyryl]phenoxyacetic acid hydrochloride in the form of a white solid. After two recrystallizations from a mixture of methanol and ether, the product melts at 165° to 167°C.Step C: Preparation of 2,3-Dichloro-4-(2-Methylenebutyryl) Phenoxyacetic Acid - The Mannich compound obtained as described above is treated with aqueous sodium bicarbonate to form 2,3-dichloro-4-(2- methylenebutyryl)phenoxyacetic acid, MP 115° to 118°C. Two recrystallizations from a mixture of benzene and cyclohexane give white solid material melting at 118.5° to 120.5°C.

Brand name

Edecrin (Merck).

General Description

White solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Ethacrynic acid may react vigorously with strong oxidizing agents. Can react exothermically with reducing agents (such as alkali metals and hydrides) to release gaseous hydrogen. May react exothermically with acids. Reacts exothermically with all bases both organic (for example, the amines) and inorganic.

Fire Hazard

Ethacrynic acid is probably combustible.

Biochem/physiol Actions

Ethacrynic acid is non sulfonamide loop diuretic that is used to treat high blood pressure and the swelling caused by diseases like congestive heart failure. Ethacrynic acid blocks sodium-potassium-chloride cotransport. Also, Ethacrynic acid potently inhibits glutathione S-transferase family members. Studies show that ethacrynic acid potently inhibits Tgase-2 (transglutaminase-2) dependent metastasis of cancer cells including lung and pancreatic cancers.

Mechanism of action

The mechanism of action of ethacrynic acid appears to be more complex than the simple addition of sulfhydryl groups of the enzyme to the drug molecule. When the double bond of ethacrynic acid is reduced, the resultant compound is still active, although the diuretic activity is diminished. The sulfhydryl groups of the enzyme would not be expected to add to the drug molecule in the absence of the α,β-unsaturated ketone.These compounds are potent high-ceiling diuretics that resemble ethacrynic acid in their mechanism of action. The ethyl ester group represents a pro-drug that can be easily hydrolyzed to the free carboxyl group. As in ethacrynic acid, a 2,3-dichloro substitution is necessary. In addition, a para-hydroxyl group and an unsubstituted aminomethyl group on the benzene ring are highly beneficial. The carbonyl group can be replaced with an ether or sulfide group. These compounds have no ability to add the sulfhydryl groups of the kidney enzymes. The complete mechanism of action of these compounds remains in doubt.

Synthesis

Ethacrynic acid—[2,3-dichloro-4-(2-methylenbutyryl)phenoxy]acetic acid (21.4.9), is synthesized from 2,3-dichlorophenoxyacetic acid. This is acylated with butyroyl chloride, forming 4-butyroyl-2,3-dichlorophenoxyacetic acid (21.4.7), which is further aminomethylated under Mannich reaction conditions using dimethylamine and formaldehyde. The resulting product (21.4.8) undergoes further thermal degredation, forming an unsaturated ketone—ethacrynic acid (21.4.9).

Veterinary Drugs and Treatments

Ethacrynic acid is a loop diuretic that shares the same indications as furosemide (congestive cardiomyopathy, pulmonary edema, hypercalcuric nephropathy, uremia, as adjunctive therapy in hyperkalemia and, occasionally, as an antihypertensive agent). Its use has been largely supplanted in the armamentarium by furosemide for these indications. Ethacrynic acid may be useful in the treatment of nephrogenic diabetes insipidus as it may cause a paradoxical decrease in urine volume. Other uses include the adjunctive treatment of hypercalcemia and to increase the excretion of bromide in the treatment of bromide toxicity.

Check Digit Verification of cas no

The CAS Registry Mumber 58-54-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 8 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 58-54:
(4*5)+(3*8)+(2*5)+(1*4)=58
58 % 10 = 8
So 58-54-8 is a valid CAS Registry Number.
InChI:InChI=1/C13H12Cl2O4/c1-3-7(2)13(18)8-4-5-9(12(15)11(8)14)19-6-10(16)17/h4-5H,2-3,6H2,1H3,(H,16,17)

58-54-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Sigma-Aldrich

  • (Y0001263)  Etacrynic acid for system suitability  European Pharmacopoeia (EP) Reference Standard

  • 58-54-8

  • Y0001263

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (E1800000)  Ethacrynicacid  European Pharmacopoeia (EP) Reference Standard

  • 58-54-8

  • E1800000

  • 1,880.19CNY

  • Detail
  • USP

  • (1256004)  Ethacrynicacid  United States Pharmacopeia (USP) Reference Standard

  • 58-54-8

  • 1256004-200MG

  • 4,326.66CNY

  • Detail
  • Sigma

  • (SML1083)  Ethacrynicacid  ≥97% (HPLC)

  • 58-54-8

  • SML1083-10MG

  • 376.74CNY

  • Detail

58-54-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name etacrynic acid

1.2 Other means of identification

Product number -
Other names Ethacrynic Acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:58-54-8 SDS

58-54-8Synthetic route

formaldehyd
50-00-0

formaldehyd

<2,3-dichloro-4-(1-oxobutyl)phenyloxy>acetic acid
1217-67-0

<2,3-dichloro-4-(1-oxobutyl)phenyloxy>acetic acid

ethacrynic acid
58-54-8

ethacrynic acid

Conditions
ConditionsYield
With potassium carbonate In ethanol; water at 90℃; for 10h;80.5%
t-butylamine salt of ethacrynic acid

t-butylamine salt of ethacrynic acid

ethacrynic acid
58-54-8

ethacrynic acid

Conditions
ConditionsYield
With hydrogenchloride In water; ethyl acetate at 30℃; for 0.5h; pH=2 - 3;60.1%
2,3-dichloro-4-(2-methylenebutyryl)-phenol
4115-00-8

2,3-dichloro-4-(2-methylenebutyryl)-phenol

ethacrynic acid
58-54-8

ethacrynic acid

formaldehyd
50-00-0

formaldehyd

2,3-Dichlor-4-butyryl-phenoxyessigsaeure-aethylester
2977-51-7

2,3-Dichlor-4-butyryl-phenoxyessigsaeure-aethylester

ethacrynic acid
58-54-8

ethacrynic acid

Conditions
ConditionsYield
Stage #1: formaldehyd; 2,3-Dichlor-4-butyryl-phenoxyessigsaeure-aethylester With potassium carbonate Aldol condensation;
Stage #2: With hydrogenchloride; water
With potassium carbonate In ethanol; water for 24h; Aldol Condensation; Reflux;
2',3'-dichloro-4'-hydroxybutyrophenone
2350-46-1

2',3'-dichloro-4'-hydroxybutyrophenone

ethacrynic acid
58-54-8

ethacrynic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / toluene / 48 h / Reflux
2: potassium carbonate / ethanol; water / 24 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate; potassium iodide / acetone / 0.5 h
1.2: 4 h / 60 °C
1.3: 2 h / 20 °C
2.1: potassium carbonate / ethanol; water / 10 h / 90 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / ethanol / 0.33 h / 30 °C
1.2: 12 h / 30 - 83 °C
2.1: N,N-dimethyl-formamide / 0.17 h / 30 °C
2.2: 12 h / 100 °C
3.1: N,N-dimethyl-formamide; toluene / 5 h / 20 - 30 °C
4.1: hydrogenchloride / ethyl acetate; water / 0.5 h / 30 °C / pH 2 - 3
View Scheme
2,3-dichlorophenol
576-24-9

2,3-dichlorophenol

ethacrynic acid
58-54-8

ethacrynic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aluminum (III) chloride / carbon disulfide
2: potassium carbonate / toluene / 48 h / Reflux
3: potassium carbonate / ethanol; water / 24 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / acetone / 0.5 h
1.2: 3 h / 60 °C
2.1: aluminum (III) chloride / dichloromethane / 3.5 h / 0 - 40 °C
2.2: 3 h / 20 °C / Cooling with ice
3.1: potassium carbonate; potassium iodide / acetone / 0.5 h
3.2: 4 h / 60 °C
3.3: 2 h / 20 °C
4.1: potassium carbonate / ethanol; water / 10 h / 90 °C
View Scheme
Os(η6-p-cymene)(acetylacetonato)(2-(2,3-dichloro-4-(2-ethylenebutanoyl)phenoxy)acetato)

Os(η6-p-cymene)(acetylacetonato)(2-(2,3-dichloro-4-(2-ethylenebutanoyl)phenoxy)acetato)

A

[(η6-p-cymene)Os(acetylacetonato)Cl]

[(η6-p-cymene)Os(acetylacetonato)Cl]

B

ethacrynic acid
58-54-8

ethacrynic acid

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 37℃; for 72h;
2,3-dichloroanisole
1984-59-4

2,3-dichloroanisole

ethacrynic acid
58-54-8

ethacrynic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: aluminum (III) chloride / dichloromethane / 3.5 h / 0 - 40 °C
1.2: 3 h / 20 °C / Cooling with ice
2.1: potassium carbonate; potassium iodide / acetone / 0.5 h
2.2: 4 h / 60 °C
2.3: 2 h / 20 °C
3.1: potassium carbonate / ethanol; water / 10 h / 90 °C
View Scheme
Multi-step reaction with 5 steps
1.1: aluminum (III) chloride / dichloromethane / 0.17 h / 30 °C
1.2: 8 h / 20 - 30 °C
1.3: 8 h / 30 - 42 °C
2.1: potassium carbonate / ethanol / 0.33 h / 30 °C
2.2: 12 h / 30 - 83 °C
3.1: N,N-dimethyl-formamide / 0.17 h / 30 °C
3.2: 12 h / 100 °C
4.1: N,N-dimethyl-formamide; toluene / 5 h / 20 - 30 °C
5.1: hydrogenchloride / ethyl acetate; water / 0.5 h / 30 °C / pH 2 - 3
View Scheme
C26H22Cl12Nb2O8

C26H22Cl12Nb2O8

ethacrynic acid
58-54-8

ethacrynic acid

Conditions
ConditionsYield
In diethyl ether; water at 20℃; for 48h; Inert atmosphere;
<2,3-dichloro-4-(1-oxobutyl)phenyloxy>acetic acid
1217-67-0

<2,3-dichloro-4-(1-oxobutyl)phenyloxy>acetic acid

ethacrynic acid
58-54-8

ethacrynic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N,N-dimethyl-formamide / 0.17 h / 30 °C
1.2: 12 h / 100 °C
2.1: N,N-dimethyl-formamide; toluene / 5 h / 20 - 30 °C
3.1: hydrogenchloride / ethyl acetate; water / 0.5 h / 30 °C / pH 2 - 3
View Scheme
(2,3-dichloro-4-[2-dimethylaminomethyl-butyryl]phenoxy)acetic acid
1160-10-7

(2,3-dichloro-4-[2-dimethylaminomethyl-butyryl]phenoxy)acetic acid

ethacrynic acid
58-54-8

ethacrynic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide; toluene / 5 h / 20 - 30 °C
2: hydrogenchloride / ethyl acetate; water / 0.5 h / 30 °C / pH 2 - 3
View Scheme
ethacraplatin
847227-34-3

ethacraplatin

B

ethacrynic acid
58-54-8

ethacrynic acid

Conditions
ConditionsYield
With sodium L-ascorbate In tetrahydrofuran; aq. phosphate buffer; dimethyl sulfoxide at 20℃; pH=7.4; Kinetics;
C13H18Cl4N2O5Pt

C13H18Cl4N2O5Pt

B

ethacrynic acid
58-54-8

ethacrynic acid

Conditions
ConditionsYield
With sodium L-ascorbate In aq. phosphate buffer at 20℃; pH=7.4; Kinetics;
ethacrynic acid
58-54-8

ethacrynic acid

2-(2,3-dichloro-4-(2-methylbutanoyl)phenoxy)acetic acid
5378-94-9

2-(2,3-dichloro-4-(2-methylbutanoyl)phenoxy)acetic acid

Conditions
ConditionsYield
With hydrogen; palladium In methanol at 20℃; for 12h;100%
With palladium on activated charcoal; hydrogen In isopropyl alcohol under 2250.23 Torr; for 0.333333h; Inert atmosphere;100%
With L-Selectride In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;56%
ethacrynic acid
58-54-8

ethacrynic acid

<2,3-dichloro-4-(2-methylenebutyryl)phenoxy>acetyl chloride
113239-57-9

<2,3-dichloro-4-(2-methylenebutyryl)phenoxy>acetyl chloride

Conditions
ConditionsYield
With oxalyl dichloride at 70℃; for 1h;98.13%
With thionyl chloride In benzene for 1.25h; Heating;
With oxalyl dichloride In toluene Heating;
ethacrynic acid
58-54-8

ethacrynic acid

methyl (E)-3-aminocrotonate
14205-39-1

methyl (E)-3-aminocrotonate

<2,3-Dichlor-4-(3-ethyl-5-methoxycarbonyl-6-methyl-pyridin-2-yl)phenoxy>-essigsaeure
104684-27-7

<2,3-Dichlor-4-(3-ethyl-5-methoxycarbonyl-6-methyl-pyridin-2-yl)phenoxy>-essigsaeure

Conditions
ConditionsYield
at 120℃; for 0.5h;98%
ethacrynic acid
58-54-8

ethacrynic acid

diethyl malonate
105-53-3

diethyl malonate

2-[2-(4-Carboxymethoxy-2,3-dichloro-benzoyl)-butyl]-malonic acid diethyl ester
183430-20-8

2-[2-(4-Carboxymethoxy-2,3-dichloro-benzoyl)-butyl]-malonic acid diethyl ester

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 0.0833333h; Ambient temperature;98%
ethacrynic acid
58-54-8

ethacrynic acid

ethyl acetoacetate
141-97-9

ethyl acetoacetate

2-Acetyl-4-(4-carboxymethoxy-2,3-dichloro-benzoyl)-hexanoic acid ethyl ester

2-Acetyl-4-(4-carboxymethoxy-2,3-dichloro-benzoyl)-hexanoic acid ethyl ester

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 0.25h; Ambient temperature;93%
ethacrynic acid
58-54-8

ethacrynic acid

tert-butyl N-(6-aminohexyl)carbamate
51857-17-1

tert-butyl N-(6-aminohexyl)carbamate

C24H34Cl2N2O5

C24H34Cl2N2O5

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;93%
p-hydroxyphenethyl alcohol
501-94-0

p-hydroxyphenethyl alcohol

ethacrynic acid
58-54-8

ethacrynic acid

4-hydroxyphenethyl 2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy)acetate

4-hydroxyphenethyl 2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy)acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane for 12h; Inert atmosphere;92%
With toluene-4-sulfonic acid In dichloromethane at 0 - 50℃; for 12h;92%
ethacrynic acid
58-54-8

ethacrynic acid

1-Adamantanamine
768-94-5

1-Adamantanamine

C23H27Cl2NO3

C23H27Cl2NO3

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;92%
ethacrynic acid
58-54-8

ethacrynic acid

[2,3-Dichloro-4-(4-ethyl-4,5-dihydro-1H-pyrazol-3-yl)-phenoxy]-acetic acid

[2,3-Dichloro-4-(4-ethyl-4,5-dihydro-1H-pyrazol-3-yl)-phenoxy]-acetic acid

Conditions
ConditionsYield
With hydrazine hydrate; N-ethyl-N,N-diisopropylamine In methanol at 60℃; for 12h;89%
ethacrynic acid
58-54-8

ethacrynic acid

4-(hydroxymethyl)-4'-methyl-2,2'-bipyridine
81998-04-1

4-(hydroxymethyl)-4'-methyl-2,2'-bipyridine

(4′-methyl-[2,2′-bipyridin]-4-yl)methyl-2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy)acetate

(4′-methyl-[2,2′-bipyridin]-4-yl)methyl-2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy)acetate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; Schlenk technique; Inert atmosphere;88%
ethacrynic acid
58-54-8

ethacrynic acid

4-azidobutan-1-amine
88192-20-5

4-azidobutan-1-amine

1-{4-[(4-azidobutylaminooxy)methyl]-2,3-dichlorophenyl}-2-methylenebutan-1-one
1284258-80-5

1-{4-[(4-azidobutylaminooxy)methyl]-2,3-dichlorophenyl}-2-methylenebutan-1-one

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; Inert atmosphere;86%
ethacrynic acid
58-54-8

ethacrynic acid

(o-hydroxyphenyl)diphenylphosphine
60254-10-6

(o-hydroxyphenyl)diphenylphosphine

C31H25Cl2O4P

C31H25Cl2O4P

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; Inert atmosphere; Schlenk technique;86%
nitromethane
75-52-5

nitromethane

ethacrynic acid
58-54-8

ethacrynic acid

<2,3-Dichlor-4-(2-ethyl-4-nitrobutyryl)phenoxy>essigsaeure
138470-10-7

<2,3-Dichlor-4-(2-ethyl-4-nitrobutyryl)phenoxy>essigsaeure

Conditions
ConditionsYield
With sodium methylate In methanol for 0.0833333h; Ambient temperature;83%
other nitroalkanes;
ethacrynic acid
58-54-8

ethacrynic acid

N-(4-aminobutyl)carbaminsaeure-(tert-butyl)ester-hydrochlorid
33545-98-1

N-(4-aminobutyl)carbaminsaeure-(tert-butyl)ester-hydrochlorid

C22H30Cl2N2O5

C22H30Cl2N2O5

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;83%
ethacrynic acid
58-54-8

ethacrynic acid

6-amino-9-(4-(aminomethyl)benzyl)-2-(2-methoxyethoxy)-9H-purin-8-ol

6-amino-9-(4-(aminomethyl)benzyl)-2-(2-methoxyethoxy)-9H-purin-8-ol

C29H30Cl2N6O6

C29H30Cl2N6O6

Conditions
ConditionsYield
With dmap; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl acetamide at 20℃; for 10h; Concentration; Solvent; Time;80.7%
ethacrynic acid
58-54-8

ethacrynic acid

4-diphenylphosphanobenzoic acid
2129-31-9

4-diphenylphosphanobenzoic acid

2-((4-(diphenylphosphanyl)benzyl)oxy)ethyl-2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy) acetate

2-((4-(diphenylphosphanyl)benzyl)oxy)ethyl-2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy) acetate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 6.5h; Inert atmosphere; Schlenk technique;79%
pyridine-4-methanol
586-95-8

pyridine-4-methanol

ethacrynic acid
58-54-8

ethacrynic acid

pyridin-4-yl-methyl 2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy)acetate

pyridin-4-yl-methyl 2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy)acetate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;77%
ethacrynic acid
58-54-8

ethacrynic acid

sodium cyanide
143-33-9

sodium cyanide

<2,3-Dichlor-4-(2-cyanmethylbutyryl)phenoxy>essigsaeure
138470-12-9

<2,3-Dichlor-4-(2-cyanmethylbutyryl)phenoxy>essigsaeure

Conditions
ConditionsYield
In ethanol for 12h; Ambient temperature;76%
ethacrynic acid
58-54-8

ethacrynic acid

ethylene glycol
107-21-1

ethylene glycol

2-hydroxyethyl-2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy)acetate

2-hydroxyethyl-2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy)acetate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; Schlenk technique; Inert atmosphere;76%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;75%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃; for 2.5h;64%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃; for 15h; Schlenk technique;26%
(S)-Ethyl lactate
687-47-8

(S)-Ethyl lactate

ethacrynic acid
58-54-8

ethacrynic acid

(S)-2-(2,3-Dichlor-4-(2-methylen-1-oxobutyl)-phenoxyacetyl)-oxypropionsaeureethylester

(S)-2-(2,3-Dichlor-4-(2-methylen-1-oxobutyl)-phenoxyacetyl)-oxypropionsaeureethylester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide; dmap In dichloromethane -10 to -5 deg C, 30 min then room temp.;75.7%
(η6-p-cymene)bis(acetylacetonato)osmium

(η6-p-cymene)bis(acetylacetonato)osmium

ethacrynic acid
58-54-8

ethacrynic acid

Os(η6-p-cymene)(acetylacetonato)(2-(2,3-dichloro-4-(2-ethylenebutanoyl)phenoxy)acetato)

Os(η6-p-cymene)(acetylacetonato)(2-(2,3-dichloro-4-(2-ethylenebutanoyl)phenoxy)acetato)

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;75%
ethacrynic acid
58-54-8

ethacrynic acid

N-BOC-1,2-diaminoethane
57260-73-8

N-BOC-1,2-diaminoethane

C20H26Cl2N2O5

C20H26Cl2N2O5

Conditions
ConditionsYield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;73%
ethacrynic acid
58-54-8

ethacrynic acid

ethyl acetoacetate
141-97-9

ethyl acetoacetate

[2,3-dichloro-4-(6ethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid
183430-18-4

[2,3-dichloro-4-(6ethyl-3-oxo-1-cyclohexen-1-yl)phenoxy]acetic acid

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol for 3h; Heating;72%
With sodium methylate In ethanol; water
ethacrynic acid
58-54-8

ethacrynic acid

niobium pentachloride
10026-12-7

niobium pentachloride

C26H22Cl12Nb2O8

C26H22Cl12Nb2O8

Conditions
ConditionsYield
In dichloromethane at 20℃; for 4h; Schlenk technique; Inert atmosphere;72%
ethacrynic acid
58-54-8

ethacrynic acid

2-[2-(adamantan-1-yloxy)-ethoxy]-ethanol
1266678-98-1

2-[2-(adamantan-1-yloxy)-ethoxy]-ethanol

C27H34Cl2O6

C27H34Cl2O6

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;72%
Nitroethane
79-24-3

Nitroethane

ethacrynic acid
58-54-8

ethacrynic acid

<2,3-Dichlor-4-(2-ethyl-4-nitrovaleryl)phenoxy>essigsaeure
138470-11-8

<2,3-Dichlor-4-(2-ethyl-4-nitrovaleryl)phenoxy>essigsaeure

Conditions
ConditionsYield
With sodium methylate In methanol for 4h; Heating;71%

58-54-8Relevant articles and documents

Arene Osmium Complexes with Ethacrynic Acid-Modified Ligands: Synthesis, Characterization, and Evaluation of Intracellular Glutathione S-Transferase Inhibition and Antiproliferative Activity

Agonigi, Gabriele,Riedel, Tina,Gay, M. Pilar,Biancalana, Lorenzo,O?ate, Enrique,Dyson, Paul J.,Pampaloni, Guido,Pǎunescu, Emilia,Esteruelas, Miguel A.,Marchetti, Fabio

, p. 1046 - 1056 (2016)

Four arene osmium complexes were prepared containing derivatives of ethacrynic acid, a potent inhibitor of glutathione S-transferases, either by direct coordination or via N- or P-donor ligands. The complexes were characterized by spectroscopic and analytical methods and, for Os(η6-p-cymene)(acetylacetonato)(2-(2,3-dichloro-4-(2-ethylenebutanoyl)phenoxy)acetato) and Os(η6-p-cymene)Cl2(2-(2-(2,3-dichloro-4-(2-methylenebutanoyl)phenoxy)acetoxy)ethyl nicotinato), by single-crystal X-ray diffraction. The cytotoxicity of the complexes toward human ovarian cancer cells and nontumorous human embryonic kidney cells was investigated, and two of the complexes, for which ruthenium analogues are known, helped to delineate the influence of the metal ion. Inhibition studies of intracellular glutathione S-transferases (GSTs, detoxification enzymes implicated in drug resistance) indicate that the observed cytotoxicity of the complexes involves GST inhibition, as well as other targets following dissociation of the ethacrynic acid group from the osmium(II) ion.

Process for the Preparation of Ethacrynic Acid

-

Paragraph 0080, (2018/05/03)

The invention provides an improved process for preparing Ethacrynic acid of formula I, including the steps of: (a) reacting 4-butyryl-2,3-dichloro-phenoxy acetic acid of formula II with dimethylamine or its salt to obtain [2,3-dichloro-4-[2-dimethylaminomethyl butyryl phenoxy acetic acid of formula III or its salt; (b) hydrolysing [2,3-dichloro-4-[2-dimethylaminomethyl butyryl phenoxy acetic acid hydrochloride of formula III obtained in step a) with t-butyl amine to obtain t-butyl amine salt of Ethacrynic acid; (c) acidifying the t-butyl amine salt of Ethacrynic acid formed in step b) to obtain Ethacrynic acid of formula I; and(d) optionally purifying the obtained Ethacrynic acid with a solvent mixture of alkyl acetate and hydrocarbon solvent. The invention also provides crystalline t-butylamine salt of Ethacrynic acid and process thereof. Also provide compound Ethacrynic acid having a purity of greater than or equal to 99% and a composition including the compound.

Environmental-protection preparation method for high yielding of 1,2,4-oxadiazole compounds containing alpha,beta-unsaturated ketones

-

, (2017/08/30)

The invention provides an environmental-protection preparation method for high yielding of 1,2,4-oxadiazole compounds containing alpha,beta-unsaturated ketones; with 2,3-dichlorophenol as a raw material, an intermediate 5 is obtained through methylation and protection of phenolic hydroxyl groups, Friedel-Crafts acylation, methyl protecting group removal, nucleophilic substitution, ester hydrolysis, aldol condensation and dehydration reaction and then undergoes cyclization reaction with substituted amine oxime to obtain the target products 6r, 6s and 6u. The method has the advantages of mild reaction conditions, has no use of first-class reagents and other reagents harmful on the environment and operating personnel, fewer by-products, stable and controllable reactions, simple postprocessing, high yield and purity, and easy industrialized production.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 58-54-8