Ethacrynic acid supplier

Name
Ethacrynic acid
EINECS 200-384-1
CAS No. 58-54-8
Article Data32
CAS DataBase
Density 1.35g/cm³
Solubility Soluble in ethanol, chloroform, ether, ammonia, carbonates, and methanol. Insoluble in water.
Melting Point 122
Formula C13H12 Cl2 O4
Boiling Point 480°Cat760mmHg
Molecular Weight 303.142
Flash Point 244.1°C
Transport Information
Appearance White solid.
Safety Poison by intravenous route. Moderately toxic by ingestion. Human systemic effects by ingestion and intravenous routes: urine volume increase, impaired hearing, and tinnitus (ringing in the ears). A diuretic. When heated to decomposition it emits toxic fumes of Cl⁻.
Risk Codes R20/21/22;R36/37/38
Molecular Structure
Hazard Symbols
Synonyms Aceticacid, [2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]- (9CI); Acetic acid,[2,3-dichloro-4-(2-methylenebutyryl)phenoxy]- (8CI);2,3-Dichloro-4-(2-ethyl-1-oxo-2-propenyl)-phenoxyacetic acid; Crinuril;Edecril; Edecrin; Edecrina; Endecril; Etacrynic acid; Etakrinic acid;Ethacrynic acid; Hidromedin; Hydromedin; MK 595; Mingit; NSC 624008; NSC 85791;Otacril; Reomax; Taladren; Uregit;[2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy]acetic acid;[2,3-Dichloro-4-(2-methylenebutyryl)phenoxy]acetic acid;[4-(2-Methylenebutyryl)-2,3-dichlorophenoxy]acetic acid
PSA 63.60000
LogP 3.60570

Synthetic route

: 50-00-0
formaldehyd

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

: 58-54-8
ethacrynic acid

Conditions

Conditions	Yield
With potassium carbonate In ethanol; water at 90℃; for 10h;	80.5%

: t-butylamine salt of ethacrynic acid

: 58-54-8
ethacrynic acid

Conditions

Conditions	Yield
With hydrogenchloride In water; ethyl acetate at 30℃; for 0.5h; pH=2 - 3;	60.1%

: 4115-00-8
2,3-dichloro-4-(2-methylenebutyryl)-phenol

: 58-54-8
ethacrynic acid

: 50-00-0
formaldehyd

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

: 58-54-8
ethacrynic acid

Conditions

Conditions	Yield
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;

: 2350-46-1
2',3'-dichloro-4'-hydroxybutyrophenone

: 58-54-8
ethacrynic acid

Conditions

Conditions	Yield
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

: 576-24-9
2,3-dichlorophenol

: 58-54-8
ethacrynic acid

Conditions

Conditions	Yield
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)

A: [(η6-p-cymene)Os(acetylacetonato)Cl]

B: 58-54-8
ethacrynic acid

Conditions

Conditions	Yield
In water; dimethyl sulfoxide at 37℃; for 72h;

: 1984-59-4
2,3-dichloroanisole

: 58-54-8
ethacrynic acid

Conditions

Conditions	Yield
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

Yield

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

: 58-54-8
ethacrynic acid

Conditions

Conditions	Yield
In diethyl ether; water at 20℃; for 48h; Inert atmosphere;

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

: 58-54-8
ethacrynic acid

Conditions

Conditions	Yield
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

: 1160-10-7
(2,3-dichloro-4-[2-dimethylaminomethyl-butyryl]phenoxy)acetic acid

: 58-54-8
ethacrynic acid

Conditions

Conditions	Yield
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

: 847227-34-3
ethacraplatin

A: 26035-31-4, 14913-33-8, 15663-27-1
cisplatine

B: 58-54-8
ethacrynic acid

Conditions

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

: C13H18Cl4N2O5Pt

A: 26035-31-4, 14913-33-8, 15663-27-1
cisplatine

B: 58-54-8
ethacrynic acid

Conditions

Conditions	Yield
With sodium L-ascorbate In aq. phosphate buffer at 20℃; pH=7.4; Kinetics;

: 58-54-8
ethacrynic acid

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

Conditions

Conditions	Yield
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%

: 58-54-8
ethacrynic acid

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

Conditions

Conditions	Yield
With oxalyl dichloride at 70℃; for 1h;	98.13%
With thionyl chloride In benzene for 1.25h; Heating;
With oxalyl dichloride In toluene Heating;

: 58-54-8
ethacrynic acid

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

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

Conditions

Conditions	Yield
at 120℃; for 0.5h;	98%

: 58-54-8
ethacrynic acid

: 105-53-3
diethyl malonate

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

Conditions

Conditions	Yield
With sodium ethanolate In ethanol for 0.0833333h; Ambient temperature;	98%

: 58-54-8
ethacrynic acid

: 141-97-9
ethyl acetoacetate

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

Conditions

Conditions	Yield
With sodium ethanolate In ethanol for 0.25h; Ambient temperature;	93%

: 58-54-8
ethacrynic acid

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

: C24H34Cl2N2O5

Conditions

Conditions	Yield
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	93%

: 501-94-0
p-hydroxyphenethyl alcohol

: 58-54-8
ethacrynic acid

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

Conditions

Conditions	Yield
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%

: 58-54-8
ethacrynic acid

: 768-94-5
1-Adamantanamine

: C23H27Cl2NO3

Conditions

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

: 58-54-8
ethacrynic acid

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

Conditions

Conditions	Yield
With hydrazine hydrate; N-ethyl-N,N-diisopropylamine In methanol at 60℃; for 12h;	89%

: 58-54-8
ethacrynic acid

: 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

Conditions

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

: 58-54-8
ethacrynic acid

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

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

Conditions

Conditions	Yield
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%

: 58-54-8
ethacrynic acid

: 60254-10-6
(o-hydroxyphenyl)diphenylphosphine

: C31H25Cl2O4P

Conditions

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

: 75-52-5
nitromethane

: 58-54-8
ethacrynic acid

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

Conditions

Conditions	Yield
With sodium methylate In methanol for 0.0833333h; Ambient temperature;	83%
other nitroalkanes;

: 58-54-8
ethacrynic acid

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

: C22H30Cl2N2O5

Conditions

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

: 58-54-8
ethacrynic acid

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

: C29H30Cl2N6O6

Conditions

Conditions	Yield
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%

: 58-54-8
ethacrynic acid

: 2129-31-9
4-diphenylphosphanobenzoic acid

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

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 6.5h; Inert atmosphere; Schlenk technique;	79%

: 586-95-8
pyridine-4-methanol

: 58-54-8
ethacrynic acid

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

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;	77%

: 58-54-8
ethacrynic acid

: 143-33-9
sodium cyanide

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

Conditions

Conditions	Yield
In ethanol for 12h; Ambient temperature;	76%

: 58-54-8
ethacrynic acid

: 107-21-1
ethylene glycol

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

Conditions

Conditions	Yield
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%

: 687-47-8
(S)-Ethyl lactate

: 58-54-8
ethacrynic acid

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

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide; dmap In dichloromethane -10 to -5 deg C, 30 min then room temp.;	75.7%

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

: 58-54-8
ethacrynic acid

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

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 24h;	75%

: 58-54-8
ethacrynic acid

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

: C20H26Cl2N2O5

Conditions

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

: 58-54-8
ethacrynic acid

: 141-97-9
ethyl acetoacetate

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

Conditions

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

: 58-54-8
ethacrynic acid

: 10026-12-7
niobium pentachloride

: C26H22Cl12Nb2O8

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 4h; Schlenk technique; Inert atmosphere;	72%

: 58-54-8
ethacrynic acid

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

: C27H34Cl2O6

Conditions

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

: 79-24-3
Nitroethane

: 58-54-8
ethacrynic acid

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

Conditions

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

Ethacrynic acid Chemical Properties

IUPAC Name: 2-[2,3-Dichloro-4-(2-methylidenebutanoyl)phenoxy]acetic acid
Product Name: Ethacrynic acid
The MF of Ethacrynic acid (CAS NO.58-54-8) is C₁₃H₁₂Cl₂O₄.

The MW of Ethacrynic acid (CAS NO.58-54-8) is 303.14.
Synonyms of Ethacrynic acid (CAS NO.58-54-8): (2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)-aceticacid ; (2,3-Dichloro-4-(2-methylene-1-oxobutyl)phenoxy)aceticacid ; (4-(2-Methylenebutyryl)-2,3-dichlorophenoxy)aceticacid ; [2,3-Dichloro-4-(2-methylene-1-oxobutyl)phe-noxy]aceticacid ; Crinuryl ; Edecril ; Edecrin
Index of Refraction: 1.558
Apperance: White solid
EINECS: 200-384-1
Density: 1.35 g/ml
Flash Point: 244.1 °C
Boiling Point: 480 °C
Melting Point: 125 °C
Merck: 3717

Ethacrynic acid Uses

Ethacrynic acid (CAS NO.58-54-8) is strong diuretic inhibiting renal tubular sodium and chloride re-absorption.The role is strong and fast and a serious edema required for drugs, but the toxicity is large.

Ethacrynic acid Production

Raw materials: Sodium hydroxide-->Hydrochloric acid-->Methanol-->Diethyl ether-->Sulfuric acid -->Acetic acid glacial-->Sodium sulfate-->Sodium bicarbonate-->Benzene-->Aluminium chloride-->Sodium acetate-->Carbon disulphide-->Paraformaldehyde-->Chloroacetic acid-->Cyclohexane-->Ethyl bromoacetate-->Heptane-->Butyryl chloride-->Carbon-->Dimethylamine hydrochloride-->Methylcyclohexane-->2,3-Dichlorophenol-->2,6-Dichloroanisole-->Butyrophenone-->Ethyl phenoxyacetate-->2,3-Dichlorophenoxyacetic Acid

Ethacrynic acid Toxicity Data With Reference

1.	orl-wmn TDLo:4 mg/kg:EAR	AIMDAP Archives of Internal Medicine. 117 (1966),715.
2.	orl-man TDLo:3 mg/kg:EAR,KID	AIMDAP Archives of Internal Medicine. 117 (1966),715.
3.	ivn-wmn TDLo:3 mg/kg:EAR	AIMDAP Archives of Internal Medicine. 117 (1966),715.
4.	orl-rat LD50:1 g/kg	YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. 21 (1979),775.
5.	ipr-rat LD50:43 mg/kg	OYYAA2 Oyo Yakuri. Pharmacometrics. 2 (1968),411.
6.	orl-mus LD50:627 mg/kg	MEIEDD Merck Index. 10 (1983),539.
7.	ivn-mus LD50:176 mg/kg	MEIEDD Merck Index. 10 (1983),539.

Ethacrynic acid Safety Profile

Poison by intravenous route. Moderately toxic by ingestion. Human systemic effects by ingestion and intravenous routes: urine volume increase, impaired hearing, and tinnitus (ringing in the ears). A diuretic. When heated to decomposition it emits toxic fumes of Cl⁻.Safety information of Ethacrynic acid (CAS NO.58-54-8):
Hazard Codes Harmful Xn
Risk Statements
20/21/22 Harmful by inhalation, in contact with skin and if swallowed
36/37/38 Irritating to eyes, respiratory system and skin
Safety Statements
26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36 Wear suitable protective clothing
WGK Germany 3
RTECS AG6600000

Ethacrynic acid Specification

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.

Product Name

Ethacrynic acid

Synthetic route

Ethacrynic acid Chemical Properties

Ethacrynic acid Uses

Ethacrynic acid Production

Ethacrynic acid Toxicity Data With Reference

Ethacrynic acid Safety Profile

Ethacrynic acid Specification

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