Name: Ethacrynic acid
SKU: 58-54-8

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Basic Information

Molecular Structure:
CAS No.:	58-54-8
Name:	Ethacrynic acid
Article Data:	32

Formula:	C13H12 Cl2 O4
Molecular Weight:	303.142
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
EINECS:	200-384-1
Density:	1.35g/cm³
Melting Point:	122
Boiling Point:	480°Cat760mmHg
Flash Point:	244.1°C
Solubility:	Soluble in ethanol, chloroform, ether, ammonia, carbonates, and methanol. Insoluble in water.
Appearance:	White solid.
Hazard Symbols:
Risk Codes:	R20/21/22;R36/37/38
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⁻.
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

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

Raw Materials

576-24-9

50-00-0

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Chemistry

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

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.

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

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.

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

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.