540-82-9

Basic information

• Product Name: ethyl hydrogen sulphate
• Synonyms: ethyl hydrogen sulphate;Ethy Hydrogen Sulphate;Sulfuric acid, monoethyl ester;Sulfethylic acid;Sulfovinic acid;Sulfuric acid hydrogen ethyl ester;sulfuric acid ethyl ester;Ethyl sulfate free-forM
• CAS NO: 540-82-9
• Molecular Formula: C₂H₆O₄S
• Molecular Weight: 126.13164
• EINECS: 208-758-6
• Product Categories: Pharmaceutical Intermediates
• Mol File: 540-82-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: -32°C (estimate)
• Boiling Point: 280°C
• Appearance: /liquid (estimate)
• Density: 1.458
• Refractive Index: 1.4105
• PKA: -3.14±0.15(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents, metals
• CAS DataBase Reference: ethyl hydrogen sulphate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl hydrogen sulphate(540-82-9)
• EPA Substance Registry System: ethyl hydrogen sulphate(540-82-9)

Safety Data

• RIDADR: 2571
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 540-82-9(Hazardous Substances Data)

Usage

Chemical Properties

Colorless, oily liquid; boils at 280°C (536°F)(decomposes); density 1.367; highly solublein water; hydrolyzes forming sulfuric acid.

Uses

Ethyl hydrogen sulfate is used as an intermediate in the synthesis of ethanol from ethylene.

General Description

ethyl hydrogen sulphate are colorless, oily liquids. They are soluble in water and weigh more than water. Contact with the material may cause severe irritation to skin, eyes, and mucous membranes. ethyl hydrogen sulphate may be toxic by ingestion, inhalation and skin absorption. ethyl hydrogen sulphate is used to make other chemicals.

Air & Water Reactions

They are soluble in water and weigh more than water. Heat may be generated by dissolution into water.

Health Hazard

Different sources of media describe the Health Hazard of 540-82-9 differently. You can refer to the following data:
1. TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
2. The liquid is a strong irritant to skin. Suchirritant property may be attributed to sulfuric acid resulting from the reaction withthe moisture in the skin. The vapors of thissubstance are highly irritating to the res-piratory tract. It readily forms salts withgroup IIA metals. The barium salt, bariumethyl sulfate is highly toxic.

Fire Hazard

Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

InChI:InChI=1/C2H6O4S/c1-2-6-7(3,4)5/h2H2,1H3,(H,3,4,5)

Synthetic route

N-sulfonoxy-p-chloroacetanilide pyridinium salt (91631-54-8) → ethyl sulfate (540-82-9) + N-(4-chlorophenyl)-N-hydroxyacetamide (1503-91-9)

Conditions	Yield
In ethanol at 40℃;	A 83% B n/a
In ethanol at 40℃;	A n/a B 83%

diethyl sulfate (64-67-5) + ethanol (64-17-5) → diethyl ether (60-29-7) + ethyl sulfate (540-82-9)

diethyl sulfate (64-67-5) → ethyl sulfate (540-82-9)

Conditions	Yield
With sodium hydroxide at 150 - 200℃;
With ethanol; sodium ethanolate
With sodium ethanolate; toluene

diethyl ether (60-29-7) → ethyl sulfate (540-82-9)

Conditions	Yield
With sulfuric acid

ethanol (64-17-5) → diethyl sulfate (64-67-5) + ethyl sulfate (540-82-9)

Conditions	Yield
With chlorosulfonic acid

ethanol (64-17-5) → ethyl sulfate (540-82-9)

Conditions	Yield
With sulphur monochloride
With chlorosulfonic acid
With sulfuric acid

ethene (74-85-1) → diethyl sulfate (64-67-5) + ethyl sulfate (540-82-9)

Conditions	Yield
With sulfuric acid

ethene (74-85-1) → ethyl sulfate (540-82-9)

Conditions	Yield
With sulfuric acid
With sulfuric acid; silver
With silver salt; sulfuric acid

ethyl iodide (75-03-6) → ethyl sulfate (540-82-9)

Conditions	Yield
With silver hydrogensulfate

Thiophosphorsaeure-O,O-diethylester (2465-65-8) → ethyl sulfate (540-82-9)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In ethanol at -60 - 20℃;

ethanol (64-17-5) + diammonium salt of phenyl phosphatosulfate (32599-82-9) → ethyl sulfate (540-82-9) + phosphoric acid monophenyl ester (701-64-4) + ethyl phenyl hydrogen phosphate (46207-73-2)

Conditions	Yield
With N-ethylmorpholine;; magnesium(II) perchlorate at 55℃; Rate constant;

chlorobenzene (108-90-7) + ethyl ester of p-toluenesulfonic acid (80-40-0) → ethyl sulfate (540-82-9) + 4-methylphenyl-4-chlorophenyl sulfone (5184-71-4)

Conditions	Yield
With sulfur trioxide 1.) room temperature, 1h; Multistep reaction;

ethylnitramine (19091-98-6) → ethyl sulfate (540-82-9)

Conditions	Yield
With sulfuric acid at 25 - 85℃; Kinetics; Mechanism; Thermodynamic data; ΔH(excit.), -ΔS(excit.);

diethyl sulfate (64-67-5) + water (7732-18-5) → ethyl sulfate (540-82-9) + ethanol (64-17-5)

Conditions	Yield
anschliessend entsteht auch H2SO4;

chloral ethyl hemiacetal (515-83-3) + sulfuric acid (7664-93-9) → ethyl sulfate (540-82-9) + chloral (75-87-6)

ethyl bromide (74-96-4) + sulfuric acid (7664-93-9) + silver sulfate → ethyl sulfate (540-82-9) + silver bromide

ethanol (64-17-5) + sulfuric acid (7664-93-9) → ethyl sulfate (540-82-9)

Conditions	Yield
Electrolysis;

ethanol (64-17-5) + sodium disulfate → ethyl sulfate (540-82-9)

1,2-dichloro-2-ethoxyethane (623-46-1) + sulfuric acid (7664-93-9) → 2-chloroethanal (107-20-0) + hydrogenchloride (7647-01-0) + ethyl sulfate (540-82-9)

diethyl ether (60-29-7) + sulfuric acid (7664-93-9) → diethyl sulfate (64-67-5) + ethyl sulfate (540-82-9)

Conditions	Yield
at 100℃; bei hoeherer Temp. entsteht Aethylen und schwefliger Saeure;

ethyl hydroperoxide (3031-74-1) + sulphurous acid (7782-99-2) → ethyl sulfate (540-82-9) + sulfuric acid (7664-93-9)

ethanol (64-17-5) → ethyl sulfate (540-82-9) + water (7732-18-5)

Conditions	Yield
With sulfuric acid at 25℃;

pyridine-SO3 complex (42824-16-8) + ethanol (64-17-5) → ethyl sulfate (540-82-9) + pyridine sulfate

2-oxo-1-phenylpropane-1-sulfonic acid (99179-77-8) + hydrogen chloride containing ethanol → ethyl sulfate (540-82-9) + 1-phenyl-acetone (103-79-7)

water (7732-18-5) + sulfuric acid diethyl ester; ferrisulfuric acid ethyl ester → ethyl sulfate (540-82-9) + ethanol (64-17-5) + ferrisulfate

ethanol (64-17-5) + sulfur trioxide pyridine complex (26412-87-3) → ethyl sulfate (540-82-9) + pyridine sulfate

diethyl sulfate (64-67-5) + 4-acetamino-2-amino-methoxyethoxybenzene + 2-chloro-4,6-dinitroaniline (3531-19-9) → ethyl sulfate (540-82-9)

Conditions	Yield
In sulfuric acid; water

ethanol (64-17-5) + sulfur trioxide (7446-11-9) → diethyl sulfate (64-67-5) + ethyl sulfate (540-82-9) + 2-sulfooxy-ethanesulfonic acid (461-42-7)

Conditions	Yield
In liquid sulphur dioxide
In sulfur dioxide

sulfuric acid diethyl ester; ferrisulfuric acid ethyl ester → iron(III) sulfate + ethyl sulfate (540-82-9) + ethanol (64-17-5)

Conditions	Yield
In water decomposition in water;;

8-mercapto-2H-3,4-dihydro-1,5-benzodioxepine-6-carboxylic acid + ethyl sulfate (540-82-9) → 8-ethylthio-2H-3,4-dihydro-1,5-benzodioxepine-6-carboxylic acid

Conditions	Yield
With hydrogenchloride In water	91%

7-mercapto-1,4-benzodioxane-5-carboxylic acid (66410-43-3) + ethyl sulfate (540-82-9) → 7-ethylthio-1,4-benzodioxane-5-carboxylic acid (66410-44-4)

Conditions	Yield
With hydrogenchloride In water	81%

ethyl sulfate (540-82-9) + 7,8-dichloro-6-nitro-4-oxo-1,4-dihydroquinoline (560059-35-0) → 7,8-dichloro-4-ethoxy-6-nitroquinoline

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 60℃;	60%

ethyl sulfate (540-82-9) → diethyl sulfate (64-67-5)

Conditions	Yield
at 120 - 165℃; under 4.50045E-06 Torr;	43%
bei der Destillation im Vakuum;
With sodium sulfate durch Destillation unter vermindertem Druck;
With sodium ethyl sulfate durch Destillation unter vermindertem Druck;
bei der Destillation im Vakuum;

ethyl sulfate (540-82-9) + (E)-3-(4-(Diethylamino)phenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-8-yl)prop-2-en-1-one → (E)-3-(4-(diethylamino)phenyl)-1-(5-ethoxy-2,2-dimethyl-2H-chromen-8-yl)prop-2-en-1-one

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 12h;	39%

ethyl sulfate (540-82-9) + 2-methyl-4,5-diphenylthiazole + 3,1',3'-triethyl-4-keto-5-acetanilinomethylene-5'-chlorothiazolinoimidacyanine perchlorate → 3,1',3'-triethyl-4-keto-5'-chloro-5-(3-ethyl-4,5-diphenylthiazolinylidene-2-ethylidene)thiazolinoimidacyanine perchlorate

Conditions	Yield
With sodium perchlorate; triethylamine In ethanol for 6h; Heating;	27%

2(RS)-(2-hydroxyethyl)piperidine (1484-84-0) + ethyl sulfate (540-82-9) → 2-(1-ethyl-[2]piperidyl)-ethanol (876488-02-7)

Conditions	Yield
With water; potassium

diethyl sulfate (64-67-5) + ethyl sulfate (540-82-9) + 1-chloro-2-(dimethylamino)benzene (698-01-1) → N-ethyl-2-chloro-N,N-dimethyl-anilinium; perchlorate

Conditions	Yield
anschliessendes Behandeln mit wss.HClO4;

β-Propiolactone (57-57-8) + ethyl sulfate (540-82-9) + ethanol (64-17-5) → ethyl acrylate (140-88-5)

Conditions	Yield
With iron(II) sulfate at 140℃;

ethyl sulfate (540-82-9) + 1,4-diamino-9,10-anthraquinone (128-95-0) → 1,4-bisethylamino-anthraquinone (6994-46-3)

Conditions	Yield
at 140℃;

ethyl sulfate (540-82-9) → ethyl chlorosulfate (625-01-4)

Conditions	Yield
With phosphorus pentachloride

ethyl sulfate (540-82-9) → ethanol (64-17-5)

Conditions	Yield
With steam; ammonia
With ammonia; water

ethyl sulfate (540-82-9) → ethene (74-85-1)

Conditions	Yield
With diethyl sulfate; phosphorite; sulfuric acid at 250 - 300℃;
With sodium sulfate at 300℃;
With sodium chloride at 300℃;

ethyl sulfate (540-82-9) → chloroethane (75-00-3)

Conditions	Yield
With hydrogenchloride at 140℃; unter Druck;
With hydrogenchloride at 140℃; unter Druck;

ethyl sulfate (540-82-9) → acetic acid (64-19-7)

Conditions	Yield
With chromium(VI) oxide; water; iron(III) chloride Electrolysis;
With manganese(IV) oxide; water; iron(III) chloride Electrolysis;
With chromium(VI) oxide; water; iron(III) chloride Electrolysis;
With manganese(IV) oxide; water; iron(III) chloride Electrolysis;

ethyl sulfate (540-82-9) + chloroformic acid ethyl ester (541-41-3) → diethyl sulfate (64-67-5) + chloroethane (75-00-3)

Conditions	Yield
at 40 - 50℃;
at 40 - 50℃;

ethyl sulfate (540-82-9) + acrylonitrile (107-13-1) → ethyl acrylate (140-88-5)

Conditions	Yield
With water at 110℃;

ethyl sulfate (540-82-9) + methyl chloroformate (79-22-1) → ethyl methane sulfate (814-40-4)

Conditions	Yield
at 50 - 80℃;
at 50 - 80℃;

ethyl sulfate (540-82-9) + 2-amino-2-cyanopropane (19355-69-2) → methyl methacrylate (97-63-2)

Conditions	Yield
Einw. von NaNO2-Loesung auf das Reaktionsprodukt;

methylperoxy-methanol (40116-50-5) + ethyl sulfate (540-82-9) → methylperoxymethoxy-ethane (58712-33-7)

Conditions	Yield
In diethyl ether

1-tert-butylperoxy-ethanol (4202-06-6) + ethyl sulfate (540-82-9) → tert-butyl 1-ethoxy-ethyl peroxide (10312-63-7)

Conditions	Yield
In diethyl ether

Upstream product

• 64-67-5 diethyl sulfate 
• 64-17-5 ethanol 
• 2465-65-8 Thiophosphorsaeure-O,O-diethylester 
• 19091-98-6 ethylnitramine 
• 515-83-3 chloral ethyl hemiacetal 
• 7664-93-9 sulfuric acid 
• 74-96-4 ethyl bromide 
• 3031-74-1 ethyl hydroperoxide 
• 7782-99-2 sulphurous acid 
• 42824-16-8 pyridine-SO₃ complex 
• 74-85-1 ethene 
• 74-84-0 ethane 
• 7446-11-9 sulfur trioxide 
• 3531-19-9 2-chloro-4,6-dinitroaniline 

Downstream Products

• 97-63-2 methyl methacrylate 
• 109-95-5 ethyl nitrite 
• 79-24-3 Nitroethane 
• 627-05-4 1-nitrobutane 
• 64-67-5 diethyl sulfate 
• 7664-93-9 sulfuric acid 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 74-85-1 ethene 
• 103-73-1 Phenetole 
• 854645-32-2 ethyl 2-ethoxy-5-methylbenzoate 
• 183666-73-1 2,6-di-tert-butyl-4-(4-nitrobenzylidene)cyclohexa-2,5-diene-1-one 
• 861205-83-6 (1R,2R,3S)-2-ethoxymethyl-3-(3,4-dichlorophenyl)-tropane citrate 
• 75-04-7 ethylamine 

Relevant articles and documents

EQUILIBRIA IN SOLUTIONS OF METHANOL OR ETHANOL, SULFURIC ACID, AND ALKYL SULFATES

Equilibria in reactions of methanol and ethanol with sulfuric acid or in hydrolyses of alkyl sulfates were followed using 13C NMR, anion-exchange HPLC, and titrations.Variations of equilibrium constant K = (ester)(H2O)/(ROH)(HSO4(1-)) with acidity indicate participation of reactions ROH2(1+) + HSO4(1-) ROH(1+)SO3(1-) + H2O, accompanied by acid base equilibra involving the alcohol and ester.For mixtures containing initially 20percent (w/w) alcohol, pKMeOH2(1+) = -4.2, pKEtOH2(1+) = -3.7, pKMeOH(1+)SO3(1-) = -3.3 and pKEtOH(1+)SO3(1-) = -2.7.

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A capillary electrophoresis study of the synthesis and stability of 1,2-decanedisulfate, 1-hydroxy-2-decanesulfate, and 2-hydroxy-1-decanesulfate

Capillary zone electrophoresis (CZE) was used to study the preparation of 1,2-decanedisulfate from 1,2-decanediol and determine the stability of the two-headed surfactant and the corresponding hydroxydecanesulfates under both acidic and basic conditions. The optimum buffer for the CZE determination was found to be diethylbarbiturate. Resolution of the hydroxydecanesulfate constitutional isomers was facilitated by the addition of magnesium ions. Decanedisulfate was stable in base but hydrolyzed in acid. The hydroxysulfates hydrolyzed much more rapidly, and in both acid and base. Mechanisms were postulated based on differential rates of formation and hydrolysis of the hydroxydecanesulfate constitutional isomers.

Mg2+-Promoted P-O vs. S-O Bond Cleavage in the Alcoholyses of Phenyl Phosphatosulfate

In order to obtain insight into the selectivity of Mg2+ at the site of bond cleavage of P-O and S-O of the P-O-S linkage, metal ion-promoted alcoholyses of phenyl phosphatosulfate were studied.Mg2+ quantitatively promoted P-O bond cleavage in the methanolysis, but mixed cleavage of the P-O bond, which occurred partly due to hydrolysis by trace water and the S-O bond in the reaction of ethanol, 1- or 2-propanol.The ratio of the S-O bond cleavage against the mixed cleavage increased in a order EtOH (11.5percent) 2+ and Zn2+ promoted selective P-O and S-O bond cleavage, respectively, in the reaction of 2-propanol as well as methanolysis.The medium-dependent change in the selectivity of Mg2+ at the site of bond cleavage was discussed.