926-39-6

Basic information

• Product Name: 2-AMINOETHYL HYDROGEN SULFATE
• Synonyms: 2-amino-ethanohydrogensulfate(ester);2-Aminoethanolhydrogensulfateester;2-AMINOETHYL HYDROGEN SULPHATE;2-AMINOETHYL SULFATE;2-AMINOETHYL SULFURIC ACID;AMINOETHYL HYDROGEN SULFATE;SULFURIC ACID MONO(2-AMINOETHYL) ESTER;aminoethylsulfuric acid
• CAS NO: 926-39-6
• Molecular Formula: C₂H₇NO₄S
• Molecular Weight: 141.15
• EINECS: 213-135-7
• Mol File: 926-39-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 277 °C (dec.)(lit.)
• Boiling Point: 296.49℃[at 101 325 Pa]
• Appearance: White to slightly beige/Fine Crystalline Powder
• Density: 1.344 (estimate)
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.5130 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -4.33±0.18(Predicted)
• Water Solubility: almost transparency
• BRN: 1704079
• CAS DataBase Reference: 2-AMINOETHYL HYDROGEN SULFATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINOETHYL HYDROGEN SULFATE(926-39-6)
• EPA Substance Registry System: 2-AMINOETHYL HYDROGEN SULFATE(926-39-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: KJ6371000
• Hazardous Substances Data: 926-39-6(Hazardous Substances Data)

Usage

Uses

2-Aminoethyl Sulfate, is a building block used for the synthesis of various pharmaceutical and biologically active compounds, including inhibitors and therapeutic compounds. It can be used in the preparation of Taurine (T007850).

Purification Methods

Crystallise the sulfate ester from water or dissolve it in water and add EtOH. [Beilstein 4 III 1414.]

InChI:InChI=1/C2H7NO4S/c3-1-2-7-8(4,5)6/h1-3H2,(H,4,5,6)

Synthetic route

ethanolamine (141-43-5) → sulfuric acid mono-(2-amino-ethyl ester) (926-39-6)

Conditions	Yield
With sulfuric acid; tetrabutylammomium bromide In toluene at 40℃; for 1.5h;	99%
With sulfuric acid In water at -5 - 5℃; for 0.5h;	90.72%
With sulfuric acid	89%

ethyleneimine (151-56-4) → sulfuric acid mono-(2-amino-ethyl ester) (926-39-6)

Conditions	Yield
With sulfuric acid

dimethylenecyclourethane (497-25-6) → sulfuric acid mono-(2-amino-ethyl ester) (926-39-6)

Conditions	Yield
With sulfuric acid

2-bromoethylamine hydrobromide (2576-47-8) → sulfuric acid mono-(2-amino-ethyl ester) (926-39-6)

Conditions	Yield
With silver sulfate

ethanolamine (141-43-5) + dimethyl sulfate (77-78-1) → sulfuric acid mono-(2-amino-ethyl ester) (926-39-6)

(2-amino-ethyl)-nitroso-amidosulfuric acid (861555-02-4) + phenol (108-95-2) → sulfuric acid mono-(2-amino-ethyl ester) (926-39-6)

ethyleneglycol sulfate (1072-53-3) → sulfuric acid mono-(2-amino-ethyl ester) (926-39-6)

Conditions	Yield
With ammonia In dichloromethane

ethyleneimine (151-56-4) + sulfuric acid (7664-93-9) → sulfuric acid mono-(2-amino-ethyl ester) (926-39-6)

sulfuric acid (7664-93-9) + sulfur trioxide (7446-11-9) + ethanolamine (141-43-5) → sulfuric acid mono-(2-amino-ethyl ester) (926-39-6)

N-nitroso-ethylenediamine-N-sulfonic acid → sulfuric acid mono-(2-amino-ethyl ester) (926-39-6)

Conditions	Yield
With phenol

ammonium bisulfate (7803-63-6) + ethanolamine (141-43-5) → sulfuric acid mono-(2-amino-ethyl ester) (926-39-6)

Conditions	Yield
With ammonium sulfate

N-β-aminoethylcarbamic acid (109-58-0) + carbamic acid-(2-amino-ethyl ester) (142-27-8) → sulfuric acid mono-(2-amino-ethyl ester) (926-39-6)

sulfuric acid (7664-93-9) + ethanolamine (141-43-5) → sulfuric acid mono-(2-amino-ethyl ester) (926-39-6)

Conditions	Yield
at 270 - 280℃; Product distribution / selectivity;

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + salicylaldehyde (90-02-8) → C9H10NO5S(1-)*Na(1+) (110925-66-1)

Conditions	Yield
With sodium hydroxide In ethanol	95%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + vanillin (121-33-5) → C10H12NO6S(1-)*Na(1+) (110925-69-4)

Conditions	Yield
With sodium hydroxide In ethanol	94%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) → Tau (107-35-7)

Conditions	Yield
Stage #1: sulfuric acid mono-(2-amino-ethyl ester) With ammonium sulfite monohydrate at 120℃; for 18h; Autoclave; Stage #2: With ammonium sulfite monohydrate; sodium hydroxide In water pH=7.2; Temperature;	88.1%
With water; sodium sulfite

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → C13H12NO5S(1-)*Na(1+) (110925-71-8)

Conditions	Yield
With sodium hydroxide In ethanol	88%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + (-)-(2S,3S)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide (98769-72-3, 98819-72-8) → 2-{[(2S,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]amino}ethyl hydrogen sulfate (1250978-71-2) + C36H43NO10S (1250978-88-1)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol; toluene	A 86% B n/a
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 70℃;	A 92 %Chromat. B 6 %Chromat.

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + ethanolamine (141-43-5) → Tau (107-35-7)

Conditions	Yield
With ammonium sulfate; sulfuric acid; ammonium sulfite monohydrate In water at 110℃; for 24h; pH=6.2 - 7.2; Autoclave;	85%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + 4-methoxy-benzaldehyde (123-11-5) → C10H12NO5S(1-)*Na(1+) (110925-68-3)

Conditions	Yield
With sodium hydroxide In ethanol	83%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + 3,4-dimethoxy-benzaldehyde (120-14-9) → C11H14NO6S(1-)*Na(1+) (110925-70-7)

Conditions	Yield
With sodium hydroxide In ethanol	80.2%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + (-)-(2S,3S)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide (98769-72-3, 98819-72-8) → 2-{[(2S,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]amino}ethyl hydrogen sulfate (1250978-71-2)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Inert atmosphere;	78%
Stage #1: sulfuric acid mono-(2-amino-ethyl ester) With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol; toluene at 65℃; for 1h; Stage #2: (-)-(2S,3S)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide In ethanol; toluene at 65 - 70℃; for 3h;	74%
Stage #1: sulfuric acid mono-(2-amino-ethyl ester) With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol; toluene at 65℃; for 1h; Stage #2: (-)-(2S,3S)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide In ethanol; toluene at 70℃; for 3h;	1.1 kg
With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethanol; toluene at 65 - 70℃;

(2R,3S)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide (1452772-76-7) + sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) → {[(2R,3S)-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropyl]amino}ethyl hydrogen sulfate (1356958-71-8)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Inert atmosphere;	78%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + 1-(inden-7-yloxy)-2,3-epoxypropane (30190-85-3) → 2-(7-indenyloxymethyl)-morpholine hydrochloride (65043-22-3)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In methanol 1.) 55 deg C, 16 h; 2.) iso-PrOH, acetone, 0-5 deg C, 15 min.;	73%

carbon disulfide (75-15-0) + sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) → thiazolidine-2-thione (134469-06-0)

Conditions	Yield
With potassium hydroxide	68%
With sodium hydroxide In ethanol at 40℃; for 3h;	68%
With sodium hydroxide In ethanol; water for 0.666667h; Heating;
With potassium hydroxide

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + (+/-)-2-(2-ethoxy-4-iodophenyloxymethyl)oxirane (721453-42-5) → (+/-)-2-[(2-ethoxy-4-iodophenoxy)methyl]morpholine (721453-43-6)

Conditions	Yield
With sodium hydroxide In isopropyl alcohol for 8h; Heating;	67%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + (+/-)-2-(5-chloro-2-methoxyphenyloxymethyl)oxirane (721453-55-0) → (+/-)-2-[(5-chloro-2-methoxyphenoxy)methyl]morpholine (721453-56-1)

Conditions	Yield
With sodium hydroxide In isopropyl alcohol Heating;	65%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + 1-isothiocyanatonaphthalene (551-06-4) → (4,5-dihydro-thiazol-2-yl)-naphthalen-1-yl-amine (35160-17-9)

Conditions	Yield
With sodium hydroxide; ethanol	64%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + (R)-benzyl glycidol (14618-80-5) → (2R)-2-[(benzyloxy)methyl]morpholine (135065-70-2)

Conditions	Yield
With sodium hydroxide In water at 50 - 55℃; for 21h;	62%
With sodium hydroxide In methanol; water at 50℃;	49%
With sodium hydroxide In methanol; water at 50℃;	49%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) → ethyleneimine (151-56-4)

Conditions	Yield
With sodium hydroxide In water Heating;	60%
With sodium hydroxide
With potassium hydroxide

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + 2-methoxy-1-naphthaldehyde (5392-12-1) → 2-Methoxy-1-naphthalideneiminoethyl hydrogen sulfate sodium salt (110925-72-9)

Conditions	Yield
With sodium hydroxide In ethanol	58.1%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) → hypotaurine (300-84-5)

Conditions	Yield
With sodium dithionite; water at 90 - 100℃; for 12h; Temperature; Inert atmosphere;	53.87%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + (R)-1-chloro-3-(3,5-dichlorophenyl)propan-2-ol → (R)-2-(3,5-dichlorobenzyl)morpholine

Conditions	Yield
With sodium hydroxide In methanol; water; toluene at 40 - 65℃; for 21.5h;	53%

(R)-1-chloro-3-(2-methoxyphenyl)-2-propanol + sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) → (R)-2-(2-methoxybenzyl)morpholine

Conditions	Yield
With sodium hydroxide In methanol; water; toluene at 20 - 65℃; for 19.0833h;	50%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + (S)-benzyl glycidyl ether (2930-05-4, 14618-80-5, 89616-40-0, 16495-13-9) → (+)-2(S)-(phenylmethyloxymethyl)morpholine (167357-55-3)

Conditions	Yield
With sodium hydroxide In methanol; water at 50 - 55℃; for 17h;	49%
With sodium hydroxide In methanol; water at 50 - 55℃; for 17h;	49%
Stage #1: sulfuric acid mono-(2-amino-ethyl ester); (S)-benzyl glycidyl ether With sodium hydroxide In methanol; water at 40℃; for 4h; Stage #2: With sodium hydroxide In methanol; water; toluene at 65℃; for 12h;

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + (R)-1-chloro-3-thiophen-2-yl-propan-2-ol (1598383-26-6) → (R)-2-(thiophen-2-ylmethyl)-morpholine (1598383-27-7)

Conditions	Yield
Stage #1: (R)-1-chloro-3-thiophen-2-yl-propan-2-ol With sodium hydroxide In methanol; water at 20℃; for 0.0833333h; Stage #2: sulfuric acid mono-(2-amino-ethyl ester) In methanol; water at 45℃; for 2.75h; Stage #3: With sodium hydroxide In methanol; water; toluene at 65℃;	48%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + 1-isothiocyanato-4-methylbenzene (622-59-3) → N-(4-Methylphenyl)-4,5-dihydro-2-thiazolamine (102942-89-2)

Conditions	Yield
With sodium hydroxide; ethanol	44%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + 2,4-Dihydroxybenzaldehyde (95-01-2) → C9H10NO6S(1-)*Na(1+) (110925-67-2)

Conditions	Yield
With sodium hydroxide In ethanol	44%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + maleic acid (110-16-7) → 2-(benzyloxymethyl)morpholine hydrogen maleate

Conditions	Yield
With sulfuric acid In methanol; water; toluene	40%

1,2-Anhydro-3-O-(o-ethoxyphenyl)-glycerol (5296-35-5) + sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) → viloxazine (46817-91-8)

Conditions	Yield
With potassium hydroxide In methanol; water Product distribution / selectivity;	39.8%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + (2-nitro-4-trifluoromethylphenyl)isothiocyanate (137935-40-1) → (4,5-Dihydro-thiazol-2-yl)-(2-nitro-4-trifluoromethyl-phenyl)-amine (137935-32-1)

Conditions	Yield
With sodium hydroxide; ethanol	39%

sulfuric acid mono-(2-amino-ethyl ester) (926-39-6) + benzaldehyde (100-52-7) → C9H10NO4S(1-)*Na(1+) (110925-65-0)

Conditions	Yield
With sodium hydroxide In ethanol at 60 - 70℃; for 2h;	38.2%

Upstream product

• 151-56-4 ethyleneimine 
• 497-25-6 dimethylenecyclourethane 
• 141-43-5 ethanolamine 
• 7664-93-9 sulfuric acid 
• 7446-11-9 sulfur trioxide 
• 7803-63-6 ammonium bisulfate 
• 83259-42-1 monoethanolamine sulfate 
• 20261-59-0 monoethanolammonium hydrogensulfate 
• 109-58-0 N-β-aminoethylcarbamic acid 
• 142-27-8 carbamic acid-(2-amino-ethyl ester) 
• 1072-53-3 ethyleneglycol sulfate 
• 861555-02-4 (2-amino-ethyl)-nitroso-amidosulfuric acid 
• 108-95-2 phenol 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 36517-93-8 2-propylsulfanylethylamine 
• 111-41-1 2-(2-Aminoethylamino)ethanol 
• 22572-38-9 2-(tert-butylsulfanyl)ethan-1-amine 
• 19522-69-1 N-butylethylenediamine 
• 56205-96-0 (2-amino-ethyl)-(2-butylamino-ethyl)-amine 
• 7426-75-7 1,4-bis(4,5-dihydro-2-oxazolyl)benzene 
• 927-69-5 2-isopropylsulfanyl-ethylamine 
• 110925-66-1 C₉H₁₀NO₅S^(1-)*Na⁽¹⁺⁾ 
• 204917-29-3 sulfuric acid mono-{2-[3-(4-chloro-phenoxy)-2-hydroxy-propylamino]-ethyl} ester 
• 107-15-3 ethylenediamine 
• 111-40-0 3-azapentane-1,5-diamine 
• 385802-02-8 2-benzhydrylmorpholine 
• 107-35-7 Tau 

Relevant articles and documents

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Cyclic process for producing taurine from monoethanolamine

There is disclosed a cyclic process for producing taurine from monoethanolamine comprising the steps of: (a) recovering monoethanolamine sulfate from an aqueous mother liquor solution; (b) reacting the monoethanolamine sulfate with sulfuric acid to form an aqueous solution comprised of monoethanolamine bisulfate; (c) heating the aqueous solution comprised of the monoethanolamine sulfate and optionally added monoethanolamine sulfate to yield 2-aminoethyl hydrogen sulfate ester; (d) reacting the ester with ammonium sulfite or an alkali sulfite to yield taurine and ammonium or alkali sulfate; (e) separating taurine and ammonium or alkali sulfate to give an aqueous mother liquor solution; and (f) recovering the monoethanolamine sulfate from the aqueous mother liquor solution and recycling to the monoethanolamine sulfate to step (b).

Synthesis method of taurine precursor 2-aminoethanol sulfate

The invention relates to a synthesis method of taurine precursor 2-aminoethanol sulfate, and the synthesis method takes ethanolamine as an initial raw material to synthesize the 2-aminoethanol sulfatein the presence of sulfuric acid and phase transfer catalyst tetrabutyl ammonium bromide. The synthesis method of the 2-aminoethanol sulfate has the advantages of shorter synthesis circuit and higherreaction efficiency; meanwhile, the obtained product has better purity and higher yield. In addition, the synthesis method does not need special production equipment with high price, has wide raw material sources and low price, thereby effectively reducing the production cost and obtaining good economic benefits.

One-step synthesis of 6-acetamido-3-(N-(2-(dimethylamino) ethyl) sulfamoyl) naphthalene-1-yl 7-acetamido-4-hydroxynaphthalene-2-sulfonate and its characterization with 1D and 2D NMR techniques

A one-step method was reported for the synthesis of 6-acetamido-3-(N-(2- (dimethylamino) ethyl) sulfamoyl) naphthalene-1-yl 7-acetamido-4- hydroxynaphthalene-2-sulfonate by treating 7-acetamido-4-hydroxy-2- naphthalenesulfonyl chloride with equal moles of N, N-dimethylethylenediamine in acetonitrile in the presence of K2CO3. The chemical structure of the obtained compounds was characterized by MS, FTIR, 1H NMR, 13C NMR, gCOSY, TOCSY, gHSQC, and gHMBC. The chemical shift differences of 1H and 13C being δ 0.04 and 0.2, respectively, were unambiguously differentiated. Copyright 2013 John Wiley & Sons, Ltd. 6-Acetamido-3-(N-(2-(dimethylamino) ethyl) sulfamoyl) naphthalene-1-yl 7-acetamido-4-hydroxynaphthalene-2-sulfonate was prepared by a one-step method. The structure of the compound was elucidated by 1D and 2D NMR. The chemical shift differences of 1H and 13C being δ 0.04 and 0.2, respectively, were unambiguously differentiated. Copyright