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Chemical Structure| 926-39-6 Chemical Structure| 926-39-6

Structure of Aminoethyl sulfate
CAS No.: 926-39-6

Chemical Structure| 926-39-6

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Product Citations

Product Citations

Chi-Cheng Ma ; Derek Butler ; Veronica Milligan ; Blake A. Hammann ; Hao Luo ; James F. Brazdil , et al.

Abstract: Taurine, 2-aminoethane-1-sulfonic acid, is a commercial amino acid manufactured from either ethylene oxide or monoethanolamine (MEA). Taurine is a valuable nutritional additive that is widely used in the production of energy drinks, pet food, nutritional supplements, and infant formula. The industrial production of taurine from MEA is a two-step batch process in which the first step is the reaction of MEA with sulfuric acid to produce the ester 2-aminoethyl hydrogen sulfate (AES) and the second step is the reaction of AES with a sulfite reagent. This report summarizes the results of a study of the fundamental chemistry for this two-step MEA-based chemical route to taurine as well as the application of this fundamental understanding to a process design for a scalable and cost-advantaged continuous process that is capable of commercial-scale production of taurine on a multikiloton scale. In order to maximize taurine yields, the water formed during the first esterification step must be effectively removed to avoid equilibrium limitations on the conversions of MEA and sulfuric acid to form the solid AES intermediate product. For the second AES sulfonation step in aqueous medium, we found that operation above 100 °C under a moderate pressure of an inert gas resulted in significantly higher taurine yields (>80 mol %) compared to those reported in current commercial production technology (typically 55–65 mol %).

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Product Details of [ 926-39-6 ]

CAS No. :926-39-6
Formula : C2H7NO4S
M.W : 141.15
SMILES Code : [S](=O)(=O)(OCCN)O
MDL No. :MFCD00008179
InChI Key :WSYUEVRAMDSJKL-UHFFFAOYSA-N
Pubchem ID :70223

Safety of [ 926-39-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 926-39-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 3
Num. H-bond acceptors 5.0
Num. H-bond donors 2.0
Molar Refractivity 26.06
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

98.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

-0.04
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-4.06
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

-0.15
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-1.94
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.35
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-1.51

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

2.04
Solubility 15500.0 mg/ml ; 110.0 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Highly soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

2.6
Solubility 56700.0 mg/ml ; 402.0 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Highly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.6
Solubility 568.0 mg/ml ; 4.03 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-10.04 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

3.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.37

Application In Synthesis of [ 926-39-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 926-39-6 ]

[ 926-39-6 ] Synthesis Path-Downstream   1~41

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  • sulfuric acid mono-[2-(4,6-dimethoxy-[1,3,5]triazin-2-ylamino)-ethyl ester]; sodium-salt [ No CAS ]
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YieldReaction ConditionsOperation in experiment
~ 60% With sodium hydroxide; In water;Heating; Aziridine or ethylenimine is a well-known compound. It can be prepared from 2-haloethylamine hydrohalides with strong base such as silver oxide; sodium or <n="85"/>potassium hydroxide in aqueous solution. Synthesis of aziridine by treating 2- aminoethyl hydrogen sulfate with sodium hydroxide was recommended by Organic Synthesis (Allen, et al., "Organic Synthesis", V. 30, John Wiley and Son, Inc., New York, N.Y., 1950, pp. 38-40) and is the most common preparation method. Due to its high tendency to polymerize, the yield of preparation is low. A yield of 37percent of aziridine was reported by Organic Synthesis and is considered a good yield.[0222] Since aziridine is not commercially available now, the literature method (Reeves et al., J. Amer. Chem. Soc, 1951, 73, 3522) was adopted with slight modifications to synthesize this compound. The key issue of the synthesis is to generate and vaporize the aziridine instantaneously and distill rapidly to reduce undesirable polymerization.[0223] A 5-Liter, 3-neck flask fitted with a giant magnetic stir bar, a 250 mL dropping funnel and a prolonged condenser (composed of three condensers) arranged for distillation with a heating mantle was set in a well-ventilated hood (Figure 5). 100 mL of 14percent sodium hydroxide solution was placed in the 5 -Liter flask, and was heated in a metal heater controlled by a regulator. The solution was heated at full capacity until the distillation was proceeding at a rapid rate. A cool solution made from 63 g 2-aminoethyl hydrogen sulfate, 78 g of sodium hydroxide and 270 mL water was added to the distillation flask through the dropping funnel at a rate such that the amount of liquid in the flask remained about constant. The superheated distillate that came over at 100 to 115 0C was collected in a receiving flask and which was immersed in an ice-bath. The flask has a side arm connected to an amine gas trap filled with dilute sulfuric acid.[0224] In the literature, the distillate was treated with a huge amount of sodium hydroxide to salt out the raw aziridine, and it was redistilled to ensure the purity of the product. A large quantity of toxic, strongly basic waste would be generated and the re-distillation of the highly toxic and volatile aziridine is not advisable. Because the boiling point of aziridine and its dimer, the major contaminant, are 56-58° and 126-127.5°C respectively, it is possible to control the purity of aziridine by only collecting the distillate that boils at 50-115°C. The distilled dilute aziridine solution was used directly for preparing Boc-aziridine and CBZ-aziridine without further treatment. The yield of aziridine was estimated around 60percent. For characterization, a <n="86"/>fraction of the distillate was saturated with excess sodium hydroxide, and the aziridine was separated as a thick oil. Its purity was confirmed by NMR spectroscopy.[0225] 1H NMR (500 MHz, CDCl3, 25 0C): delta, 0.56 (s, br, IH, NH), 1.56 (s, 4H, CH2). 13C NMR (500 MHz, CDCl3): delta, 18.03.
  • 11
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YieldReaction ConditionsOperation in experiment
88.1% 10051] These examples demonstrate the cyclic use of mother liquor in the preparation of taurine. Using the same one-liter autoclave, the starting materials given in the table were reacted at 120°C. for 18 hours. Afierwards, the solution is cooled to 10° C. to crystallize taurine and ammonium sulfate, which are filtered off and washed with a solution saturated with ammonium sulfate. The mother liquor ischarged with ammonium sulfite monohydrate and then adjusted to pH 7.2 with aqueous ammonium hydroxide. AES is then charged and pH rechecked and if necessary readjusted to 7.2 with ammonium hydroxide or dilute sulfuric acid. The results are shown in the following table.10052] The solid filtrate, comprised of taurine and ammonium sulfate, from each batch, is combined and stirred as a suspension in water to dissolve ammonium sulfate. After filtration, crude taurine is washed with water and recrystallized from deionized water. Yield: 379.7 g (81.0percent).10053] An additional 15.2 g (3.2percent) of taurine is recovered from the mother liquor afier recrystallization and separation of ammonium sulfate.
  • 12
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  • sulfuric acid mono-(2-dichloroamino-ethyl ester) [ No CAS ]
  • 13
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YieldReaction ConditionsOperation in experiment
90.72% With sulfuric acid; In water; at -5 - 5℃; for 0.5h; In a 100 mL three-necked flask equipped with a constant pressure dropping funnel, a thermometer, and a magnet,Add 9 mL (0.15 mol) of aminoethanol and 9 mL of water,Using a cryogenic cooling circulating pump to cool the solution to -5 to 5°C and maintain it,Concentrated sulfuric acid and water are mixed in equal volumes, and 16.3 mL of the mixture is slowly added dropwise to the three-necked flask.After stirring for 0.5h, it is replaced by a vacuum distillation device.The natural temperature was raised to room temperature and the water was distilled off (the oil pump showed 15 mbar). The residue was poured into 60 mL of absolute ethanol, stirred, mixed and filtered. The filter cake was washed with 3×15 mL of anhydrous ethanol and dried to give 19.2 g of a white solid, which was 2 Aminoethanol hydrogen sulfate, yield 90.72percent.
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  • [ 50-00-0 ]
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  • [ 1950-25-0 ]
  • sulfuric acid mono-[2-(5-benzyl-6-thioxo-[1,3,5]thiadiazinan-3-yl)-ethyl] ester [ No CAS ]
  • 31
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  • sulfuric acid mono-[2-(5-phenethyl-6-thioxo-[1,3,5]thiadiazinan-3-yl)-ethyl] ester [ No CAS ]
  • 32
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  • [ 13036-89-0 ]
  • 5,5'-bis-(2-sulfooxy-ethyl)-3,3'-ethane-1,2-diyl-bis-[1,3,5]thiadiazinane-2-thione [ No CAS ]
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Historical Records

Technical Information

Categories

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[ 926-39-6 ]

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