ChemicalBook > CAS DataBase List > (S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine

(S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine

Product Name
(S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine
CAS No.
608141-42-0
Chemical Name
(S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine
Synonyms
(S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethan-1-amine;Apremilast inter2;Apremilast Impurity 55;Apremilast Intermediate II;Apremilast Intermediates 2;Apremilast Impurity HS093220;Apremilast Desphthalyl Amine;RSSYY(Lurasidone Hydrochloride)-14;Apremilast EP Impurity H (S)-Isomer;(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethanamine
CBNumber
CB82661858
Molecular Formula
C12H19NO4S
Formula Weight
273.35
MOL File
608141-42-0.mol
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(S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine Property

Melting point:
106-108oC
Boiling point:
469.6±45.0 °C(Predicted)
Density 
1.195±0.06 g/cm3(Predicted)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
Chloroform (Slightly), Methanol (Slightly)
pka
6.84±0.10(Predicted)
form 
Solid
color 
White to Off-White
InChI
InChI=1/C12H19NO4S/c1-4-17-12-7-9(5-6-11(12)16-2)10(13)8-18(3,14)15/h5-7,10H,4,8,13H2,1-3H3/t10-/s3
InChIKey
BXUJVINGXQGNFD-JQHDBZEONA-N
SMILES
[C@@H](C1C=CC(OC)=C(OCC)C=1)(N)CS(=O)(=O)C |&1:0,r|
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Safety

HS Code 
2930909899
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC
Product number
M266045
Product name
(1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine
Packaging
100mg
Price
$130
Updated
2021/12/16
AK Scientific
Product number
2841AH
Product name
(1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine
Packaging
1g
Price
$91
Updated
2021/12/16
AK Scientific
Product number
2841AH
Product name
(1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine
Packaging
5g
Price
$184
Updated
2021/12/16
AK Scientific
Product number
2841AH
Product name
(1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine
Packaging
10g
Price
$303
Updated
2021/12/16
AK Scientific
Product number
2841AH
Product name
(1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine
Packaging
25g
Price
$587
Updated
2021/12/16
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(S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine Chemical Properties,Usage,Production

Chemical Properties

APREMILAST intermediate is slightly soluble in dichloromethane and soluble in methanol. It is mainly used to synthesize APREMILAST. In addition, it can also regulate intracellular pro-inflammatory and anti-inflammatory factor effects through specificity for cyclic adenosine monophosphate (c AMP), which increases intracellular cAMP levels.

Uses

(1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine is an Apremilast (A729700) intermediate. Apremilast, an oral phosphodiesterase 4 inhibitor is used in the treatment of psoriatic arthritis.

Synthesis

1450657-31-4

608141-42-0

The general procedure for the synthesis of (S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethylamine from the compound (CAS: 1450657-31-4) was as follows: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate (36 mg, 0.074 mmol) and (S)-1-[(R)-2- ( diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine (40 mg, 0.074 mmol) were dissolved in 25 mL of 2,2,2-trifluoroethanol. Subsequently, 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethylamine (2.0 g, 7.4 mmol) was added to this solution. The reaction mixture was heated to 50 °C and hydrogenated under hydrogen pressure of 90 psig. After 18 h, the mixture was cooled to room temperature and removed from the hydrogenation unit. The solvent was removed by rotary evaporation and the residue was purified by chromatography on a C18 reversed-phase column using a water-acetonitrile gradient elution. The fraction containing the target product was collected and concentrated to about 150 mL. saturated brine (20 mL) was added to the concentrate and subsequently extracted with ethyl acetate (3 x 50 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, filtered and concentrated to give a white crystalline solid product (1.4 g, 70% yield). The product was analyzed by non-chiral HPLC (Hypersil BDSC8, 5.0 μm, 250 × 4.6 mm, 1.5 mL/min, 278 nm, 90/10 to 80/20 0.1% TFA aqueous solution/methanol gradient elution for 10 min, followed by a gradient up to 10/90 0.1% TFA aqueous solution/methanol for the next 15 min). Retention time was 9.11 min (99.6% purity); chiral HPLC (Chiralpak AD-H 5.0 μm Daicel, 250 × 4.6 mm, 1.0 mL/min, 280 nm, 70:30:0.1 heptane-isopropanol-diethylamine) analyzed with retention times of 7.32 min (97.5%) and 8.26 min ( 2.47%).1H NMR (DMSO-d6) δ 1.32 (t, J = 7.0 Hz, 3H), 2.08 (s, 2H), 2.96 (s, 3H), 3.23 (dd, J = 3.6, 14.4 Hz, 1H), 3.41 (dd, J = 9.4, 14.4 Hz, 1H), 3.73 (s, 3H), 4.02 (q , J = 7.0 Hz, 2H), 4.26 (dd, J = 3.7, 9.3 Hz, 1H), 6.89 (s, 2H), 7.02 (s, 1H); 13C NMR (DMSO-d6) δ 14.77, 41.98, 50.89, 55.54, 62.03, 63.68, 111.48, 111.77, 118.36, 137.30, 147.93, 148.09.

References

[1] Patent: US2014/81032, 2014, A1. Location in patent: Paragraph 0318; 0319
[2] Patent: US2013/217919, 2013, A1. Location in patent: Paragraph 0280
[3] Patent: WO2016/199031, 2016, A1

(S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine Preparation Products And Raw materials

Raw materials

Preparation Products

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(S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine Suppliers

China 208 India 10 United Kingdom 1 United States 8 Global 227
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Pharmaffiliates Analytics and Synthetics P. Ltd
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View Lastest Price from (S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine manufacturers

Hefei Lbao Physical & Chemical Science Co.,Ltd
Product
(S)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine 608141-42-0
Price
US $0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
Customise
Release date
2025-11-27
ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD
Product
(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethanamine 608141-42-0
Price
US $2.00-6.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2025-08-08
Hebei Ganmiao New material Technology Co., LTD
Product
(S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine 608141-42-0
Price
US $10.00-7.00/kg
Min. Order
1kg
Purity
99.9%
Supply Ability
20ton
Release date
2024-06-06

608141-42-0, (S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMineRelated Search:

1,3-Dioxo-2-isoindolineaceticacid 3,5-Cyclohexadiene-1,2-dione, 4-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]- Apremilast 1,2-Benzenedicarboxylicacid,3-(hydroxyamino)-(9CI) Apremilast Impurity 3 3-oxo-1,3-dihydro-benzo[c]isoxazole-4-carboxylic acid 6H,12H-Indazolo[2,1-a]indazole-1,7-dicarboxylic acid, 6,12-dioxo- (S)-N-(2-(1-(3,4-dihydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide Apremilast APST-ZA (R)-N-(2-(1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide (S)-N-(2-(1-(3-ethoxy-4-hydroxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide Apremilast Impurity 4 2-CHLORO-4'-HYDROXYACETOPHENONE (S)-1-(4-chloro-3-fluorophenyl)ethane-1,2-diol (S)-4-Bromo-alpha-methylbenzyl alcohol (S)-1-(3-bromo-2-methoxyphenyl)ethan-1-ol 1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl) ethanone

  • (S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine
  • (S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethylaMine
  • (alphaS)-3-Ethoxy-4-methoxy-alpha-[(methylsulfonyl)methyl]-benzenemethanamine
  • (S)-2-(3-ethoxy-4-Methoxyphenyl)-1-(Methylsulphonyl)-eth-1-ylaMine
  • Apremilast Intermediate II
  • (1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethanamine
  • 1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine-N- acetyl –L-Leucine salt
  • (1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine
  • (S)-2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)-eth-2-ylamine
  • (S)-3-Ethoxy-4-methoxy-α-[(methylsulfonyl)methyl]benzenemethanamine
  • (S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethan-1-amine
  • Apremilast inter2
  • Apremilast Intermediates 2
  • (1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethan-1-amine
  • (S)-2-[1 (3-ethoxy-4-methoxyphenyl)]-1-methanesulfonyl-2-ethylamine
  • Apremilast Impurity HS093220
  • Benzenemethanamine, 3-ethoxy-4-methoxy-α-[(methylsulfonyl)methyl]-, (αS)-
  • Apremilast Impurity 55
  • (S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamin...
  • (alphaS)-3- ethoxy -4- methoxy -alpha-[ (methylsulfonyl) methyl]-benzylamine
  • RSSYY(Lurasidone Hydrochloride)-14
  • (αS)-3-Ethoxy-4-methoxy-α-[(methylsulfonyl)methyl]benzenemethanamine
  • Apremilast Impurity 1 3-Ethoxy-4-methoxy-[(methylsulfonyl)methyl]-(S)- benzenemethanamine
  • Apremilast EP Impurity H (S)-Isomer
  • Apremilast Desphthalyl Amine
  • 608141-42-0
  • apremilast intermediates