(S)-(-)-3-(N-methylamino)-1-(2-thienyl)-1-propanol

Base Information

• Chemical Name: (S)-(-)-3-(N-methylamino)-1-(2-thienyl)-1-propanol
• CAS No.: 116539-55-0
• Molecular Formula: C8H13NOS
• Molecular Weight: 171.263
• Hs Code.: 2934999090
• UNII: 43P2XE546O
• DSSTox Substance ID: DTXSID20151422
• Nikkaji Number: J1.907.774H
• Wikidata: Q27258657
• Mol file: 116539-55-0.mol

Synonyms:116539-55-0;(S)-(-)-3-(N-methylamino)-1-(2-thienyl)-1-propanol;(1S)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol;(S)-3-(Methylamino)-1-(thiophen-2-yl)propan-1-ol;3-(N-Methylamino)-1-(2-thienyl)-1-propanol, (-)-;(S)-3-(Methylamino)-1-(2-thienyl)-1-propanol;(S)-(-)-3-methylamino-1-(2-thienyl)propan-1-ol;UNII-43P2XE546O;43P2XE546O;(S)-3-(Methylamino)-1-(2-thienyl)propan-1-ol;(1S)-3-(methylamino)-1-thiophen-2-ylpropan-1-ol;N-Methyl-(S)-(-)-3-hydroxy-3-(2-thiophen)propylamine;(1S)-(-)-3-(Methylamino)-1-(thien-2-yl)propan-1-ol;Duloxetine hydrochloride impurity B [EP];EC 601-437-5;(1S)-3-methylamino-1-(2-thienyl)-1-propanol;(S)-3-(n-methylamino)-1-(2-thienyl)-1-propanol;(S)-3-Methylamino-1-(thiophene-2-yl)propan-1-ol;(S)-1-beta-Hydroxy-1-(2-thienyl)-3-methylaminopropane;2-Thiophenemethanol, alpha-(2-(methylamino)ethyl)-, (alphaS)-;Duloxetine EP IMpurity B;2-Thiophenemethanol, alpha-[2-(methylamino)ethyl]-, (alphaS)-;MFCD07357308;(S)-3-METHYLAMINO-1-THIOPHEN-2-YL-PROPAN-1-OL;SCHEMBL98019;DTXSID20151422;YEJVVFOJMOHFRL-ZETCQYMHSA-N;CS-M3028;AKOS006284313;AC-5321;DS-1147;M2157;EN300-7357294;(1S)-3-(methylamino)-1-(2-thienyl)-1-propanol;(S) -3-Methyl-amino-1-(2-thienyl)-1-propanol;(s)-n-methyl-3-hydroxy-3-(2-thienyl)propylamine;(-)-3-(N-methylamino)-1-(2-thienyl)-1-propanol;(S)-2-[3-(Methylamino)-1-hydroxypropyl]thiophene;(S)-(-)-3-methylamino-1-(2-thienyl)-propan-1-ol;(S)-3-METHYLAMINO-1-(2-THIENYL)-1-PROPANOL;(S)-N-methyl-3-hydroxy-3-(2-thienyl)-1-propanamine;Q27258657;DULOXETINE HYDROCHLORIDE IMPURITY B [EP IMPURITY];2-THIOPHENEMETHANOL, .ALPHA.-(2-(METHYLAMINO)ETHYL)-, (.ALPHA.S)-

Chemical Property of (S)-(-)-3-(N-methylamino)-1-(2-thienyl)-1-propanol

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 72.0 to 76.0 °C
• Refractive Index: 1.553
• Boiling Point: 294.288 °C at 760 mmHg
• PKA: 13.77±0.20(Predicted)
• Flash Point: 131.781 °C
• PSA: 60.50000
• Density: 1.128 g/cm³
• LogP: 1.78190
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 171.07178521
• Heavy Atom Count: 11
• Complexity: 110

Purity/Quality:

99% ^*data from raw suppliers

(S)-1-β-Hydroxy-1-(2-thienyl)-3-methylaminopropane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCCC(C1=CC=CS1)O
• Isomeric SMILES: CNCC[C@@H](C1=CC=CS1)O
• Uses: A Duloxetine intermediate. Duloxetine EP Impurity B. A Duloxetine intermediate.

Technology Process of (S)-(-)-3-(N-methylamino)-1-(2-thienyl)-1-propanol

There total 84 articles about (S)-(-)-3-(N-methylamino)-1-(2-thienyl)-1-propanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

C8H13NO2S (1035456-55-3) → (S)-3-methylamino-1-(2-thienyl)-1-propanol (116539-55-0)

Guidance literature:

C₈H₁₃NO₂S; With acetic acid; zinc; In water; at 50 ℃; for 1.5h;

With sodium hydroxide; In water;

Reference yield: 98.0%

(S)-3-hydroxy-N-methyl-3-(thiophen-2-yl)propanamide (603959-56-4) → (S)-3-methylamino-1-(2-thienyl)-1-propanol (116539-55-0)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 20 ℃; for 4h; Reagent/catalyst;

Reference yield: 94.0%

N-methyl-3-(thien-2-yl)-3-morpholino-propylamine hydrochloride (645411-16-1) → (S)-3-methylamino-1-(2-thienyl)-1-propanol (116539-55-0)

Guidance literature:

With Rh[((S,S)-BenzP*)(cod)]SbF₆; hydrogen; caesium carbonate; zinc(II) chloride; In methanol; at 20 ℃; for 20h; under 19001.3 Torr; Reagent/catalyst; Solvent; enantioselective reaction; Autoclave;

DOI:10.1002/anie.201411384

upstream raw materials:

S-(-)-3-iodo-1-(2-thienyl)-1-propanol

methylamine

(S)-3-hydroxy-3-(2-thienyl)propyl methanesulfonate

((S)-3-Hydroxy-3-thiophen-2-yl-propyl)-carbamic acid ethyl ester

Downstream raw materials:

Duloxetine

Duloxetine oxalate

(R)-Duloxetine

(S)-3-dimethylamino-1-(2-thienyl)propan-1-ol

Refernces

• 1、 Kamal, Ahmed,Khanna, G. B. Ramesh,Ramu,Krishnaji. "Chemoenzymatic synthesis of duloxetine and its enantiomer: Lipase-catalyzed resolution of 3-hydroxy-3-(2-thienyl) propanenitrile". . p. 4783 - 4787. Retrieved 2003.
• 2、 -. "Method for synthesizing (S)-3-methylamino-1-(thiophene-2-yl) propyl alcohol". Paragraph 0040-0042; 0045-0047. . Retrieved 2018/04/21.
• 3、 -. "(S)- (-) - 3 - methylamino - 1 - (2 - thienyl) - 1 - propanol synthetic method". Paragraph 0075; 0084; 0085; 0086; 0087; 0088; 0089. . Retrieved 2017/08/25.