Isotimolol

Base Information

• Chemical Name: Isotimolol
• CAS No.: 59697-06-2
• Molecular Formula: C13H24N4O3S
• Molecular Weight: 316.425
• Hs Code.: 2934990002
• European Community (EC) Number: 642-072-1,806-079-5
• UNII: 66OA8AMH50
• Nikkaji Number: J1.931.945H
• Wikidata: Q27264005
• Mol file: 59697-06-2.mol

Synonyms:Isotimolol;59697-06-2;rac-Isotimolol;3-(tert-butylamino)-2-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)propan-1-ol;3-(tert-butylamino)-2-[(4-morpholin-4-yl-1,2,5-thiadiazol-3-yl)oxy]propan-1-ol;66OA8AMH50;(S)-Isotimolol (Timolol Impurity B);1-Propanol, 3-((1,1-dimethylethyl)amino)-2-((4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl)oxy)-;1-Propanol,3-[(1,1-dimethylethyl)amino]-2-[[4-(4-morpholinyl)-1,2,5-thiadiazol-3-yl]-oxy]-;158636-96-5;UNII-66OA8AMH50;Timolol maleate specified impurity B [EP];SCHEMBL16655912;FT-0670571;F76124;TIMOLOL MALEATE IMPURITY B [EP IMPURITY];Q27264005

Chemical Property of Isotimolol

Chemical Property:

• Melting Point: 120.0-121.5 °C(Solv: hexane (110-54-3))
• Boiling Point: 484.7±45.0 °C(Predicted)
• PKA: 13.84±0.10(Predicted)
• PSA: 107.98000
• Density: 1.224±0.06 g/cm3(Predicted)
• LogP: 0.95840
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 316.15691181
• Heavy Atom Count: 21
• Complexity: 310

Purity/Quality:

97% ^*data from raw suppliers

rac-Isotimolol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)NCC(CO)OC1=NSN=C1N2CCOCC2
• Uses: rac-Isotimolol (Timolol EP Impurity B; Timolol BP Impurity B; Timolol USP Related Compound B) is an analog of Timolol (T443700); an antihypertensive, antiarrhythmic (class II), antianginal, and antiglaucoma agent.

Technology Process of Isotimolol

There total 2 articles about Isotimolol 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:

3-Morpholino-4-chloro-1,2,5-thiadiazole (30165-96-9) + ((2Ξ,5S)-3-tert-butyl-2-phenyl-oxazolidin-5-yl)-methanol (194861-99-9) → 3-tert-butylamino-2-(4-morpholin-4-yl-[1,2,5]thiadiazol-3-yloxy)-propan-1-ol (59697-06-2,158636-96-5) + timolol (26839-75-8,47148-57-2)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; at 25 ℃; for 16h;

DOI:10.1021/jo00881a011

Reference yield:

(S)-1-tert-butylamino-2,3-dihydroxypropane (30315-46-9) → 3-tert-butylamino-2-(4-morpholin-4-yl-[1,2,5]thiadiazol-3-yloxy)-propan-1-ol (59697-06-2,158636-96-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 150 °C

2: KOtBu / 2-methyl-propan-2-ol / 16 h / 25 °C

With potassium tert-butylate; In tert-butyl alcohol;

DOI:10.1021/jo00881a011

upstream raw materials:

3-Morpholino-4-chloro-1,2,5-thiadiazole

((2Ξ,5S)-3-tert-butyl-2-phenyl-oxazolidin-5-yl)-methanol

(S)-1-tert-butylamino-2,3-dihydroxypropane

Refernces