(R)-betaxolol

Base Information

• Chemical Name: (R)-betaxolol
• CAS No.: 91878-53-4
• Molecular Formula: C18H29 N O3
• Molecular Weight: 307.43
• UNII: 759O83814X
• DSSTox Substance ID: DTXSID50873206
• Nikkaji Number: J491.311F
• Wikidata: Q27126571
• Pharos Ligand ID: WDJJHV4GH1RR
• Metabolomics Workbench ID: 60503
• ChEMBL ID: CHEMBL1369414
• Mol file: 91878-53-4.mol

Synonyms:(R)-betaxolol;91878-53-4;Betaxolol, (R)-;Betaxolol, (+)-;Dextrobetaxolol;UNII-759O83814X;759O83814X;CHEMBL1369414;CHEBI:59251;(2R)-1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-(propan-2-ylamino)propan-2-ol;2-Propanol, 1-(4-(2-(cyclopropylmethoxy)ethyl)phenoxy)-3-((1-methylethyl)amino)-, (2R)-;(R)-1-(isopropylamino)-3-[p-(cyclopropylmethoxyethyl)phenoxy]-2-propanol;(2R)-1-{4-[2-(cyclopropylmethoxy)ethyl]phenoxy}-3-(propan-2-ylamino)propan-2-ol;(R)-Betaxolol;(+)-Betaxolol;d-Betaxolol;Tocris-0906;Lopac-B-5683;SCHEMBL23531;DTXSID50873206;BDBM50404948;NCGC00015159-01;NCGC00015159-02;NCGC00015159-03;NCGC00015159-07;NCGC00016904-01;NCGC00024863-01;PD132910;CAS-63659-19-8;Q27126571

Chemical Property of (R)-betaxolol

Chemical Property:

• Boiling Point: 448.0±40.0 °C (760 mmHg)
• PSA: 50.72000
• Density: 1.067±0.06 g/cm3 (20 °C, 760 mmHg)
• LogP: 2.78430
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 307.21474379
• Heavy Atom Count: 22
• Complexity: 286

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=C(C=C1)CCOCC2CC2)O
• Isomeric SMILES: CC(C)NC[C@H](COC1=CC=C(C=C1)CCOCC2CC2)O
• Recent ClinicalTrials: Safety and Efficacy Study of BETOPTIC S 0.25% and Timolol Gel-forming Solution 0.25% and 0.5% in Pediatric Patients With Glaucoma or Ocular Hypertension

Technology Process of (R)-betaxolol

There total 11 articles about (R)-betaxolol 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:

1-benzyloxy-4-(2-cyclopropylmethoxyethyl)benzene (63659-15-4) → (+)-Betaxolol (91878-53-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 50 - 60 °C / 2585.7 Torr

2: NaOH / ethanol / 24 h / Heating

3: water, HCl

4: 71 percent / pyridine / 5 h / 0 °C

5: 100 percent / Na / methanol; diethyl ether / 12 h / 0 °C

6: 96 h / Heating

With pyridine; hydrogenchloride; sodium hydroxide; water; hydrogen; sodium; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol;

DOI:10.1021/jm00389a008

Reference yield:

2-(4-benzyloxyphenyl)ethanol (61439-59-6) → (+)-Betaxolol (91878-53-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH / 1.) DMF, 2.) DMF, 60 deg, 18 h

2: 84 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 50 - 60 °C / 2585.7 Torr

3: NaOH / ethanol / 24 h / Heating

4: water, HCl

5: 71 percent / pyridine / 5 h / 0 °C

6: 100 percent / Na / methanol; diethyl ether / 12 h / 0 °C

7: 96 h / Heating

With pyridine; hydrogenchloride; sodium hydroxide; water; hydrogen; sodium; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol;

DOI:10.1021/jm00389a008

Reference yield:

2-<4-(phenylmethoxy)phenyl>acetic acid ethyl ester (56441-69-1) → (+)-Betaxolol (91878-53-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 86 percent / LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

2: 1.) NaH / 1.) DMF, 2.) DMF, 60 deg, 18 h

3: 84 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 50 - 60 °C / 2585.7 Torr

4: NaOH / ethanol / 24 h / Heating

5: water, HCl

6: 71 percent / pyridine / 5 h / 0 °C

7: 100 percent / Na / methanol; diethyl ether / 12 h / 0 °C

8: 96 h / Heating

With pyridine; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; water; hydrogen; sodium; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol;

DOI:10.1021/jm00389a008

upstream raw materials:

isopropylamine

(R)-4-<2-(cyclopropylmethoxy)ethyl>phenyl 2,3-epoxypropyl ether

Acetic acid (S)-1-chloromethyl-2-[4-(2-cyclopropylmethoxy-ethyl)-phenoxy]-ethyl ester

Acetic acid (S)-2-(acetyl-isopropyl-amino)-1-[4-(2-cyclopropylmethoxy-ethyl)-phenoxymethyl]-ethyl ester