93221-48-8

Basic information

• Product Name: LEVOBETAXOLOL
• Synonyms: (2S)-1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-(isopropylamino)propan-2-ol;(2S)-1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-(propan-2-ylamino)propan-2-ol;(S)-1-[4-[2-(Cyclopropylmethoxy)ethyl]phenoxy]-3-[(1-methylethyl)amino]-2-propanol;Levoβxolol HCl;LEVOBETAXOLOL;(S)-(-)-Betaxolol;(S)-Betaxolol;2-Propanol, 1-[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]-3-[(1-methylethyl)amino]-, (2S)-
• CAS NO: 93221-48-8
• Molecular Formula: C₁₈H₂₉NO₃
• Molecular Weight: 307.43
• Mol File: 93221-48-8.mol

Chemical Properties

• Melting Point: 71-72℃
• Boiling Point: 448°C at 760 mmHg
• Flash Point: 224.7°C
• Appearance: /
• Density: 1.067
• Vapor Pressure: 8.26E-09mmHg at 25°C
• Refractive Index: 1.529
• PKA: 13.89±0.20(Predicted)
• CAS DataBase Reference: LEVOBETAXOLOL(CAS DataBase Reference)
• NIST Chemistry Reference: LEVOBETAXOLOL(93221-48-8)
• EPA Substance Registry System: LEVOBETAXOLOL(93221-48-8)

Safety Data

• Hazardous Substances Data: 93221-48-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H29NO3/c1-14(2)19-11-17(20)13-22-18-7-5-15(6-8-18)9-10-21-12-16-3-4-16/h5-8,14,16-17,19-20H,3-4,9-13H2,1-2H3/t17-/m0/s1

Upstream product

• 874809-42-4 (S)-2-[4-(2-cyclopropylmethoxy ethyl)phenoxymethyl]oxirane 
• 75-31-0 isopropylamine 
• 100-00-5 4-chlorobenzonitrile 
• 874112-86-4 S-(-)-1-{4-[2-(allyloxy)-ethyl]phenoxy}-3-isopropylamino propan-2-ol 
• 75-11-6 diiodomethane 
• 63659-18-7 betaxolol 
• 947340-61-6 (5S)-2-(4-((3-isopropyl-2-phenyloxazolidin)-5-methoxy)phenyl)-4-ethanol 
• 62572-94-5 (+/-)-O-Demethylmetoprolol 
• 169613-97-2 Acetic acid (S)-2-(acetyl-isopropyl-amino)-1-[4-(2-cyclopropylmethoxy-ethyl)-phenoxymethyl]-ethyl ester 
• 169613-96-1 1-(N-acetyl-N-isopropyl)amino-3-<4-(2-cyclopropylmethoxy)ethyl>phenoxyprop-2-yl acetate 
• 7051-34-5 cyclopropylcarbinyl bromide 
• 131564-69-7 (-)-O-Demethylmetoprolol 
• 1312687-84-5 C₁₈H₂₇NO₅ 
• 959279-50-6 C₂₀H₂₉NO₆ 

Downstream Products

• 93221-49-9 (S)-(-)-3-<4-<2-(cyclopropylmethoxy)ethyl>phenoxy>-1-(isopropylamino)-2-propanol maleate 

Relevant articles and documents

Technique for synthesizing levorotatory betaxolol hydrochloride (by machine translation)

The invention discloses a technique for synthesizing levorotatory betaxolol hydrochloride, the process adopts to hydroxy phenylacetic alcohol and R- epoxy halogen propane is used as starting material, under certain conditions after alkylation, amination,

Effect of basic and acidic additives on the separation of some basic drug enantiomers on polysaccharide-based chiral columns with acetonitrile as mobile phase

The separation of enantiomers of 16 basic drugs was studied using polysaccharide-based chiral selectors and acetonitrile as mobile phase with emphasis on the role of basic and acidic additives on the separation and elution order of enantiomers. Out of the studied chiral selectors, amylose phenylcarbamate-based ones more often showed a chiral recognition ability compared to cellulose phenylcarbamate derivatives. An interesting effect was observed with formic acid as additive on enantiomer resolution and enantiomer elution order for some basic drugs. Thus, for instance, the enantioseparation of several β-blockers (atenolol, sotalol, toliprolol) improved not only by the addition of a more conventional basic additive to the mobile phase, but also by the addition of an acidic additive. Moreover, an opposite elution order of enantiomers was observed depending on the nature of the additive (basic or acidic) in the mobile phase.

Chemoenzymatic route to S-betaxolol

An efficient chemoenzymatic route to S-betaxolol is reported. A strain (Rhodotorula mucilaginosa DQ832198) screened from soil was used as biocatalyst for the kinetic resolution of the key acetylated intermediates. Excellent enantiomeric excess (ee99%) was

Concise synthesis of β-blockers (S)-metoprolol and (S)-betaxolol using hydrolytic kinetic resolution

Enantiopure (S)-metoprolol and (S)-betaxolol were prepared in an extremely simple and practical way using Jacobsen's hydrolytic kinetic resolution of terminal epoxides in isopropanol.

PROCESS FOR PREPARATION OF S-(-)-BETAXOLOL AND SALTS THEREOF

The present invention relates to an improved process for preparation of S-(?)-betaxolol salts. More particularly the present invention relates to the preparation of hydrochloride salt of S-(?)-betaxolol of formula (1).

S-(?)-1-{4-[2-(allyloxy)-ethyl]phenoxy}-3-isopropylamino propan-2-ol, process for preparation thereof and process for preparation of S-(?)betaxolo

The present invention relates to a novel compound S-(?)-1-{4-[2-(allyloxy)-ethyl] phenoxy}-3-isopropylamino propan-2-ol of formula 1 and to a process for the preparation thereof. More particularly the present invention relates to a process for preparing S

Selective terminal heck arylation of vinyl ethers with aryl chlorides: A combined experimental-computational approach including synthesis of betaxolol

Reaction conditions have been developed for palladium-catalyzed terminal (β-) arylation of acyclic vinyl ethers with high regioselectivity using inexpensive aryl chlorides as starting materials and the P(t-Bu)3 releasing preligand [(t-Bu3)PH]BF4 as the key additive. This swift and straightforward protocol exploits non-inert conditions and controlled microwave heating to minimize handling and processing times and uses aqueous DMF or environmentally friendly PEG-200 as the reaction medium. The selectivity for linear β-product in PEG-200 is slightly higher than in aqueous DMF. DFT calculations support a ligand-driven selectivity rationale, where the electronic and steric influence of bulky P(t-Bu)3 ligand provides improved β-selectivity in the essential insertion step also with electron-rich aryl chlorides. A tentative computational rationalization of the improved selectivity in non-methylated PEG is discussed. Finally the synthetic methodology was used to provide efficient access to linear p-[2- (cyclopropylmethoxy)-ethyl] phenol from p-nitrophenyl chloride, a key intermediate in the synthesis of the β-adrenergic blocking agent Betaxolol.

A convenient synthesis of the enantiomerically pure β-blocker (S)-betaxolol using hydrolytic kinetic resolution

Enantiopure (S)-betaxolol was prepared in an extremely simple and practical way using hydrolytic kinetic resolution of a terminal epoxide by Jacobsen's catalyst. High enantiomeric purity (99% ee) has been achieved and the method is amenable to industrial scale-up.

A chemoenzymatic route to both enantiomers of betaxolol

Evaluation of some of the possible lipase-catalyzed transformations has been done in order to prepare both enantiomers of betaxolol. Resolution of betaxolol by lipase-catalyzed hydrolysis of its bisacetylated derivatives 4 led to (-)- and (+)-enantiomers with an ee of 20 and 60%, respectively. When the resolution was performed on the chlorohydrin precursor 6 of betaxolol, (-)- and (+)-enantiomers were obtained with an ee of 91 and 75%, respectively.