Dexpropranolol hydrochloride

Base Information

• Chemical Name: Dexpropranolol hydrochloride
• CAS No.: 13071-11-9
• Molecular Formula: C₁₆H₂₁NO₂*ClH
• Molecular Weight: 295.809
• Hs Code.: 2922 19 00
• European Community (EC) Number: 235-961-7
• UNII: AB9DB0NX46
• DSSTox Substance ID: DTXSID30873365
• Wikidata: Q27122453
• NCI Thesaurus Code: C77945
• ChEMBL ID: CHEMBL1358662
• Mol file: 13071-11-9.mol

Synonyms:Anaprilin;Anapriline;Avlocardyl;AY 20694;AY-20694;AY20694;Betadren;Dexpropranolol;Dociton;Hydrochloride, Propranolol;Inderal;Obsidan;Obzidan;Propanolol;Propranolol;Propranolol Hydrochloride;Rexigen

Chemical Property of Dexpropranolol hydrochloride

Chemical Property:

• Vapor Pressure: 2.48E-08mmHg at 25°C
• Melting Point: 196-198 °C(lit.)
• Boiling Point: 434.9 °C at 760 mmHg
• Flash Point: 216.8 °C
• PSA: 41.49000
• LogP: 3.77040
• Storage Temp.: 2-8°C
• Solubility.: ethanol: 10 mg/mL
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 295.1339066
• Heavy Atom Count: 20
• Complexity: 257

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-(+)-Propranolol hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O.Cl
• Isomeric SMILES: CC(C)NC[C@H](COC1=CC=CC2=CC=CC=C21)O.Cl
• Description: (R)-Propranolol hydrochloride is the less active enantiomer of the anti-adrenoceptor (β-adrenoceptor) antagonist propranolol (HY-B0573). Propranolol is a nonselective β-adrenergic receptor (βAR) antagonist with high affinity for β1AR and β2AR with Ki values of 1.8 nM and 0.8 nM, respectively.
• Physical Properties: (R)-Propranolol's solubility:ethanol: 10 mg/mLDMSO: <14.5 mg/mLH2O: 50 mg/mL (With heat. Aqueous solutions are most stable at pH 3.0 and decompose rapidly at basic pH. Decomposition is accompanied by discoloration of the solution.)
• Uses: less active enantiomer The R-enantiomer of Propranolol (P831800). β?Adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II).

Technology Process of Dexpropranolol hydrochloride

There total 9 articles about Dexpropranolol hydrochloride 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%

isopropylamine (75-31-0) + (S)-(+)-1-chloro-3-(1-naphthyloxy)-2-propanol (132005-35-7) → (R)-propranolol hydrochloride (318-98-9,3506-09-0,4199-10-4,13071-11-9)

Guidance literature:

With sodium hydroxide; water; for 16h; Ambient temperature;

DOI:10.1021/jo00018a032

Reference yield: 89.0%

<2R-(2α(R*),3aα,4α,7α,7aα)>-N-(1-Methylethyl)-3-(1-naphthoxy)-2-<(octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl)oxy>-1-propanamin → (R)-propranolol hydrochloride (318-98-9,3506-09-0,4199-10-4,13071-11-9)

Guidance literature:

With hydrogenchloride; In methanol; diethyl ether;

DOI:10.1007/BF00807429

Reference yield:

Inderal (318-98-9) → (S)-(-)-propanolol hydrochloride (4199-10-4) + (R)-propranolol hydrochloride (318-98-9,3506-09-0,4199-10-4,13071-11-9)

Guidance literature:

With sodium dihydrogenphosphate; phosphoric acid; In methanol; water; pH=2.75; Reagent/catalyst; Ionic liquid; Resolution of racemate;

DOI:10.1002/chir.22168

upstream raw materials:

isopropylamine

(S)-(+)-1-chloro-3-(1-naphthyloxy)-2-propanol

3-(1-naphthyloxy)-1,2-epoxypropane

α-naphthol

Downstream raw materials:

(+)-5-Hydroxypropranolol

(R)-N-desisopropylpropranolol

(R)-2-Phenyl-butyric acid (R)-1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester

(S)-2-Phenyl-butyric acid (R)-1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester

Refernces

• 1、 Xu, Guangfu,Du, Yingxiang,Du, Fan,Chen, Jiaquan,Yu, Tao,Zhang, Qi,Zhang, Jinjing,Du, Shuaijing,Feng, Zijie. "Establishment and Evaluation of the Novel Tetramethylammonium-L-Hydroxyproline Chiral Ionic Liquid Synergistic System Based on Clindamycin Phosphate for Enantioseparation by Capillary Electrophoresis". . p. 598 - 604. Retrieved 2015.
• 2、 Zhang, Mei,Zi, Min,Wang, Bang-Jin,Yuan, Li-Ming. "Uridine, thymidine and inosine used as chiral stationary phases in HPLC". . p. 2226 - 2228. Retrieved 2014/06/09.