Bambuterol hydrochloride

Base Information

• Chemical Name: Bambuterol hydrochloride
• CAS No.: 81732-46-9
• Molecular Formula: C₁₈H₂₉N₃O₅*ClH
• Molecular Weight: 403.906
• Hs Code.: 29242990
• European Community (EC) Number: 643-060-9
• NSC Number: 758916
• UNII: 786Q84QZ3F
• DSSTox Substance ID: DTXSID8045515
• Wikidata: Q27126505
• ChEMBL ID: CHEMBL1603534
• Mol file: 81732-46-9.mol

Synonyms:5-(2-(tert-butylamino)-1-hydroxyethyl)-3-phenylene bis(dimethylcarbamate);bambuterol;bambuterol hydrochloride

Chemical Property of Bambuterol hydrochloride

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 7.49E-11mmHg at 25°C
• Melting Point: 222-224 °C
• Refractive Index: 1.533
• Boiling Point: 500.9 °C at 760 mmHg
• Flash Point: 256.7 °C
• PSA: 91.34000
• Density: 1.154g/cm3
• LogP: 3.42180
• Storage Temp.: -20°C Freezer
• Solubility.: H2O: ~33 mg/mL, soluble
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 403.1873988
• Heavy Atom Count: 27
• Complexity: 446

Purity/Quality:

99% ^*data from raw suppliers

Bambuterol hydrochloride ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)NCC(C1=CC(=CC(=C1)OC(=O)N(C)C)OC(=O)N(C)C)O.Cl
• Recent ClinicalTrials: The Effect of Bronchodilator on Eosinophilic Bronchitis and Cough Variant Asthma
• Uses: Ester prodrug of the ?-adrenergic agonist terbutaline Ester prodrug of the ?2-adrenergic agonist terbutaline. beta adrenergic agonist, bronchodilator, cholinesterase inhibitor

Technology Process of Bambuterol hydrochloride

There total 8 articles about Bambuterol 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: 68.9%

2-[3,5-di(N,N-dimethylcarbamyloxy)phenyl]oxirane (1392302-60-1) + tert-butylamine (75-64-9) → Bambuterol hydrochloride (81732-46-9)

Guidance literature:

2-[3,5-di(N,N-dimethylcarbamyloxy)phenyl]oxirane; tert-butylamine; With triethylamine; In isopropyl alcohol; for 8h; Reflux; Green chemistry;

With hydrogenchloride; In ethyl acetate; pH=2; Solvent; Cooling with ice; Green chemistry;

Reference yield: 67.0%

bis-3',5'-(N,N-dimethylcarbamoyloxy)-ω-N-benzyl-tert-butylaminoacetophenone → Bambuterol hydrochloride (81732-46-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; benzyl chloride; In ethanol; at 50 ℃; for 22h; under 2068.65 - 2585.81 Torr;

Reference yield:

Bambuterol hydrochloride (81732-46-9) → (S)-bambuterol hydrochloride (1020652-57-6,81732-46-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / water / 0.5 h

2.1: ethyl acetate / 2 h / 50 - 60 °C / Green chemistry

3.1: potassium carbonate / water / 0.5 h

3.2: 1 h / pH 1 / Cooling with ice

With potassium carbonate; In water; ethyl acetate;

DOI:10.1002/chir.22573

upstream raw materials:

2-[3,5-di(N,N-dimethylcarbamyloxy)phenyl]oxirane

tert-butylamine

Downstream raw materials:

(S)-bambuterol hydrochloride

(R)-bambuterol hydrochloride

(RS)-[3-[-2-(tert-butylamino)-1-hydroxyethyl]-5-hydroxyphenyl] N,N-dimethylcarbamate hydrochloride

Refernces

• 1、 -. "Synthetic process of Bambuterol hydrochloride". Paragraph 0029; 0032; 0038-0039; 0040; 0046-0047; 0060. . Retrieved 2019/07/08.