1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride

Base Information

• Chemical Name: 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride
• CAS No.: 16899-81-3
• Molecular Formula: C11H15 N O3 . Cl H
• Molecular Weight: 245.706
• Hs Code.: 2922509090
• European Community (EC) Number: 240-943-7
• NSC Number: 23623
• UNII: X4JS3SRV5Y
• ChEMBL ID: CHEMBL1736975
• Mol file: 16899-81-3.mol

Synonyms:Acetophenone,3',4'-dihydroxy-2-(isopropylamino)-, hydrochloride (8CI); Ethanone,1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino]-, hydrochloride (9CI);3,4-Dihydroxy-a-(isopropylamino)acetophenonehydrochloride; U 12844A

Chemical Property of 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride

Chemical Property:

• Vapor Pressure: 2.69E-07mmHg at 25°C
• Melting Point: 255-257℃
• Boiling Point: 409.7°Cat760mmHg
• Flash Point: 201.6°C
• PSA: 69.56000
• Density: 1.185g/cm³
• LogP: 2.47140
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 245.0818711
• Heavy Atom Count: 16
• Complexity: 218

Purity/Quality:

99.5% ^*data from raw suppliers

Isoprenaline impurity A European Pharmacopoeia (EP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Moderately toxic.
• Hazard Codes: Moderately toxic.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)NCC(=O)C1=CC(=C(C=C1)O)O.Cl
• Uses: 1-(3,4-Dihydroxyphenyl)-2-[(1-methylethyl)amino]-ethanone is an impurity of Isoprenaline (I874200, HCl salt) which is non-selective beta-adrenergic agonist. Isoprenaline is used in the treatment of bradycardia.

Technology Process of 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] hydrochloride

There total 5 articles about 1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino] 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: 85.3%

2-chloro-3',4'-dihydroxyacetophenone (99-40-1) → Isoproterenone hydrochloride (16899-81-3)

Guidance literature:

With isopropylamine; In toluene; at 5 - 25 ℃; for 5h;

Reference yield: 84.3%

isopropyl chloride (75-29-6) + arterenone (499-61-6) → Isoproterenone hydrochloride (16899-81-3)

Guidance literature:

isopropyl chloride; With triethylamine; In ethanol; at 10 - 15 ℃;

arterenone; In ethanol; at 40 ℃; for 10h; Concentration;

Reference yield:

benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → Isoproterenone hydrochloride (16899-81-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: zinc(II) chloride / 1,2-dichloro-ethane / 0.5 h / 10 - 70 °C

1.2: 20 h / Reflux

2.1: triethylamine / ethanol / 10 - 15 °C

2.2: 10 h / 40 °C

With triethylamine; zinc(II) chloride; In ethanol; 1,2-dichloro-ethane;

upstream raw materials:

2-chloro-3',4'-dihydroxyacetophenone

isopropylamine

isopropyl chloride

arterenone

Downstream raw materials:

(+)-Isoproterenol hydrochloride

isoproterenol hydrochloride

3,4-O-diacetylisoproterenol hydrochloride

3',4'-diacetoxy-2-(isopropylamino)acetophenone hydrochloride

Refernces

• 1、 -. "Hydrochloric acid isopropyl adrenergic preparation method". Paragraph 0014; 0017-0018; 0021; 0024-0025; 0028; 0031-0032. . Retrieved 2019/03/31.
• 2、 Brazzell,Kostenbauder. "Isolated perfused rabbit lung as a model for intravascular and intrabronchial administration of bronchodilator drugs II: isoproterenol prodrugs". . p. 1274 - 1281. Retrieved 2007/10/02.