2-AMINO-1-(3-CHLOROPHENYL)-1-ETHANOL

Base Information

• Chemical Name: 2-AMINO-1-(3-CHLOROPHENYL)-1-ETHANOL
• CAS No.: 53360-89-7
• Molecular Formula: C8H10ClNO
• Molecular Weight: 171.626
• Hs Code.: 2922199090
• Mol file: 53360-89-7.mol

Synonyms:1-(3-Chlorophenyl)-2-aminoethanol;2-(3-Chlorophenyl)-2-hydroxyethanamine;2-(3-Chlorophenyl)-2-hydroxyethylamine;2-Amino-1-(3-chlorophenyl)-1-ethanol;2-Amino-1-(3-chlorophenyl)ethanol;S16483-6;R)-3-Chlorophenylglycinol;

Chemical Property of 2-AMINO-1-(3-CHLOROPHENYL)-1-ETHANOL

Chemical Property:

• Vapor Pressure: 0.000138mmHg at 25°C
• Refractive Index: 1.587
• Boiling Point: 319.8 °C at 760 mmHg
• PKA: 11.77±0.35(Predicted)
• Flash Point: 147.2 °C
• PSA: 46.25000
• Density: 1.26 g/cm³
• LogP: 2.03240

Purity/Quality:

99% ^*data from raw suppliers

BENZENEMETHANOL,α-(AMINOMETHYL)-3-CHLORO- 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 2-Amino-1-(3-chlorophenyl)-1-ethanol is a key intermediate in the synthesis of oxazolidine derivatives with potential beta₃-adrenoceptor agonist activity. Its structural features, including the chlorophenyl and amino groups, are essential for forming cyclic compounds that may exhibit thermogenic and lipolytic effects, making it valuable for developing anti-obesity agents. 2-AMINO-1-(3-CHLOROPHENYL)-1-ETHANOL undergoes cyclization reactions, such as with formaldehyde, to construct the core oxazolidine framework of these bioactive derivatives.

Technology Process of 2-AMINO-1-(3-CHLOROPHENYL)-1-ETHANOL

There total 11 articles about 2-AMINO-1-(3-CHLOROPHENYL)-1-ETHANOL 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: 70.0%

2-(3-chlorophenyl)-2-hydroxyacetonitrile (97070-75-2,122047-10-3,137766-66-6,53313-92-1) → 2-amino-1-(3-chloro-phenyl)-ethanol (53360-89-7)

Guidance literature:

2-(3-chlorophenyl)-2-hydroxyacetonitrile; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 60 ℃; for 2h; Inert atmosphere;

With sodium hydroxide; In tetrahydrofuran; at 0 ℃;

Reference yield: 70.0%

m-Chlorobenzaldehyde (587-04-2) → 2-amino-1-(3-chloro-phenyl)-ethanol (53360-89-7)

Guidance literature:

Reference yield:

O-trimethyl-silyl-3-chloromandelonitrile → 2-amino-1-(3-chloro-phenyl)-ethanol (53360-89-7)

Guidance literature:

With hydrogenchloride; sodium hydroxide; sodium borohydrid; trifluoroacetic acid; In tetrahydrofuran; water;

upstream raw materials:

2-(3-chlorophenyl)-2-hydroxyacetonitrile

trimethylsilyl cyanide

m-Chlorobenzaldehyde

2-(3-chloro-phenyl)-2-triethylsilanyloxy-ethylamine

Downstream raw materials:

5-(3-chloro-phenyl)-4,5-dihydro-oxazol-2-ylamine

5-(3-chlorophenyl)oxazolidine

(+/-)-2-{4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-7-methyl-3H-benzimidazole-5-carbonitrile

5-(4-{2-[2-(3-chlorophenyl)-2-hydroxyethylamino]propoxy}benzyl)thiazolidine-2,4-dione

Refernces

Synthesis of new oxazolidine, oxazolidin-2-one and perhydro-1,4-oxazine derivatives of arylethanolamine as potential beta₃-adrenoceptor agonists

10.1002/jhet.5570320504

The research focuses on the synthesis of new cyclic compounds, specifically arylethanolamine derivatives, with potential beta-adrenergic agonist selectivity. These compounds are associated with thermogenesis and regulation of insulin release, and their synthesis involves creating oxazolidine, oxazolidin-2-one, and perhydro-1,4-oxazine derivatives. The study aims to develop new potential beta-adrenergic agonists that could be useful in treating obesity due to their lipid mobilization and thermogenic activities with fewer undesirable effects than other lipolytic substances. 2-amino-1-(3-chlorophenyl)-1-ethanol plays a crucial role as a key starting material for the synthesis of the oxazolidine derivatives. It is used to form the core structure of the target compounds through cyclization reactions. Specifically, it is reacted with formaldehyde under reflux conditions to form the oxazolidine ring, which is a fundamental part of the cyclic compounds being synthesized. This compound is essential for introducing the chlorophenyl and amino groups into the structure, which are critical for the potential beta-adrenergic agonist activity of the final products.

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