5-(Bromoacetyl)-2-(phenylmethoxy)benzamide

Base Information

• Chemical Name: 5-(Bromoacetyl)-2-(phenylmethoxy)benzamide
• CAS No.: 72370-19-5
• Molecular Formula: C16H14 Br N O3
• Molecular Weight: 348.196
• European Community (EC) Number: 276-604-5
• DSSTox Substance ID: DTXSID80993163
• Nikkaji Number: J299.098I
• Wikidata: Q82983727
• Mol file: 72370-19-5.mol

Synonyms:5-(Bromoacetyl)-2-(phenylmethoxy)benzamide;72370-19-5;5-(2-bromoacetyl)-2-phenylmethoxybenzamide;EINECS 276-604-5;Benzamide,5-(2-bromoacetyl)-2-(phenylmethoxy)-;Benzamide, 5-(bromoacetyl)-2-(phenylmethoxy)-;C16H14BrNO3;5-(2-Bromoacetyl)-2-(phenylmethoxy)benzamide;SCHEMBL6895376;C16-H14-Br-N-O3;DTXSID80993163;LUQQESVFZAPODX-UHFFFAOYSA-N;2-benzyloxy-5-(bromoacetyl)benzamide;AKOS030255006;2-(Benzyloxy)-5-(2-bromoacetyl)benzamide;2-(Benzyloxy)-5-(bromoacetyl)benzene-1-carboximidic acid

Chemical Property of 5-(Bromoacetyl)-2-(phenylmethoxy)benzamide

Chemical Property:

• Vapor Pressure: 7.12E-10mmHg at 25°C
• Melting Point: 150-152 °C
• Boiling Point: 493.3°C at 760 mmHg
• PKA: 14.87±0.50(Predicted)
• Flash Point: 252.1°C
• PSA: 70.38000
• Density: 1.465g/cm³
• LogP: 3.82630
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 347.01571
• Heavy Atom Count: 21
• Complexity: 369

Purity/Quality:

99% ^*data from raw suppliers

5-(2-Bromoacetyl)-2-(phenylmethoxy)benzamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=C(C=C(C=C2)C(=O)CBr)C(=O)N
• Uses: 5-(2-Bromoacetyl)-2-(phenylmethoxy)benzamide is an intermediate of (R,R)-Labetalol (L096500), a specific competitive antagonist at both α-and β-adrenergic receptor sites. (R,R)-Labetalol is used as an antihypertensive.

Technology Process of 5-(Bromoacetyl)-2-(phenylmethoxy)benzamide

There total 4 articles about 5-(Bromoacetyl)-2-(phenylmethoxy)benzamide 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: 87.0%

5-acetyl-2-(phenylmethoxy)benzamide (75637-30-8) → 5-(bromoacetyl)-2-(phenylmethoxy)benzamide (72370-19-5)

Guidance literature:

With bromine; In chloroform;

DOI:10.1016/S0960-894X(01)00645-X

Reference yield:

5-acetylsalicylamide (40187-51-7) → 5-(bromoacetyl)-2-(phenylmethoxy)benzamide (72370-19-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / NaOMe / methanol

2: 87 percent / Br₂ / CHCl₃

With bromine; sodium methylate; In methanol; chloroform;

DOI:10.1016/S0960-894X(01)00645-X

Reference yield:

benzyl chloride (100-44-7) → 5-(bromoacetyl)-2-(phenylmethoxy)benzamide (72370-19-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaOCH₃ / 1.) DMF, 2.) DMF, heating, 7 h

2: Br₂ / CHCl₃ / 0.17 h / Heating

With bromine; sodium methylate; In chloroform;

DOI:10.1021/jm00353a017

upstream raw materials:

5-acetyl-2-(phenylmethoxy)benzamide

5-acetylsalicylamide

benzyl bromide

benzyl chloride

Downstream raw materials:

(-)-2-hydroxy-5-<(R)-1-hydroxy-2-<(S)-(1-methyl-3-phenylpropyl)amino>ethyl>benzamide hydrochloride

*)>-2-hydroxy-5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)amino>ethyl>benzamide hydrochloride

*,R^*)>-5-<1-hydroxy-2-ethyl>-2-(phenylmethoxy)benzamide

*,R^*)>-5-<1-hydroxy-2-ethyl>-2-(phenylmethoxy)benzamide

Refernces

• 1、 Ashwell, Mark A,Solvibile Jr., William R,Han, Stella,Largis, Elwood,Mulvey, Ruth,Tillet, Jeffrey. "4-Aminopiperidine ureas as potent selective agonists of the human β3-Adrenergic receptor". . p. 3123 - 3127. Retrieved 2007/10/03.