2-Amino-5-nitrobenzophenone

Base Information

• Chemical Name: 2-Amino-5-nitrobenzophenone
• CAS No.: 1775-95-7
• Molecular Formula: C13H10N2O3
• Molecular Weight: 242.234
• Hs Code.: 29223990
• European Community (EC) Number: 217-207-9
• UNII: G2X8PCQ4GY
• DSSTox Substance ID: DTXSID40170317
• Nikkaji Number: J80.313H
• Wikidata: Q72439978
• Mol file: 1775-95-7.mol

Synonyms:2-amino-5-nitrobenzophenone

Chemical Property of 2-Amino-5-nitrobenzophenone

Chemical Property:

• Appearance/Colour: yellow solid
• Vapor Pressure: 2.65E-09mmHg at 25°C
• Melting Point: 166-168 °C(lit.)
• Refractive Index: 1.657
• Boiling Point: 478.1 °C at 760 mmHg
• PKA: -2.26±0.36(Predicted)
• Flash Point: 242.9 °C
• PSA: 88.91000
• Density: 1.333 g/cm³
• LogP: 3.51240
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
• Water Solubility.: 3 mg/L (20 C)
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 242.06914219
• Heavy Atom Count: 18
• Complexity: 321

Purity/Quality:

99% ^*data from raw suppliers

5-Amino-2-nitrobenzophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)C2=C(C=CC(=C2)[N+](=O)[O-])N
• Uses: 2-Amino-5-nitrobenzophenone was used in the synthesis of [5-(4-nitrophenyl)-2-furyl]acrylic acid substituted benzophenone (anti-malarial agent). A metabolite of Nitrazepam

Technology Process of 2-Amino-5-nitrobenzophenone

There total 27 articles about 2-Amino-5-nitrobenzophenone 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: 99.0%

5-nitro-3-phenyl-2,1-benzisoxazole (38735-62-5) → 2-amino-5-nitrobenzophenone (1775-95-7)

Guidance literature:

With trimethylsilyl iodide; water; In acetonitrile; at 20 ℃; for 0.5h;

Reference yield: 97.0%

5-nitroanthranilonitrile (17420-30-3) + phenylboronic acid (98-80-6) → 2-amino-5-nitrobenzophenone (1775-95-7)

Guidance literature:

With 5,5'-dimethyl-2,2'-bipyridine; methanesulfonic acid; palladium(II) trifluoroacetate; water; In 2-methyltetrahydrofuran; at 80 ℃; for 36h; Schlenk technique;

DOI:10.1039/c4ob00978a

Reference yield: 96.0%

5-nitroanthranilonitrile (17420-30-3) + sodium benzenesulfonate (873-55-2) → 2-amino-5-nitrobenzophenone (1775-95-7)

Guidance literature:

With p-nitrobenzenesulfonic acid; palladium diacetate; In tetrahydrofuran; water; at 80 ℃; for 48h; Inert atmosphere; Schlenk technique;

DOI:10.3390/molecules19056439

upstream raw materials:

N-(2-Benzoyl-4-nitro-phenyl)-acetamide

2-chloro-5-nitrobenzophenone

N-(2-benzoyl-4-nitrophenyl)benzamide

p-nitrobenzanilide

Downstream raw materials:

2-(2,2,2-trifluoroethylamino)-5-nitrobenzophenone

N-(2-Benzoyl-4-nitro-phenyl)-acetamide

2-(2-Amino-5-nitro-α-phenylbenzylidenamino)ethanol

2-N-carbethoxymethyl-5-nitrobenzophenone

Refernces

Structure-activity relationships of novel anti-malarial agents: Part 5. N-(4-acylamino-3-benzoylphenyl)-[5-(4-nitrophenyl)-2-furyl]acrylic acid amides

10.1016/S0960-894X(02)01003-X

The study focuses on the structure-activity relationships of novel anti-malarial agents, specifically N-(4-acylamino-3-benzoylphenyl)-[5-(4-nitrophenyl)-2furyl]acrylic acid amides. The researchers developed a lead compound, benzophenone 4g, which was modified by replacing the tolylacetyl residue at the 2-amino group with various acyl residues to determine their influence on anti-malarial activity. The chemicals used included 2-amino-5-nitrobenzophenone, acid chlorides for acylation, SnCl2?2H2O for reduction, and 3-[5-(4-nitrophenyl)-2-furyl]acrylic acid chloride for further acylation. The purpose of these chemicals was to synthesize and test a series of compounds to identify the optimal acyl residue structure for high anti-malarial activity, with the aim of overcoming drug resistance in Plasmodium falciparum, the causative agent of malaria. The study found that a phenylacetic acid substructure substituted in its para-position with methyl or similar-sized substituents was essential for high activity, with the trifluoromethyl-substituted derivative showing the most potent activity.