2-Nitrochalcone

Base Information

• Chemical Name: 2-Nitrochalcone
• CAS No.: 7473-93-0
• Molecular Formula: C₁₅H₁₁NO₃
• Molecular Weight: 253.257
• Hs Code.: 2914790090
• European Community (EC) Number: 676-894-7
• NSC Number: 636937,401727
• UNII: MH3MVT883Z
• DSSTox Substance ID: DTXSID201247532
• Nikkaji Number: J860.912H,J103.563K
• Wikidata: Q106902662
• Pharos Ligand ID: KY19L9669ZXP
• ChEMBL ID: CHEMBL323025
• Mol file: 7473-93-0.mol

Synonyms:2-Nitrochalcone;7473-93-0;Chalcone, 2-nitro-;2-Nitrobenzylideneacetophenone;2-Propen-1-one, 3-(2-nitrophenyl)-1-phenyl-;(E)-3-(2-nitrophenyl)-1-phenylprop-2-en-1-one;(2E)-3-(2-nitrophenyl)-1-phenylprop-2-en-1-one;CCRIS 1671;NSC 401727;CHEMBL323025;53744-31-3;3-(2-nitrophenyl)-1-phenylprop-2-en-1-one;(E)-3-(2-Nitrophenyl)-1-phenyl-2-propen-1-one;NSC636937;NSC-401727;(2E)-3-(2-Nitrophenyl)-1-phenyl-2-propen-1-one;(E)-3-(2-nitrophenyl)-1-phenyl-prop-2-en-1-one;2-Propen-1-one, 3-(2-nitrophenyl)-1-phenyl-, (E)-;(E)-3-(2-Nitro-phenyl)-1-phenyl-propenone;trans-2-Nitrochalcone;(E)-2-Nitrochalcone;2-Nitro-trans-chalcone;MH3MVT883Z;Chalcone, 2-nitro- (8CI);SCHEMBL5474931;SCHEMBL5474937;2-propen-1-one, 3-(2-nitrophenyl)-1-phenyl-, (2E)-;KTXHLWZQKQDFRF-ZHACJKMWSA-N;DTXSID201247532;SMSF0003641;BDBM50572881;MFCD00031069;NSC401727;STK033694;1-(2-Nitrophenyl)-2-benzoyl-ethene;AKOS000483284;NSC-636937;PS-10394;BIM-0009065.P001;LS-188406;A838214;SR-01000196595;SR-01000196595-1;(2E)-3-(2-Nitrophenyl)-1-phenyl-2-propen-1-one #

Chemical Property of 2-Nitrochalcone

Chemical Property:

• Vapor Pressure: 1.7E-07mmHg at 25°C
• Melting Point: 124-128oC
• Boiling Point: 427°Cat760mmHg
• Flash Point: 205.5°C
• PSA: 62.89000
• Density: 1.255g/cm³
• LogP: 4.01410
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 253.07389321
• Heavy Atom Count: 19
• Complexity: 353

Purity/Quality:

97% ^*data from raw suppliers

2-Nitrochalcone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)C=CC2=CC=CC=C2[N+](=O)[O-]
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)/C=C/C2=CC=CC=C2[N+](=O)[O-]
• General Description: 2-Nitrochalcone is a versatile chemical intermediate used in redox-neutral, atom-economical synthesis of sultams when reacted with elemental sulfur under basic conditions, as well as in the chemoselective preparation of quinoline N-oxides via reductive cyclization. Its reactivity allows for environmentally friendly and efficient transformations, making it valuable in medicinal chemistry and heterocyclic synthesis.

Technology Process of 2-Nitrochalcone

There total 19 articles about 2-Nitrochalcone 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: 91.0%

phenylacetylene (536-74-3) + 2-nitro-benzaldehyde (552-89-6) → (E)-3-(2-nitrophenyl)-1-phenylprop-2-en-1-one (7473-93-0,53744-31-3)

Guidance literature:

With phosphonic Acid; In water; at 110 ℃; for 24h; Schlenk technique; Green chemistry;

DOI:10.1055/s-0035-1560832

Reference yield: 90.0%

acetophenone (98-86-2) + 2-nitro-benzaldehyde (552-89-6) → (E)-3-(2-nitrophenyl)-1-phenylprop-2-en-1-one (7473-93-0,53744-31-3)

Guidance literature:

acetophenone; 2-nitro-benzaldehyde; With sodium hydroxide; In ethanol; at 25 ℃; for 8h;

With sulfuric acid; In ethanol; at 80 ℃; for 2h;

DOI:10.1002/anie.201600257

Reference yield: 88.0%

[(2S,3R)-3-(2-Nitro-phenyl)-aziridin-2-yl]-phenyl-methanone (101854-90-4) → (E)-3-(2-nitrophenyl)-1-phenylprop-2-en-1-one (7473-93-0,53744-31-3)

Guidance literature:

With N-Bromosuccinimide; ammonium cerium (IV) nitrate; In water; acetonitrile; at 20 ℃; for 1.5h;

DOI:10.3184/174751914X14176157994656

upstream raw materials:

2-Nitrochalkondibromid

ortho-nitrobenzoic acid

1-phenyl-propan-1-one

(Benzoylmethylene)triphenylphosphorane

Downstream raw materials:

2-Phenylquinoline

2-Nitrochalkondibromid

1,2,3,7-Tetrahydro-8-(2-imidazolin-2-yl)-7-(2-nitrophenyl)-5-phenylimidazo<1,2-a>pyridin-hydrochlorid

benzil

Refernces

Redox-Neutral Access to Sultams from 2-Nitrochalcones and Sulfur with Complete Atom Economy

10.1021/acs.orglett.7b01766

The research focuses on the development of a novel, catalyst-free, redox-neutral, and atom-economical method for synthesizing sultams from 2-nitrochalcones and elemental sulfur. The experiments involve heating 2-nitrochalcones with sulfur in the presence of a base such as 3-picoline or N-methylmorpholine, leading to the formation of sultams with complete atom economy. The reaction conditions were optimized through a series of tests, varying the base, temperature, and amount of sulfur. The scope of the reaction was explored with various chalcones bearing different substituents on the benzoyl and nitrobenzene rings. The connectivity of the synthesized sultams was confirmed by X-ray diffraction studies and NMR spectroscopy. The study also investigated the reaction mechanism and found that the choice of basic additive was crucial for the success of the reaction. The research demonstrates a versatile and environmentally friendly approach to synthesizing sultams, which are important scaffolds in medicinal chemistry.

Chemoselective synthesis of quinoline N-oxides from 3-(2-nitrophenyl)-3- hydroxypropanones

10.1002/jhet.485

The study presents a chemoselective method for the synthesis of quinoline N-oxides from 3-(2-nitrophenyl)-3-hydroxypropanones using Zn/NH4Cl as the reducing agent, achieving high yields (80–90%). The process involves the reduction of the nitro group to a hydroxylamine, which then intramolecularly condenses and dehydrates to form the quinoline N-oxide. The researchers also explored the use of Sn/NH4Cl for the reductive cyclization of 2-nitrochalcones, yielding quinoline N-oxides in good yields. This method offers a more efficient and direct route for the synthesis of quinoline N-oxides compared to previous methods, which often required harsher conditions or multiple steps. The study includes detailed experimental procedures, reaction conditions, and product characterizations, highlighting the versatility and scope of this approach for the synthesis of various quinoline N-oxide derivatives.