2,3-Epoxy-3-(o-nitrophenyl)propiophenone

Base Information

• Chemical Name: 2,3-Epoxy-3-(o-nitrophenyl)propiophenone
• CAS No.: 7152-68-3
• Molecular Formula: C15H11NO4
• Molecular Weight: 269.257
• NSC Number: 41597,24798
• DSSTox Substance ID: DTXSID70992004
• Nikkaji Number: J51.118H
• Mol file: 7152-68-3.mol

Synonyms:7152-68-3;[3-(2-nitrophenyl)oxiran-2-yl](phenyl)methanone;2,3-Epoxy-3-(o-nitrophenyl)propiophenone;[3-(2-nitrophenyl)oxiran-2-yl]-phenylmethanone;2-Benzoyl-3-(2-nitrophenyl)oxirane;Methanone, [3-(2-nitrophenyl)oxiranyl]phenyl-;Methanone, (3-(2-nitrophenyl)oxiranyl)phenyl-;WLN: T3OTJ BVR& CR BNW;NSC 41597;Propiophenone,3-epoxy-3-(o-nitrophenyl)-;NSC 24798;2-Benzoyl-3-(2-nitrophenyl)-oxirane;Propiophenone, 2,3-epoxy-3-(o-nitrophenyl)-;SCHEMBL3994076;DTXSID70992004;YYDCQFLIOWAXNZ-UHFFFAOYSA-N;NSC24798;NSC41597;MFCD01695208;NSC-24798;NSC-41597;AKOS003368274;LS-08246;[3-(2-nitrophenyl)oxiran-2-yl]phenylmethanone;[3-(2-Nitrophenyl)-2-oxiranyl](phenyl)methanone #

Chemical Property of 2,3-Epoxy-3-(o-nitrophenyl)propiophenone

Chemical Property:

• Vapor Pressure: 1.05E-07mmHg at 25°C
• Boiling Point: 433.2°C at 760 mmHg
• Flash Point: 194.7°C
• PSA: 75.42000
• Density: 1.364g/cm³
• LogP: 3.44080
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 269.06880783
• Heavy Atom Count: 20
• Complexity: 386

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)C2C(O2)C3=CC=CC=C3[N+](=O)[O-]

Technology Process of 2,3-Epoxy-3-(o-nitrophenyl)propiophenone

There total 16 articles about 2,3-Epoxy-3-(o-nitrophenyl)propiophenone 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%

1-chloroacetophenone (532-27-4,108321-66-0,164322-25-2) + 2-nitro-benzaldehyde (552-89-6) → trans-2,3-epoxy-1-(2-nitrophenyl)-3-phenylpropan-1-one (7152-68-3,28812-34-2,28812-35-3,128672-46-8)

Guidance literature:

With potassium fluoride on basic alumina; at 20 ℃;

DOI:10.1080/00397910701316292

Reference yield: 96.0%

acetophenone (98-86-2) + 2-nitro-benzaldehyde (552-89-6) → trans-(2S,3R)-epoxy-3-(2-nitrophenyl)-1-phenyl-1-propan-1-one (7152-68-3,28812-34-2,28812-35-3,128672-46-8)

Guidance literature:

acetophenone; 2-nitro-benzaldehyde; at 60 ℃; for 3h;

With tetrabutylammomium bromide; dihydrogen peroxide; sodium hydroxide; In toluene; at 20 ℃; for 1.5h; enantioselective reaction;

DOI:10.1016/j.jcat.2015.11.020

Reference yield: 79.0%

trans-2,3-epoxy-1-(2-nitrophenyl)-3-phenylpropan-1-one (7152-68-3,28812-34-2,28812-35-3,128672-46-8) → (2RS,3RS)-2,3-epoxy-3-(2-nitro-phenyl)-1-phenyl-propan-1-one (7152-68-3,28812-34-2,28812-35-3,128672-46-8)

Guidance literature:

With sodium methylate; In methanol;

upstream raw materials:

α-bromoacetophenone

2-nitro-benzaldehyde

1-chloroacetophenone

carbon dioxide

Downstream raw materials:

5-(2-nitrophenyl)-1,3-diphenyl-1H-pyrazole

3-hydroxy-2-phenylquinoline

5-(2-nitrophenyl)-3-phenylisoxazole

C₁₅H₁₀⁽²⁾HNO₄

Refernces

• 1、 Gubaidullin, A. T.,Khikmatova, G. Z.,Korshin, D. E.,Krivolapov, D. B.,Mahrous, E. M.,Mamedov, V. A.,Mamedova, V. L.,Sinyashin, O. G.. "Acid catalyzed rearrangements of aryl 3-(2-nitroaryl)oxiran-2-yl ketones". . p. 510 - 516. Retrieved 2020/04/17.
• 2、 Mamedov, Vakhid A.,Mamedova, Vera L.,Syakaev, Victor V.,Korshin, Dmitry E.,Khikmatova, Gul'naz Z.,Mironova, Ekaterina V.,Bazanova, Olga B.,Rizvanov, Il'dar Kh.,Latypov, Shamil K.. "Simple synthesis of 3-hydroxyquinolines via Na2S2O4-mediated reductive cyclization of (2-(2-nitrophenyl)oxiran-1-yl)(aryl)methanones (o-nitrobenzalacetophenone oxides)". . p. 5082 - 5090. Retrieved 2017/07/28.