2-Acetyl-5-nitrofuran

Base Information

• Chemical Name: 2-Acetyl-5-nitrofuran
• CAS No.: 5275-69-4
• Molecular Formula: C6H5 N O4
• Molecular Weight: 155.11
• Hs Code.: 2932190090
• NSC Number: 40160,6455
• UNII: CF78LD3XCG
• DSSTox Substance ID: DTXSID10200736
• Nikkaji Number: J49.583B
• Wikidata: Q83073903
• Mol file: 5275-69-4.mol

Synonyms:1-(5-nitrofuran-2-yl)ethanone;2-Acetyl-5-nitrofuran;5275-69-4;Ketone, methyl 5-nitro-2-furyl;Furan, 2-acetyl-5-nitro-;Ethanone, 1-(5-nitro-2-furanyl)-;5-Nitro-2-furyl methyl ketone;KETONE, (5-NITRO-2-FURYL) METHYL;NSC 6455;AI3-17337;5-nitro-2-acetylfuran;NSC 40160;CF78LD3XCG;NSC-6455;NSC-40160;WLN: T5OJ BV1 ENW;UNII-CF78LD3XCG;Acetyl-5-nitrofuran, 2-;SCHEMBL6734715;SCHEMBL14489520;1-(5-Nitro-2-furanyl)ethanone;DTXSID10200736;NSC6455;NSC40160;AKOS000279015;AKOS005166954;AKOS040764864;1-(5-NITRO-2-FURYL)ETHANONE;SB61929;LS-87337

Chemical Property of 2-Acetyl-5-nitrofuran

Chemical Property:

• Vapor Pressure: 0.086mmHg at 25°C
• Melting Point: 78.5 °C
• Refractive Index: 1.5423 (estimate)
• Boiling Point: 225.5°Cat760mmHg
• Flash Point: 90.2°C
• PSA: 76.03000
• Density: 1.341g/cm³
• LogP: 1.91360
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 155.02185764
• Heavy Atom Count: 11
• Complexity: 186

Purity/Quality:

99%, ^*data from raw suppliers

2-ACETYL-5-NITROFURAN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC=C(O1)[N+](=O)[O-]

Technology Process of 2-Acetyl-5-nitrofuran

There total 10 articles about 2-Acetyl-5-nitrofuran 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: 94.0%

1-(5-nitrofuran-2-yl)ethan-1-ol (18753-50-9) → 5-nitro-2-acetylfuran (5275-69-4)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 1h; Inert atmosphere;

DOI:10.1016/j.bmcl.2016.11.093

Reference yield: 68.0%

(5-acetylfuran-2-yl)boronic acid (1107580-77-7) → 5-nitro-2-acetylfuran (5275-69-4)

Guidance literature:

With 1,1,1,3',3',3'-hexafluoro-propanol; 2-nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide; at 60 ℃; for 19h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.0c00671

Reference yield: 26.0%

1-(2-furyl)-1-ethanone (1192-62-7,80145-44-4) → 5-nitro-2-acetylfuran (5275-69-4)

Guidance literature:

1-(2-furyl)-1-ethanone; With nitric acid; acetic anhydride; at 0 - 20 ℃;

With triethylamine; at 20 ℃; for 1h;

DOI:10.1039/b813394h

upstream raw materials:

diazomethane

5-nitrofurane-2-carboxaldehyde

1-(2-furyl)-1-ethanone

acetic anhydride

Downstream raw materials:

(6-Chloro-2-{[1-(5-nitro-furan-2-yl)-eth-(E)-ylidene]-hydrazono}-benzothiazol-3-yl)-acetic acid ethyl ester

(E)-3-(4-Chloro-phenyl)-1-(5-nitro-furan-2-yl)-propenone

(E)-3-(4-Bromo-phenyl)-1-(5-nitro-furan-2-yl)-propenone

1-(5-nitro-furan-2-yl)-5-phenyl-penta-2,4-dien-1-one

Refernces

• 1、 Hayes,O'Keefe. "-". . p. 1897,1900. Retrieved 1954.
• 2、 Budinská, Alena,Katayev, Dmitry,Passera, Alessandro,Zhang, Kun. "N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids". supporting information. . Retrieved 2020/03/30.
• 3、 Aridoss, Gopalakrishnan,Laali, Kenneth K.. "Ethylammonium nitrate (EAN)/Tf2O and EAN/TFAA: Ionic liquid based systems for aromatic nitration". experimental part. p. 8088 - 8094. Retrieved 2011/11/13.