5-NITRO-2-FUROYL CHLORIDE

Base Information

• Chemical Name: 5-NITRO-2-FUROYL CHLORIDE
• CAS No.: 25084-14-4
• Molecular Formula: C5H2 Cl N O4
• Molecular Weight: 175.528
• Hs Code.: 2932190090
• European Community (EC) Number: 246-607-6
• NSC Number: 74620
• DSSTox Substance ID: DTXSID30179778
• Nikkaji Number: J236.048I
• Wikidata: Q83050298
• ChEMBL ID: CHEMBL449237
• Mol file: 25084-14-4.mol

Synonyms:2-Furoylchloride, 5-nitro- (6CI,7CI,8CI); 2-(Chlorocarbonyl)-5-nitrofuran;5-Nitro-2-furancarbonyl chloride; 5-Nitro-2-furoyl chloride; 5-Nitrofuroylchloride; NSC 74620

Chemical Property of 5-NITRO-2-FUROYL CHLORIDE

Chemical Property:

• Vapor Pressure: 0.00598mmHg at 25°C
• Melting Point: 38-40oC
• Boiling Point: 272.7°Cat760mmHg
• Flash Point: 118.7°C
• PSA: 76.03000
• Density: 1.588g/cm³
• LogP: 2.09000
• Sensitive.: Moisture Sensitive
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 174.9672352
• Heavy Atom Count: 11
• Complexity: 189

Purity/Quality:

99% ^*data from raw suppliers

5-Nitro-2-furoyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(OC(=C1)[N+](=O)[O-])C(=O)Cl
• Description: 5-Nitrofuroyl chloride is a furan chain bound to an acyl and a nitro group. Nitrofuran derivatives have been used as antibiotic and antimicrobial drugs but the acyl group bound to furan (furoyl chloride) is an intermediate for the synthesis of pharmaceuticals (e.g. antibiotics). 5-Nitrofuroyl chloride has been used as a reagent for the synthesis of some compounds with antibacterial properties and other chemicals.
• Uses: 5-Nitrofuroyl chloride has been used in the synthesis of certain ureides of furanmonocarboxylic acid and in the synthesis of two salts of the mesoionic compound with an influence on the effectiveness of norfloxacin, tetracycline, and erythromycin. There is a study on the antibacterial effects of some 5-nirtofuroyl derivatives but not on 5-nitrofuroyl chloride. There are no reports on its commercial use. 5-Nitro-2-furoyl Chloride is used as reactant in the synthesis of several therapeutic agents.

Technology Process of 5-NITRO-2-FUROYL CHLORIDE

There total 8 articles about 5-NITRO-2-FUROYL CHLORIDE 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: 100.0%

5-nitro-2-furoic acid (645-12-5) → 5-nitrofuran-2-carboxylic chloride (25084-14-4)

Guidance literature:

With oxalyl dichloride; In dichloromethane; at 0 - 20 ℃; for 3h;

Reference yield:

indole (120-72-9) + oxalyl dichloride (79-37-8) + 5-nitro-2-furoic acid (645-12-5) → 5-nitrofuran-2-carboxylic chloride (25084-14-4) + 3-(5-nitro-2-furoyl)indole (139156-17-5)

Guidance literature:

aluminium trichloride; In dichloromethane;

Reference yield:

5-nitro-2-furoic acid (645-12-5) + Chloro-oxo-acetic acid (4732-69-8) → 5-nitrofuran-2-carboxylic chloride (25084-14-4)

Guidance literature:

In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; N,N-dimethyl-formamide;

upstream raw materials:

5-nitro-2-furoic acid

Chloro-oxo-acetic acid

thionyl chloride

indole

Downstream raw materials:

5-nitro-furan-2-carboxylic acid 4-(4-decyl-phenyl)-thiazol-2-ylamide

[2-(5-Nitro-furan-2-carbonyloxy)-benzyl]-triphenyl-phosphonium; bromide

[5-Methoxy-2-(5-nitro-furan-2-carbonyloxy)-benzyl]-triphenyl-phosphonium; bromide

2-[6-Methoxy-3-(5-nitro-furan-2-carbonyl)-3H-pyrimidin-(4Z)-ylidene]-1-phenyl-ethanone; hydrochloride

Refernces

• 1、 De Almeida, Mauro V.,Le Hyaric, Mireille,Siqueira, Leonardo J. A.,Pinto, Luciana D.,Valle, Marcelo S.,Alves, Wendel A.. "Synthesis of furan derivatives condensed with carbohydrates". . p. 728 - 735. Retrieved 2001.
• 2、 Foscolos, Angeliki-Sofia,Papanastasiou, Ioannis,Tsotinis, Andrew,Taylor, Martin C.,Kelly, John M.. "Synthesis and Evaluation of Nifurtimox–Adamantane Adducts with Trypanocidal Activity". supporting information. p. 1227 - 1231. Retrieved 2019/07/09.