Nitrofurazone

Base Information

• Chemical Name: Nitrofurazone
• CAS No.: 59-87-0
• Deprecated CAS: 60051-85-6,8027-71-2
• Molecular Formula: C6H6N4O4
• Molecular Weight: 198.138
• Hs Code.: 29321900
• European Community (EC) Number: 200-443-1
• NSC Number: 757244,2100,1602
• UNII: X8XI70B5Z6
• Wikipedia: Nitrofurazone
• Wikidata: Q103965033
• NCI Thesaurus Code: C73150
• Metabolomics Workbench ID: 42715
• ChEMBL ID: CHEMBL869
• Mol file: 59-87-0.mol

Synonyms:Furacilin;Furacillin;Furacin;Nitrofural;Nitrofurazone;Nitrofurazone, Calcium (2:1) Salt

Chemical Property of Nitrofurazone

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 242-244 °C(lit.)
• Refractive Index: 1.674
• Boiling Point: 236-240oC
• PKA: pKa 9.28± 0.03( EtOH,t =35±0.1,I=0.00) (Uncertain)
• Flash Point: 2 °C
• PSA: 126.44000
• Density: 1.7 g/cm³
• LogP: 1.80440
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Very slightly soluble in water, slightly soluble in ethanol (96 per cent).
• Water Solubility.: <0.1 g/100 mL at 19℃
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 198.03890469
• Heavy Atom Count: 14
• Complexity: 261

Purity/Quality:

99% ^*data from raw suppliers

Nitrofurazone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,F
• Statements: 22-36-20/21/22-11
• Safety Statements: 36-36/37-26-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Animal Feed Additives
• Canonical SMILES: C1=C(OC(=C1)[N+](=O)[O-])C=NNC(=O)N
• Isomeric SMILES: C1=C(OC(=C1)[N+](=O)[O-])/C=N/NC(=O)N
• Recent EU Clinical Trials: Clinical Trial to determine efficacy and safety of healing with platelet-rich
• Description: Nitrofurazone is an antibacterial agent used in animal feed. Occupational dermatitis was reported in cattle breeders and farmers.
• Uses: Anti-infective (topical). Antimicrobial.Environmental contaminants; Food contaminants; Heat processing contaminants Anti-infective (topical). Antimicrobial. Nitrofurazone is a topical anti-infective and bactericide for most pathogens commonly causing surface infections; in the adjunctive therapy of patients with second and third degree bums when bacterial resistance to other agents is areal or potential problem; in skin grafting where bacterial contamination may cause graft rejection and/or donor-site infection; antibacterial agent for the treatment or prevention of infections in a variety of conditions involving skin, eyes, ears, nose and genito-urinary tract; used on pyodermas, ulcers, and wounds; affects some protozoa and is an effective prophylaxis against nosocomial infections; antiseptic lubricant for trans urethral resection; anti-microbial in veterinary medicine.
• Indications: Nitrofurazone (Furacin), a synthetic nitrofuran derivative with a broad antibacterial spectrum. Although its exact mechanism of action is unknown, it is thought to inhibit bacterial enzymes involved in carbohydrate metabolism. It is not effective against fungal or viral organisms. It is used as adjunctive therapy in patients with second- and third-degree burns when bacterial resistance to other antiinfective agents is a potential problem. It is not effective in the treatment ofminor burns or superficial bacterial infections involving wounds, cutaneous ulcers, or various pyodermas. It is rarely used by dermatologists as it carries a high risk of acquired contact sensitivity.
• Therapeutic Function: Topical antiinfective
• Clinical Use: 5-Nitro-2-furaldehyde semicarbazone (Furacin) occurs asa lemon-yellow crystalline solid that is sparingly solublein water and practically insoluble in organic solvents.Nitrofurazone is chemically stable, but moderately lightsensitive.It is used topically in the treatment of burns, especiallywhen bacterial resistance to other agents may be a concern.It may also be used to prevent bacterial infection associatedwith skin grafts. Nitrofurazone has a broad spectrumof activity against Gram-positive and Gram-negative bacteria,but it is not active against fungi. It is bactericidalagainst most bacteria commonly causing surface infections,including S. aureus, Streptococcus spp., E. coli,Clostridium perfringens, Enterobacter (Aerobacter) aerogenes,and Proteus spp.; however, P. aeruginosa strainsare resistant.Nitrofurazone is marketed in solutions, ointments, andsuppositories in a usual concentration of 0.2%.

Technology Process of Nitrofurazone

There total 17 articles about Nitrofurazone 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-nitrofurfural nitrosemicarbazone → nitrofurazone (59-87-0)

Guidance literature:

With ammonia; In water; Reflux;

DOI:10.1007/s11172-016-1336-9

Reference yield: 97.0%

5-nitrofurane-2-carboxaldehyde (698-63-5) + hydrazine carboxamide (4426-72-6,51433-48-8,57-56-7) → nitrofurazone (59-87-0)

Guidance literature:

hydrazine carboxamide; With acetic acid; In water; for 0.0833333h; Sonication;

5-nitrofurane-2-carboxaldehyde; In dimethyl sulfoxide; at 20 ℃; for 0.5h; Sonication;

DOI:10.1016/j.taap.2020.115104

Reference yield: 91.0%

5-nitrofurane-2-carboxaldehyde (698-63-5) + hydrazine carboxamide (4426-72-6,51433-48-8,57-56-7) → nitrofurazone (59-87-0)

Guidance literature:

With hydrogenchloride; at 30 ℃; for 2h; Temperature;

upstream raw materials:

butan-2-one semicarbazone

5-nitro-2-furfuraldehyde diacetate

semicarbazide hydrochloride

hydrazine carboxamide

Downstream raw materials:

5-nitro-2-furaldehyde azine

syn isomer of nitrofurazone

semicarbazide hydrochloride

Hydroxymethylnitrofurazone

Refernces

• 1、 Gavars, R.,Stradins, J.,Baumane, L.,Baider, L.. "ESR SPECTRA OF ELECTROCHEMICALLY GENERATED ANION RADICALS OF THE NITROFURAN SERIES". . p. 183 - 198. Retrieved 1983.
• 2、 Raffauf,Austin. "-". . p. 756. Retrieved 1950.
• 3、 Fesenko, Anastasia A.,Yankov, Alexander N.,Shutalev, Anatoly D.. "A general and convenient synthesis of 4-(tosylmethyl)semicarbazones and their use in amidoalkylation of hydrogen, heteroatom, and carbon nucleophiles". . . Retrieved 2019/10/14.
• 4、 -. "Method for synthesizing furacilin under catalysis of supported catalyst". Paragraph 0006; 0017; 0021; 0023; 0027; 0028; 0032. . Retrieved 2018/06/26.