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Basic Information
CAS No.: 59-87-0
Name: Furacilin
Molecular Structure:
Molecular Structure of 59-87-0 (Furacilin)
Formula: C6H6N4O4
Molecular Weight: 198.138
Synonyms: 2-Furaldehyde,5-nitro-, semicarbazone (6CI,7CI,8CI);Semioxamazide, 1-(5-nitrofurfurylidene)-(5CI);(5-Nitro-2-furfurylidenamino)urea;1-(5-Nitro-2-furfurylidene)semicarbazide;2-Furancarboxaldehyde, 5-nitro-,semicarbazone;5-Nitro-2-furaldehyde semicarbazone;5-Nitro-2-furfuralsemicarbazone;5-Nitro-2-furfuraldehyde semicarbazone;5-Nitrofurazone;5-Nitrofurfural semicarbazone;Aldomycin;Alfucin;Amifur;Babrocid;Chemofuran;Coxistat;Fura-Septin;FuraZin;Furacilinum;Furacin;Furacine;Furacinetten;Furacoccid;Furacycline;Furalcyn;Furaldon;Furaplast;Furaseen;Furaskin;Furaziline;Furazol W;Furesol;Mammex;Mastofuran;Monafuracin;NFS;Nefco;Nfz mix;Nifucin;Nifuzon;Nitrofural;Nitrofuraldehyde semicarbazone;Nitrofuran;Nitrofuran(bactericide);Nitrofurazone;Nitrozone;Otofural;Topifuran;Vabrocid;Veterinarynitrofurazone;
EINECS: 200-443-1
Density: 1.7 g/cm3
Melting Point: 242-244 °C(lit.)
Boiling Point: 236-240oC
Flash Point: 2 °C
Solubility: <0.1 g/100 mL at 19 °C in water
Appearance: white to light yellow crystal powder
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 36
PSA: 126.44000
LogP: 1.80440
Synthetic route
698-63-5

5-nitrofurane-2-carboxaldehyde

4426-72-6, 51433-48-8

hydrazine carboxamide

59-87-0

nitrofurazone

Conditions
ConditionsYield
Stage #1: hydrazine carboxamide With acetic acid In water for 0.0833333h; Sonication;
Stage #2: 5-nitrofurane-2-carboxaldehyde In dimethyl sulfoxide at 20℃; for 0.5h; Sonication;
97%
aniline at 25℃; Rate constant; var. concentrations of aniline and semicarbazine;
698-63-5

5-nitrofurane-2-carboxaldehyde

563-41-7

semicarbazide hydrochloride

59-87-0

nitrofurazone

Conditions
ConditionsYield
Stage #1: semicarbazide hydrochloride With sodium hydride In dimethyl sulfoxide for 5h;
Stage #2: 5-nitrofurane-2-carboxaldehyde In dimethyl sulfoxide at 20℃; for 18h; Further stages.;
55%
With sodium acetate In ethanol; water
624-46-4

butan-2-one semicarbazone

59-87-0

nitrofurazone

Conditions
ConditionsYield
With sulfuric acid 5-nitro-furfural semicarbazone of mp: 240 degree;
92-55-7

5-nitro-2-furfuraldehyde diacetate

563-41-7

semicarbazide hydrochloride

59-87-0

nitrofurazone

Conditions
ConditionsYield
With mineral acid 5-nitro-furfural semicarbazone of mp: 240 degree;
92-55-7

5-nitro-2-furfuraldehyde diacetate

4426-72-6, 51433-48-8

hydrazine carboxamide

59-87-0

nitrofurazone

Conditions
ConditionsYield
With mineral acid 5-nitro-furfural semicarbazone of mp: 240 degree;
92-55-7

5-nitro-2-furfuraldehyde diacetate

110-20-3

acetone semicarbazone

59-87-0

nitrofurazone

Conditions
ConditionsYield
With sulfuric acid 5-nitro-furfural semicarbazone of mp: 240 degree;
1574-10-3

benzaldehyde semicarbazone

59-87-0

nitrofurazone

Conditions
ConditionsYield
With sulfuric acid 5-nitro-furfural semicarbazone of mp: 240 degree;

C6H6N4O4(1-)

59-87-0

nitrofurazone

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide Rate constant; effect of water content in DMF;
698-63-5

5-nitrofurane-2-carboxaldehyde

aqueous semicarbazide hydrochloride

aqueous semicarbazide hydrochloride

59-87-0

nitrofurazone

Conditions
ConditionsYield
With methanol 5-nitro-furfural semicarbazone of mp: 232 degree;
With ethanol 5-nitro-furfural semicarbazone of mp: 232 degree;
110-53-2

1-Bromopentane

59-87-0

nitrofurazone

C16H26N4O4

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide at 60℃; for 2h;99%
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Chemistry

Molecular Structure of Furacilin (CAS NO.59-87-0):

IUPAC Name: [(E)-(5-nitrofuran-2-yl)methylideneamino]urea
Molecular Formula: C6H6N4O4
Formula Weight: 198.14
Melting point: 242-244 °C(lit.)
Flash Point: 2 °C
H bond acceptors: 8
H bond donors: 3
Freely Rotating Bonds: 3
Polar Surface Area: 94.87 Å2
Index of Refraction: 1.674
Molar Refractivity: 43.56 cm3
Molar Volume: 116 cm3
Surface Tension: 81 dyne/cm
Density: 1.7 g/cm3
Storage temp: 2-8°C
Water Solubility: <0.1 g/100 mL at 19 oC
Sensitive: Light Sensitive
EINECS: 200-443-1
Product Categories: Furan&Benzofuran; NA - NIAntibiotics; Alphabetic; Chemical Structure; N; Others

Production

FURFURAL by nitration, esterification, hydrolysis, System 5-nitro - FURFURAL, and with condensation hydrochloride derived amino Nitrofurazone.

Toxicity Data With Reference

1.    

dnd-esc 1 mg/L

    MUREAV    Mutation Research. 107 (1983),1.
2.    

dnd-hmn:oth 250 μmol/L

    CNREA8    Cancer Research. 35 (1975),781.
3.    

orl-rat LD50:590 mg/kg

    JAMAAP    JAMA, Journal of the American Medical Association. 133 (1947),299.
4.    

ipr-rat LDLo:150 mg/kg

    BCPCA6    Biochemical Pharmacology. 13 (1964),285.
5.    

scu-rat LD50:3000 mg/kg

    JAMAAP    JAMA, Journal of the American Medical Association. 133 (1947),299.
6.    

orl-mus LD50:249 mg/kg

    TRSTAZ    Transactions of the Royal Society of Tropical Medicine and Hygiene. 74 (1980),43.
7.    

ipr-mus LD50:96 mg/kg

    JMCMAR    Journal of Medicinal Chemistry. 10 (1967),530.
8.    

scu-mus LD50:753 mg/kg

    JPETAB    Journal of Pharmacology and Experimental Therapeutics. 102 (1951),185.

Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of chemicals to Man . 50 ,1990,p. 195.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of chemicals to Man . 50 ,1990,p. 195.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of chemicals to Man . 7 ,1974,p. 171.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human No Adequate Data IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of chemicals to Man . 7 ,1974,p. 171.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of chemicals to Man . 50 ,1990,p. 195.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in NTP Carcinogenesis Studies (feed); Clear Evidence: rat, mouse NTPTR*    National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-337 ,1988. . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Safety Profile

Hazard Codes: HarmfulXnFlammableF
Risk Statements: 22-36-20/21/22-11 
R22:Harmful if swallowed. 
R36:Irritating to eyes. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R11:Highly flammable.
Safety Statements: 36-36/37-26 
S36:Wear suitable protective clothing. 
S36/37:Wear suitable protective clothing and gloves. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: 3249
WGK Germany: 3
RTECS: LT7700000
F: 8
HazardClass: 6.1(b)
PackingGroup: III
Poison by ingestion and intraperitoneal routes. Moderately toxic by subcutaneous route. Questionable carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. Experimental reproductive effects. A human sensitizer. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Specification

  Furacilin , with CAS number of 59-87-0, can be called Nitrofuraldehyde semicarbazone ; Nitrofuran ; Nitrofurazone ; Nitrofuran(bactericide) ; Veterinarynitrofurazone ; Mammex ; 5-Nitro-2-furfuraldehyde semicarbazone ; 5-Nitro-2-furfuralsemicarbazone ; 5-Nitro-2-furaldehyde semicarbazone ; 2-Furancarboxaldehyde, 5-nitro-,semicarbazone ; 2-Furaldehyde,5-nitro-, semicarbazone (6CI,7CI,8CI) . Furacilin (CAS NO.59-87-0) is used as an antibiotic most commonly in the form of ointments. Its use in medicine has become less frequent as safer and more effective products have become available.