Product Name

  • Name

    Furacilin

  • EINECS 200-443-1
  • CAS No. 59-87-0
  • Article Data18
  • CAS DataBase
  • Density 1.7 g/cm3
  • Solubility <0.1 g/100 mL at 19 °C in water
  • Melting Point 242-244 °C(lit.)
  • Formula C6H6N4O4
  • Boiling Point 236-240oC
  • Molecular Weight 198.138
  • Flash Point 2 °C
  • Transport Information
  • Appearance white to light yellow crystal powder
  • Safety 36
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 59-87-0 (Furacilin)
  • Hazard Symbols HarmfulXn
  • 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;
  • PSA 126.44000
  • LogP 1.80440

Synthetic route

5-nitrofurane-2-carboxaldehyde
698-63-5

5-nitrofurane-2-carboxaldehyde

hydrazine carboxamide
4426-72-6, 51433-48-8

hydrazine carboxamide

nitrofurazone
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;
5-nitrofurane-2-carboxaldehyde
698-63-5

5-nitrofurane-2-carboxaldehyde

semicarbazide hydrochloride
563-41-7

semicarbazide hydrochloride

nitrofurazone
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
butan-2-one semicarbazone
624-46-4

butan-2-one semicarbazone

nitrofurazone
59-87-0

nitrofurazone

Conditions
ConditionsYield
With sulfuric acid 5-nitro-furfural semicarbazone of mp: 240 degree;
5-nitro-2-furfuraldehyde diacetate
92-55-7

5-nitro-2-furfuraldehyde diacetate

semicarbazide hydrochloride
563-41-7

semicarbazide hydrochloride

nitrofurazone
59-87-0

nitrofurazone

Conditions
ConditionsYield
With mineral acid 5-nitro-furfural semicarbazone of mp: 240 degree;
5-nitro-2-furfuraldehyde diacetate
92-55-7

5-nitro-2-furfuraldehyde diacetate

hydrazine carboxamide
4426-72-6, 51433-48-8

hydrazine carboxamide

nitrofurazone
59-87-0

nitrofurazone

Conditions
ConditionsYield
With mineral acid 5-nitro-furfural semicarbazone of mp: 240 degree;
5-nitro-2-furfuraldehyde diacetate
92-55-7

5-nitro-2-furfuraldehyde diacetate

acetone semicarbazone
110-20-3

acetone semicarbazone

nitrofurazone
59-87-0

nitrofurazone

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

benzaldehyde semicarbazone

nitrofurazone
59-87-0

nitrofurazone

Conditions
ConditionsYield
With sulfuric acid 5-nitro-furfural semicarbazone of mp: 240 degree;
C6H6N4O4(1-)

C6H6N4O4(1-)

nitrofurazone
59-87-0

nitrofurazone

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide Rate constant; effect of water content in DMF;
5-nitrofurane-2-carboxaldehyde
698-63-5

5-nitrofurane-2-carboxaldehyde

aqueous semicarbazide hydrochloride

aqueous semicarbazide hydrochloride

nitrofurazone
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;
1-Bromopentane
110-53-2

1-Bromopentane

nitrofurazone
59-87-0

nitrofurazone

C16H26N4O4

C16H26N4O4

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide at 60℃; for 2h;99%
1-bromo-butane
109-65-9

1-bromo-butane

nitrofurazone
59-87-0

nitrofurazone

C14H22N4O4

C14H22N4O4

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide at 60℃; for 2h;99%
p-toluene sulfinic acid
536-57-2

p-toluene sulfinic acid

butyraldehyde
123-72-8

butyraldehyde

nitrofurazone
59-87-0

nitrofurazone

(E)-1-[(5-nitro-2-furyl)methylene]-4-(1-tosylbut-1-yl)semicarbazide

(E)-1-[(5-nitro-2-furyl)methylene]-4-(1-tosylbut-1-yl)semicarbazide

Conditions
ConditionsYield
Stage #1: p-toluene sulfinic acid; butyraldehyde In formic acid; water at 20℃; for 0.25h;
Stage #2: nitrofurazone In formic acid; water at 20℃; for 24h;
92%
p-toluene sulfinic acid
536-57-2

p-toluene sulfinic acid

propionaldehyde
123-38-6

propionaldehyde

nitrofurazone
59-87-0

nitrofurazone

(E)-1-[(5-nitro-2-furyl)methylene]-4-(1-tosylprop-1-yl)semicarbazide

(E)-1-[(5-nitro-2-furyl)methylene]-4-(1-tosylprop-1-yl)semicarbazide

Conditions
ConditionsYield
Stage #1: p-toluene sulfinic acid; propionaldehyde In formic acid; water at 20℃; for 0.25h;
Stage #2: nitrofurazone In formic acid; water at 20℃; for 24h;
91%
p-toluene sulfinic acid
536-57-2

p-toluene sulfinic acid

isobutyraldehyde
78-84-2

isobutyraldehyde

nitrofurazone
59-87-0

nitrofurazone

(E)-4-[(2-methyl-1-tosyl)prop-1-yl]-1-[(5-nitro-2-furyl)methylene]semicarbazide

(E)-4-[(2-methyl-1-tosyl)prop-1-yl]-1-[(5-nitro-2-furyl)methylene]semicarbazide

Conditions
ConditionsYield
Stage #1: p-toluene sulfinic acid; isobutyraldehyde In formic acid; water at 20℃; for 0.25h;
Stage #2: nitrofurazone In formic acid; water at 20℃; for 24h;
89%
5-nitrofurane-2-carboxaldehyde
698-63-5

5-nitrofurane-2-carboxaldehyde

p-toluene sulfinic acid
536-57-2

p-toluene sulfinic acid

nitrofurazone
59-87-0

nitrofurazone

(E)-1-[(5-nitro-2-furyl)methylene]-4-[(5-nitro-2-furyl)(tosyl)methyl]semicarbazide

(E)-1-[(5-nitro-2-furyl)methylene]-4-[(5-nitro-2-furyl)(tosyl)methyl]semicarbazide

Conditions
ConditionsYield
Stage #1: 5-nitrofurane-2-carboxaldehyde; p-toluene sulfinic acid In formic acid; water at 20℃; for 0.25h;
Stage #2: nitrofurazone In formic acid; water at 20℃; for 24h; Enzymatic reaction;
83%
1-Bromopentane
110-53-2

1-Bromopentane

nitrofurazone
59-87-0

nitrofurazone

C11H16N4O4

C11H16N4O4

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 36h;75%
1-bromo-butane
109-65-9

1-bromo-butane

nitrofurazone
59-87-0

nitrofurazone

5-nitro-furfural-(2-butyl semicarbazone)

5-nitro-furfural-(2-butyl semicarbazone)

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 36h;75%
formaldehyd
50-00-0

formaldehyd

nitrofurazone
59-87-0

nitrofurazone

C7H8N4O5

C7H8N4O5

Conditions
ConditionsYield
With potassium carbonate In water at 20℃; for 49h;56%
nitrofurazone
59-87-0

nitrofurazone

5-imino-4,5-dihydro-furfural semicarbazone

5-imino-4,5-dihydro-furfural semicarbazone

Conditions
ConditionsYield
With water; nickel Hydrogenation;
With aerobacter aerogenes Reduktion;
With palladium on activated charcoal; ethanol Hydrogenation;
nitrofurazone
59-87-0

nitrofurazone

4-oxo-5-semicarbazono-valeronitrile
87015-72-3

4-oxo-5-semicarbazono-valeronitrile

Conditions
ConditionsYield
With water; nickel Hydrogenation;
nitrofurazone
59-87-0

nitrofurazone

A

5-nitro-2-furaldehyde azine
112537-96-9

5-nitro-2-furaldehyde azine

B

syn isomer of nitrofurazone
112574-40-0

syn isomer of nitrofurazone

Conditions
ConditionsYield
In water for 0.0833333h; Product distribution; Irradiation; further nitrofuran derivatives, various solvents, temperatures, time;
water
7732-18-5

water

nitrofurazone
59-87-0

nitrofurazone

Raney nickel

Raney nickel

4-oxo-5-semicarbazono-valeronitrile
87015-72-3

4-oxo-5-semicarbazono-valeronitrile

Conditions
ConditionsYield
Einstellung der Reaktionsloesung auf pH 8,5-9,2.Hydrogenation; 5-nitro-furfural semicarbazone of mp: 232 degree;
ethanol
64-17-5

ethanol

nitrofurazone
59-87-0

nitrofurazone

palladium

palladium

5-amino-furfural semicarbazone

5-amino-furfural semicarbazone

Conditions
ConditionsYield
Hydrogenation; 5-nitro-furfural semicarbazone of mp: 232 degree;
nitrofurazone
59-87-0

nitrofurazone

4,5-disemicarbazono-valeronitrile
98335-88-7

4,5-disemicarbazono-valeronitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Raney nickel; water / Hydrogenation
View Scheme
nitrofurazone
59-87-0

nitrofurazone

(E)-4-[(5-nitro-2-furyl)methyl]-1-[(5-nitro-2-furyl)methylene]semicarbazide

(E)-4-[(5-nitro-2-furyl)methyl]-1-[(5-nitro-2-furyl)methylene]semicarbazide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: water; formic acid / 0.25 h / 20 °C
1.2: 24 h / 20 °C / Enzymatic reaction
2.1: sodium tetrahydroborate / ethanol / 1.5 h / 0 - 20 °C
View Scheme
nitrofurazone
59-87-0

nitrofurazone

(E)-1-[(5-nitro-2-furyl)methylene]-4-propylsemicarbazide

(E)-1-[(5-nitro-2-furyl)methylene]-4-propylsemicarbazide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: water; formic acid / 0.25 h / 20 °C
1.2: 24 h / 20 °C
2.1: sodium tetrahydroborate / ethanol / 1.5 h / 20 °C
View Scheme
nitrofurazone
59-87-0

nitrofurazone

(E)-4-butyl-1-[(5-nitro-2-furyl)methylene]semicarbazide

(E)-4-butyl-1-[(5-nitro-2-furyl)methylene]semicarbazide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: water; formic acid / 0.25 h / 20 °C
1.2: 24 h / 20 °C
2.1: sodium tetrahydroborate / ethanol / 1.5 h / 20 °C
View Scheme
nitrofurazone
59-87-0

nitrofurazone

(E)-4-isobutyl-1-[(5-nitro-2-furyl)methylene]semicarbazide

(E)-4-isobutyl-1-[(5-nitro-2-furyl)methylene]semicarbazide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: water; formic acid / 0.25 h / 20 °C
1.2: 24 h / 20 °C
2.1: sodium tetrahydroborate / ethanol / 1.5 h / 20 °C
View Scheme

Furacilin Chemical Properties

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

Furacilin Production

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

Furacilin 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.

Furacilin 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.

Furacilin 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.

Furacilin 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.

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