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67-20-9

Basic Information
CAS No.: 67-20-9
Name: Nitrofurantoin
Molecular Structure:
Molecular Structure of 67-20-9 (Nitrofurantoin)
Formula: C8H6N4O5
Molecular Weight: 238.16
Synonyms: Furadonin;Uerineks;Sodium nitrofurantoin;Berkfuran;Macrodantina;1-[[(5-Nitro-2-furanyl)methylene]amino]-2,4-imidazolidinedione;Urantoin;2,4-Imidazolidinedione,1-[[(5-nitro-2- furanyl)methylene]amino]-;1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dione;Urolisa;Furatoin;NSC-2107;Furadantin;N-Toin;1-(5-Nitro-2-furfurylidenamino)hydantoin;54-87-5;5-Nitrofurantoin;Furadonine;2,4-Imidazolidinedione, 1-[[ (5-nitro-2-furanyl)methylene]amino]-;Macrofurin;Trantoin;Urodin;Furina;Hydantoin, 1-(5-nitro-furfurylideneamino)-;Macpac;Hydantoin, 1-((5-nitrofurfurylidene)amino)-;Zoofurin;PiyEloseptyl;Ceduran;Urofuran;Welfurin;N-(5-Nitrofurfurylidene)-1-aminohydantoin;ND-7248;Furadontin;Furadantin Retard;Urolong;Furadantin (TN);Cistofuran;Furadantine mc;Nifurantin;Siraliden;Urofurin;Nitrofuradantin;Alfuran;Furophen T;Parfuran;Macrobid;Ro-Antoin;Nitoin;Benkfuran;2,4-Imidazolidenedione, 1-(((5-nitro-2-furanyl)methylene)amino)-;Chemiofuran;
EINECS: 200-646-5
Density: 1.81 g/cm3
Melting Point: 268 °C
Boiling Point: 380.75°C (rough estimate)
Flash Point:
Solubility: <0.01 g/100 mL at 19 °C in water
Appearance: lemon yellow crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-42/43
Safety: 22-36/37-45
Transport Information: UN 2811
PSA: 120.73000
LogP: 0.86340
Synthetic route
698-63-5

5-nitrofurane-2-carboxaldehyde

2827-56-7

1-aminohydantoin hydrochloride

67-20-9

Nitrofurantoin

Conditions
ConditionsYield
With zirconium(IV) oxide for 0.25h;95%
6301-02-6

1-aminohydantoin

698-63-5

5-nitrofurane-2-carboxaldehyde

67-20-9

Nitrofurantoin

Conditions
ConditionsYield
Stage #1: 1-aminohydantoin With acetic acid In water for 0.0833333h; Sonication;
Stage #2: 5-nitrofurane-2-carboxaldehyde In dimethyl sulfoxide at 20℃; for 0.5h; Sonication;
95%
6301-02-6

1-aminohydantoin

92-55-7

5-nitro-2-furfuraldehyde diacetate

67-20-9

Nitrofurantoin

63981-22-6

3-(5-nitrofurfurylideneamino)hydantoic acid

67-20-9

Nitrofurantoin

Conditions
ConditionsYield
With mineral acid
3-<5-nitro-furfurylidenamino>-hydantoic acid alkyl ester

3-<5-nitro-furfurylidenamino>-hydantoic acid alkyl ester

67-20-9

Nitrofurantoin

Conditions
ConditionsYield
With mineral acid
698-63-5

5-nitrofurane-2-carboxaldehyde

67-20-9

Nitrofurantoin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium cyanate; water; aqueous sulfuric acid
2: mineral acid
View Scheme
936326-60-2

phenyl(2,4,6-trimethoxyphenyl)iodonium 4-methylbenzenesulfonate

67-20-9

Nitrofurantoin

1-(5-nitrofurfurylideneamino)-3-phenylhydantoin

Conditions
ConditionsYield
With copper nitrate hemi(pentahydrate); triethylamine In toluene at 70℃; for 24h; regioselective reaction;78%
67-20-9

Nitrofurantoin

(4-((N-phthalimidyl)benzyl))(2,4,6-trimethoxyphenyl)iodonium tosylate

1-(5-nitrofurfurylideneamino)-3-(4-(phthalimidyl)benzyl)hydantoin

Conditions
ConditionsYield
With copper nitrate hemi(pentahydrate); triethylamine In toluene at 70℃; for 24h; regioselective reaction;75%
74-83-9

methyl bromide

67-20-9

Nitrofurantoin

(E)-3-methyl-1-([(5′-nitrofuran-2′-yl)methylene]amino)imidazolidine-2,4-dione

Conditions
ConditionsYield
Stage #1: Nitrofurantoin With trialkylamine In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: methyl bromide In N,N-dimethyl-formamide at 20℃;
67%
67-20-9

Nitrofurantoin

104-81-4

4-Methylbenzyl bromide

(E)-3-(p-methylbenzyl)-1-([(5′-nitrofuran-2′-yl)methylene]amino)imidazolidine-2,4-dione

Conditions
ConditionsYield
Stage #1: Nitrofurantoin With trialkylamine In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: 4-Methylbenzyl bromide In N,N-dimethyl-formamide at 20℃;
65%
67-20-9

Nitrofurantoin

[4-(methoxycarbonyl)phenyl](2,4,6-trimethoxyphenyl)iodonium tosylate

1-(5-nitrofurfurylideneamino)-3-(4-methoxycarbonyl)phenylhydantoin

Conditions
ConditionsYield
With copper nitrate hemi(pentahydrate); triethylamine In toluene at 70℃; for 24h; regioselective reaction;65%
110-53-2

1-Bromopentane

67-20-9

Nitrofurantoin

(E)-1-([(5′-nitrofuran-2′-yl)methylene]amino)-3-pentylimidazolidine-2,4-dione

Conditions
ConditionsYield
Stage #1: Nitrofurantoin With trialkylamine In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: 1-Bromopentane In N,N-dimethyl-formamide at 20℃;
64%
637-59-2

1-Bromo-3-phenylpropane

67-20-9

Nitrofurantoin

(E)-1-([(5′-nitrofuran-2′-yl)methylene]amino)-3-(3″-phenylpropyl)imidazolidine-2,4-dione

Conditions
ConditionsYield
Stage #1: Nitrofurantoin With trialkylamine In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: 1-Bromo-3-phenylpropane In N,N-dimethyl-formamide at 20℃;
63%
111-25-1

1-bromo-hexane

67-20-9

Nitrofurantoin

(E)-3-hexyl-1-([(5′-nitrofuran-2′-yl)methylene]amino)imidazolidine-2,4-dione

Conditions
ConditionsYield
Stage #1: Nitrofurantoin With trialkylamine In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: 1-bromo-hexane In N,N-dimethyl-formamide at 20℃;
61%
629-04-9

1-Bromoheptane

67-20-9

Nitrofurantoin

(E)-3-heptyl-1-([(5′-nitrofuran-2′-yl)methylene]amino)imidazolidine-2,4-dione

Conditions
ConditionsYield
Stage #1: Nitrofurantoin With trialkylamine In N,N-dimethyl-formamide at 20℃; for 0.25h;
Stage #2: 1-Bromoheptane In N,N-dimethyl-formamide at 20℃;
58%
67-20-9

Nitrofurantoin

88585-78-8

<4S,5R,6S(R)>-3-(hydroxymethyl)-6-<1-<(tert-butyldimethylsilyl)oxy>ethyl>-7-oxo-4-thia-1-azabicyclo<3.2.0>hept-2-enecarboxylic acid 2-allyl ester

103109-62-2

(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(3-{[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amino}-2,5-dioxo-imidazolidin-1-ylmethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Ambient temperature; Yield given;
67-20-9

Nitrofurantoin

sodium salt of 3-(5-nitrofurfurylideneamino)hydantoic acid

Conditions
ConditionsYield
With saccharin sodium salt; sodium citrate; citric acid In water 1.) reflux, 13 h, 2.) room temperature, 24 h;
67-20-9

Nitrofurantoin

63981-22-6

3-(5-nitrofurfurylideneamino)hydantoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium citrate dihydrate, citric acid, sodium saccharin dihydrate / H2O / 1.) reflux, 13 h, 2.) room temperature, 24 h
2: 3 M HCl
View Scheme
67-20-9

Nitrofurantoin

103109-68-8

(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-(3-{[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amino}-2,5-dioxo-imidazolidin-1-ylmethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / Ambient temperature
2: tetrabutylammonium fluoride / acetic acid; tetrahydrofuran
View Scheme
67-20-9

Nitrofurantoin

Sodium; (5R,6S)-6-((R)-1-hydroxy-ethyl)-3-(3-{[1-(5-nitro-furan-2-yl)-meth-(E)-ylidene]-amino}-2,5-dioxo-imidazolidin-1-ylmethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / Ambient temperature
2: tetrabutylammonium fluoride / acetic acid; tetrahydrofuran
3: Pd(PPh3)4, PPh3, sodium 2-ethylhexanoate / CH2Cl2; tetrahydrofuran
View Scheme
127-19-5

N,N-dimethyl acetamide

67-20-9

Nitrofurantoin

nitrofurantoin dimethylacetamide monosolvates

Conditions
ConditionsYield
With 1-carbamimidamido-N-(4-fluorophenyl)methanimidamide hydrochloride at 20℃;
127-19-5

N,N-dimethyl acetamide

67-20-9

Nitrofurantoin

nitrofurantoin dimethylacetamide disolvate

Conditions
ConditionsYield
With N,N'-(2,6-pyridinediyl)bis(acetamide) at 3.84℃;
67-20-9

Nitrofurantoin

5441-02-1

N,N'-(2,6-pyridinediyl)bis(acetamide)

1305253-65-9

nitrofurantoin 2,6-diacetamidopyridine cocrystal

Conditions
ConditionsYield
With N,N-dimethyl acetamide at 49.84℃;
67-20-9

Nitrofurantoin

67-68-5

dimethyl sulfoxide

nitrofurantoin dimethyl sulfoxide monosolvate

Conditions
ConditionsYield
With 1-carbamimidamido-N-(4-fluorophenyl)methanimidamide hydrochloride at 3.84℃;
67-20-9

Nitrofurantoin

67-68-5

dimethyl sulfoxide

nitrofurantoin dimethyl sulfoxide hemisolvate

Conditions
ConditionsYield
With N,N'-(2,6-pyridinediyl)bis(acetamide) at 20℃;
108-99-6

3-Methylpyridine

67-20-9

Nitrofurantoin

1443274-83-6

C8H6N4O5*C6H7N

Conditions
ConditionsYield
With water
67-20-9

Nitrofurantoin

1443274-88-1

C8H6N4O5*C7H10N2

Conditions
ConditionsYield
In acetonitrile
67-20-9

Nitrofurantoin

6301-02-6

1-aminohydantoin

Conditions
ConditionsYield
With cytochrome P450 monooxygenase at 37℃; for 0.5h;
With water Photolysis;
Downstream Products
6301-02-6
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    Introduction Product Name Nitrofurantoin Molecular Formula C8H6N4O5 Molecular Weight 238.157 CAS Registry Number 67-20-9 EINECS 200-646-5 Density 1.81g/cm3 Melting point 268°C Refractive index 1.744 Water solubility <0.01 g/100 mL

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Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 50 ,1990,p. 211; Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 50 ,1990,p. 211; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 50 ,1990,p. 211. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Specification

The IUPAC name of Nitrofurantoin is 1-[(E)-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione. With the CAS registry number 67-20-9, it is also named as 1-((5-Nitrofurfurylidene)amino)hydantoin. The product's categories are Furan & Benzofuran; Peptide Synthesis / Antibiotics. Besides, it is lemon yellow crystalline powder, which should be stored in cool, dark and sealed place at 0-6 °C. It is stable, and incompatible with strong oxidizing agents, strong alkalies, strong acids. In addition, its molecular formula is C8H6N4O5 and molecular weight is 238.16.

The other characteristics of this product can be summarized as: (1)EINECS: 200-646-5; (2)ACD/LogP: -0.03; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): -0.03; (5)ACD/LogD (pH 7.4): -0.21; (6)ACD/BCF (pH 5.5): 1; (7)ACD/BCF (pH 7.4): 1; (8)ACD/KOC (pH 5.5): 22.81; (9)ACD/KOC (pH 7.4): 15.23; (10)#H bond acceptors: 9; (11)#H bond donors: 1; (12)#Freely Rotating Bonds: 3; (13)Polar Surface Area: 111.94 Å2; (14)Index of Refraction: 1.744; (15)Molar Refractivity: 53.13 cm3; (16)Molar Volume: 131 cm3; (17)Polarizability: 21.06×10-24cm3; (18)Surface Tension: 89.5 dyne/cm; (19)Density: 1.81 g/cm3; (20)Melting point: 268 °C; (21)Water solubility: <0.01 g/100 mL at 19 °C.

Preparation and Uses of Nitrofurantoin: frist, you can produce Aminohydantoin by the reaction of Hydrazine hydrate and Urea. And then you can obtain this chemical by condensation of Aminohydantoin and 5-Nitro-2-furaldehyde diacetate. Furthermore, this chemical is an antibiotic which is usually used in treating urinary tract infection. It is often used against E. coli.

When you are using this chemical, please be cautious about it as the following: it is harmful in contact with skin and if swallowed. It also may cause sensitization by inhalation and skin contact. Please do not breathe dust. And you should wear suitable protective clothing and gloves. Moreover, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
(1)SMILES: O=[N+]([O-])c2oc(/C=N/N1C(=O)NC(=O)C1)cc2
(2)InChI: InChI=1/C8H6N4O5/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(15)16/h1-3H,4H2,(H,10,13,14)/b9-3+
(3)InChIKey: NXFQHRVNIOXGAQ-YCRREMRBBU
(4)Std. InChI: InChI=1S/C8H6N4O5/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(15)16/h1-3H,4H2,(H,10,13,14)/b9-3+
(5)Std. InChIKey: NXFQHRVNIOXGAQ-YCRREMRBSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD50 oral 53mg/kg (53mg/kg)   Journal of Nutrition. Vol. 112, Pg. 1741, 1982.
human TDLo oral 80mg/kg (80mg/kg) PERIPHERAL NERVE AND SENSATION: RECORDING FROM PERIPHERAL MOTOR NERVE

BEHAVIORAL: ATAXIA
Archives of Neurology Vol. 18, Pg. 680, 1968.
human TDLo unreported 60mg/kg (60mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION British Medical Journal. Vol. 2, Pg. 1044, 1976.
mammal (species unspecified) LDLo oral 250mg/kg (250mg/kg)   Bollettino Chimico Farmaceutico. Vol. 102, Pg. 505, 1963.
man TDLo oral 29mg/kg/20D-I (29mg/kg) BRAIN AND COVERINGS: INCREASED INTRACRANIAL PRESSURE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE
Drug Intelligence and Clinical Pharmacy. Vol. 22, Pg. 345, 1988.
man TDLo oral 40mg/kg/2W-I (40mg/kg) KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS

KIDNEY, URETER, AND BLADDER: PROTEINURIS

BLOOD: CHANGES IN LEUCOCYTE (WBC) COUNT
Lancet. Vol. 348, Pg. 1177, 1996.
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 oral 360mg/kg (360mg/kg)   Journal of Medicinal Chemistry. Vol. 16, Pg. 312, 1973.
rat LD50 intraperitoneal 112mg/kg (112mg/kg)   Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 303, 1970.
rat LD50 oral 604mg/kg (604mg/kg)   Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 303, 1970.
women TDLo oral 24mg/kg (24mg/kg) BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA American Journal of Clinical Pathology. Vol. 58, Pg. 408, 1972.
women TDLo oral 42mg/kg/6W-I (42mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

LIVER: LIVER FUNCTION TESTS IMPAIRED

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"
Medical Journal of Australia. Vol. 156, Pg. 347, 1992.
women TDLo oral 365mg/kg/1Y-I (365mg/kg) LUNGS, THORAX, OR RESPIRATION: FIBROSIS (INTERSTITIAL)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LIVER: LIVER FUNCTION TESTS IMPAIRED
Postgraduate Medical Journal. Vol. 73, Pg. 519, 1997.