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Basic Information

Molecular Structure:
CAS No.:	67-20-9
Name:	Nitrofurantoin
Article Data:	30

Formula:	C₈H₆N₄O₅
Molecular Weight:	238.159
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)
Solubility:	<0.01 g/100 mL at 19 °C in water
Appearance:	lemon yellow crystalline powder
Hazard Symbols:	Xn
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With mineral acid

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

: 67-20-9
Nitrofurantoin

Conditions

Conditions	Yield
With mineral acid

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

: 67-20-9
Nitrofurantoin

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

Raw Materials

6301-02-6

92-55-7

63981-22-6

698-63-5

Downstream Products

6301-02-6

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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.