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CAS No.: | 67-20-9 |
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Name: | Nitrofurantoin |
Article Data: | 30 |
Molecular Structure: | |
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 |
Conditions | Yield |
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With zirconium(IV) oxide for 0.25h; | 95% |
Conditions | Yield |
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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% |
3-(5-nitrofurfurylideneamino)hydantoic acid
Nitrofurantoin
Conditions | Yield |
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With mineral acid |
Nitrofurantoin
Conditions | Yield |
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With mineral acid |
Conditions | Yield |
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Multi-step reaction with 2 steps 1: potassium cyanate; water; aqueous sulfuric acid 2: mineral acid View Scheme |
phenyl(2,4,6-trimethoxyphenyl)iodonium 4-methylbenzenesulfonate
Nitrofurantoin
Conditions | Yield |
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With copper nitrate hemi(pentahydrate); triethylamine In toluene at 70℃; for 24h; regioselective reaction; | 78% |
Nitrofurantoin
Conditions | Yield |
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With copper nitrate hemi(pentahydrate); triethylamine In toluene at 70℃; for 24h; regioselective reaction; | 75% |
Conditions | Yield |
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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% |
Conditions | Yield |
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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% |
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. |