Name: Furazolidone
SKU: 67-45-8

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Basic Information

Molecular Structure:
CAS No.:	67-45-8
Name:	Furazolidone
Article Data:	33

Formula:	C₈H₇N₃O₅
Molecular Weight:	225.161
Synonyms:	Nitrofurazolidone;Giarlam;Furazolidon;Furazon;Furall;Roptazol;Coryzium;3-[(5-Nitrofurylidene)amino]-2-oxazolidone;3-[(5-Nitrofurfurylidene)amino]-2-oxazolidinone;Furoxane;Furaxone;2-Oxazolidinone, 3-[ (5-nitrofurfurylidene)amino]-;Furoxal;2-Oxazolidinone,3-[[(5-nitro-2-furanyl)methylene] amino]-;Neftin;Nitrofuroxon;Furoxon;Nicolen;2-Oxazolidinone, 3-[[ (5-nitro-2-furanyl)methylene]amino]-;Puradin;Medaron;2-Oxazolidinone, 3-[(5-nitrofurfurylidine)amino]-;2-Furanmethanimine, 5-nitro-N-(2-oxo-3-oxazolidinyl)-;Furazol;Furazolidine;N-(5-Nitro-2-furfurylidene)-3-amino-2-oxazolidone;Diafuron;Furozolidine;Prestwick_1067;3-[(5-nitro-2-furyl)methylideneamino]oxazolidin-2-one;3-[[(5-Nitro-2-furanyl)methylene]amino]-2-oxazolidinone;Trichofuron;Optazol;3-(5-Nitrofurfuralamino)-2-oxazolidone;Furoxone (TN);Furazolidone (USP);Furazolidone;NG-180;
EINECS:	200-653-3
Density:	1.6 g/cm³
Melting Point:	254-256°C (dec.)
Boiling Point:	342.6 °C at 760 mmHg
Flash Point:	161 °C
Solubility:	极微溶于氯仿、水、乙醇和四氯化碳，1L水中溶40mg该品。稍溶于二甲基甲酰胺。
Appearance:	solid
Hazard Symbols:	Xn
Risk Codes:	62-40
Safety:	36-22
PSA:	100.86000
LogP:	1.43500

Synthetic route

: 80-65-9
3-amino-2-oxazolidinone

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

: 67-45-8
furazolidone

Conditions

Conditions	Yield
With aqueous acid

: 75-44-5
phosgene

: 28127-20-0
2-(2-(propan-2-ylidene)hydrazinyl)ethanol

: 67-45-8
furazolidone

Conditions

Conditions	Yield
With acetone Behandeln des Reaktionsprodukts in H2O mit 5-Nitro-furfural in Isopropylalkohol;

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

: 109-84-2
2-hydroxyethylhydrazine

: 67-45-8
furazolidone

Conditions

Conditions	Yield
Reaktion ueber mehrere Stufen;

: 109-84-2
2-hydroxyethylhydrazine

: 92-55-7
5-nitro-2-furfuraldehyde diacetate

: 67-45-8
furazolidone

Conditions

Conditions	Yield
With sulfuric acid; isopropyl alcohol

: 5407-76-1
(2-imino-oxazolidin-3-yl)-(5-nitro-[2]furfuryliden)-amine

: 67-45-8
furazolidone

Conditions

Conditions	Yield
With acetic acid; sodium nitrite
With sulfuric acid; water

: 6270-33-3
3-furfurylideneamino-oxazolidin-2-one

: 67-45-8
furazolidone

Conditions

Conditions	Yield
With sulfuric acid; nitric acid

: 109-84-2
2-hydroxyethylhydrazine

: 105-58-8
Diethyl carbonate

: 67-45-8
furazolidone

Conditions

Conditions	Yield
With methanol; sodium methylate anschliessend Behandeln mit 5-Nitro-furfural in wss.-aethanol HCl;

: 3-{[1-(5-Nitro-furan-2-yl)-meth-(E)-ylidene]-amino}-oxazolidin-2-one

: 67-45-8
furazolidone

Conditions

Conditions	Yield
In water; N,N-dimethyl-formamide Rate constant; effect of water content in DMF;

: 405-22-1
5-nitro-furfural-[2-(2-hydroxy-ethyl)-semicarbazone]

: 67-45-8
furazolidone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2; benzene 2: H2O; aqueous H2SO4 View Scheme

: 67-45-8
furazolidone

: 13641-84-4
N-(5-amino-2-furfurylidene)-3-amino-2-oxazolidone

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol

Raw Materials

6270-33-3

5407-76-1

405-22-1

28127-20-0

80-65-9

109-84-2

698-63-5

92-55-7

Downstream Products

13641-84-4

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Chemistry

Molecular Structure of 3-(5'-Nitrofurfuralamino)-2-oxazolidone (CAS NO.67-45-8):

IUPAC Name: 3-[(E)-(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one
Empirical Formula: C₉H₈N₂O₅
Molecular Weight: 224.1702
H bond acceptors: 7
H bond donors: 0
Freely Rotating Bonds: 3
Polar Surface Area: 88.5 Å²
Index of Refraction: 1.718
Molar Refractivity: 55.23 cm³
Molar Volume: 140 cm³
Surface Tension: 85.7 dyne/cm
Density: 1.6 g/cm³
Flash Point: 161 °C
Enthalpy of Vaporization: 58.63 kJ/mol
Boiling Point: 342.6 °C at 760 mmHg
Vapour Pressure: 7.47E-05 mmHg at 25°C
EINECS: 200-653-3
Melting pointt: 254-256°C (dec.)
Storage temp: 0-6°C
Merck: 13,4321
Stability: Stable. Combustible. Incompatible with strong oxidizing agents
Product Categories: Active Pharmaceutical Ingredients
InChI
InChI=1/C8H7N3O5/c12-8-10(3-4-15-8)9-5-6-1-2-7(16-6)11(13)14/h1-2,5H,3-4H2/b9-5+
Smiles
C1COC(N1\N=C\c1ccc(o1)[N+]([O-])=O)=O

Toxicity Data With Reference

1.	pic-esc 2 mg/L	MUREAV Mutation Research. 156 (1985),69.
2.	cyt-hmn:lym 2 mg/L/72H	MUREAV Mutation Research. 59 (1979),139.
3.	orl-man TDLo:11 mg/kg:PUL,BLD	ARDSBL American Review of Respiratory Disease. 105 (1972),823.
4.	orl-rat LD50:2336 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 18 (1971),185.
5.	orl-mus LD50:1782 mg/kg	TRSTAZ Transactions of the Royal Society of Tropical Medicine and Hygiene. 74 (1980),43.
6.	ipr-mus LD50:300 mg/kg	PMDCAY Progress in Medical Chemistry. 5 (1967),320.
7.	orl-ckn LDLo:150 mg/kg CLDND*

Consensus Reports

IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(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 . 31 ,1983,p. 141.(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 EPA TSCA Inventory. EPA Genetic Toxicology Program.

Safety Profile

Poison by ingestion and intraperitoneal routes. Human systemic effects by ingestion: dyspnea, respiratory depression, and eosinophilia. Experimental reproductive effects. Human mutation data reported. Questionable carcinogen. When heated to decomposition it emits toxic fumes of NO_x.
Hazard Codes: Harmful Xn
Risk Statements: 62-40
R62:Risk of impaired fertility.
R40:Limited evidence of a carcinogenic effect.
Safety Statements: 36-22
S36:Wear suitable protective clothing.
S22:Do not breathe dust.
WGK Germany: 3

Specification

3-(5'-Nitrofurfuralamino)-2-oxazolidone , with CAS number of 67-45-8, can be called N-(5-Nitro-2-furfurylidene)-3-amino-2-oxazolidone ; N-(5-Nitro-2-furfurylidene)-3-aminooxazolidine-2-one ; Nicolen ; Nifurazolidonum ; Optazol ; Furox Aerosol Powder (Veterinary) ; 5-Nitro-N-(2-oxo-3-oxazolidinyl)-2-furanmethanimine ; 3-(((5-Nitro-2-furanyl)methylene)amino)-2-oxazolidinone ; 2-Oxazolidinone, 3-(((5-nitro-2-furanyl)methylene)amino)- ; 2-Oxazolidinone, 3-((5-nitrofurfurylidine)amino)- ; 2-Furanmethanimine, 5-nitro-N-(2-oxo-3-oxazolidinyl)- . 3-(5'-Nitrofurfuralamino)-2-oxazolidone (CAS NO.67-45-8) is a fungicide with wide antimicrobial spectrum, be used as anti-infection drugs, used in the treatment of bacterial dysentery, enteritis, also used for treatment of vaginal infection, in recent years, also used for Typhoid, and the effect is good.

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Chemistry

Toxicity Data With Reference

Consensus Reports

Safety Profile

Specification