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Nifurzide

Nifurzide structure

CAS No:
39978-42-2
Formula:
C12H8N4O6S
Chemical Name:
Nifurzide
Synonyms:
2-Thiophenecarboxylic acid,5-nitro-,2-[3-(5-nitro-2-furanyl)-2-propen-1-ylidene]hydrazide;2-Thiophenecarboxylic acid,5-nitro-,[3-(5-nitro-2-furanyl)-2-propenylidene]hydrazide;N1-(5-Nitro-2-thenoyl)-N2-(5-nitro-2-furylacrylidene)hydrazine;N1-(5′-Nitro-2′-thenoyl)-N2-(5′′-nitro-2′′-furylacrylidene)hydrazine;Nifurzide;Ricridene
Categories:
Organic Chemistry > Nitro Compounds

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Nifurzide Basic Attributes

Molecular Weight：

336.28

Exact Mass：

336.28

EC Number：

254-728-0

ATC Code：

A - Alimentary tract and metabolism

Characteristics

PSA：

175 Å²

Density：

1.62±0.1 g/cm3

Melting Point：

235.5 °C

Toxicity：

LD50 orally in mice: 3200 mg/kg (Szarvasi, Fontaine, 1972)

PKA：

10.31±0.46

Drug Information

MeSH Entry Terms：

5-nitro-2-thiophenecarboxylic acid-(3-(5-nitro-2-furanyl)-2-propenylidene)hydrazide

Nifurzide Use and Manufacturing

(a) Ethyl-5-nitro-2-thiophene carboxylate: 17.4 g (mol/10 = 17.31 g) of 5-nitrothiophene carboxylic acid are dissolved in 85 ml of absolute ethanol. A stream of gaseous hydrochloric acid is caused to enter the boiling solution to the point of saturation, and for 5 hours. Evaporation to dryness takes place and then the solid residue is washed with a sodium bicarbonate solution. It is suction-filtered and washed with water. After drying, there are obtained 17.7 g of a yellow product with a melting point of 63°C to 65°C and the yield is 88% (theoretical yield = 88%). The N'-(5'-nitro-2'-thenoyl)hydrazide is prepared by reacting hydrazine with ethyl 5-nitro-2-thiophene carboxylate. (b) 6.3 g (mol/30 = 6.5 g) of N1-[5'-nitro-2'-thenoyl]hydrazide are dissolved in 100 ml of dry tetrahydrofuran. 5.6 g (mol/30 = 5.55 g) of 5-nitro-2-furyl acrolein in 56 ml of tetrahydrofuran are added. Heating under reflux takes place for 1 hour and, 25 minutes after starting the heating, the crystallization commences; the crystals are suction-filtered, washed with ether and dried. There are obtained 7.9 g (yield 70%-theoretical yield = 11.2 g) of a yellow solid of melting point 235°C to 236°C. Recrystallization (tepid dimethylformamide + ether) leaves the melting point unchanged.

Computed Properties

Molecular Weight:336.28
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:4
Exact Mass:336.01645516
Monoisotopic Mass:336.01645516
Topological Polar Surface Area:175
Heavy Atom Count:23
Complexity:529
Undefined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 39978-42-2

Grade: Industrial Grade

Content: 99%

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