1689-89-0

Basic information

• Product Name: Nitroxinil
• Synonyms: NITROXINIL;NITROXYNIL;4-hydroxy-3-iodo-5-nitro-benzonitril;dovenix;4-CYANO-2-IODO-6-NITROPHENOL;4-HYDROXY-3-IODO-5-NITROBENZONITRILE;NITROXINYL;Benzonitrile, 4-hydroxy-3-iodo-5-nitro-
• CAS NO: 1689-89-0
• Molecular Formula: C₇H₃IN₂O₃
• Molecular Weight: 290.01
• EINECS: 216-884-8
• Product Categories: Aromatic Nitriles
• Mol File: 1689-89-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 137-138°
• Boiling Point: 280.1 °C at 760 mmHg
• Flash Point: 123.2 °C
• Appearance: white to yellow powder
• Density: 2.1385 (estimate)
• Vapor Pressure: 0.00227mmHg at 25°C
• Refractive Index: 1.735
• Storage Temp.: 0-6°C
• PKA: 3.00±0.38(Predicted)
• CAS DataBase Reference: Nitroxinil(CAS DataBase Reference)
• NIST Chemistry Reference: Nitroxinil(1689-89-0)
• EPA Substance Registry System: Nitroxinil(1689-89-0)

Safety Data

• Hazard Codes: T
• Statements: 25-36/37/38-43
• Safety Statements: 26-36/37-45
• RIDADR: UN2811 6.1/PG 3
• WGK Germany: 3
• RTECS: DI4600000
• Hazardous Substances Data: 1689-89-0(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

Different sources of media describe the Uses of 1689-89-0 differently. You can refer to the following data:
1. Nitroxinil is an anthelmintic used in the treatment of liver fluke. Nitroxinil is used for the treatment of fascioliasis in cattle and sheep.
2. categorized under the category of Anthelmintic / Anti parasitic ( for veterinary use)

InChI:InChI=1/C7H3IN2O3/c8-5-1-4(3-9)2-6(7(5)11)10(12)13/h1-2,11H

Upstream product

• 2296-23-3 2-iodo-4-cyanophenol 
• 3861-59-4 3-Jod-4-hydroxy-5-nitro-benzalhydroxylamin 
• 3272-08-0 4-hydroxy-3-nitrobenzonitrile 

Downstream Products

• 25801-30-3 3-iodo-4-methoxy-5-nitrobenzonitrile 
• 26034-12-8 benzoate de nitroxinil 
• 87047-19-6 D,L-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]-thiazolium 4-cyano-2-iodo-6-nitrophenoxide 
• 26168-89-8 3-iodo-4-methoxy-5-aminobenzonitrile 
• 10463-17-9 3-iodo-4-hydroxy-5-nitrobenzoic acid 
• 25845-22-1 3-iodo-4-hydroxy-5-nitrobenzamide 
• 25845-15-2 3-iodo-4-hydroxy-5-aminobenzonitrile 
• 1093397-33-1 4-[5-cyano-7-(2-fluorophenyl)-1,3-benzoxazol-2-yl]-N-({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)benzamide 
• 1093397-20-6 lithium 4-(5-cyano-7-methyl-1,3-benzoxazol-2-yl)benzoate 
• 1093397-25-1 4-hydroxy-3-nitro-5-[(1E)-prop-1-en-1-yl]benzonitrile 
• 942216-08-2 4-hydroxy-3-isopropenyl-5-nitrobenzonitrile 
• 1093397-18-2 methyl 4-(5-cyano-7-methyl-1,3-benzoxazol-2-yl)benzoate 
• 942215-54-5 3-amino-4-hydroxy-5-methylbenzonitrile 
• 1292821-26-1 C₂₇H₂₁F₃N₄O₂ 

Relevant articles and documents

3-(Ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium cation: A green alternative to tert-butyl nitrite for synthesis of nitro-group-containing arenes and drugs at room temperature

Due to their remarkable properties, task-specific ionic liquids have turned out to be progressively popular over the last few years in the field of green organic synthesis. Herein, for the first time, we report that a new task-specific nitrite-based ionic liquid such as 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imides (TS-N-IL) derived from biodegradable ethyl nicotinate indeed acted as an efficient and eco-friendly reagent for the synthesis of highly valuable nitroaromatic compounds and drugs including nitroxynil, tolcapone, niclofolan, flutamide, niclosamide and nitrazepam. The bridging of an ionic liquid with nitrite group not only increases the yield and rate of direct C[sbnd]N bond formation reaction but also allows easy product separation and recyclability of a byproduct. Nonvolatile nature, easy synthesis, merely stoichiometric need and mildness are a portion of the extra focal points of TS-N-IL while contrasted with tert-butyl nitrite an outstanding and highly-flammable reagent utilized largely in organic synthesis.

In vitro metabolism of aromatic nitriles

Studies on the metabolic fate of aromatic nitriles, in contrast to their aliphatic counterparts, have been minimal and the subject of controversy. The in vitro metabolic fate of several aromatic nitriles with varying substituents was investigated by using rat liver subcellular fractions, with a particular emphasis on the nitrile moiety. Benzonitriles and 4-cyanophenols underwent oxidative metabolism to produce ring-hydroxylated metabolites. On the other hand, 2-cyanophenol was resistant to metabolism. o-Tolunitrile was metabolized and produced o-cyanobenzyl alcohol and phthalide. Phthalide, however, was chemically derived from o-cyanobenzyl alcohol, the initial metabolite. 4-Nitrobenzonitrile was resistant to oxidation on the ring, but was readily reduced to the corresponding amine metabolite under both aerobic and anaerobic conditions. Nitroxynil (3-iodo-4-hydroxy-5-nitrobenzonitrile) was metabolized to produce 3-iodo-4-hydroxy-5-nitrobenzamide and 3-iodo-4- hydroxy-5-nitrobenzoic acid. The enzyme(s) responsible for this hydrolytic metabolism was primarily localized in the cytosol. Among the nitriles tested, o-tolunitrile and nitroxynil produced metabolites in which the nitrile moiety was modified. Nitroxynil, however, was the only compound that was directly metabolized on the nitrile moiety by the rat liver enzyme(s).