2315-80-2

Basic information

• Product Name: Benzonitrile, 4-hydroxy-3,5-dinitro-
• Synonyms: Benzonitrile, 4-hydroxy-3,5-dinitro-;4-hydroxy-3,5-dinitrobenzonitrile
• CAS NO: 2315-80-2
• Molecular Formula: C₇H₃N₃O₅
• Molecular Weight: 209.11582
• Mol File: 2315-80-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 278.3°Cat760mmHg
• Flash Point: 122.1°C
• Appearance: /
• Density: 1.72g/cm³
• Vapor Pressure: 0.00254mmHg at 25°C
• Refractive Index: 1.662
• CAS DataBase Reference: Benzonitrile, 4-hydroxy-3,5-dinitro-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-hydroxy-3,5-dinitro-(2315-80-2)
• EPA Substance Registry System: Benzonitrile, 4-hydroxy-3,5-dinitro-(2315-80-2)

Safety Data

• Hazardous Substances Data: 2315-80-2(Hazardous Substances Data)

Usage

General Description

Benzonitrile, 4-hydroxy-3,5-dinitro- is a chemical compound and nitrophenol derivative with the molecular formula C7H4N2O5. It is a yellow crystalline solid that is used in the production of dyes and pigments. It is also known as 4-hydroxy-3,5-dinitrobenzonitrile or HDNB. Benzonitrile, 4-hydroxy-3,5-dinitro- is commonly used as a starting material in the synthesis of various organic compounds and is also used as a reagent in chemical reactions. It is important to handle and use this compound with caution, as it can be toxic and may cause irritation to the skin and eyes.

InChI:InChI=1/C7H3N3O5/c8-3-4-1-5(9(12)13)7(11)6(2-4)10(14)15/h1-2,11H

Upstream product

• 767-00-0 4-cyanophenol 
• 19018-96-3 2,6-dinitro-4-cyanoanisole 

Relevant articles and documents

PEG-N2O4: An efficient nitrating agent for the selective mono- and dinitration of phenols under mild conditions

N2O4 was easily impregnated on polyethyleneglycol to give a stable reagent. The polyethyleneglycol-N2O4 (PEG-N2O4) system was used as an effective nitrating agent for the nitration of phenols. Mono- and dinitrophenols can be obtained via direct nitration of phenols in the presence of PEG-N2O4 at room temperature in moderate to high yields. Copyright Taylor & Francis Group, LLC.

Stereoelectronic and Conformational Effects in Meisenheimer Complexes. Intrinsic Reactivities of Spiro vs. 1,1-Dimethoxy and 1-Methoxy-1-phenoxy Complexes

Rate and equilibrium constants of formation of spiro Meisenheimer complexes derived from 1-(2-hydroxyethoxy)-2,6-dinitro-4-X-benzenes in aqueous solution are compared with those for 1,1-dimethoxy Meisenheimer complexes derived from 2,4-dinitro-4-X-anisoles.Hammett ρ values for the equilibrium constants are 8.2 for the dimethoxy and 5.9 for the spiro complexes, while the normalized ρ values for the rate constants of complex formation (cleavage) are 0.44 (-0.56) for the dimethoxy and 0.58 (-0.42) for the spiro complexes.The large difference in the equilibrium ρ values is attributed to a conformation of a dimethoxy complexes in which there is repulsion between the lone pairs on the ketal and the o-nitro group oxygens.A procedure for making the reactions in the two families thermodynamically comparable by correcting the rate and equilibrium constants for the pKa difference in the nucleophile and for intramolecularity of spiro complex formation was applied.The corrected parameters show that the spiro complexes form and decompose much faster than the dimethoxy complexes.This enhanced reactivity, ΔΔG, is attributed to a stereoelectronic effect or p-? overlap between a lone pair orbital of the nonreacting oxygen and the benzene ring, which is only feasible in the transition state of the spiro complex reaction (14) but not in the thransition state of the dimethoxy complex reaction (15).This interpretation is strongly supported by the fact that ΔΔG increases with increasing electron-withdrawing strength of X substituent.The enhanced rate of formation and decomposition of the spiro complex from catehol 2,4,6-trinitrophenyl ether compared to that of the corresponding 1-methoxy-1-phenoxy complex can be explained in a similar way.