91997-67-0

Basic information

• Product Name: 3,10-dinitroperylene
• Synonyms: 3,10-Dinitroperylene; Perylene, 3,10-dinitro-
• CAS NO: 91997-67-0
• Molecular Formula: C₂₀H₁₀N₂O₄
• Molecular Weight: 342.3044
• Mol File: 91997-67-0.mol

Chemical Properties

• Boiling Point: 597.1°C at 760 mmHg
• Flash Point: 298°C
• Density: 1.557g/cm³
• Vapor Pressure: 1.37E-13mmHg at 25°C
• Refractive Index: 1.914
• CAS DataBase Reference: 3,10-dinitroperylene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,10-dinitroperylene(91997-67-0)
• EPA Substance Registry System: 3,10-dinitroperylene(91997-67-0)

Safety Data

• Hazardous Substances Data: 91997-67-0(Hazardous Substances Data)

Upstream product

• 198-55-0 PERYLENE 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 
• 56-23-5 tetrachloromethane 
• 7697-37-2 nitric acid 

Relevant articles and documents

Electrophilic substitution of two monohomoperylenes and perylene

Various types of electrophilic substitution of monohomoperylene (1) and its 11,11-difluoro derivative (2) have been studied, viz, bromination, nitration, acylation, formylation and sulfonation.Bromination with N-bromosuccinimide (NBS) of 1 in dichloromethane leads to initial substitution mainly at the α position 2 and 10, i.e., of the annuleno moiety, followed by further substitution of the β positions 4 and 8 of the same moiety, and of the α positions 2' and 10' of the naphthaleno moiety.Reaction of 1 with 5.0 mol-equiv. of NBS yields 2,4,8,10,2'-pentabromo-1 in 46percent yield.Sulfonation of 1 with SO3 in dichloromethane using 1.2 mol-equiv. of dioxane as reactivity moderator leads to the formation of 1-2-sulfonic acid (1-2-S), 1-2,10-S2, and the intermediate ? complex 6.Sulfonation of the 11,11-difluoro derivative 2 leads to the formation of 2-2-S, 2-2,10-S2 and 2-2,10-disulfonic anhydride (7), together with small amounts of 2-2,2'-S2 or/and 2-2,10'-S2.The other types of electrophilic substitution of 1 and 2 studied were found to proceed similarly, in that the initial substitution occurs at the 2-position and the subsequent one at the 10-position, i.e., peri to the primarily introduced substituent.The chemical behaviour (i.e., the substitution pattern and relative reactivity) of the two monohomoperylenes 1 and 2 have been compared with that of 1,6-methanoannulene (3), its 11,11-difluoro derivative (4), and perylene (5).For example, the sulfonation reactivity ratio of the naphthalene to the annuleno moiety is significantly greater for 2 than 1, as predicted on the basis of the higher sulfonation reactivity of 3 compared to 4.

Preparation and characterization of dinitroperylenes.

Dinitroperylenes have been synthesized and purified by HPLC. Based on NMR, MS and UV data, the main isomers were identified as 3,6-,3,7-,3,9- and 3,10-dinitroperylene.