616-69-3

Basic information

• Product Name: 3-NIRO-O-XYLENE
• Synonyms: 3-NIRO-O-XYLENE;3,5-Dinitro-o-xylene;4,5-Dimethyl-1,3-dinitrobenzene;1,2-diMethyl-3,5-dinitrobezene
• CAS NO: 616-69-3
• Molecular Formula: C₈H₈N₂O₄
• Molecular Weight: 196.16
• Mol File: 616-69-3.mol

Chemical Properties

• Boiling Point: 334.9 °C at 760 mmHg
• Flash Point: 165.6 °C
• Appearance: /
• Density: 1.346 g/cm³
• Vapor Pressure: 0.000241mmHg at 25°C
• Refractive Index: 1.587
• CAS DataBase Reference: 3-NIRO-O-XYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-NIRO-O-XYLENE(616-69-3)
• EPA Substance Registry System: 3-NIRO-O-XYLENE(616-69-3)

Safety Data

• Hazardous Substances Data: 616-69-3(Hazardous Substances Data)

Usage

Uses

Used in Dye Production:
3-NIRO-O-XYLENE is used as a key intermediate for the production of dyes, contributing to the development of colorants that are essential in various industries.
Used in Polymer Synthesis:
3-NIRO-O-XYLENE is employed as an intermediate in the synthesis of polymers, which are crucial in the manufacturing of plastics, textiles, and other materials.
Used in Resin Production:
3-NIRO-O-XYLENE is used as an intermediate in the production of resins, which are vital components in the formulation of adhesives, coatings, and composite materials.
Used in Pharmaceutical Industry:
3-NIRO-O-XYLENE is used as an intermediate in the synthesis of pharmaceuticals, playing a significant role in the development of new drugs and medications.
Used in Agricultural Chemicals:
3-NIRO-O-XYLENE is utilized as an intermediate in the production of agricultural chemicals, such as pesticides and fertilizers, which are essential for crop protection and yield enhancement.
Used in Organic Chemicals:
3-NIRO-O-XYLENE is used as an intermediate in the synthesis of other organic chemicals, highlighting its importance in the chemical industry.

InChI:InChI=1/C8H8N2O4/c1-5-3-7(9(11)12)4-8(6(5)2)10(13)14/h3-4H,1-2H3

Upstream product

• 99-51-4 4-nitro-o-xylene 
• 860752-01-8 (2-methyl-4,6-dinitro-phenyl)-acetic acid 
• 95-47-6 o-xylene 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 83-41-0 2,3-dimethylnitrobenzene 
• 2198-54-1 N-(3,4-dimethylphenyl)acetamide 
• 99321-70-7 5,6-dimethyl-2,6-dinitrocyclohexa-2,4-dienyl methyl ether 
• 99321-75-2 5,6-dimethyl-2,6-dinitrocyclohexa-2,4-dienyl acetate 
• 861545-90-6 (2-methyl-4,6-dinitro-phenyl)-malonic acid diethyl ester 
• 18905-50-5 2-chloro-1-methyl-3,5-dinitrobenzene 

Downstream Products

• 64823-22-9 3,4-dimethyl-5-nitro-aniline 
• 106837-44-9 2,3-dimethyl-5-nitro-phenylamine 
• 75038-11-8 1,2-dimethyl-3,4,5-trinitro-benzene 
• 102312-36-7 2,3-dimethyl-1,4,5-trinitro-benzene 
• 65151-58-8 3,4-dimethyl-5-nitrophenol 
• 92505-48-1 3-Amino-4,5-dimethylphenol 
• 52911-61-2 3,4-dimethyl-5-nitrobenzonitrile 
• 52911-59-8 2,3-dimethyl-5-nitrobenzonitrile 
• 90922-71-7 methyl 2,3-dimethyl-5-nitrobenzoate 
• 90557-88-3 3,4-Dimethyl-5-nitro-benzamid 
• 90557-86-1 2,3-Dimethyl-5-nitro-benzamid 
• 110969-50-1 acide dimethyl-2,3 nitro-5 benzoique 
• 5628-58-0 methyl 5-hydroxy-2,3-dimethylbenzoate 
• 5628-57-9 5-hydroxy-2,3-dimethyl-benzoic acid 

Relevant articles and documents

Nitration of deactivated aromatic compounds via mechanochemical reaction

A variety of deactivated arenes were nitrated to their corresponding nitro derivatives in excellent yields under high-speed ball milling condition using Fe(NO3)3·9H2O/P2O5 as nitrating reagent. A radical involved mechanism was proposed for this facial, eco-friendly, safe, and effective nitration reaction.

Continuous-Flow Nitration of o-Xylene: Effect of Nitrating Agent and Feasibility of Tubular Reactors for Scale-Up

Continuous-flow nitration of o-xylene has been studied with different nitrating agents over a wide range of conditions for different parameters such as temperature, residence time, and concentrations. A nitrating mixture comprising sulfuric acid and fuming nitric acid was seen to yield higher selectivity for the isomer 1,2-dimethyl-3-nitrobenzene over the isomer 1,2-dimethyl-4-nitrobenzene and also a non-negligible quantity of dinitro derivatives of o-xylene. With only fuming nitric acid as the nitrating agent, the reaction was selective for 1,2-dimethyl-4-nitrobenzene over 1,2-dimethyl-3-nitrobenzene. Impurities mainly come from nitration of mononitro derivatives, and this occurs more from nitration of the 3-nitro isomer because of its higher reactivity with nitric acid. An economic analysis of the continuous-flow reactor for the production of 1,2-dimethyl-4-nitrobenzene at 100 and 500 kg/h in a jacketed tubular reactor showed that numbering-up is a more economical approach for higher production capacity. A combination of large- and small-sized tubes depending upon the relative rates of heat generation during a reaction will achieve more profit and a shorter payback period than having the entire reactor made of a single tube size.

The dinitration of dimethylacetanilides

The orientation of dinitration of the dimethylacetanilides has been examined by 1H NMR methods and a possible enhancement of the hyperconjugative influence of a methyl group has been considered as an additional factor augmenting the effect of the steric i

Ozone-mediated Nitration of Alkylbenzenes and Related Compounds with Nitrogen Dioxide

In the presence of ozone, nitrogen dioxide exhibits a strong nitrating ability for alkylbenzenes at low temperatures, converting them into the corresponding nitro derivatives in high yield.The addition of a protonic acid as catalyst enhances considerably the ability of this nitrating system and leads to a good yield of polynitro compounds.The reaction is clean and proceeds rapidly without any accompanying side-chain substitution or aryl-aryl coupling.It shows no kinetic dependence on the concentration of substrates and, as far as can be judged from relative reactivities and isomer distributions of products, it gives the appearance of being an electrophilic aromatic process.A possible role for nitrogen trioxide has been suggested as the initial electrophilic agent for the nitration of alkylbenzenes.

ipso Nitration. XXVI. Nitration of 1,2-dimethyl-4-nitrobenzene. Formation and reactions of adducts

Nitration of 1,2-dimethyl-4-nitrobenzene in a mixture of acetic anhydride and trifluoroacetic anhydride gives the diastereoisomers of 4,5-dimethyl-2,4-dinitrocyclohexa-2,5-dienyl acetate (50percent), in addition to the 1,2-dimethyldinitrobenzenes.In moderate and more strongly acid conditions the adduct gives 4-nitro-, 3,4-dinitro-, and 3,5-dinitro-o-xylene.In neutral and weakly acid solutions 4-nitro- and 3,5-dinitro-o-xylene are formed by a radical and a sigmatropic pathway.The adduct reacts facilely with nucleophiles by allylic substitution to give a 5,6-dimethyl-6-nitrocyclohexa-2,4-dienyl derivative which, in many instances, undergoes a second allylic substitution to a new 4,5-dimethyl-2,4-dinitrocyclohexa-2,5-dienyl derivative.Depending on the nature of the introduced substituent, these 2,4- and 2,5-dienyl products may eliminate nitrous acid, under the reaction conditions, to give the corresponding aromatic compound.The dienyl acetates undergo acid-catalysed transesterification to the corresponding dienols.