1,3-Dinitrobenzene

Base Information

• Chemical Name: 1,3-Dinitrobenzene
• CAS No.: 99-65-0
• Molecular Formula: C6H4N2O4
• Molecular Weight: 168.109
• Hs Code.: 29042090
• European Community (EC) Number: 202-776-8
• ICSC Number: 0691
• NSC Number: 7189
• UN Number: 1597,3443
• UNII: DK8B627BU0
• DSSTox Substance ID: DTXSID9024065
• Nikkaji Number: J1.177K,J2.476.350A
• Wikipedia: 1,3-Dinitrobenzene
• Wikidata: Q2653558
• Metabolomics Workbench ID: 57728
• ChEMBL ID: CHEMBL114070
• Mol file: 99-65-0.mol

Synonyms:1,3-dinitrobenzene;3-dinitrobenzene;m-dinitrobenzene;meta-dinitrobenzene

Chemical Property of 1,3-Dinitrobenzene

Chemical Property:

• Appearance/Colour: orange to yellow crystalline powder
• Vapor Pressure: 0.00188mmHg at 25°C
• Melting Point: 86 °C
• Refractive Index: 1.612
• Boiling Point: 301.5 °C at 760 mmHg
• Flash Point: 136.9 °C
• PSA: 91.64000
• Density: 1.486 g/cm³
• LogP: 2.54940
• Storage Temp.: 2-8°C
• Water Solubility.: 500 mg/L (20 ºC)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 168.01710661
• Heavy Atom Count: 12
• Complexity: 175
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

1,3-Dinitrobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,N
• Hazard Codes: T+,N,T,F,Xn
• Statements: 26/27/28-33-50/53-40-36/37/38-23/24/25-11-52/53-36-20/21/22
• Safety Statements: 28-36/37-45-60-61-28A-27-16-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitros, Aromatic
• Canonical SMILES: C1=CC(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-]
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and respiratory tract. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: The substance may have effects on the blood. This may result in anaemia. The substance may have effects on the liver. This may result in liver impairment. The substance may have effects on the nervous system. Animal tests show that this substance possibly causes toxicity to human reproduction or development. May cause impaired vision.
• Description: 1,3-Dinitrobenzene (1,3-DNB) is an impurity present in the manufacture of 2,4,6-trinitrotoluene. Workers in munitions plants are at risk of exposure. While it does not bioaccumulate, it persists in the environments (air, water, and soil) with slow rates of degradation. Metabolism in animals (rabbits) results in reduction of the nitro functionalities to amine functionalities to produce 2,4-diaminophenol, m-nitroaniline, m-phenylenediamine, and 2-amino-4-nitrophenol. Human exposure is generally dermal contact or inhalation of vapor.
• Uses: 1,3-Dinitrobenzene (1,3-DNB) is an impurity present in the manufacture of 2,4,6-trinitrotoluene. Dinitrobenzene (as a mixture of 1,2-dinitro- 1,3-dinitro- and 1,4-dinitro-isomers) is used in the manufacture of dyes and explosives, and in organic syntheses.

Technology Process of 1,3-Dinitrobenzene

There total 153 articles about 1,3-Dinitrobenzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → meta-dinitrobenzene (99-65-0) + para-dinitrobenzene (100-25-4)

Guidance literature:

With Perfluorooctanesulfonic acid; nitric acid; ytterbium(III) perfluorooctanesulfonate; In hexane; at 60 ℃; for 16h;

DOI:10.1080/00397910600773700

Reference yield: 86.0%

nitrobenzene (98-95-3,26969-40-4) → meta-dinitrobenzene (99-65-0) + para-dinitrobenzene (100-25-4) + 1,2-Dinitrobenzene (528-29-0)

Guidance literature:

With Iron(III) nitrate nonahydrate; phosphorus pentoxide; In neat (no solvent); at 20 ℃; for 6h; Overall yield = 98 percent; Milling; Green chemistry;

DOI:10.1016/j.tetlet.2021.153087

Reference yield: 85.0%

C8H9N5O4 (401631-88-7) → meta-dinitrobenzene (99-65-0) + 2,4-dinitrobromobenzene (584-48-5)

Guidance literature:

With tetrafluoroboric acid diethyl ether; tetrabutylammomium bromide; In acetonitrile; at 60 ℃; for 1h;

DOI:10.1055/s-2001-18072

upstream raw materials:

benzenesulfonic acid-[N'-(2,4-dinitro-phenyl)-hydrazide]

2,6-dinitroaniline

1-iodyl-2,4-dinitro-benzene

triphenylbismuthane

Downstream raw materials:

furfural

benzophenone

(E/Z)-3,7-dimethyl-2,6-octadienal

isobutene

Refernces

• 1、 Moneo, Alvaro,Telo, Joao P.. "Electron transfer within 1,3-dinitrobenzene radical anions: Electron hopping or superexchange?". . p. 1139 - 1143. Retrieved 2012.
• 2、 Daher, Samer S.,Lee, Miseon,Jin, Xiao,Teijaro, Christiana N.,Wheeler, Steven E.,Jacobson, Marlene A.,Buttaro, Bettina,Andrade, Rodrigo B.. "Synthesis, Biological Evaluation, and Computational Analysis of Biaryl Side-Chain Analogs of Solithromycin". supporting information. p. 3368 - 3373. Retrieved 2021/09/06.
• 3、 Fauziev, Ruslan V.,Kharchenko, Alexandr K.,Kuchurov, Ilya V.,Zharkov, Mikhail N.,Zlotin, Sergei G.. "Nitration of aromatics with dinitrogen pentoxide in a liquefied 1,1,1,2-tetrafluoroethane medium". . p. 25841 - 25847. Retrieved 2021/08/09.