1,4-Dinitrobenzene

Base Information

• Chemical Name: 1,4-Dinitrobenzene
• CAS No.: 100-25-4
• Molecular Formula: C6H4 N2 O4
• Molecular Weight: 168.109
• Hs Code.: 29042090
• European Community (EC) Number: 202-833-7
• ICSC Number: 0692
• NSC Number: 3809
• UN Number: 3443,1597
• UNII: 784Q9O56S9
• DSSTox Substance ID: DTXSID0021836
• Nikkaji Number: J1.178I,J2.152.479D
• Wikipedia: 1,4-Dinitrobenzene
• Wikidata: Q2403718
• Metabolomics Workbench ID: 57729
• ChEMBL ID: CHEMBL349400
• Mol file: 100-25-4.mol

Synonyms:1,4-dinitrobenzene;p-dinitrobenzene

Chemical Property of 1,4-Dinitrobenzene

Chemical Property:

• Appearance/Colour: light yellow powder
• Vapor Pressure: 0.00206mmHg at 25°C
• Melting Point: 170-173 °C(lit.)
• Refractive Index: 1.725 (589.3 nm)
• Boiling Point: 183.4 °C34 mm Hg(lit.)
• Flash Point: 154.4°C
• PSA: 91.64000
• Density: 1.486g/cm³
• LogP: 2.54940
• Storage Temp.: 2-8°C
• Solubility.: alcohol: soluble1g in 300ml
• Water Solubility.: Soluble in water. (0.8 g/L) at 20°C.
• 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: 165
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

1,4-Dinitrobenzene >99.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A suspected carcinogen and poison by ingestion. TWA 0.15 ppm (skin). Mixture with nitric acid is a high explosive.
• Hazard Codes: T+,N,T,F
• Statements: 26/27/28-33-34-50/53-52/53-39/23/24/25-23/24/25-11
• Safety Statements: 28-36/37-45-60-61-16

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.
• Physical properties: Clear, colorless to white crystalline solid or monoclinic crystals. Slowly turns yellow on exposure to air.
• Uses: 1,4-Dinitrobenzene is used in a study to evaluate the ionization mechanism and solvent effect by novel atmospheric pressure photoionization mass spectrometry in negative ion mode for analysis of some compounds. 1,4-Dinitrobenzene can be used in synthesis of dyes and dye intermediates. manufacture of dyes, dye intermediates, explosives, plastics.

Technology Process of 1,4-Dinitrobenzene

There total 117 articles about 1,4-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: 98.0%

(4-nitrophenyl)(phenyl)iodonium tetrafluoroborate → p-nitrobenzene iodide (636-98-6) + para-dinitrobenzene (100-25-4) + iodobenzene (591-50-4) + nitrobenzene (98-95-3,26969-40-4)

Guidance literature:

With sodium nitrite; In chloroform; water; at 56 ℃; for 1h;

DOI:10.1007/BF00954097

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: 82.0%

3,3-dimethyldioxirane (74087-85-7) + benzene-1,4-diamine hydrochloride (624-18-0,55972-71-9) → para-dinitrobenzene (100-25-4)

Guidance literature:

In water; acetone; for 23h; Ambient temperature;

DOI:10.1021/jo00285a027

upstream raw materials:

peracetic acid

N-(4-Nitrophenyl)acetamide

p-nitrobenzene iodide

p-dinitrosobenzene

Downstream raw materials:

4-nitro-aniline

bis(4-nitrophenyl)diazene

para-methoxynitrobenzene

4,4'-azoxy anisole

Refernces

• 1、 Westheimer,Kharasch. "-". . p. 1871,1873. Retrieved 1946.
• 2、 Fujitsuka, Mamoru,Sato, Tadatake,Shimidzu, Takeo,Watanabe, Akira,Ito, Osamu. "Photochemical generation of radical cations of dithienothiophenes, condensed thiophene trimers, studied by laser flash photolysis". . p. 1056 - 1061. Retrieved 1997.
• 3、 Nagi, Sh. M.,Zubkov, E. A.,Shubin, V. G.. "NITRATION OF AROMATIC COMPOUNDS CATALYZED BY ZrO2/SO42-". . p. 1500 - 1502. Retrieved 1990.
• 4、 Fujiwara, Kenji,Andoh, Takayuki,Arai, Mitsuru,Tamura, Masamitsu,Yoshida, Tadao. "Solvent Effects in the Nitration of Nitrobenzene". . p. 4973 - 4976. Retrieved 1980.
• 5、 Nelsen, Stephen F.,Konradsson, Asgeir E.,Weaver, Michael N.,Telo, Joao P.. "Intervalence near-IR spectra of delocalized dinitroaromatic radical anions". . p. 12493 - 12501. Retrieved 2003.
• 6、 Telo,Grampp,Shohoji. "Solvent effects on intramolecular electron exchange in the 1,4- dinitrobenzene radical anion". . p. 99 - 104. Retrieved 1999.
• 7、 Starkey. "-". . . Retrieved 1937.
• 8、 Cao, Dezhong,Xiao, Hongdi,Xu, Hangzhou,Cui, Jishi,Gao, Qingxue,Pei, Haiyan. "Enhancing the photocatalytic activity of GaN by electrochemical etching". . p. 881 - 886. Retrieved 2015.
• 9、 Capperucci, Antonella,Dalia, Camilla,Tanini, Damiano. "The polyhedral nature of selenium-catalysed reactions: Se(iv) species instead of Se(vi) species make the difference in the on water selenium-mediated oxidation of arylamines". supporting information. p. 5680 - 5686. Retrieved 2021/08/16.