1,2-Dinitrobenzene

Base Information

• Chemical Name: 1,2-Dinitrobenzene
• CAS No.: 528-29-0
• Molecular Formula: C6H4N2O4
• Molecular Weight: 168.109
• Hs Code.: 29042000
• European Community (EC) Number: 208-431-8
• ICSC Number: 0460
• NSC Number: 60682
• UN Number: 3443,1597
• UNII: 35XUO924Y0
• DSSTox Substance ID: DTXSID4024066
• Nikkaji Number: J1.209B
• Wikipedia: 1,2-Dinitrobenzene
• Wikidata: Q2238767
• ChEMBL ID: CHEMBL168075
• Mol file: 528-29-0.mol

Synonyms:1,2-dinitrobenzene;o-dinitrobenzene;ortho-dinitrobenzene

Chemical Property of 1,2-Dinitrobenzene

Chemical Property:

• Appearance/Colour: light yellow-brown powder
• Melting Point: 116 °C
• Refractive Index: 1.5650
• Boiling Point: 319.9 °C at 760 mmHg
• Flash Point: 169.2 °C
• PSA: 91.64000
• Density: 1.486 g/cm³
• LogP: 2.54940
• Solubility.: chloroform: soluble5%, clear, yellow-green
• Water Solubility.: 150 mg/L (20 ºC)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 168.01710661
• Heavy Atom Count: 12
• Complexity: 173

Purity/Quality:

99% ^*data from raw suppliers

1,2-Dinitrobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,N
• Hazard Codes: T+,N
• Statements: 26/27/28-33-50/53
• Safety Statements: 28-36/37-45-60-61-28A

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitros, Aromatic
• Canonical SMILES: C1=CC=C(C(=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 liver. This may result in liver impairment. The substance may have effects on the blood. This may result in anaemia.
• Uses: 1,2-Dinitrobenzene was used as internal standard for analysis of the explosives, TNT, RDX, and tetryl in sea water by vapor phase chromatography with the nickel-63 electron capture detector.

Technology Process of 1,2-Dinitrobenzene

There total 69 articles about 1,2-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: 88.0%

2-nitro-aniline (88-74-4) → 1,2-Dinitrobenzene (528-29-0)

Guidance literature:

With sulfuric acid; acetic acid; tetra-n-propylammonium bromate; for 1.25h; Heating;

DOI:10.1081/SCC-120039488

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%

1,2-diamino-benzene (95-54-5) → 1,2-Dinitrobenzene (528-29-0)

Guidance literature:

With water; fluorine; In chloroform; acetonitrile; at -15 ℃; for 0.0333333h;

DOI:10.1039/c39910000567

upstream raw materials:

o-nitroacetanilide

2,3-dinitroaniline

3,4-dinitroaniline

triphenylbismuthane

Downstream raw materials:

N,N-dimethyl-2-nitro-benzenamine

2-nitro-N-phenylaniline

2-Nitroanisole

N,O-bis-(1-cyano-1-methyl-ethyl)-N-(2-nitro-phenyl)-hydroxylamine

Refernces

• 1、 Ichikawa. "-". . p. 253,257. Retrieved 1937.
• 2、 Wu, Jian-Wei,Zhang, Pu,Guo, Zhi-Xin. "Nitration of deactivated aromatic compounds via mechanochemical reaction". supporting information. . Retrieved 2021/05/05.
• 3、 Van Loo, Bert,Berry, Ryan,Boonyuen, Usa,Mohamed, Mark F.,Golicnik, Marko,Hengge, AlVan C.,Hollfelder, Florian. "Transition-State Interactions in a Promiscuous Enzyme: Sulfate and Phosphate Monoester Hydrolysis by Pseudomonas aeruginosa Arylsulfatase". . p. 1363 - 1378. Retrieved 2019/03/11.