D194255

1,3-Dinitrobenzene

97% anhydrous basis

• Synonym(s): 1,3-Dinitrobenzene, DNB, Meta-dinitrobenzene, m-Dinitrobenzene
• Linear Formula: C₆H₄(NO₂)₂
• CAS Number: 99-65-0
• Molecular Weight: 168.11
• Beilstein/REAXYS Number: 1105654
• EC Number: 202-776-8
• MDL number: MFCD00007222
• UNSPSC Code: 12352100
• PubChem Substance ID: 24893577
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 97% anhydrous basis
• form: solid
• impurities: ≤10.0% H₂O
• bp: 297 °C (lit.)
• mp: 84-86 °C (lit.)
• density: 1.368 g/mL at 25 °C (lit.)
• SMILES string: [O-][N+](=O)c1cccc(c1)[N+]([O-])=O
• InChI: 1S/C6H4N2O4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H
• InChI key: WDCYWAQPCXBPJA-UHFFFAOYSA-N

Description

General description

1,3-Dinitrobenzene can undergo reductive degradation by alkaline ascorbic acid to produce 1,3-phenylenediamine.

Application

1,3-Dinitrobenzene can be used as a reactant to synthesize:      

• 2′,6′- dinitrobiphenyl-4-ol and 1-nitrodibenzofuran via copper-catalyzed regioselective cross-coupling reaction with 4-iodophenol and 2-iodophenol respectively.      
• 1H-indazole derivatives by reacting with various N-tosylhydrazones in the presence of a base catalyst.      
• 3-(1H-Tetrazol-1-yl)benzenamine by reacting with triethyl orthoformate and NaN₃ in the presence of a three-functional redox catalytic system.

Safety Information

• pictograms: GHS06,GHS08,GHS09
• signalword: Danger
• hcodes: H300 + H310 + H330,H373,H410
• pcodes: P262 - P264 - P273 - P280 - P302 + P352 + P310 - P304 + P340 + P310
• Hazard Classifications: Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 3
• flash_point_f: 302.0 °F - closed cup
• flash_point_c: 150 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges