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D194255

Sigma-Aldrich

1,3-Dinitrobenzene

97% anhydrous basis

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Linear Formula:
C6H4(NO2)2
CAS Number:
99-65-0
Molecular Weight:
168.11
Beilstein:
1105654
EC Number:
202-776-8
MDL number:
MFCD00007222
PubChem Substance ID:
24893577

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

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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.

Signal Word

Danger

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 Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

302.0 °F - closed cup

Flash Point(C)

150 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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1, 3-Dinitrobenzene reductive degradation by alkaline ascorbic acid--Reaction mechanisms, degradation pathways and reagent optimization
Ciou C,et al.
Chemosphere, 166, 482-488 (2017)
Copper-Mediated Vicarious Substitution of 1, 3-Dinitrobenzene with lodophenols or lodomethyl Phenyl Sulfoxide/Sulfone
Haglund O, et al.
Synthesis, 1990(10), 942-944 (1990)
Zhenxing Liu et al.
Chemical communications (Cambridge, England), 50(39), 5061-5063 (2014-04-10)
A new method for the synthesis of 1H-indazoles from readily available N-tosylhydrazones and nitroaromatic compounds has been developed. This transformation occurs under transition-metal-free conditions and shows a wide substrate scope. The method has been successfully applied to the formal synthesis
Oxidation/MCR domino protocol for direct transformation of methyl benzene, alcohol, and nitro compounds to the corresponding tetrazole using a three-functional redox catalytic system bearing TEMPO/Co (III)-porphyrin/Ni (II) complex
Mahmoudi B, et al.
Molecular Catalysis, 499, 111311-111311 (2021)
Chenyu Lin et al.
BMC chemistry, 14(1), 66-66 (2020-12-10)
For analysis of weak π-π complexes proton-nuclear magnetic resonance (proton-NMR) simultaneously provides information of stacking configurations and association constants [Formula: see text] However, an apparent issue for this approach is inconsistent/impossible constant estimation which often leads to unreasonable interpretation for
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