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102369

Sigma-Aldrich

1,4-Dinitrobenzene

98%

Synonym(s):

p-dinitrobenzene, para-Dinitrobenzene

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About This Item

Linear Formula:
C6H4(NO2)2
CAS Number:
100-25-4
Molecular Weight:
168.11
Beilstein:
1105828
EC Number:
202-833-7
MDL number:
MFCD00007314
UNSPSC Code:
12352100
PubChem Substance ID:
24846575
NACRES:
NA.22

Assay

98%

bp

183.4 °C/34 mmHg (lit.)

mp

170-173 °C (lit.)

solubility

alcohol: soluble 1g in 300ml
boiling water: soluble 1g in 555ml
cold water: soluble 1g in 12,500ml
benzene: very slightly soluble
chloroform: very slightly soluble
ethyl acetate: very slightly soluble

density

1.625 g/mL at 25 °C (lit.)

functional group

nitro

SMILES string

[O-][N+](=O)c1ccc(cc1)[N+]([O-])=O

InChI

1S/C6H4N2O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H

InChI key

FYFDQJRXFWGIBS-UHFFFAOYSA-N

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General description

Dinitrobenzene is commonly used in industrial explosives containing ammonium nitrate. 1,4-Dinitrobenzene forms negative molecular ion M-· by electron capture or charge exchange.

Application

1,4-Dinitrobenzene was 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.

Preparation Note

One gram of 1,4-Dinitrobenzene dissolves in 12,500 ml cold water, 555 ml boiling water and 300 ml alcohol.

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tiina J Kauppila et al.
Journal of the American Society for Mass Spectrometry, 15(2), 203-211 (2004-02-10)
The ionization mechanism in the novel atmospheric pressure photoionization mass spectrometry (APPI-MS) in negative ion mode was studied thoroughly by the analysis of seven compounds in 17 solvent systems. The compounds possessed either gas-phase acidity or positive electron affinity, whereas
Polymer sensors for nitroaromatic explosives detection.
Toal SJ and Trogler WC.
Journal of Materials Chemistry, 16(28), 2871-2883 (2006)
Silvia M Barolo et al.
The Journal of organic chemistry, 71(22), 8493-8499 (2006-10-27)
The photostimulated intramolecular ortho-arylation reactions of bromoarenes linked with pendant phenoxy containing N-substituted tetrahydroisoquinolines in liquid ammonia afforded aporphine (54-82% yield) alkaloid derivatives via SRN1 reactions. This strategy was extended for the first time to the synthesis of a homoaporphine
N Kessler et al.
Proteins, 34(3), 383-394 (1999-02-19)
The sequences of the variable regions of three monoclonal antibodies with different specificities to cholesterol monohydrate and 1,4-dinitrobenzene crystals were determined. The structures of their binding sites were then modeled, based on homology to other antibodies of known structure. Two
Akio Kamimura et al.
Molecules (Basel, Switzerland), 17(5), 4782-4790 (2012-04-27)
S(RN)1-type coupling adducts are readily prepared by the reaction between a-sulfonylesters or a-cyanosulfones and gem-dinitro compounds in ionic liquids. The reactions progress smoothly and recovered ionic liquids can be used for several iterations, as long as they are washed with
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