1-chloro-2,4-dinitrobenzene

• ChemBase ID: 78438
• Molecular Formular: C6H3ClN2O4
• Molecular Mass: 202.55202
• Monoisotopic Mass: 201.97813427
• SMILES: Clc1c(cc(cc1)[N+](=O)[O-])[N+](=O)[O-]
• Canonical SMILES: [O-][N+](=O)c1ccc(c(c1)[N+](=O)[O-])Cl
• InChI: InChI=1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H
• InChIKey: VYZAHLCBVHPDDF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-chloro-2,4-dinitrobenzene
• IUPAC Traditional name: Cdnb; dinitrochlorobenzene
• Synonyms: CDNB; 1-Chloro-2,4-dinitrobenzene; Dinitrochlorobenzene; Chlorodinitrobenzene; 2,4-Dinitrophenyl chloride; 2,4-Dinitrochlorobenzene; 1-Chloro-2,4-dinitrobenzene; 2,4-Dinitrochlorobenzene 98%; 1-CHLORO-2,4-DINITROBENZENE PRACTICAL GRADE; 4-Chloro-1,3-Dinitrobenzene; 6-Chloro-1,3-dinitrobenzene; Dinitrochlorobenzol; DNCB; 2,4-Dinitrochlorobenzene; 1-CHLORO-2,4-DINITROBENZENE; 2,4-二硝基氯苯; 1-氯-2,4-二硝基苯

Database IDs

• CAS Number: 97-00-7
• EC Number: 202-551-4
• MDL Number: MFCD00007075
• Beilstein Number: 613161
• Merck Index: 142136
• PubChem SID: 24848362; 24854237; 162043205
• PubChem CID: 6
• Chemspider ID: 5
• Wikipedia Title: 2,4-Dinitrochlorobenzene

CALCULATED PROPERTIES

• Acid pKa: 19.2014
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.457259
• LogD (pH = 7.4): 2.457259
• Log P: 2.457259
• Molar Refractivity: 43.5038 cm^3
• Polarizability: 16.25405 Å^3
• Polar Surface Area: 86.28 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: cast in container
• Melting Point: 48-50 °C(lit.); 48-51 °C; 48-52 °C; 48-52°C; 49.5 °C; 49.5°C; 50-54°C
• Boiling Point: > 300 °C with decomposition; 314-316°C; 315 °C(lit.); 315°C
• Flash Point: 179 °C (method not stated); 186°C(366°F); 194 °C; 194°C; 381.2 °F
• Density: 1.498; 1.52 g/cm^3 at 60 °C; 1.700
• Vapor Pressure: .0001 hPa at 20 °C

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Toxic/Harmful/Corrosive
• RTECS: CZ0525000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 1577; 3441; UN3441
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 2; II
• Australian Hazchem: 2W
• Risk Statements: 23/24/25-33-50/53; R:22-27-43
• Safety Statements: 28-36/37-45-60-61; S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 153
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• Explode Limits: 22 %
• GHS Hazard statements: H301-H311-H315-H318-H331-H373-H410; H301-H311-H331-H373-H400-H410
• GHS Precautionary statements: P260-P301+P310-P361-P302+P352-P405-P501A; P261-P273-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3441 6.1/PG 2

Product Information

• Purity: ≥98.0% (GC); ≥99%; ≥99.0% (GC); 95%; 97%; 98%; 99%
• Grade: PRACTICAL; puriss.; purum
• Linear Formula: ClC6H3(NO2)2

DETAILS

MP Biomedicals - 02150611

Purity: 99%
Reported to be a substrate for glutathione S-transferases^1 and used to form o-DNP-tyrosine derivatives.^2

MP Biomedicals - 05201206

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02150612

Practical Grade
Purity: 95%
Sensitizing agent that induces allergic contact dermatitis.

Sigma Aldrich - 138630

Packaging
2 kg in glass bottle
5, 100, 500 g in glass bottle

Sigma Aldrich - 24440

Other Notes
Activating agent used in the synthesis of glutaconic aldehyde derivatives from pyridine1

Sigma Aldrich - 237329

Packaging
10, 50 g in glass bottle

REFERENCES

• Biochem J. ,189 : 135 (1980).
• Biochem J. , 39 : 507 (1945).
• J. Invest. Dermatol. , 62 : 2 (1974).
• The doubly-activated chloro-substituent is readily displaced by nucleophiles, e.g.:
• Ammonia/ammonium acetate to give 2,4-dinitroaniline: Org. Synth. Coll., 2, 221 (1943); or with ammonia gas in toluene in the presence of TBAB which improves the solubility of ammonia in the organic medium and accelerates the reaction: J. Chem. Soc., Chem. Commun., 1267 (1987). Benzyl mercaptan to give the thioether: Org. Synth. Coll., 5, 474 (1973). Iodide ion to give 2,4-dinitro-1-iodobenzene: Org. Synth. Coll., 5, 478 (1973). Nitrite in toluene (phase-transfer) to give 1,2,4-trinitrobenzene (caution!): J. Org. Chem., 56, 4967 (1991).