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2,4-Dinitrochlorobenzene Basic information
Product Name:2,4-Dinitrochlorobenzene
Synonyms:Chlorodinitrobenzene;2,4-DINITROCHLOROBENZENE;2,4 DINITRO-1-CHLOROBENZENE;1,3-dinitro-4-chlorobenzene;4-Chloro-1,3-dinitrobenzene;6-Chloro-1,3-dinitrobenzene;Benzene,1-chloro-2,4-dinitro-;Dinitrochlorobenzol
Product Categories:Dyestuff Intermediates;Benzene derivates;Intermediates of Dyes and Pigments;blocks;NitroCompounds;Organics
Mol File:97-00-7.mol
2,4-Dinitrochlorobenzene Structure
2,4-Dinitrochlorobenzene Chemical Properties
Melting point 48-50 °C(lit.)
Boiling point 315 °C(lit.)
density 314
vapor density 6.98 (vs air)
vapor pressure 1 hPa (106 °C)
refractive index 1.5857
Fp 367 °F
storage temp. Store below +30°C.
solubility alcohol: very slightly soluble (cold)(lit.)
form Crystalline Mass, Chunks or Crystals and Powder
color Yellow to brown
explosive limit1.9-22%(V)
Water Solubility insoluble
Merck 14,2136
BRN 613161
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, ammonia. Reacts violently with hydrazine hydrate.
LogP2.24 at 23.3℃ and pH3.5-5.5
CAS DataBase Reference97-00-7(CAS DataBase Reference)
NIST Chemistry ReferenceBenzene, 1-chloro-2,4-dinitro-(97-00-7)
EPA Substance Registry System2,4-Dinitrochlorobenzene (97-00-7)
Safety Information
Hazard Codes T,N
Risk Statements 23/24/25-33-50/53-43-41-38
Safety Statements 28-36/37-45-60-61-28A-24
RIDADR UN 3441 6.1/PG 2
WGK Germany 2
RTECS CZ0525000
Autoignition Temperature464 °C
Hazard Note Toxic
HS Code 2904 99 00
HazardClass 6.1
PackingGroup II
Hazardous Substances Data97-00-7(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 640 mg/kg LD50 dermal Rabbit 130 mg/kg
MSDS Information
SigmaAldrich English
ALFA English
2,4-Dinitrochlorobenzene Usage And Synthesis
Chemical Propertiesyellow crystals with an almond odour
Uses1-Chloro-2,4-dinitrobenzene is used as a reagent for the detection and determination of pyridine compounds. It has been used as alkylating agent to evaluate the depletion of intracellular erythrocyte glutathione (GSH). It is an irreversible inhibitor of human thioredoxin reductase.
Uses1-Chloro-2,4-dinitrobenzene is a benzene derivative and is used in biochemical research as a substrate for glutathione S-transferase.
DefinitionChEBI: 2,4-Dinitrochlorobenzene is a C-nitro compound that is chlorobenzene carrying a nitro substituent at each of the 2- and 4-positions. It has a role as an epitope, an allergen and a sensitiser. It is a C-nitro compound and a member of monochlorobenzenes.
General DescriptionPale yellow needles, almond odor.
Reactivity ProfileSelf-reactive, [Halpern, Chem. and Eng. News, 29:2666(1951)]. The mixture of 2,4-Dinitrochlorobenzene with hydrazine hydrate caused a violent reaction.
HazardToxic by ingestion, inhalation, and skin absorption. Combustible. Upper explosive limit 22%. A skin irritant.
Health HazardTOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire HazardCombustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
Contact allergensThis substance is one of the strongest primary skin irritants known, and a universal contact allergen. Occupational dermatitis has been reported, but current use is decreasing or performed with completely closed systems. DNCB is sometimes used for topical treatment of alopecia areata, severe warts, and cutaneous metastasis of malignant melanoma
Safety ProfilePoison by skin contact and intraperitoneal routes. Moderately toxic by ingestion. A severe human skin and eye irritant. Acts as a primary irritant as well as a sensitizer of skin. An allergen. Mutation data reported. Combustible when exposed to heat or flame. A moderate explosion hazard when exposed to flame, sparks, heated to 1 50°, or when shocked in a sealed container. Explosive reaction with ammonia at 17O℃/40 bar. To fight fire, use CO2, dry chemical. Reacts violently with hydrazine sulfate or hydrazine hydrate. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS.
Purification MethodsUsually it is recrystallised from EtOH or MeOH. It has also been crystallised from Et2O, *C6H6, *C6H6/pet ether or isopropyl alcohol. A preliminary purification step is to pass its solution in *benzene through an alumina column. It has also been purified by zone refining. It exists in three forms: one stable and two unstable. The stable form crystallises as yellow needles from Et2O, m 51o, b 315o/760mm with some decomposition, and is soluble in EtOH. A labile form also crystallises from Et2O, m 43o, and is more soluble in organic solvents. The second labile form has m 27o. [Hoffman & Dame, J Am Chem Soc 41 1015 1919, Welsh J Am Chem Soc 63 3276 1941, J Chem Soc 2476 1957, Beilstein 5 IV 744.]
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