Names | |
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Preferred IUPAC name 1-Chloro-2,4-dinitrobenzene | |
Other names Dinitrochlorobenzene Chlorodinitrobenzene 2,4-Dinitrochlorobenzene 2,4-Dinitrophenyl chloride 4-Chloro-1,3-dinitrobenzene | |
Identifiers | |
3D model (JSmol) | |
Abbreviations | CDNB; DNCB |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.002.321 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C6H3ClN2O4 | |
Molar mass | 202.55 g·mol−1 |
Appearance | yellow crystals |
Odor | almond-like |
Density | 1.6867 g/cm3 |
Melting point | 54 °C (129 °F; 327 K) |
Boiling point | 315 °C (599 °F; 588 K) |
Insoluble [1] | |
Solubility | soluble in ether, benzene, CS2 |
Refractive index (nD) | 1.5857 (60 °C) |
Hazards | |
NFPA 704 (fire diamond) | |
Explosive limits | 2–22% |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 1.07 g/kg (rat, oral) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
2,4-Dinitrochlorobenzene (DNCB) is an organic compound with the chemical formula (O2N)2C6H3Cl. It is a yellow solid that is soluble in organic solvents. It is an important intermediate for the industrial production of other compounds. [2]
DNCB is produced commercially by the nitration of p-nitrochlorobenzene with a mixture of nitric and sulfuric acids. Other methods afford the compound less efficiently include the chlorination of 1,3-dinitrobenzene, nitration of o-nitrochlorobenzene and the dinitration of chlorobenzene. [3]
By virtue of the two nitro groups, the chloride is susceptible to nucleophilic substitution. In this way, the compound is a precursor to many other compounds. [4] [5] [6]
DNCB is used as a substrate in GST enzyme activity assays. [7] The molecule is conjugated to a single molecule of reduced glutathione which then absorbs at 340 nm. Affinity of CDNB for each class of GST varies and so it is not a good measure of activity for some forms (e.g. GSTT and GSTZ).[ citation needed ]
DNCB can be used to treat warts with an effective cure rate of 80%. [8] DNCB induces an allergic immune response toward the wart-causing virus. [8]
DNCB induces a type IV hypersensitivity reaction in almost all people exposed to it, so it is used medically to assess the T cell activity in patients. This is a useful diagnostic test for immunocompromised patients. It can also be used to treat warts. [9]
DNCB can cause contact dermatitis. [10]
N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It is a tertiary amine, featuring a dimethylamino group attached to a phenyl group. This oily liquid is colourless when pure, but commercial samples are often yellow. It is an important precursor to dyes such as crystal violet.
In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.
In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and nitric acid. The difference between the resulting molecular structures of nitro compounds and nitrates is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, whereas in nitrate esters, the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom.
In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups. The nitro group is one of the most common explosophores used globally. The nitro group is also strongly electron-withdrawing. Because of this property, C−H bonds alpha (adjacent) to the nitro group can be acidic. For similar reasons, the presence of nitro groups in aromatic compounds retards electrophilic aromatic substitution but facilitates nucleophilic aromatic substitution. Nitro groups are rarely found in nature. They are almost invariably produced by nitration reactions starting with nitric acid.
o-Phenylenediamine (OPD) is an organic compound with the formula C6H4(NH2)2. This aromatic diamine is an important precursor to many heterocyclic compounds. OPD is a white compound although samples appear darker owing to oxidation by air. It is isomeric with m-phenylenediamine and p-phenylenediamine.
Diethylamine is an organic compound with the formula (CH3CH2)2NH. It is classified as a secondary amine. It is a flammable, volatile weakly alkaline liquid that is miscible with most solvents. It is a colorless liquid, but commercial samples often appear brown due to impurities. It has a strong ammonia-like odor.
Nitrophenols are compounds of the formula HOC6H5−x(NO2)x. The conjugate bases are called nitrophenolates. Nitrophenols are more acidic than phenol itself.
Allyl bromide (3-bromopropene) is an organic halide. It is an alkylating agent used in synthesis of polymers, pharmaceuticals, perfumes and other organic compounds. Allyl bromide is a colorless liquid, although commercial samples appear yellow or brown. It is an irritant and a potentially dangerous alkylating agent. Allyl bromide is more reactive but more expensive than allyl chloride, and these considerations guide its use.
The reduction of nitro compounds are chemical reactions of wide interest in organic chemistry. The conversion can be effected by many reagents. The nitro group was one of the first functional groups to be reduced. Alkyl and aryl nitro compounds behave differently. Most useful is the reduction of aryl nitro compounds.
The Béchamp reduction is a chemical reaction that converts aromatic nitro compounds to their corresponding anilines using iron as the reductant:
2-Nitroaniline is an organic compound with the formula H2NC6H4NO2. It is a derivative of aniline, carrying a nitro functional group in position 2. It is mainly used as a precursor to o-phenylenediamine.
4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2. A yellow solid, it is one of three isomers of nitroaniline. It is an intermediate in the production of dyes, antioxidants, pharmaceuticals, gasoline, gum inhibitors, poultry medicines, and as a corrosion inhibitor.
1-Fluoro-2,4-dinitrobenzene is a chemical that reacts with the N-terminal amino acid of polypeptides. This can be helpful for sequencing proteins.
4-Nitrochlorobenzene is the organic compound with the formula ClC6H4NO2. It is a pale yellow solid. 4-Nitrochlorobenzene is a common intermediate in the production of a number of industrially useful compounds, including antioxidants commonly found in rubber. Other isomers with the formula ClC6H4NO2 include 2-nitrochlorobenzene and 3-nitrochlorobenzene.
4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene.
2,4-Dinitroanisole (DNAN) is a low sensitivity organic compound. It has an anisole (methoxybenzene) core, with two nitro groups (–NO2) attached.
2-Nitrochlorobenzene is an organic compound with the formula ClC6H4NO2. It is one of three isomeric nitrochlorobenzenes. It is a yellow crystalline solid that is important as a precursor to other compounds due to its two functional groups.
2-Methylanthraquinone, also known as β-methylanthraquinone and tectoquinone, is an organic compound which is a methylated derivative of anthraquinone. An off-white solid, it is an important precursor to many dyes. It is present in the wood of the teak tree, where it gives the tree resistance to insects.
In chemistry, the Halex process is used to convert aromatic chlorides to the corresponding aromatic fluorides. The process entails Halide exchange, hence the name. The reaction conditions call for hot (150-250 °C) solution of the aryl chloride and anhydrous potassium fluoride. Typical solvents are dimethylsulfoxide, dimethylformamide, and sulfolane. Potassium chloride is generated in the process. The reaction is mainly applied to nitro-substituted aryl chlorides. Sometimes more soluble fluorides, such as caesium fluoride and TBAF are used.
α-Halo carboxylic acids and esters are organic compounds with the respective formulas RCHXCO2H and RCHXCO2R' where R and R' are organic substituents. The X in these compounds is a halide, usually chloride and bromide. These compounds are often used as intermediates in the preparation of more elaborate derivatives. They are often potent alkylating agents. The mono halide derivatives are chiral.