3,5-Dichloroaniline

Last updated
3,5-Dichloroaniline
3,5-Dichloranilin.svg
Names
Other names
1-amino-3,5- dichlorobenzene
Identifiers
3D model (JSmol)
636492
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.954 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 210-948-9
363409
PubChem CID
UNII
  • InChI=1S/C6H5Cl2N/c7-4-1-5(8)3-6(9)2-4/h1-3H,9H2
    Key: UQRLKWGPEVNVHT-UHFFFAOYSA-N
  • C1=C(C=C(C=C1Cl)Cl)N
Properties
C6H5Cl2N
Molar mass 162.01 g·mol−1
Appearancecolorless solid
Density 1.58 g/cm3
Melting point 51–53 °C (124–127 °F; 324–326 K)
Boiling point 260 °C (500 °F; 533 K) 741 torr
Hazards
GHS labelling: [1]
GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H301, H311, H331, H373, H410
P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3,5-Dichloroaniline is an organic compound with the formula C6H3Cl2(NH2). It is one of several isomers of dichloroaniline. It is a colorless solid although commercial samples often appear colored. It is produced by hydrogenation of 3,5-dichloronitrobenzene. [2] It is a precursor to the fungicide vinclozolin.

Safety and environmental aspects

Its 72-h EC50 in an algal growth inhibition assay is 4.39 mg/L. [3] Biodegradation of dichloroanilines usually proceeds via initial ring hydroxylation. [4]

Related Research Articles

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<span class="mw-page-title-main">Biodegradation</span> Decomposition by living organisms

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<span class="mw-page-title-main">Bioremediation</span> Process used to treat contaminated media such as water and soil

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<span class="mw-page-title-main">Nonylphenol</span> Chemical compound

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<span class="mw-page-title-main">1,3,5-Trichlorobenzene</span> Chemical compound

1,3,5-Trichlorobenzene is an organochlorine compound. It is one of the three isomers of trichlorobenzene. Being more symmetrical than the other isomers, it exists as colourless crystals whereas the other isomers are liquids at room temperature.

Carbocatalysis is a form of catalysis that uses heterogeneous carbon materials for the transformation or synthesis of organic or inorganic substrates. The catalysts are characterized by their high surface areas, surface functionality, and large, aromatic basal planes. Carbocatalysis can be distinguishable from supported catalysis in that no metal is present, or if metals are present they are not the active species.

<span class="mw-page-title-main">1,4-Dichloro-2-nitrobenzene</span> Chemical compound

1,4-Dichloro-2-nitrobenzene is an organic compound with the formula C6H3Cl2NO2. One of several isomers of dichloronitrobenzene, it is a yellow solid that is insoluble in water. It is produced by nitration of 1,4-dichlorobenzene. It is a precursor to many derivatives of commercial interest. Hydrogenation gives 1,4-dichloroaniline. Nucleophiles displace the chloride adjacent to the nitro group: ammonia gives the aniline derivative, aqueous base gives the phenol derivative, and methoxide gives the anisole derivative. These compounds are respectively 4-chloro-2-nitroaniline, 4-chloro-2-nitrophenol, and 4-chloro-2-nitroanisole.

<span class="mw-page-title-main">Dichloroaniline</span>

Dichloroanilines are chemical compounds which consist of an aniline ring substituted with two chlorine atoms and have the molecular formula C6H5Cl2N. There are six isomers, varying in the positions of the chlorine atoms around the ring relative to the amino group. As aniline derivatives, they are named with the amino group in position 1. They are all colorless, although commercial samples can appear colored due to the presence of impurities. Several derivatives are used in the production of dyes and herbicides.

<span class="mw-page-title-main">3,5-Lutidine</span> Chemical compound

3,5-Lutidine is a heterocyclic organic compound with the formula (CH3)2C5H3N. It is one of several dimethyl-substituted derivatives of pyridine, all of which are referred to as lutidines. It is a colorless liquid with mildly basic properties and a pungent odor. The compound is a precursor to the drug omeprazole.

4-Fluoronitrobenzene is an organic compound with the formula FC6H4NO2. It is one of three isomeric fluoronitrobenzenes. A yellow oil, it is prepared from 4-nitrochlorobenzene using the Halex process:

4-Fluoroaniline is an organofluorine compound with the formula FC6H4NH2. A colorless liquid, it is one of three isomers of fluoroaniline. It is used as a precursor to various potential and real applications.

3,4-Dichloroaniline is an organic compound with the formula C6H3Cl2(NH2). It is one of several isomers of dichloroaniline. It is a white solid although commercial samples often appear gray. It is a precursor to dyes, agricultural chemicals, and drugs including the antimalarial chlorproguanil and the herbicides propanil, linuron, DCMU, and diuron.

<span class="mw-page-title-main">2,3-Dichloroaniline</span> Chemical compound

2,3-Dichloroaniline is an organic compound with the formula C6H3Cl2(NH2). It is one of several isomers of dichloroaniline. It is a colorless oil although commercial samples often appear colored. It is produced by hydrogenation of 2,3-dichloronitrobenzene.

References

  1. "3,5-Dichloroaniline". pubchem.ncbi.nlm.nih.gov.
  2. Jagadeesh, Rajenahally V.; Surkus, Annette-Enrica; Junge, Henrik; Pohl, Marga-Martina; Radnik, Jörg; Rabeah, Jabor; Huan, Heming; Schünemann, Volker; Brückner, Angelika; Beller, Matthias (2013). "Nanoscale Fe2O3-Based Catalysts for Selective Hydrogenation of Nitroarenes to Anilines". Science. 342 (6162): 1073–1076. Bibcode:2013Sci...342.1073J. doi:10.1126/science.1242005. PMID   24288327.
  3. Aruoja, Villem; Sihtmäe, Mariliis; Dubourguier, Henri-Charles; Kahru, Anne (2011). "Toxicity of 58 substituted anilines and phenols to algae Pseudokirchneriella subcapitata and bacteria Vibrio fischeri: Comparison with published data and QSARs". Chemosphere. 84 (10): 1310–1320. Bibcode:2011Chmsp..84.1310A. doi:10.1016/j.chemosphere.2011.05.023. PMID   21664645.
  4. Suchana, Shamsunnahar; Araujo, Sofia Pimentel; Lomheim, Line; Mack, E. Erin; Spain, Jim C.; Edwards, Elizabeth; Passeport, Elodie (2024). "Compound-Specific Carbon, Nitrogen, and Hydrogen Isotope Analysis to Characterize Aerobic Biodegradation of 2,3-Dichloroaniline by a Mixed Enrichment Culture". Environmental Science & Technology. 58 (27): 12042–12050. Bibcode:2024EnST...5812042S. doi:10.1021/acs.est.4c02173. PMID   38934904.