3-Chloroaniline
| File:3-chlooraniline t.png | |
| Names | |
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| IUPAC name
3-chloroaniline
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Other names
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
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| E number | Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C6H6ClN | |
| Appearance | Colorless to amber liquid, darkens in storage |
| Density | 1.2150 g/mL at 22 °C |
| Melting point | −10.4 °C (13.3 °F; 262.8 K) |
| Boiling point | 230.5 °C (446.9 °F; 503.6 K) |
| 5.4 g/L (20 °C) | |
| Solubility | Miscible in ethanol, ether, and acetone |
| log P | 1.88 |
| Vapor pressure | 0.066 mmHg (25 °C) |
| Acidity (pKa) | 3.521 (conjugate acid) (25 °C) |
| Hazards | |
| GHS pictograms |    
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| GHS Signal word | |
| <abbr class="abbr" title="Error in hazard statements">HH301+H311, <abbr class="abbr" title="Error in hazard statements">HH301, <abbr class="abbr" title="Error in hazard statements">HH311, <abbr class="abbr" title="Error in hazard statements">HH317, <abbr class="abbr" title="Error in hazard statements">HH319, <abbr class="abbr" title="Error in hazard statements">HH330, <abbr class="abbr" title="Error in hazard statements">HH331, <abbr class="abbr" title="Error in hazard statements">HH350, <abbr class="abbr" title="Error in hazard statements">HH372, <abbr class="abbr" title="Error in hazard statements">HH373, <abbr class="abbr" title="Error in hazard statements">HH400, <abbr class="abbr" title="Error in hazard statements">HH410 | |
| <abbr class="abbr" title="Error in hazard statements">PP203, <abbr class="abbr" title="Error in hazard statements">PP260, <abbr class="abbr" title="Error in hazard statements">PP261, <abbr class="abbr" title="Error in hazard statements">PP262, <abbr class="abbr" title="Error in hazard statements">PP264, <abbr class="abbr" title="Error in hazard statements">PP264+265, <abbr class="abbr" title="Error in hazard statements">PP270, <abbr class="abbr" title="Error in hazard statements">PP271, <abbr class="abbr" title="Error in hazard statements">PP272, <abbr class="abbr" title="Error in hazard statements">PP273, <abbr class="abbr" title="Error in hazard statements">PP280, <abbr class="abbr" title="Error in hazard statements">PP284, <abbr class="abbr" title="Error in hazard statements">PP301+P316, <abbr class="abbr" title="Error in hazard statements">PP302+P352, <abbr class="abbr" title="Error in hazard statements">PP304+P340, <abbr class="abbr" title="Error in hazard statements">PP305+P351+P338, <abbr class="abbr" title="Error in hazard statements">PP316, <abbr class="abbr" title="Error in hazard statements">P318, <abbr class="abbr" title="Error in hazard statements">PP319, <abbr class="abbr" title="Error in hazard statements">PP320, <abbr class="abbr" title="Error in hazard statements">PP321, <abbr class="abbr" title="Error in hazard statements">PP330, <abbr class="abbr" title="Error in hazard statements">PP333+P317, <abbr class="abbr" title="Error in hazard statements">PP361, <abbr class="abbr" title="Error in hazard statements">PP364 | |
| Flash point | 118 °C (244 °F; 391 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
3-Chloroaniline or meta-chloroaniline is an organochlorine compound with the formula ClC6H4NH2. It is one of three structural isomers of chloroaniline. It is a colorless to light amber liquid.[1]
Preparation
3-Chloroaniline is prepared by hydrogenation of 3-nitrochlorobenzene. This process employs noble metal or noble metal sulfides as catalysts, as well as metal oxides to prevent dehalogenation. The yield is about 98%. Alternatively, 3-nitrochlorobenzene can be produced by reduction with sodium hydrosulfide.[2]
Uses
3-Chloroaniline is used as a chemical intermediate. It is used to produce herbicides such as chlorpropham and m-chlorophenyl isocyanurate. It is also used in production of pharmaceuticals, azo dyes, and insecticides.[2][3]
Toxicity
3-Chloroaniline causes methemoglobinemia and can cause acute contact dermatitis. Inhalation can cause symptoms such as dizziness, vomiting, and unconsciousness.[4][2]
References
- ↑ 1.0 1.1 "3-Chloroaniline (compound)". PubChem. Retrieved 27 June 2026.
- ↑ 2.0 2.1 2.2 "3-Chloroaniline: Applications in the Chemical Industry, Production Methods and Toxic Properties". chemicalbook.com. Retrieved 27 June 2026.
- ↑ "3-chloroaniline". atamanchemicals.com. Retrieved 27 June 2026.
- ↑ "3-Chloroaniline". haz-map.com. Retrieved 27 June 2026.
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