2-Chloroaniline
Comment: Non-notable substance based on the sources provided. Refs. 1, 2, and 4 are primary sources (databases and catalogs), and Ref. 3 is obviously LLM-generated SEO-spam. WeirdNAnnoyed (talk) 11:13, 8 July 2026 (UTC)
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| Identifiers | |
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3D model (JSmol)
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| 606077 | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). |
| E number | Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). |
PubChem CID
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| UNII | |
| UN number | 2019 |
CompTox Dashboard (EPA)
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| Properties | |
| C6H6ClN | |
| Molar mass | 127.57 g·mol−1 |
| Appearance | Colorless to tan liquid |
| Odor | sweet or amine |
| Density | 1.213 |
| Melting point | 0–3 °C (32–37 °F; 273–276 K) |
| Boiling point | 208–210 °C (406–410 °F; 481–483 K) |
Refractive index (nD)
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1.589 |
| Hazards | |
| GHS pictograms |    
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| GHS Signal word | |
| H301, H311, H319, H331, H341, H373, H410 | |
| <abbr class="abbr" title="Error in hazard statements">P203, P261, P262, P264, <abbr class="abbr" title="Error in hazard statements">P264+265, P270, P271, P273, P280, <abbr class="abbr" title="Error in hazard statements">P301+316, P302+352, P304+340, P305+351+338, <abbr class="abbr" title="Error in hazard statements">P316, <abbr class="abbr" title="Error in hazard statements">P318, <abbr class="abbr" title="Error in hazard statements">P319, P321, P330, <abbr class="abbr" title="Error in hazard statements">P337+317, <abbr class="abbr" title="Error in hazard statements">P361+364, P391, P403+233, P405, P501 | |
| Related compounds | |
Related compounds
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3-Chloroaniline; 4-Chloroaniline; Aniline; Chlorobenzene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
2-Chloroaniline or ortho-chloroaniline is an organochlorine compound with the formula ClC6H4NH2. It is one of three structural isomers of chloroaniline. It is colorless to tan in color.[1]
Preparation
2-Chloroaniline is prepared by reflux of 2-nitrochlorobenzene with iron filings, dilute hydrochloric acid, and water to reduce the nitro group to an amine group:
Distillations are used to obtain the final product.[2] Direct chlorination of aniline would lead to poor yield due to 4-chloroaniline and over-chlorination side reactions.
Uses
2-Chloroaniline is a versatile chemical intermediate. It is used in production of chlorsulfuron, an herbicide as well as dyes and pigments such as azo dyes or tartrazine. Other uses include pharmaceuticals, where it is used for producing active pharmaceutical ingredients. Additionally, it is used to produce synthetic resins and polyurethane elastomers, particularly as a chain extender.[3][4]
References
- ↑ 1.0 1.1 "2-Chloroaniline (compound)". PubChem. Retrieved 25 June 2026.
- ↑ "2-Chloroaniline". chemicalbook.com. Retrieved 25 June 2026.
- ↑ "The Essential Role of 2-Chloroaniline in Modern Chemical Manufacturing". nbinno.com. Retrieved 25 June 2026.
- ↑ "2-Chloroaniline". sigmaaldrich.com. Retrieved 27 June 2026.
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