3-Chloroaniline

3-Chloroaniline
Names
	IUPAC name 3-chloroaniline
	Other names m-chloroaniline;
Identifiers
CAS Number	108-42-9;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:229245;
ChEMBL	ChEMBL325415;
ChemSpider	13869451;
ECHA InfoCard	100.003.256
EC Number	203-581-0;
PubChem CID	7932;
UNII	6GKR52SKIY;
UN number	2019
CompTox Dashboard (EPA)	DTXSID0024761 ;
	InChI Key: PNPCRKVUWYDDST-UHFFFAOYSA-N; InChI=1S/C6H6ClN/c7-5-2-1-3-6(8)4-5/h1-4H,8H2;
	SMILES C1=CC(=CC(=C1)Cl)N;
Properties
Chemical formula	C6H6ClN
Appearance	Colorless to amber liquid, darkens in storage
Odor	Sweet
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)
Solubility in water	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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H301+H311, H311, H317, H319, H330, H331, H350, H372, H373, H410
Precautionary statements	P203, P260, P262, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P320, P321, P330, P333+P317, P361, P362+P364, P364, P391, P403+P233, P405, P501
Flash point	118 °C (244 °F; 391 K)
Autoignition; temperature	>540 °C (1,004 °F; 813 K)
Related compounds
Related compounds	4-Chloroaniline 2,4,6-trichloroaniline
	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 with a sweet odor.^[7]

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.^[8]

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.^[8]^[9]

Toxicity

3-Chloroaniline causes methemoglobinemia and can cause acute contact dermatitis. Inhalation can cause symptoms such as dizziness, vomiting, and unconsciousness.^[10]^[8]

References

1 2 3 O’Neil, M. J. (2001). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. p. 365.
↑ Chiou, CT; et al. (1982). "Partitioning of Organic Compounds in Octanol-Water Systems". Environmental Science & Technology. 16 (1): 4–10. Bibcode:1982EnST...16....4C. doi:10.1021/es00095a005.
↑ Lide, DR (2000). CRC Handbook of Chemistry and Physics (81 ed.). Boca Raton, Florida: CRC Press LLC. pp. 3–21.
↑ Hansch, C.; Leo, A.; Hoekman, D. (1995). Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society. p. 19.
↑ Daubert, T.E.; Danner, R.P. (1989). Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, DC: Taylor and Francis.
↑ Perrin, D.D. (1972). Dissociation Constants of Organic Bases in Aqueous Solution. London: Buttersworth.
↑ "M-CHLOROANILINE". cameochemicals.noaa.gov. Retrieved 6 July 2026.
1 2 3 "3-Chloroaniline: Applications in the Chemical Industry, Production Methods and Toxic Properties". chemicalbook.com. Retrieved 27 June 2026.
↑ Venkateswara Rao, P.; Venkatramana, L.; Gowrisankar, M.; Ravindranath, K. (March 2016). "Volumetric, acoustic and spectroscopic properties of 3-chloroaniline with substituted ethanols at various temperatures". The Journal of Chemical Thermodynamics. 94: 186–196. Bibcode:2016JChTh..94..186V. doi:10.1016/j.jct.2015.11.012. Retrieved 6 July 2026.
↑ "3-chloroaniline". chemicalsafety.ilo.org. Retrieved 6 July 2026.

[“merck365”-1] 1 2 3 O’Neil, M. J. (2001). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. p. 365.

[2] Chiou, CT; et al. (1982). "Partitioning of Organic Compounds in Octanol-Water Systems". Environmental Science & Technology. 16 (1): 4–10. Bibcode:1982EnST...16....4C. doi:10.1021/es00095a005.

[3] Lide, DR (2000). CRC Handbook of Chemistry and Physics (81 ed.). Boca Raton, Florida: CRC Press LLC. pp. 3–21.

[4] Hansch, C.; Leo, A.; Hoekman, D. (1995). Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society. p. 19.

[5] Daubert, T.E.; Danner, R.P. (1989). Physical and Thermodynamic Properties of Pure Chemicals Data Compilation. Washington, DC: Taylor and Francis.

[6] Perrin, D.D. (1972). Dissociation Constants of Organic Bases in Aqueous Solution. London: Buttersworth.

[7] "M-CHLOROANILINE". cameochemicals.noaa.gov. Retrieved 6 July 2026.

[chemicalbook-8] 1 2 3 "3-Chloroaniline: Applications in the Chemical Industry, Production Methods and Toxic Properties". chemicalbook.com. Retrieved 27 June 2026.

[9] Venkateswara Rao, P.; Venkatramana, L.; Gowrisankar, M.; Ravindranath, K. (March 2016). "Volumetric, acoustic and spectroscopic properties of 3-chloroaniline with substituted ethanols at various temperatures". The Journal of Chemical Thermodynamics. 94: 186–196. Bibcode:2016JChTh..94..186V. doi:10.1016/j.jct.2015.11.012. Retrieved 6 July 2026.

[10] "3-chloroaniline". chemicalsafety.ilo.org. Retrieved 6 July 2026.

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