Anilinium chloride

Anilinium chloride
Identifiers
CAS Number	142-04-1 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3182415;
ChemSpider	8536;
ECHA InfoCard	100.005.018
EC Number	205-519-8;
PubChem CID	8870;
UNII	576R1193YL;
UN number	1548
CompTox Dashboard (EPA)	DTXSID3020091 ;
	InChI InChI=1S/C6H7N.ClH/c7-6-4-2-1-3-5-6;/h1-5H,7H2;1H Key: MMCPOSDMTGQNKG-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)N.Cl;
Properties
Chemical formula	C6H5NH+3Cl−
Molar mass	129.59 g·mol−1
Appearance	white solid
Density	1.68 g/cm3
Melting point	196 °C (385 °F; 469 K)
Boiling point	245 °C (473 °F; 518 K)
Solubility in water	1070 g/l
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H317, H318, H331, H341, H351, H372, H400
Precautionary statements	P203, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P281, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P333+P313, P361+P364, P362+P364, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)	3 1 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Anilinium chloride is the organic compound with the formula C₆H₅NH+3Cl⁻. A white solid, it is the chloride salt of anilinium, which is the conjugate acid of aniline, C₆H₅NH₂. Anilinium chloride is produced by treatment of aniline with hydrochloric acid. The cation consists of a phenyl ring attached to a tetrahedral ammonium center. The C-N bond elongates from 1.41 Å in aniline to 1.474 Å in anilinium.^[2]

Uses

Anilinium chloride is used as a precursor to diphenylamine by heating with aniline:^[3]

C₆H₅NH₂ + C₆H₅NH₃Cl → (C₆H₅)₂NH + NH₃ + HCl

It reacts with formaldehyde to give methylenedianiline, a precursor to commercial polymers.^[3]

References

^ "Aniline hydrochloride". pubchem.ncbi.nlm.nih.gov. Retrieved 31 August 2023.
^ Anderson, Kirsty M.; Goeta, Andres E.; Hancock, Kirsty S. B.; Steed, Jonathan W. (2006). "Unusual variations in the incidence of Z? > 1 in oxo-anion structures". Chemical Communications (20): 2138–2140. doi:10.1039/b602492k. PMID 16703133.
^ ^a ^b Amini, Bijan; Lowenkron, Steven (2003). "Aniline and Its Derivatives". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0114091201130914.a01.pub2. ISBN 978-0-471-48494-3.

[1] "Aniline hydrochloride". pubchem.ncbi.nlm.nih.gov. Retrieved 31 August 2023.

[2] Anderson, Kirsty M.; Goeta, Andres E.; Hancock, Kirsty S. B.; Steed, Jonathan W. (2006). "Unusual variations in the incidence of Z? > 1 in oxo-anion structures". Chemical Communications (20): 2138–2140. doi:10.1039/b602492k. PMID 16703133.

[KO-3] Amini, Bijan; Lowenkron, Steven (2003). "Aniline and Its Derivatives". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0114091201130914.a01.pub2. ISBN 978-0-471-48494-3.

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