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Anilinium chloride

From Wikipedia, the free encyclopedia
(Redirected from C6H8ClN)
Anilinium chloride
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.018 Edit this at Wikidata
EC Number
  • 205-519-8
UNII
UN number 1548
  • InChI=1S/C6H7N.ClH/c7-6-4-2-1-3-5-6;/h1-5H,7H2;1H
    Key: MMCPOSDMTGQNKG-UHFFFAOYSA-N
  • C1=CC=C(C=C1)N.Cl
Properties
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)
1070 g/l
Hazards
GHS labelling:[1]
GHS02: FlammableGHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H301, H311, H317, H318, H331, H341, H351, H372, H400
P203, P260, 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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Anilinium chloride is the organic compound with the formula C6H5NH+3Cl−. It is a white solid and 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

[edit]

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

[edit]
  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.
  3. 1 2 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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