p-Phenetidine

p-Phenetidine (4-ethoxyaniline) is a chemical compound with the molecular formula C8H11NO. It is one of the three isomers of phenetidine. It is used as an intermediate in the synthesis of pharmaceutical drugs, dyes, and the sweetener dulcin.[1]

p-Phenetidine
Names
Preferred IUPAC name
4-Ethoxyaniline
Other names
para-Phenetidine; 4-Aminophenetole
Identifiers
3D model (JSmol)
ECHA InfoCard 100.005.324
EC Number
  • 205-855-5
RTECS number
  • SI6465500
UNII
  • InChI=1S/C8H11NO/c1-2-10-8-5-3-7(9)4-6-8/h3-6H,2,9H2,1H3
    Key: IMPPGHMHELILKG-UHFFFAOYSA-N
  • CCOC1=CC=C(C=C1)N
Properties
C8H11NO
Molar mass 137.182 g·mol−1
Appearance Colorless liquid; turns red to brown on exposure to air[1]
Density 1.07 g/mL[2]
Melting point 3 °C (37 °F; 276 K)[2]
Boiling point 254 °C (489 °F; 527 K)[2]
20 g/L (20 °C)[2]
Hazards
Flash point 116 °C (241 °F; 389 K)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

p-Phenetidine is a metabolite of the pharmaceutical drugs bucetin and phenacetin[3] and of the preservative ethoxyquin.[4] It is also used as a chemical intermediate in the manufacture of bucetin, phenacetin, ethoxyquin, and phenacaine.

p-Phenetidine has high renal toxicity[3] and it is believed to be responsible for the adverse effects that led to the withdrawal of phenacetin and bucetin from pharmaceutical use. p-Phenetidine is also a possible mutagen.[4]

References
  1. Merck Index (12th ed.). p. 1244. 7373. p-Phenetidine.
  2. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. Kankuri, Esko; Solatunturi, Erkka; Vapaatalo, Heikki (2003). "Effects of phenacetin and its metabolite p-phenetidine on COX-1 and COX-2 activities and expression in vitro". Thrombosis Research. 110 (5–6): 299–303. doi:10.1016/S0049-3848(03)00416-X. PMID 14592552.
  4. "Ethoxyquin: EFSA safety assessment inconclusive". European Food Safety Authority. 2015-11-18.
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