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p-Anisidine

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p-Anisidine
Skeletal formula of p-anisidine
Ball-and-stick model of p-anisidine
Names
IUPAC name
4-Methoxyaniline
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.959 Edit this at Wikidata
EC Number
  • 203-254-2
KEGG
UN number 2431
  • InChI=1S/C7H9NO/c1-9-7-4-2-6(8)3-5-7/h2-5H,8H2,1H3 checkY
    Key: BHAAPTBBJKJZER-UHFFFAOYSA-N checkY
  • InChI=1/C7H9NO/c1-9-7-4-2-6(8)3-5-7/h2-5H,8H2,1H3
  • COc1ccc(cc1)N
Properties[2]
C7H9NO
Molar mass 123.15 g/mol
Density 1.071 (57 °C)
Melting point 56 to 59 °C (133 to 138 °F; 329 to 332 K)
Boiling point 243 °C (469 °F; 516 K)
soluble
Solubility soluble in ethanol, diethyl ether, acetone, benzene
Vapor pressure 0.006 mmHg (25 °C)[1]
1.5559
Hazards
Flash point 122 °C (252 °F; 395 K)
515 °C (959 °F; 788 K)
Lethal dose or concentration (LD, LC):
2900 mg/kg (rabbit, oral)
1300 mg/kg (mouse, oral)
1400 mg/kg (rat, oral)[3]
1000 mg/kg (mouse, oral)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 0.5 mg/m3 [skin][1]
REL (Recommended)
TWA 0.5 mg/m3 [skin][1]
IDLH (Immediate danger)
50 mg/m3[1]
Related compounds
Related compounds
o-Anisidine
m-Anisidine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

para-Anisidine (p-anisidine), a grey-brown solid, is the most toxic[4] of the three isomers of anisidine and causes blood damage upon oral ingestion, inhalation or skin contact. If heated strongly, it may release very toxic fumes of nitrogen oxides.

p-Anisidine reacts with secondary oxidation products such as aldehydes and ketones in fats and oils to form products that absorb at 350 nm wavelength of light; therefore, it is used as an official method for detecting them by the American Oil Chemists' Society.[5] It is particularly good at detecting unsaturated aldehydes, which are the ones that are most likely to generate unacceptable flavors, making it particularly useful in food quality testing.[6]

References

  1. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0035". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-98. ISBN 0-8493-0462-8..
  3. ^ a b "p-Anisidine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ^ http://www.sigmaaldrich.com/catalog/product/aldrich/a88255?lang=de&region=DE
  5. ^ "AOCS Official Method Cd 18-90". American Oil Chemists' Society. Retrieved 26 February 2013.
  6. ^ Steele, Robert (2004). Understanding and Measuring the Shelf-Life of Food. Woodhead Publishing in Food Science and Technology Series. Woodhead Publishing. p. 136. ISBN 1855737329.