p-Anisidine

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p-Anisidine
Skeletal formula of p-anisidine
Ball-and-stick model of p-anisidine
Names
Preferred IUPAC name
4-Methoxyaniline
Other names
p-Anisidine (no longer recommended[1])
Identifiers
104-94-9 YesY
3D model (Jmol) Interactive image
ChEMBL ChEMBL295652 YesY
ChemSpider 13869414 YesY
ECHA InfoCard 100.002.959
EC Number 203-254-2
KEGG C19326 N
UNII 575917SNR4 N
UN number 2431
Properties[3]
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)[2]
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)[4]
1000 mg/kg (mouse, oral)[4]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 0.5 mg/m3 [skin][2]
REL (Recommended)
TWA 0.5 mg/m3 [skin][2]
IDLH (Immediate danger)
50 mg/m3[2]
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 YesYN ?)
Infobox references

para-Anisidine (p-anisidine), a grey-brown solid, is the most toxic[5] 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.[6] 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.[7]

References[edit]

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 669. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The names ‘toluidine’, ‘anisidine’, and ‘phenetidine’ for which o-, m-, and p- have been used to distinguish isomers, and ‘xylidine’ for which numerical locants, such as 2,3-, have been used, are no longer recommended, nor are the corresponding prefixes ‘toluidine’, ‘anisidino’, ‘phenetidine’, and ‘xylidino’. 
  2. ^ a b c d "NIOSH Pocket Guide to Chemical Hazards #0035". National Institute for Occupational Safety and Health (NIOSH). 
  3. ^ 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. .
  4. ^ a b "p-Anisidine". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH). 
  5. ^ http://www.sigmaaldrich.com/catalog/product/aldrich/a88255?lang=de&region=DE
  6. ^ "AOCS Official Method Cd 18-90". American Oil Chemists' Society. Retrieved 26 February 2013. 
  7. ^ 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. 

External links[edit]