p-Anisidine
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
4-Methoxyaniline | |||
| Other names
p-Anisidine (no longer recommended[1])
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| Identifiers | |||
3D model (JSmol)
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| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.002.959 | ||
| EC Number |
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| KEGG | |||
| UNII | |||
| UN number | 2431 | ||
CompTox Dashboard (EPA)
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| 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] | ||
Refractive index (nD)
|
1.5559 | ||
| Hazards | |||
| Flash point | 122 °C (252 °F; 395 K) | ||
| 515 °C (959 °F; 788 K) | |||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
|
2900 mg/kg (rabbit, oral) 1300 mg/kg (mouse, oral) 1400 mg/kg (rat, oral)[4] | ||
LDLo (lowest published)
|
1000 mg/kg (mouse, oral)[4] | ||
| NIOSH (US health exposure limits): | |||
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).
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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
- ^ 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'.
- ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0035". National Institute for Occupational Safety and Health (NIOSH).
- ^ 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..
- ^ a b "p-Anisidine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ http://www.sigmaaldrich.com/catalog/product/aldrich/a88255?lang=de®ion=DE
- ^ "AOCS Official Method Cd 18-90". American Oil Chemists' Society. Retrieved 26 February 2013.
- ^ 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
- International Chemical Safety Card 0971
- NIOSH Pocket Guide to Chemical Hazards. "#0035". National Institute for Occupational Safety and Health (NIOSH).
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