P-Anisidine

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p-Anisidine
4-Anisidine.png
P-Anisidine 3D ball.png
Names
Preferred IUPAC name
4-Methoxyaniline [1]
Other names
para-Anisidine; 4-Aminoanisole; p-Aminoanisole
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.959 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-254-2
KEGG
PubChem CID
RTECS number
  • BZ5450000
UNII
UN number 2431
  • InChI=1S/C7H9NO/c1-9-7-4-2-6(8)3-5-7/h2-5H,8H2,1H3 Yes check.svgY
    Key: BHAAPTBBJKJZER-UHFFFAOYSA-N Yes check.svgY
  • 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 123.155 g·mol−1
AppearanceLight reddish brown solid [3]
Odor Fishy [3]
Density 1.071 (at 57 °C)
Melting point 56 to 59 °C (133 to 138 °F; 329 to 332 K)
Boiling point 243 °C (469 °F; 516 K)
Sparingly soluble [3]
Solubility in other solventsSoluble in ethanol, diethyl ether, acetone, benzene
Vapor pressure 0.006 mmHg (25 °C) [4]
-80.56·10−6 cm3/mol
1.5559
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Carcinogen
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Warning
H300, H310, H330, H350, H373, H400 [5]
P201, P202, P260, P262, P264, P270, P271, P273, P280, P281, P284, P301+P310, P302+P350, P304+P340, P308+P313, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501
Flash point 122 °C (252 °F; 395 K)
515 °C (959 °F; 788 K)
Lethal dose or concentration (LD, LC):
145 mg/kg (rabbit, oral) [6]
130 mg/kg (mouse, oral)
140 mg/kg (rat, oral) [7]
100 mg/kg (mouse, oral) [7]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 0.5 mg/m3 [skin] [4]
REL (Recommended)
TWA 0.5 mg/m3 [skin] [4]
IDLH (Immediate danger)
50 mg/m3 [4]
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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p-Anisidine (or para-anisidine) is an organic compound with the formula CH3OC6H4NH2. A white solid, commercial samples can appear grey-brown owing to air oxidation. It is one of three isomers of anisidine, methoxy-containing anilines. It is prepared by reduction of 4-nitroanisole. [8]

Contents

Anisidine value

p-Anisidine condenses readily with aldehydes and ketones to form Schiff bases, which absorb at 350 nm. This colorimetric reaction is used to test for the presence of oxidation products in fats and oils, an official method for detecting them by the American Oil Chemists' Society. [9] 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. [10] [11]

Safety

p-Anisidine is a relatively toxic compound with a permissible exposure limit of 0.5 mg/m3. [3]

Related Research Articles

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<span class="mw-page-title-main">Dimethylamine</span> Chemical compound

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<i>o</i>-Xylene Chemical compound

o-Xylene (ortho-xylene) is an aromatic hydrocarbon with the formula C6H4(CH3)2, with two methyl substituents bonded to adjacent carbon atoms of a benzene ring (the ortho configuration). It is a constitutional isomer of m-xylene and p-xylene, the mixture being called xylene or xylenes. o-Xylene is a colourless slightly oily flammable liquid.

<i>m</i>-Cresol Chemical compound

meta-Cresol, also 3-methylphenol, is an organic compound with the formula CH3C6H4(OH). It is a colourless, viscous liquid that is used as an intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of p-cresol and o-cresol.

<span class="mw-page-title-main">1-Propanol</span> Primary alcohol compound

1-Propanol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colourless liquid and an isomer of 2-propanol. 1-Propanol is used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

<i>m</i>-Xylene Chemical compound

m-Xylene (meta-xylene) is an aromatic hydrocarbon. It is one of the three isomers of dimethylbenzene known collectively as xylenes. The m- stands for meta-, indicating that the two methyl groups in m-xylene occupy positions 1 and 3 on a benzene ring. It is in the positions of the two methyl groups, their arene substitution pattern, that it differs from the other isomers, o-xylene and p-xylene. All have the same chemical formula C6H4(CH3)2. All xylene isomers are colorless and highly flammable.

<span class="mw-page-title-main">Diphenylamine</span> Chemical compound

Diphenylamine is an organic compound with the formula (C6H5)2NH. The compound is a derivative of aniline, consisting of an amine bound to two phenyl groups. The compound is a colorless solid, but commercial samples are often yellow due to oxidized impurities. Diphenylamine dissolves well in many common organic solvents, and is moderately soluble in water. It is used mainly for its antioxidant properties. Diphenylamine is widely used as an industrial antioxidant, dye mordant and reagent and is also employed in agriculture as a fungicide and antihelmintic.

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<span class="mw-page-title-main">Tolidine</span> Chemical compound

2-Tolidine (orthotolidine, o-tolidine; not to be confused with o-toluidine) is an organic compound with the chemical formula (C6H4(CH3)NH2)2. Several isomers are known; the 3-tolidine derivative is also important commercially. It is a colorless compound although commercial samples are often colored. It is slightly soluble in water. It forms salts with acids, such as the hydrochloride, which is commercially available.

<i>o</i>-Anisidine Chemical compound

o-Anisidine (2-anisidine) is an organic compound with the formula CH3OC6H4NH2. A colorless liquid, commercial samples can appear yellow owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.

<i>m</i>-Anisidine Chemical compound

m-Anisidine is an organic compound with the formula CH3OC6H4NH2. A clear light yellow or amber color liquid, commercial samples can appear brown owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.

4-Nitrotoluene or para-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is a pale yellow solid. It is one of three isomers of nitrotoluene.

3-Nitrotoluene or meta-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is one of three isomers of nitrotoluene. A yellow liquid, it is used in the manufacture of meta-toluidine, which is an intermediate in the production of various dyes.

2-Nitrotoluene or ortho-nitrotoluene is an organic compound with the formula CH3C6H4NO2. It is pale yellow liquid that crystallizes in two forms, called α (−9.27 °C) and β (−3.17 °C). It is mainly a precursor to o-toluidine, which is an intermediate in the production of various dyes.

References

  1. ↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 669. doi:10.1039/9781849733069-00648. 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. ↑ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, Florida: CRC Press. p. C-98. ISBN   0-8493-0462-8.
  3. 1 2 3 4 "Occupational Safety and Health Guideline for Anisidine (o-, p-isomers)" (PDF).
  4. 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0035". National Institute for Occupational Safety and Health (NIOSH).
  5. ↑ "p-Anisidine safety and hazards". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-12-02.
  6. ↑ p-Anisidine toxicity
  7. 1 2 "p-Anisidine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  8. ↑ Mitchell, Stephen C.; Waring, Rosemary H. (2000). "Aminophenols". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a02_099. ISBN   3527306730.
  9. ↑ "AOCS Official Method Cd 18-90". American Oil Chemists' Society. Retrieved 26 February 2013.
  10. ↑ 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.
  11. ↑ A.J. Dijkstra (2016). "Vegetable Oils: Composition and Analysis". Encyclopedia of Food and Health. pp. 357–364. doi:10.1016/B978-0-12-384947-2.00708-X. ISBN   9780123849533.
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