p-Anisidine

p-Anisidine
Names
	Preferred IUPAC name 4-Methoxyaniline[1]
	Other names para-Anisidine; 4-Aminoanisole; p-Aminoanisole
Identifiers
CAS Number	104-94-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82388;
ChEMBL	ChEMBL295652 ;
ChemSpider	13869414 ;
ECHA InfoCard	100.002.959
EC Number	203-254-2;
KEGG	C19326 ;
PubChem CID	7732;
RTECS number	BZ5450000;
UNII	575917SNR4 ;
UN number	2431
CompTox Dashboard (EPA)	DTXSID7024532 ;
	InChI InChI=1S/C7H9NO/c1-9-7-4-2-6(8)3-5-7/h2-5H,8H2,1H3 Key: BHAAPTBBJKJZER-UHFFFAOYSA-N ; InChI=1/C7H9NO/c1-9-7-4-2-6(8)3-5-7/h2-5H,8H2,1H3;
	SMILES COc1ccc(cc1)N;
Properties[2]
Chemical formula	C7H9NO
Molar mass	123.155 g·mol−1
Appearance	Light 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)
Solubility in water	Sparingly soluble[3]
Solubility in other solvents	Soluble in ethanol, diethyl ether, acetone, benzene
Vapor pressure	0.006 mmHg (25 °C)[4]
Magnetic susceptibility (χ)	-80.56·10−6 cm3/mol
Refractive index (nD)	1.5559
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Carcinogen
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H300, H310, H330, H350, H373, H400[5]
Precautionary statements	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)
Autoignition; temperature	515 °C (959 °F; 788 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	145 mg/kg (rabbit, oral)[6]; 130 mg/kg (mouse, oral); 140 mg/kg (rat, oral)[7]
LDLo (lowest published)	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). verify (what is ?) Infobox references

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]

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]

References

Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 669. doi:10.1039/9781849733069-00648. 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'.
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.
"Occupational Safety and Health Guideline for Anisidine (o-, p-isomers)" (PDF).
NIOSH Pocket Guide to Chemical Hazards. "#0035". National Institute for Occupational Safety and Health (NIOSH).
"p-Anisidine safety and hazards". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-12-02.
p-Anisidine toxicity
"p-Anisidine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
Mitchell, Stephen C.; Waring, Rosemary H. (2000). "Aminophenols". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a02_099. ISBN 3527306730.
"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.
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.

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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[iupac2013-1] 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, FL: CRC Press. p. C-98. ISBN 0-8493-0462-8.

[cdc-3] "Occupational Safety and Health Guideline for Anisidine (o-, p-isomers)" (PDF).

[NIOSH-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] -Anisidine toxicity

[IDLH-7] "p-Anisidine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[Ullmann-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.

[AOCS-9] "AOCS Official Method Cd 18-90". American Oil Chemists' Society. Retrieved 26 February 2013.

[Steele-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.