4-Aminophenol

4-Aminophenol
Skeletal formula of 4-aminophenol	Space-filling model of the 4-aminophenol molecule
Names
	Preferred IUPAC name 4-Aminophenol[1]
	Other names p-Aminophenol; para-Aminophenol;
Identifiers
CAS Number	123-30-8 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	385836
ChEBI	CHEBI:17602 ;
ChEMBL	ChEMBL1142 ;
ChemSpider	392 ;
ECHA InfoCard	100.004.198
EC Number	204-616-2;
Gmelin Reference	2926
KEGG	C02372 ;
MeSH	Aminophenols
PubChem CID	403;
UNII	R7P8FRP05V ;
UN number	2512
CompTox Dashboard (EPA)	DTXSID3024499 ;
	InChI InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 Key: PLIKAWJENQZMHA-UHFFFAOYSA-N ; InChI=1/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 Key: PLIKAWJENQZMHA-UHFFFAOYAD;
	SMILES Oc1ccc(N)cc1; c1cc(ccc1N)O;
Properties
Chemical formula	C6H7NO
Molar mass	109.128 g·mol−1
Appearance	Colorless to reddish-yellow crystals
Density	1.13 g/cm3
Melting point	187.5 °C (369.5 °F; 460.6 K)
Boiling point	284 °C (543 °F; 557 K)
Solubility in water	1.5 g/100 mL
Solubility	Very soluble in dimethylsulfoxide; Soluble in acetonitrile, ethyl acetate, and acetone; Slightly soluble in toluene, diethyl ether, and ethanol; Negligible solubility in benzene and chloroform;
log P	0.04
Acidity (pKa)	5.48 (amino; H2O); 10.30 (phenol; H2O)[2];
Structure
Crystal structure	orthorhombic
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	-190.6 kJ/mol
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H302, H332, H341, H400, H410
GHS precautionary statements	P201, P202, P261, P264, P270, P271, P273, P281, P301+312, P304+312, P304+340, P308+313, P312, P330, P391, P405, P501
NFPA 704 (fire diamond)	1 2 0
Flash point	195 °C (383 °F; 468 K) (cc)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	671 mg/kg
Related compounds
Related aminophenols	2-Aminophenol; 3-Aminophenol
Related compounds	Aniline; Phenol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

4-Aminophenol (or para-aminophenol or p-aminophenol) is the organic compound with the formula H₂NC₆H₄OH. Typically available as a white powder,[3] it was commonly used as a developer for black-and-white film, marketed under the name Rodinal.

Reflecting its slightly hydrophilic character, the white powder is moderately soluble in alcohols and can be recrystallized from hot water. In the presence of a base, it oxidizes readily. The methylated derivatives N-methylaminophenol and N,N-dimethylaminophenol are of commercial value.

The compound is one of three isomeric aminophenols, the other two being 2-aminophenol and 3-aminophenol.

Preparation

From phenol

It is produced from phenol by nitration followed by reduction with iron. Alternatively, the partial hydrogenation of nitrobenzene affords phenylhydroxylamine, which rearranges primarily to 4-aminophenol:[4]

C₆H₅NO₂ + 2 H₂ → C₆H₅NHOH + H₂O

C₆H₅NHOH → HOC₆H₄NH₂

From nitrobenzene

It can be produced from nitrobenzene by electrolytic conversion to phenylhydroxylamine, which spontaneously rearranges to 4-aminophenol.[5]

Uses

4-Aminophenol is a building block used in organic chemistry. Prominently, it is the final intermediate in the industrial synthesis of paracetamol. Treating 4-aminophenol with acetic anhydride gives paracetamol:[6][7][8]

References

Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 690. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
CRC Handbook of Chemistry and Physics 65th Ed.
Mitchell, S.C. & Waring, R.H. "Aminophenols." In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, doi:10.1002/14356007.a02_099
Polat, K.; Aksu, M.L.; Pekel, A.T. (2002), "Electroreduction of nitrobenzene to p-aminophenol using voltammetric and semipilot scale preparative electrolysis techniques", Journal of Applied Electrochemistry, Kluwer Academic Publishers, 32: 217–223, doi:10.1023/A:1014725116051
Ellis, Frank (2002). Paracetamol: a curriculum resource. Cambridge: Royal Society of Chemistry. ISBN 0-85404-375-6.
Anthony S. Travis (2007). "Manufacture and uses of the anilines: A vast array of processes and products". In Zvi Rappoport (ed.). The chemistry of Anilines Part 1. Wiley. p. 764. ISBN 978-0-470-87171-3.
Elmar Friderichs; Thomas Christoph; Helmut Buschmann. "Analgesics and Antipyretics". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_269.pub2.

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[IUPAC2013_690-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 690. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[CRC97-2] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.

[crc-3] CRC Handbook of Chemistry and Physics 65th Ed.

[Mitchell_Waring-4] Mitchell, S.C. & Waring, R.H. "Aminophenols." In Ullmann’s Encyclopedia of Industrial Chemistry; 2002 Wiley-VCH, doi:10.1002/14356007.a02_099

[5] Polat, K.; Aksu, M.L.; Pekel, A.T. (2002), "Electroreduction of nitrobenzene to p-aminophenol using voltammetric and semipilot scale preparative electrolysis techniques", Journal of Applied Electrochemistry, Kluwer Academic Publishers, 32: 217–223, doi:10.1023/A:1014725116051

[6] Ellis, Frank (2002). Paracetamol: a curriculum resource. Cambridge: Royal Society of Chemistry. ISBN 0-85404-375-6.

[7] Anthony S. Travis (2007). "Manufacture and uses of the anilines: A vast array of processes and products". In Zvi Rappoport (ed.). The chemistry of Anilines Part 1. Wiley. p. 764. ISBN 978-0-470-87171-3.

[8] Elmar Friderichs; Thomas Christoph; Helmut Buschmann. "Analgesics and Antipyretics". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_269.pub2.