3-Aminophenol
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Names | |||
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Preferred IUPAC name
3-Aminophenol[2] | |||
Other names
m-Aminophenol
meta-Aminophenol 3-Hydroxyaniline m-Hydroxyaniline meta-Hydroxyaniline | |||
Identifiers | |||
3D model (JSmol)
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636059 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
EC Number |
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2913 | |||
KEGG | |||
PubChem CID
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RTECS number |
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UNII | |||
UN number | 2512 | ||
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Properties | |||
C6H7NO | |||
Molar mass | 109.128 g·mol−1 | ||
Appearance | White orthorhombic crystals | ||
Density | 1.195 g/cm3 | ||
Melting point | 120 to 124 °C (248 to 255 °F; 393 to 397 K) | ||
Boiling point | 164 °C (327 °F; 437 K) at 11 mmHg | ||
Acidity (pKa) |
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Hazards | |||
GHS labelling: | |||
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Warning | |||
H302, H332, H411 | |||
P261, P264, P270, P271, P273, P301+P312, P304+P312, P304+P340, P312, P330, P391, P501 | |||
NFPA 704 (fire diamond) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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3-Aminophenol is an organic compound with formula C6H4(NH2)(OH). It is an aromatic amine and aromatic alcohol. It is the meta isomer of 2-aminophenol and 4-aminophenol.
Preparation
3-Aminophenol can be prepared by caustic fusion of 3-aminobenzenesulfonic acid (i.e. heating with NaOH to 245 °C for 6 hours)[4] or from resorcinol via a substitution reaction with ammonium hydroxide.[5]
Uses
One of the most relevant applications of the substance is the synthesis of 3-(diethylamino)phenol, key intermediate for the preparation of several fluorescent dyes (e.g., rhodamine B). Other uses for the compound include hair dye colorants and stabilizers for chlorine-containing thermoplastics.[4]
References
- ^ [https://www.sigmaaldrich.com/US/en/product/aldrich/100242 |ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC 3-Aminophenol] at Sigma-Aldrich.
- ^ 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.
Only one name is retained, phenol, for C6H5-OH, both as a preferred name and for general nomenclature. The structure is substitutable at any position. Locants 2, 3, and 4 are recommended, not o, m, and p.
- ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
- ^ a b Mitchell, Stephen C.; Waring, Rosemary H. (2000). "Aminophenols". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a02_099.
- ^ Harada, Haruhisa; Hiroshi, Maki; Sasaki, Shigeru (1986). "Method for the production of m-aminophenol EP0197633A1". Google Patents. Sumitomo Chemical Company, Limited. Retrieved 3 February 2015.