3-Aminophenol

3-Aminophenol[1]
3-Aminophenol molecule
Names
Preferred IUPAC name
3-Aminophenol[2]
Other names
m-Aminophenol
meta-Aminophenol
3-Hydroxyaniline
m-Hydroxyaniline
meta-Hydroxyaniline
Identifiers
3D model (JSmol)
636059
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.830
EC Number
  • 209-711-2
2913
KEGG
RTECS number
  • SJ4900000
UNII
UN number 2512
  • InChI=1S/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2 checkY
    Key: CWLKGDAVCFYWJK-UHFFFAOYSA-N checkY
  • InChI=1/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2
    Key: CWLKGDAVCFYWJK-UHFFFAOYAM
  • Oc1cccc(N)c1
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)
  • 4.37 (amino; 20 °C, H2O)
  • 9.82 (phenol; 20 °C, H2O)[3]
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H332, H411
P261, P264, P270, P271, P273, P301+P312, P304+P312, P304+P340, P312, P330, P391, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

3-Aminophenol is an organic compound with formula C6H4(NH2)(OH). It is an aromatic amine and a phenol. It is the meta isomer of 2-aminophenol and 4-aminophenol.

Preparation

3-Aminophenol is prepared by reduction of 3-nitrophenol. It can also 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, which is used 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

  1. ^ "3-Aminophenol". Sigma-Aldrich.
  2. ^ 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.
  3. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
  4. ^ a b Mitchell, Stephen C.; Waring, Rosemary H. (2000). "Aminophenols". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a02_099. ISBN 9783527303854.
  5. ^ 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.
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