3-Aminophenol

3-Aminophenol^[1]

Names

Preferred IUPAC name

3-Aminophenol

Other names

m-Aminophenol (no longer recommended^[2])
3-Hydroxyaniline
m-Hydroxyaniline

Identifiers

CAS Number

591-27-5^Y

3D model (JSmol)

Interactive image

ChEBI

CHEBI:28924^Y

ChemSpider

11080^Y

209-711-2

C05058^Y

PubChem CID

11568

UNII

L3WTS6QT82^Y

InChI

InChI=1S/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2^Y
Key: CWLKGDAVCFYWJK-UHFFFAOYSA-N^Y
InChI=1/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2
Key: CWLKGDAVCFYWJK-UHFFFAOYAM

SMILES

Oc1cccc(N)c1

Properties

Chemical formula

C₆H₇NO

Molar mass

109.13 g/mol

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 (pK_a)

4.17; 9.87

Hazards

R-phrases (outdated)

R20/22 R51/53

S-phrases (outdated)

S28 S61

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

verify (what is ^YN ?)

Infobox references

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)^[3] or from resorcinol via a substitution reaction with ammonium hydroxide.^[4]

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.^[3]

References

↑ 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. ISBN 978-0-85404-182-4. doi:10.1039/9781849733069-FP001. 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.
1 2 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.

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