3-Aminophenol

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title: "3-Aminophenol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["aminophenols"] topic_path: "general/aminophenols" source: "https://en.wikipedia.org/wiki/3-Aminophenol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 477218126 | Reference = | ImageFileL1 =M-Aminophenol.svg | ImageFileR1 = 3-Aminophenol-3D-spacefill.png | ImageAltR1 = 3-Aminophenol molecule | PIN = 3-Aminophenol | OtherNames = m-Aminophenol meta-Aminophenol 3-Hydroxyaniline m-Hydroxyaniline meta-Hydroxyaniline |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 11080 | UNII_Ref = | UNII = L3WTS6QT82 | KEGG_Ref = | KEGG = C05058 | Gmelin = 2913 | Beilstein = 636059 | RTECS = SJ4900000 | UNNumber = 2512 | InChI = 1/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2 | InChIKey = CWLKGDAVCFYWJK-UHFFFAOYAM | ChEMBL_Ref = | ChEMBL = 269755 | ChEMBL2_Ref = | ChEMBL2 = 376136 | StdInChI_Ref = | StdInChI = 1S/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2 | StdInChIKey_Ref = | StdInChIKey = CWLKGDAVCFYWJK-UHFFFAOYSA-N | CASNo_Ref = | CASNo =591-27-5 | PubChem =11568 | EINECS = 209-711-2 | ChEBI_Ref = | ChEBI = 28924 | SMILES = Oc1cccc(N)c1 |Section2={{Chembox Properties | C=6 | H=7 | N=1 | O=1 | Appearance = White orthorhombic crystals | Density = 1.195 g/cm3 | MeltingPtC = 120 to 124 | MeltingPt_notes = | BoilingPtC = 164 | BoilingPt_notes = at 11 mmHg | Solubility = | pKa = {{Unbulleted list | 4.37 (amino; 20 °C, H2O) | 9.82 (phenol; 20 °C, H2O) |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | GHSPictograms = | GHSSignalWord = Warning | HPhrases = | PPhrases = | NFPA-H = 2 | NFPA-F = 0 | NFPA-R = 0 | NFPA-S =

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) or from resorcinol via a substitution reaction with ammonium hydroxide.

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.

References

References

  1. "3-Aminophenol". [[Sigma-Aldrich]].
  2. (2014). "Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
  3. (2016). "CRC Handbook of Chemistry and Physics". [[CRC Press]].
  4. (2000). "Aminophenols". Ullmann's Encyclopedia of Industrial Chemistry.
  5. (1986). "Method for the production of m-aminophenol EP0197633A1". Sumitomo Chemical Company, Limited.

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aminophenols