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词条 3-Aminophenol
释义

  1. Preparation

  2. Uses

  3. References

{{chembox
| Watchedfields = changed
| verifiedrevid = 477218126
| Reference =[1]
| ImageFileL1 =M-Aminophenol.svg
| ImageFileR1 = 3-Aminophenol-3D-spacefill.png
| ImageAltR1 = 3-Aminophenol molecule
| PIN = 3-Aminophenol
| OtherNames = m-Aminophenol (no longer recommended[2])
3-Hydroxyaniline
m-Hydroxyaniline
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 11080
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = L3WTS6QT82
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C05058
| InChI = 1/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2
| InChIKey = CWLKGDAVCFYWJK-UHFFFAOYAM
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 269755
| ChEMBL2_Ref = {{ebicite|correct|EBI}}
| ChEMBL2 = 376136
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CWLKGDAVCFYWJK-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =591-27-5
| PubChem =11568
| EINECS = 209-711-2
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28924
| SMILES = Oc1cccc(N)c1
}}
|Section2={{Chembox Properties
| Formula =C6H7NO
| MolarMass =109.13 g/mol
| Appearance = White orthorhombic crystals
| Density = 1.195 g/cm3
| MeltingPtC = 120 to 124
| MeltingPt_notes =
| BoilingPtC = 164
| BoilingPt_notes = at 11 mmHg
| Solubility =
| pKa = {{ubl
| 4.37 (amino; 20 °C, H2O)
| 9.82 (phenol; 20 °C, H2O)[3]
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
| RPhrases ={{R20/22}} {{R51/53}}
| SPhrases ={{S28}} {{S61}}
}}

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

1. ^3-Aminophenol at Sigma-Aldrich.
2. ^{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 690 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = 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. ^{{cite book | editor= Haynes, William M. | year = 2016 | title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = CRC Press | isbn = 978-1498754286 | page=5–89 | title-link = CRC Handbook of Chemistry and Physics }}
4. ^{{cite journal|last1=Mitchell|first1=Stephen C.|last2=Waring|first2=Rosemary H.|title=Aminophenols|journal=Ullmann's Encyclopedia of Industrial Chemistry|date=2000|doi=10.1002/14356007.a02_099}}
5. ^{{cite web|last1=Harada|first1=Haruhisa|last2=Hiroshi|first2=Maki|last3=Sasaki|first3=Shigeru|title=Method for the production of m-aminophenol EP0197633A1|date=1986|url=http://www.google.com/patents/EP0197633A1?cl=en|website=Google Patents|publisher=Sumitomo Chemical Company, Limited|accessdate=3 February 2015}}
{{DEFAULTSORT:Aminophenol, 3-}}

2 : Anilines|Phenols

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