P-Nitrofenoli

p-Nitrofenoli
Tunnisteet
IUPAC-nimi 4-nitrofenoli
CAS-numero 100-02-7
PubChem CID 980
SMILES C1=CC(=CC=C1[N+](=O)[O-])O[1]
Ominaisuudet
Molekyylikaava C6H5NO3
Moolimassa 139,11 g/mol
Sulamispiste 114,9–115,6 °C[2]
Kiehumispiste 279 °C[2]
Tiheys 1,479 g/cm3[2]
Liukoisuus veteen Veteen 12,4 g/l (20 °C)[3]

p-Nitrofenoli eli 4-nitrofenoli (C6H5NO3) on fenolin nitrattuihin johdannaisiin kuuluva orgaaninen yhdiste. Yhdistettä voidaan käyttää muiden orgaanisten yhdisteiden valmistuksessa lähtöaineena ja analyyttisessä kemiassa pH-indikaattorina. p-Nitrofenoli on o- ja m-nitrofenolien isomeeri.

Ominaisuudet

Huoneenlämpötilassa p-nitrofenoli on väritöntä tai keltaista kiteistä ainetta. p-Nitrofenolilla on kaksi kiderakenteeltaan eroavaa muotoa: α- ja β-muodot. Yhdiste liukenee hieman viileään veteen ja paremmin lämpimään. Aine liukenee hyvin muun muassa etanoliin, dietyylieetteriin, kloroformiin ja emäksisiin vesiliuoksiin. p-Nitrofenolin pKa-arvo on 7,15 eli se on heikko happo. Yhdiste on kuitenkin fenolia voimakkaampi happo, mikä johtuu nitroryhmän aiheuttamasta elektroneja puoleensavetävästä induktiivisestä efektistä. Lisäksi nitroryhmä konjugoituneena bentseenirenkaaseen lisää mahdollisuuksia eri resonanssimuotoihin, mikä stabiloi rakennetta. p-Nitrofenolin etanoliliuoksen muuttavat väriään värittömästä keltaiseksi pH:n ollessa välillä 5,6–7,6.[2][4][5][6][7][8] p-Nitrofenoli on myrkyllistä ja ärsyttää voimakkaasti ihoa, silmiä ja hengitysteitä. Aineelle altistuminen voi johtaa methemoglobiinin muodostumiseen veressä, mikä ilmenee ihon sinistymisenä.[3]

Valmistus ja käyttö

p-Nitrofenolia voidaan valmistaa kahdelle tavalla. Nämä ovat fenolin nitraus tai p-kloorinitrobentseenin hydrolyysi emäksisissä olosuhteissa.[4][7][9]

p-Nitrofenolia voidaan käyttää pH-indikaattorina. Siitä valmistetaan useita muita yhdisteitä kuten lääkkeinä käytettäviä amodiakiinia ja rilutsolia, maatalouskemikaaleja kuten parationia sekä väriaineita ja niiden valmistuksessa käytettäviä yhdisteitä kuten p-aminofenolia ja rikkivärejä.[4][6][7][9]

Lähteet

  1. ↑ 4-Nitrophenol – Substance summary PubChem. NCBI. Viitattu 26.8.2016.
  2. ↑ a b c d Alén, Raimo: Kokoelma orgaanisia yhdisteitä: Ominaisuudet ja käyttökohteet, s. 210. Helsinki: Consalen Consulting, 2009. ISBN 978-952-92-5627-3
  3. ↑ a b p-Nitrofenolin kansainvälinen kemikaalikortti Viitattu 26.8.2016
  4. ↑ a b c Gerald Booth: Nitro Compounds, Aromatic, Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, New York, 2000. Viitattu 26.8.2016
  5. ↑ Ram W. Sabnis, Erwin Ross, Jutta Köthe, Renate Naumann, Wolfgang Fischer, Wilhelm-Dietrich Mayer, Gerhard Wieland, Ernest J. Newman & Charles M. Wilson: Indicator Reagents, Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, New York, 2009. Viitattu 26.8.2016
  6. ↑ a b Susan Budavari (päätoim.): Merck Index, s. 1137-1138. (12th Edition) Merck & Co., 1996. ISBN 0911910-12-3 (englanniksi)
  7. ↑ a b c Thomas Scott, Mary Eagleson: Concise encyclopedia chemistry, s. 700. Määritä julkaisija! (englanniksi)
  8. ↑ Joseph M. Hornback: Organic Chemistry, s. 124. Cengage Learning, 2005. ISBN 978-0534389512 Kirja Googlen teoshaussa Viitattu 26.8.2016. (englanniksi)
  9. ↑ a b Robert D. Ashford: Ashford's Dictionary of Industrial Chemicals, s. 802. (2nd Edition) Wavelength Publications, 2001. ISBN 0-9522674-2-X (englanniksi)

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