3-klooripropaanihappo

3-klooripropaanihappo
Tunnisteet
CAS-numero 107-94-8
PubChem CID 7899
SMILES C(CCl)C(=O)O[1]
Ominaisuudet
Molekyylikaava C3H5ClO2
Moolimassa 108,52 g/mol
Sulamispiste 42 °C[2]
Kiehumispiste 204 °C (hajoaa)[2]
Liukoisuus veteen liukenee hyvin veteen

3-klooripropaanihappo eli 3-klooripropionihappo (C3H5ClO2) on halogenoituihin karboksyylihappoihin kuuluva orgaaninen yhdiste. Yhdistettä voidaan käyttää orgaanisen kemian synteeseissä valmistettaessa lääkkeitä ja muita kemikaaleja. 3-klooripropaanihappo on 2-klooripropaanihapon isomeeri.

Ominaisuudet

Huoneenlämpötilassa 3-klooripropaanihappo on värittömiä hygroskooppisia kiteitä. Yhdiste liukenee erittäin hyvin veteen, etanoliin ja kloroformiin ja vähäisemmässä määrin dietyylieetteriin. 3-klooripropaanihappo on muiden karboksyylihappojen tavoin heikko happo. Yhdisteen happovakio on 1,01 · 10−4 mol/dm3 ja pKa-arvo on 3,99. Vahvuudeltaan se on siis muurahaishapon luokkaa.[3][4][5]

3-klooripropaanihappo kykenee sitoutumaan GABA-reseptoreihin. Tämä johtuu todennäköisesti siitä, että polarisoitunut hiilen ja kloorin välinen sidos vuorovaikuttaa reseptorien kanssa ja klooriatomi toimii vetysidoksen vastaanottajana sitoutuessaan reseptoriin.[6]

Valmistus ja käyttö

Tyypillisimmin 3-klooripropaanihappoa valmistetaan käsittelemällä akryylihappoa vetykloridilla 40–45 °C:n lämpötilassa tai klooramalla propaanihappoa kloorilla UV-valon aktivoimana noin 20 °C:n lämpötilassa.[3] Muita yhdisteen syntetisointitapoja ovat 3-klooripropanaldehydin tai trimetyleenikloorihydriinin hapetus typpihapon avulla tai etyleenisyanohydriinin hydrolyysi vetykloridiliuoksessa[4].

3-klooripropaanihappoa käytetään valmistettaessa lääkeaineita kuten beklamidia tai oksolamiinia. Siitä valmistetaan myös 3-merkaptopropionaattiestereitä, joita käytetään muovien stabilisaattoreina.[3]

Lähteet

  1. ↑ 3-Chloropropanoic acid – Substance summary PubChem. NCBI. Viitattu 1.9.2015.
  2. ↑ a b Alén, Raimo: Kokoelma orgaanisia yhdisteitä: Ominaisuudet ja käyttökohteet, s. 361. Helsinki: Consalen Consulting, 2009. ISBN 978-952-92-5627-3
  3. ↑ a b c Ulf-Rainer Samel, Walter Kohler, Armin Otto Gamer, Ullrich Keuser, Shang-Tian Yang, Ying Jin, Meng Lin & Zhongqiang Wang: Propionic Acid and Derivatives, Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, New York, 2014. Viitattu 1.9.2015
  4. ↑ a b Susan Budavari (päätoim.): Merck Index, s. 360. (12th Edition) Merck & Co., 1996. ISBN 0911910-12-3 (englanniksi)
  5. ↑ Michael B. Smith: Organic Chemistry, s. 207. CRC Press, 2011. ISBN 9781420079203 Kirja Googlen teoshaussa (viitattu 1.9.2015). (englanniksi)
  6. ↑ Alba T Macias, R.Jason Hernandez, Ashok K Mehta, Alexander D MacKerell Jr., Maharaj K Ticku & Andrew Coop: 3-Chloropropanoic acid (UMB66): a ligand for the gamma-hydroxybutyric acid receptor lacking a 4-hydroxyl group. Bioorganic & Medicinal Chemistry, 2004, 12. vsk, nro 7, s. 1643–1647. Artikkelin verkkoversio. Viitattu 1.9.2015. (englanniksi)

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