Bromaceton

Bromaceton
Strukturní vzorec
Strukturní vzorec
Model molekuly
Model molekuly
Obecné
Systematický název1-brompropan-2-on
Funkční vzorecCH2BrC(O)CH3
Sumární vzorecC3H5BrO
Vzhledbezbarvá kapalina
Identifikace
Registrační číslo CAS598-31-2
PubChem11715
ChEBI51845
SMILESBrCC(=O)C
InChIInChI=1/C3H5BrO/c1-3(5)2-4/h2H2,1H3
Vlastnosti
Molární hmotnost136,98 g/mol
Teplota tání−36,5 °C (236,6 K)
Teplota varu137 °C (410 K)
Hustota1,634 g/cm3
Tlak páry1,1 kPa (20 °C)
Bezpečnost
GHS02 – hořlavé látky
GHS02
GHS06 – toxické látky
GHS06
GHS07 – dráždivé látky
GHS07
[1]
Nebezpečí[1]
Není-li uvedeno jinak, jsou použity
jednotky SI a STP (25 °C, 100 kPa).
Některá data mohou pocházet z datové položky.

Bromaceton (systematický název 1-brompropan-2-on) je organická sloučenina se vzorcem CH3C(O)CH2Br. Používá se na přípravu dalších organických látek.

Výskyt

Bromaceton se (v koncentracích pod 1 %) vyskytuje v mořské řase Asparagopsis taxiformis rostoucí v okolí Havajských ostrovů.[2]

Výroba

Bromaceton je komerčně dostupný, často bývá stabilizován oxidem hořečnatým.

Vyrábí se reakcí acetonu s bromem v kyselém prostředí.[3] Aceton se, podobně jako ostatní ketony, za přítomnosti kyseliny či zásady přeměňuje na enol. Na alfa uhlík se následně elektrofilní substitucí naváže brom; přitom může dojít k přebromování, kdy se naváže více atomů bromu, než je potřeba, čímž vznikají dibromované a tribromované produkty. V zásaditém prostředí se tvoří bromoform, jelikož dojde k haloformové reakci.[4]

Použití

Bromaceton se v první světové válce používal jako chemická zbraň. V organické syntéze se používá například na přípravu hydroxyacetonu.[5]

Odkazy

Související články

Externí odkazy

  • Logo Wikimedia Commons Obrázky, zvuky či videa k tématu Bromaceton na Wikimedia Commons

Reference

V tomto článku byl použit překlad textu z článku Bromoacetone na anglické Wikipedii.

  1. ↑ a b Bromoacetone. pubchem.ncbi.nlm.nih.gov [online]. PubChem [cit. 2021-05-24]. Dostupné online. (anglicky) 
  2. ↑ B. J. Burreson; R. E. Moore; P. P. Roller. Volatile halogen compounds in the alga Asparagopsis taxiformis (Rhodophyta). Journal of Agricultural and Food Chemistry. 1976, s. 856–861. 
  3. ↑ LEVENE, P. A. Bromoacetone. Org. Synth.. 1930, s. 12. Dostupné online. ; Coll. Vol.. S. 88. 
  4. ↑ W. Reusch. Virtual Textbook of Organic Chemistry [online]. Michigan State University, 5.5. 2013 [cit. 2007-10-27]. Kapitola Carbonyl Reactivity. Dostupné v archivu pořízeném z originálu dne 21.6. 2010. 
  5. ↑ LEVENE, P. A.; WALTI, A. Acetol. Org. Synth.. 1930, s. 1. Dostupné online. ; Coll. Vol.. S. 5. 

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