Oxalic acid bis (2,4,6-trichlorophenyl ester)

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Structural formula
Structure of oxalic acid bis (2,4,6-trichlorophenyl ester)
General
Surname Oxalic acid bis (2,4,6-trichlorophenyl ester)
other names
  • TCPO
  • Bis (2,4,6-trichlorophenyl) oxalate
Molecular formula C 14 H 4 Cl 6 O 4
Brief description

beige powder

External identifiers / databases
CAS number 1165-91-9
EC number 629-336-1
ECHA InfoCard 100.157.526
PubChem 160567
Wikidata Q3359026
properties
Molar mass 448.9 g mol −1
Physical state

firmly

density

1.703 g cm −3

Melting point

192 ° C

safety instructions
GHS labeling of hazardous substances
07 - Warning

danger

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Oxalic acid bis (2,4,6-trichlorophenyl ester) , abbreviated to TCPO , is a chemical compound , a di-ester of oxalic acid , which emits light when fluorescent dyes are present. Together with a weak base , hydrogen peroxide and the dye that determines the color, peroxyoxalate chemiluminescence occurs .

Extraction

TCPO is obtained from a mixture of 2,4,6-trichlorophenol , toluene and a base such as triethylamine at less than 10 ° C. and subsequent reaction with oxalyl chloride.

use

Of marketed light sticks chemical-based use aromatic Oxalsäureester as TCPO and DNPO . TCPO lights up longer, but weaker than DNPO. The addition of weakly basic catalysts (e.g. sodium salicylate , triethylamine ) increases the glow of TCPO at the expense of the lighting duration. Scientifically, the compound is used to recognize fluorescent compounds in liquid chromatography and protein or DNA bands in membranes.

Individual evidence

  1. ↑ a b c d data sheet bis (2,4,6-trichlorophenyl) oxalate from Sigma-Aldrich , accessed on April 24, 2013 ( PDF ).
  2. ^ Carl L. Yaws: Thermophysical Properties of Chemicals and Hydrocarbons . William Andrew, 2008, ISBN 0-08-094774-3 , pp. 267 .
  3. ↑ a b Chemical encyclopedia - entry on oxalic acid bis (2,4,6-trichlorophenyl ester) (TCPO) ( Memento from May 7, 2012 in the Internet Archive )
  4. ^ Dieter Wöhrle, Michael W. Tausch, Wolf-Dieter Stohrer: Photochemistry . John Wiley & Sons, 2012, ISBN 3-527-66107-7 , pp. 474 ( limited preview in Google Book search).
  5. ^ Philip E. Stanley, Larry J. Kricka: Bioluminescence and Chemiluminescence . World Scientific, 2002, ISBN 981-277-662-1 , pp. 343 ( limited preview in Google Book search).

Web links