Chlorbenzotrifluoride

Chlorbenzotrifluoride
Name 2-Chlorbenzotrifluorid 3-Chlorbenzotrifluorid 4-Chlorbenzotrifluorid
Andere Namen o-Chlorbenzotrifluorid
2-Chlor-α,α,α-trifluortoluol
o-Chlor-α,α,α-trifluortoluol
1-Chlor-2-(trifluormethyl)benzol 		m-Chlorbenzotrifluorid
3-Chlor-α,α,α-trifluortoluol
m-Chlor-α,α,α-trifluortoluol
1-Chlor-3-(trifluormethyl)benzol 		p-Chlorbenzotrifluorid
4-Chlor-α,α,α-trifluortoluol
p-Chlor-α,α,α-trifluortoluol
1-Chlor-4-(trifluormethyl)benzol
Strukturformel
CAS-Nummer 88-16-4 98-15-7 98-56-6
ECHA-InfoCard 100.001.641 100.002.403 100.002.438
PubChem 6921 7374 7394
Summenformel C7H4ClF3
Molare Masse 180,56 g·mol−1
Aggregatzustand flüssig
Kurzbeschreibung gelbliche, entzündliche Flüssigkeit[1] farblose, entzündliche Flüssigkeit mit aromatischem Geruch[2][3]
Schmelzpunkt −6 °C[1] −55,4 °C[2] −36 °C[3]
Siedepunkt 152 °C[1] 137–138 °C[2] 139 °C[3]
Dichte 1,37 g·cm−3 (20 °C)[1] 1,336 g·cm−3 (25 °C)[2] 1,35 g·cm−3 (20 °C)[3]
Dampfdruck 5 hPa (20 °C)[1] 8,5 hPa (20 °C)[2] 10,2 hPa (25 °C)[3]
Löslichkeit praktisch unlöslich in Wasser[1][2][3]
GHS-
Kennzeichnung
Gefahrensymbol Gefahrensymbol
Achtung[1]
Gefahrensymbol
Achtung[2]
Gefahrensymbol Gefahrensymbol

Gefahrensymbol
Achtung[3]
H- und P-Sätze 226​‐​302​‐​315​‐​319​‐​335 226​‐​412 226​‐​317​‐​411
keine EUH-Sätze keine EUH-Sätze keine EUH-Sätze
210​‐​261​‐​280​‐​301+312
302+352​‐​305+351+338 		keine P-Sätze 210​‐​273​‐​280​‐​333+313​‐​391​‐​403+235
LD50 oral Ratte > 5.000 mg·kg−1[4] > 5.000–13.000 mg·kg−1[5]

Chlorbenzotrifluoride sind chemische Verbindungen aus der Gruppe der halogenierten Benzolderivate.

Gewinnung und Darstellung

Chlorbenzotrifluoride können durch Chlorierung von Benzotrifluorid und anschließende Destillation des Isomerengemisches gewonnen werden. 4-Chlorbenzotrifluorid wird auch durch Reaktion von 4-Chlorbenzotrichlorid und Fluorwasserstoff gewonnen.

Verwendung

Chlorbenzotrifluoride werden als Zwischenprodukte bei der Herstellung von Schädlingsbekämpfungsmitteln, Farb- und Arzneistoffen (z. B. Tetrachlorbenzotrifluorid) verwendet. So wird z. B. 4-Chlorbenzotrifluorid zur Herstellung von Dinitroanilin-Herbiziden wie Trifluralin. 4-Chlorbenzotrifluorid wird auch als dielektrische Flüssigkeit und als Lösungsmittel eingesetzt.[5]

Sicherheitshinweise

Die Dämpfe von Chlorbenzotrifluoriden können mit Luft beim Erhitzen über ihren Flammpunkt (40–60 °C) hinaus ein explosionsfähiges Gemisch bilden.[1][2][3]

Einzelnachweise

  1. ↑ a b c d e f g h Eintrag zu CAS-Nr. 88-16-4 in der GESTIS-Stoffdatenbank des IFA, abgerufen am 27. Dezember 2019. (JavaScript erforderlich)
  2. ↑ a b c d e f g h Eintrag zu CAS-Nr. 98-15-7 in der GESTIS-Stoffdatenbank des IFA, abgerufen am 27. Dezember 2019. (JavaScript erforderlich)
  3. ↑ a b c d e f g h Eintrag zu CAS-Nr. 98-56-6 in der GESTIS-Stoffdatenbank des IFA, abgerufen am 27. Dezember 2019. (JavaScript erforderlich)
  4. ↑ Toxikologische Bewertung von m-Chlorbenzotrifluorid (PDF) bei der Berufsgenossenschaft Rohstoffe und chemische Industrie (BG RCI), abgerufen am 22. August 2012.
  5. ↑ a b Toxikologische Bewertung von p-Chlorbenzotrifluorid (PDF) bei der Berufsgenossenschaft Rohstoffe und chemische Industrie (BG RCI), abgerufen am 22. August 2012.

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