1,3-dichloroacetone

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Structural formula
1,3-dichloroacetone.svg
General
Surname 1,3-dichloroacetone
other names
  • 1,3-dichloro-2-propanone ( IUPAC )
  • Bis (chloromethyl) ketone
  • Symmetrical dichloroacetone
Molecular formula C 3 H 4 Cl 2 O
Brief description
  • colorless crystals
  • light brown crystals with a pungent odor
External identifiers / databases
CAS number 534-07-6
EC number 208-585-6
ECHA InfoCard 100.007.806
PubChem 10793
ChemSpider 21106513
Wikidata Q4917164
properties
Molar mass 126.97 g mol −1
Physical state

firmly

density

1.383 g cm −3 (46 ° C)

Melting point

39-43 ° C

boiling point

172.6-173 ° C

Vapor pressure

<0.1 mm Hg (20 ° C)

solubility

little in water (27.9 g l −1 at 20 ° C)

safety instructions
GHS labeling of hazardous substances
06 - Toxic or very toxic 08 - Dangerous to health 05 - Corrosive

danger

H and P phrases H: 300 + 310 + 330-314-341
P: 260-280-301 + 310 + 330-303 + 361 + 353-304 + 340 + 310-305 + 351 + 338
Toxicological data

20 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,3-dichloroacetone is a dichlorinated derivative of acetone . Like other halogenated acetones, it belongs to the group of chlorinated ketones .

properties

1,3-Dichloroacetone is in the form of colorless white crystals at room temperature . It is very soluble in alcohol or diethyl ether . According to Antoine, the vapor pressure function results from log 10 (P) = A− (B / (T + C)) (P in bar, T in K) with A = 4.90009, B = 1937.489 and C = −49.092 in the temperature range from 348 to 445 K. The heat of vaporization is 49.6 kJ · mol −1 . 1,3-dichloroacetone only forms flammable vapor-air mixtures at higher temperatures. The compound has a flash point of 95 ° C, the ignition temperature is 590 ° C.

use

1,3-dichloroacetone is used as the starting material for the production of cyclopropanols and cyclopropanones .

safety instructions

1,3-dichloroacetone is very toxic; it is also absorbed through the skin. In addition to the toxic effect, contact with skin or eyes also causes considerable irritation and even chemical burns.

Individual evidence

  1. ↑ a b Hans-Joachim Teuber, Günther Schütz, Eberhard Erkenbrecher: Vinylogous guanidines of the pyrroline series made from “dimeric” chloroacetonitrile. In: Archives of Pharmacy . 313, 1980, pp. 851-858, doi : 10.1002 / ardp.19803131007 .
  2. ↑ a b c d e f g h i Entry on 1,3-dichloroacetone in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
  3. ↑ Data sheet 1,3-dichloroacetone from Sigma-Aldrich , accessed on November 14, 2014 ( PDF ).
  4. ↑ David O Hagan, Jeffrey White, David A. Jones: Efficient routes to isotopically labeled epichlorohydrins ((chloromethyl) oxiranes). In: Journal of Labeled Compounds and Radiopharmaceuticals . 34, 1994, pp. 871-880, doi : 10.1002 / jlcr.2580340908 .
  5. ↑ Theodor Posner, Karl Rohde: About the so-called pseudo-dichloroacetone, an alleged isomer of the symmetrical dichloroacetone. In: Reports of the German Chemical Society. 42, 1909, pp. 3233-3242, doi : 10.1002 / cber.19090420349 .
  6. ↑ a b E. D. Smith, WL Thornsberry: Characterization data for chloroacetone, 1,1-dichloroacetone, and 1,3-dichloroacetone . In Journal of Chemical & Engineering Data 15 (1970) 296-297, doi : 10.1021 / je60045a002 .
  7. ↑ RM Stephenson, S. Malanowski: Handbook of the Thermodynamics of Organic Compounds , Springer 1987, ISBN 978-94-010-7923-5 , doi : 10.1007 / 978-94-009-3173-2 .
  8. ↑ a b Entry on 1,3-dichloro-2-propanone. In: Römpp Online . Georg Thieme Verlag, accessed on November 16, 2014.