Isobenzane

Structural formula
General
Surname	Isobenzane
other names	Telodrin; 1,3,4,5,6,7,8,8-octachloro-1,3,3a, 4,7,7a-hexahydro-4,7-methanoisobenzofuran; 1,3,5,7,8,9,10,10-octachloro-4-oxatricyclo [5.2.1.0 2,6 ] dec-8-en ( IUPAC );
Molecular formula	C 9 H 4 Cl 8 O
Brief description	white solid
External identifiers / databases
EC number	206-045-4
ECHA InfoCard	100.005.497
PubChem	9271
ChemSpider	8914
Wikidata	Q6085351
properties
Molar mass	411.73 g mol −1
Physical state	firmly
density	1.87 g cm −3
Melting point	120-122 ° C; 122.2 ° C;
boiling point	> 210 ° C (decomposition)
Vapor pressure	0.39 mPa (20 ° C)
solubility	practically insoluble in water (0.1 g l −1 at 20 ° C); soluble in acetone , benzene , toluene , xylene and diethyl ether ;
safety instructions
H and P phrases	H: 300-310-400
	P: 264-273-280-301 + 310-302 + 350-310
Toxicological data	4.8 mg kg −1 ( LD 50 , rat , oral ) ; 12 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Isobenzane (Telodrin) is a highly toxic organochlorine compound that has an insecticidal effect. It was only made between 1958 and 1965. Use has been discontinued. It is a persistent organic pollutant that can remain in the soil for 2 to 7 years. The biological half-life of isobenzane in human blood is estimated to be around 2.8 years.

Presentation and extraction

The precursor 4,5,6,7,10,10-hexachloro-4,7-endomethylene-4,7,8,9-tetrahydrophthalane can be obtained by two synthetic routes. In a synthesis variant published in 1954, the 1,4,5,6,7,7-hexachloro-2,3-bishydroxymethylbicyclo [ 2, 2 ] is first obtained by reacting hexachlorocyclopentadiene with cis-1,4-dihydroxybut-2-ene . 2,1 ] hept-5-ene, which is then dehydrated to the precursor. In 1961, a direct preparation of the precursor via a Diels-Alder reaction with hexachlorocyclopentadiene and 2,5-dihydrofuran was found. The target compound is then synthesized by photochlorination of the precursor.

properties

Isobenzane forms colorless crystals that melt at 122.2 ° C. The enthalpy of fusion is 26.8 kJ mol ⁻¹ . The stereochemistry was examined by means of ¹ H-NMR spectroscopy and X-ray diffractometry , as well as an oxidative degradation. It could be shown here that the compound can be classified as exo-1, exo-3,4,5,6,7,8,8-octachloro-1,3,3a, 4,7,7a-hexahydro-endo-4,7 -methanoisobenzofuran is present. The compound crystallizes in a monoclinic crystal lattice with the space group C2 / c.

Individual evidence

↑ ^a ^b ^c ^d Environmental Health Criteria (EHC) for isobenzane , accessed December 22, 2017.
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on isobenzane in the GESTIS substance database of the IFA , accessed on December 22, 2017 (JavaScript required)
↑ ^a ^b ^c Plato, C .; Glasgow, AR, Jr .: Differential scanning calorimetry as a general method for determining the purity and heat of fusion of high-purity organic chemicals. Application to 95 compounds in Anal. Chem. 41 (1969) 330-336, doi : 10.1021 / ac60271a041 .
↑ ^a ^b ^c David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 97th edition. (Internet version: 2016), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compound, pp. 3-326 - 3-327.
↑ ^a ^b R.L. Metcalf: Insect Control , in: Ullmanns Enzyklopädie der Technischen Chemie , Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2012; doi : 10.1002 / 14356007.a14_263 .
↑ Entry on isobenzane in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 28, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Patent DE15324 (Ruhrchemie AG 1954).
↑ ^a ^b Patent US3000907 (Ruhrchemie AG 1961).
↑ Riemschneider, R .; Gallert, H .; Andres, P: Zur Chemie von Polyhalocyclopentadienes, 22. Mitt .: About the production of 1,4,5,6,7,7-Hexachlorbicyclo [2.2.1] hepten- (5) -bishydroxymethylene- (2,3) in Monthly Chem. 92 (1961) 1075-1079, doi : 10.1007 / BF00924776 .
↑ Patent DE1020346 (Ruhrchemie AG 1954).
↑ Feichtinger, H .; Linden, H.-W .: Telodrin, Its Synthesis and Derivatives in Chem. Ind. 79 (1965) 1938-1940.
↑ Feichtinger, H .; Linden, H.-W .: Friedel-Crafts reactions of 1-substituted 4.5.6.7.10.10-hexachloro-4.7-methylene-4.7.8.9-tetrahydrophthalane in Chem. Ber. 97 (1964) 2779-2784, doi : 10.1002 / cber.19640971009 .
^ Singer, H .; Ballschmiter, K .: H-NMR spectroscopic investigations on 1.3-disubstituted derivatives of 4.5.6.7.8.8-hexachloro-1.3.3a.4.7.7a-hexahydro-4.7-methano-isobenzofurans in Chem. Ber. 101 (1968) 17-23, doi : 10.1002 / cber.19681010104 .
↑ ^a ^b Feichtinger, H .; Linden, H.-W .; Singer, H .: On the knowledge of halogenated 4.7.8.9-tetrahydro-4.7-methano-phthalanes, IV. On the configuration of 1.3-disubstituted 4.5.6.7.10.10-hexachloro-4.7.8.9-tetrahydro-4.7-methano-phthalanes in Chem. Ber. 101 (1968) 2776-2784, doi : 10.1002 / cber.19681010823 .
↑ ^a ^b Smith, G .; Kennard, GHL: Insecticides. XIII. Crystal structure of isobenzane (exo-1, exo-3,4,5,6,7,8,8-octachloro-1,3,3a, 4,7,7a-hexahydro-endo-4,7-methanoisobenzofuran) in Austr. J. Chem. 30 (1977) 1117-1122, doi : 10.1071 / CH9771117 .

[INCHEM-1] Environmental Health Criteria (EHC) for isobenzane , accessed December 22, 2017.

[Gestis-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on isobenzane in the GESTIS substance database of the IFA , accessed on December 22, 2017 (JavaScript required)

[Plato-3] Plato, C .; Glasgow, AR, Jr .: Differential scanning calorimetry as a general method for determining the purity and heat of fusion of high-purity organic chemicals. Application to 95 compounds in Anal. Chem. 41 (1969) 330-336, doi : 10.1021 / ac60271a041 .

[CRC_Handbook-4] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 97th edition. (Internet version: 2016), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compound, pp. 3-326 - 3-327.

[Ullmann-5] R.L. Metcalf: Insect Control , in: Ullmanns Enzyklopädie der Technischen Chemie , Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2012; doi : 10.1002 / 14356007.a14_263 .

[CLP_100.005.497-6] Entry on isobenzane in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 28, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .

[7] Patent DE15324 (Ruhrchemie AG 1954).

[Ruhrchemie1-8] Patent US3000907 (Ruhrchemie AG 1961).

[Riemschneider-9] Riemschneider, R .; Gallert, H .; Andres, P: Zur Chemie von Polyhalocyclopentadienes, 22. Mitt .: About the production of 1,4,5,6,7,7-Hexachlorbicyclo [2.2.1] hepten- (5) -bishydroxymethylene- (2,3) in Monthly Chem. 92 (1961) 1075-1079, doi : 10.1007 / BF00924776 .

[10] Patent DE1020346 (Ruhrchemie AG 1954).

[Feichtinger1-11] Feichtinger, H .; Linden, H.-W .: Telodrin, Its Synthesis and Derivatives in Chem. Ind. 79 (1965) 1938-1940.

[Feichtinger2-12] Feichtinger, H .; Linden, H.-W .: Friedel-Crafts reactions of 1-substituted 4.5.6.7.10.10-hexachloro-4.7-methylene-4.7.8.9-tetrahydrophthalane in Chem. Ber. 97 (1964) 2779-2784, doi : 10.1002 / cber.19640971009 .

[Singer-13] Singer, H .; Ballschmiter, K .: H-NMR spectroscopic investigations on 1.3-disubstituted derivatives of 4.5.6.7.8.8-hexachloro-1.3.3a.4.7.7a-hexahydro-4.7-methano-isobenzofurans in Chem. Ber. 101 (1968) 17-23, doi : 10.1002 / cber.19681010104 .

[Feichtinger3-14] Feichtinger, H .; Linden, H.-W .; Singer, H .: On the knowledge of halogenated 4.7.8.9-tetrahydro-4.7-methano-phthalanes, IV. On the configuration of 1.3-disubstituted 4.5.6.7.10.10-hexachloro-4.7.8.9-tetrahydro-4.7-methano-phthalanes in Chem. Ber. 101 (1968) 2776-2784, doi : 10.1002 / cber.19681010823 .

[Smith-15] Smith, G .; Kennard, GHL: Insecticides. XIII. Crystal structure of isobenzane (exo-1, exo-3,4,5,6,7,8,8-octachloro-1,3,3a, 4,7,7a-hexahydro-endo-4,7-methanoisobenzofuran) in Austr. J. Chem. 30 (1977) 1117-1122, doi : 10.1071 / CH9771117 .