1,3-Dihloropropen

1,3-Dihloropropen
Nazivi
	IUPAC naziv 1,3-dihloroprop-1-en
	Sistemski IUPAC naziv 1-Propen, 1,3-dihloro-, (1E)-
	Drugi nazivi AQL Agrocelhon, DD92, 1,3-D, Dorlon, Nematox, Telon, Nemex, cis-Dihloropropen, Di-Trapex CP, Vorlex 201, dihloro-1,3-propen, 1,3-dihloro-1-propen, 1,3-dihloro-2-propen, alfa-hloroalilhlorid, hloroalilhlorid, gama-hloroalilhlorid, hloroalil hlorid, hloropropenil hlorid, 1,3-dihloropropilen, 3-D, DCP, 3-hloroalil hlorid
Identifikacija
CAS broj	542-75-6 ;
3D model (Jmol)	interaktivna slika;
ChEBI	CHEBI:18918 ;
ChemSpider	23117 ;
ECHA InfoCard	100.008.024
KEGG	C18627 ;
PubChem C ID	24726;
UNII	9H780918D0 ;
	SMILES ClC\C=C\Cl; ; ; ; ; ;
Svojstva
Hemijska formula	C3H4Cl2
Molarna masa	110,970
	Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa).
	Reference infokutije

1,3-Dihloropropen je organohlorno jedinjenje, koje je u prodaji pod mnoštvom naziva. On je bezbojna tečnost prijatnog mirisa. Ovaj materijal se rastvara u vodi i lako isparava. On se uglavnom koristi u poljoprivredi kao pesticid, specifično kao presetveni fumigant i nematicid. Početak njegove poljoprivredne primene datira iz 1950-tih godina. On je u šikoroj upotrebi u SAD i nizu drugih zemlja. U Evropskoj uniji je u toku proces izvođenja iz upotrebe ovag materijala.^[4]

Proizvodnja i biodegradacija

1,3-Dihloropropen je nusproizvod hlorinacije propena pri pravljenju alil hlorida.^[5]

On se obično dobija kao smeša geometrijskih izomera, zvanih Z-1,3-dihloropropen, i E-1,3-dihloropropen. Poznata su dva puta biodegradacije ovog materijala. Jedan od njih je degradacija hlorougljenika do acetaldehida preko hloroakrilne kiseline.^[6]

Bezbednost

TLV-TWA za 1,3-dihloropropen (DCP) je 1 ppm.^[7] On je kontaktni iritant. Poznat je širok opseg komplikacija.^[8]

Karcinogenost

Evidencija karcinogenosti 1,3-dihloropropena kod ljudi je neadekvatna, mada rezultati nekoliko testova raka pružaju adedekvatne dokaze karcinogenosti kod životinja. U SAD je Ministarstvo za Zdravstvo utvrdilo da se može očekivati da je 1,3-dihloropropen karcinogen. Internacionalna agencija za istraživanje raka (IARC) je ustanovila da je moguće da je 1,3-dihloropropen karcinogen kod ljudi. EPA agencija klasifikuje 1,3-dihloropropen kao mogući ljudski karcinogen.^[8]

Osobine

1,3-Dihloropropen je organsko jedinjenje, koje sadrži 3 atoma ugljenika i ima molekulsku masu od 110,970 Da.

Osobina	Vrednost
Broj akceptora vodonika	0
Broj donora vodonika	0
Broj rotacionih veza	1
Particioni koeficijent^[9] (ALogP)	1,5
Rastvorljivost^[10] (logS, log(mol/L))	-1,7
Polarna površina^[11] (PSA, Å²)	0,0

Reference

^ Joanne Wixon; Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast. 17 (1): 48—55. doi:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
^ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди
^ Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.
^ COMMISSION DECISION of 20 September 2007 concerning the non-inclusion of 1,3-dichloropropene in Annex I to Council Directive 91/414/EEC and the withdrawal of authorisations for plant protection products containing that substance, Official Journal of the European Union, 25 September 2007.
^ Krähling, Ludger; Krey, Jürgen; Jakobson, Gerald; Grolig, Johann; Miksche, Leopold (2000). „Allyl Compounds”. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 9783527303854. doi:10.1002/14356007.a01_425.
^ Poelarends, Gerrit J.; Whitman, Christian P. (2004). „Evolution of enzymatic activity in the tautomerase superfamily: Mechanistic and structural studies of the 1,3-dichloropropene catabolic enzymes”. Bioorganic Chemistry. 32 (5): 376—392. PMID 15381403. doi:10.1016/j.bioorg.2004.05.006.
^ Metcalf, Robert L. (2000). „Insect Control”. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 9783527303854. doi:10.1002/14356007.a14_263.
^ ^а ^б Toxic Substances Portal - Dichloropropenes
^ Ghose, A.K.; Viswanadhan V.N. & Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A. 102: 3762—3772. doi:10.1021/jp980230o.
^ Tetko IV, Tanchuk VY, Kasheva TN, Villa AE (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 1488—1493. PMID 11749573. doi:10.1021/ci000392t.
^ Ertl P.; Rohde B.; Selzer P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties”. J. Med. Chem. 43: 3714—3717. PMID 11020286. doi:10.1021/jm000942e.

Literatura

Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (I изд.). Oxford University Press. ISBN 978-0-19-850346-0.
Smith, Michael B.; March, Jerry (2007). Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th изд.). New York: Wiley-Interscience. ISBN 0-471-72091-7.
Katritzky A.R.; Pozharskii A.F. (2000). Handbook of Heterocyclic Chemistry (Second изд.). Academic Press. ISBN 0080429882.

Spoljašnje veze

[1] Joanne Wixon; Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast. 17 (1): 48—55. doi:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[2] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди

[3] Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.

[4] COMMISSION DECISION of 20 September 2007 concerning the non-inclusion of 1,3-dichloropropene in Annex I to Council Directive 91/414/EEC and the withdrawal of authorisations for plant protection products containing that substance, Official Journal of the European Union, 25 September 2007.

[Ullmann-5] Krähling, Ludger; Krey, Jürgen; Jakobson, Gerald; Grolig, Johann; Miksche, Leopold (2000). „Allyl Compounds”. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 9783527303854. doi:10.1002/14356007.a01_425.

[6] Poelarends, Gerrit J.; Whitman, Christian P. (2004). „Evolution of enzymatic activity in the tautomerase superfamily: Mechanistic and structural studies of the 1,3-dichloropropene catabolic enzymes”. Bioorganic Chemistry. 32 (5): 376—392. PMID 15381403. doi:10.1016/j.bioorg.2004.05.006.

[Ullmann2-7] Metcalf, Robert L. (2000). „Insect Control”. Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. ISBN 9783527303854. doi:10.1002/14356007.a14_263.

[atsdr.cdc.gov-8] а ^б Toxic Substances Portal - Dichloropropenes

[9] Ghose, A.K.; Viswanadhan V.N. & Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A. 102: 3762—3772. doi:10.1021/jp980230o.

[10] Tetko IV, Tanchuk VY, Kasheva TN, Villa AE (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 1488—1493. PMID 11749573. doi:10.1021/ci000392t.

[11] Ertl P.; Rohde B.; Selzer P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties”. J. Med. Chem. 43: 3714—3717. PMID 11020286. doi:10.1021/jm000942e.

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