1-chloropropene

Structural formula
	Structural formulas of the trans isomer (left) and the cis isomer (right)
General
Surname	1-chloropropene
other names	1-chloroprop-1-en; 1-chloro-1-propene; Propenyl chloride;
Molecular formula	C 3 H 5 Cl
Brief description	colorless to yellowish liquid
External identifiers / databases
EC number	209-675-8
ECHA InfoCard	100,008,797
PubChem	5284364
Wikidata	Q61702553
properties
Molar mass	76.52 g mol −1
Physical state	liquid
density	0.9347 g cm −3 ( cis ); 0.9349 g cm −3 ( trans );
Melting point	−134.8 ° C ( cis ); −99 ° C ( trans );
boiling point	32.8 ° C ( cis ); 37.4 ° C ( trans );
Vapor pressure	675.8 hPa (25 ° C)
solubility	almost insoluble in water; soluble in ethanol and acetone ;
Refractive index	1.4055 (20 ° C, cis ); 1.4054 (20 ° C, trans );
safety instructions
H and P phrases	H: 225-302-315-319
	P: 210-270-280-302 + 352-332 + 313-362 + 364-305 + 351 + 338-337 + 313-370 + 378
Toxicological data	1950 mg kg −1 ( LD 50 , rat , oral ) ; 18,400 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 . Refractive index: Na-D line , 20 ° C

1-chloropropene is a chemical compound from the group of chlorinated alkenes .

Isomerism

1-Chloropropene occurs in two isomeric forms of the cis form [synonym: ( Z ) form] and the trans form [synonym: ( E ) form]. If “1-chloropropene” is mentioned in the scientific literature or in this article without reference to the cis or trans form, an unspecified mixture of cis and trans forms is meant. Structural isomers of 1-chloropropene are 2-chloropropene and 3-chloropropene (= allyl chloride).

Extraction and presentation

1-chloropropene is formed when hydrogen chloride is added to propyne . With a yield of 33%, the compound can be prepared by hydrogenation of 1,3-dichloropropane in cyclohexane at 100 ° C and 30-40 atm with an aluminum - or rhodium catalyst are presented.

It is formed as the main product from 1,1-dichloropropane with ethanolic potassium hydroxide solution.

properties

1-chloropropene is a very volatile, easily flammable, colorless to yellowish liquid that is practically insoluble in water.

use

1-chloropropene can be used to make propyne .

safety instructions

1-chloropropene forms highly flammable vapor-air mixtures. The compound has a flash point of 0 ° C. The explosion range is between 4.5% by volume as the lower explosion limit (LEL) and 16% by volume as the upper explosion limit (UEL). The compound was characterized as carcinogenic in long-term animal experiments .

literature

Beilstein Syst. No. 10: H, p. 198 .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on 1-chloropropene, cis, trans in the GESTIS substance database of the IFA , accessed on February 12, 2019(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k David R. Lide: CRC Handbook of Chemistry and Physics, 84th Edition . CRC Press, 2003, pp. 122 ( limited preview in Google Book search).
↑ Entry on 1-Propenyl Chloride (cis- and trans- mixture) at TCI Europe, accessed on February 12, 2019.
^ Daniel Bellus, Manfred Braun, Tonia Freysoldt, Richard Göttlich, Jens Hartung, Monica Härtinger, Stefan Härtinger, Paul Margaretha, Wolf-Diethard Pfeiffer, Kathrin-Maria Roy, Karola Rück-Braun, Ernst Schaumann, Theodor Troll, Henri Ulrich: Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol ... - Daniel Bellus, Manfred Braun, Tonia Freysoldt, Richard Göttlich, Jens Hartung, Monica Härtinger, Stefan Härtinger, Paul Margaretha, Wolf-Diethard Pfeiffer, Kathrin-Maria Roy, Karola Rück-Braun, Ernst Schaumann, Theodor Troll, Henri Ulrich . Georg Thieme Verlag, 2014, p. 117 ( limited preview in Google Book search).
^ Calvin L. Stevens, Carl R. Johnson, Don C. de Jongh, Norman A. Lebel, Norman L. Allinger, Michael P. Cava: Gnichtel, Horst: Organische Chemie. [Main volume] Walter de Gruyter, 1980, p. 641 ( limited preview in Google Book search).
^ Dietrich Henschler: Toxicology of organochlorine compounds . John Wiley & Sons, 2008, ISBN 3-527-62421-X , pp. 34 ( limited preview in Google Book search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on 1-chloropropene, cis, trans in the GESTIS substance database of the IFA , accessed on February 12, 2019(JavaScript required) .

[David_R._Lide-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k David R. Lide: CRC Handbook of Chemistry and Physics, 84th Edition . CRC Press, 2003, pp. 122 ( limited preview in Google Book search).

[3] Entry on 1-Propenyl Chloride (cis- and trans- mixture) at TCI Europe, accessed on February 12, 2019.

[Daniel_Bellus,_Manfred_Braun,_Tonia_Freysoldt,_Richard_Göttlich,_Jens_Hartung,_Monica_Härtinger,_Stefan_Härtinger,_Paul_Margaretha,_Wolf-Diethard_Pfeiffer,_Kathrin-Maria_Roy,_Karola_Rück-Braun,_Ernst_Schaumann,_Theodor_Troll,_Henri_Ulrich-4] Daniel Bellus, Manfred Braun, Tonia Freysoldt, Richard Göttlich, Jens Hartung, Monica Härtinger, Stefan Härtinger, Paul Margaretha, Wolf-Diethard Pfeiffer, Kathrin-Maria Roy, Karola Rück-Braun, Ernst Schaumann, Theodor Troll, Henri Ulrich: Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol ... - Daniel Bellus, Manfred Braun, Tonia Freysoldt, Richard Göttlich, Jens Hartung, Monica Härtinger, Stefan Härtinger, Paul Margaretha, Wolf-Diethard Pfeiffer, Kathrin-Maria Roy, Karola Rück-Braun, Ernst Schaumann, Theodor Troll, Henri Ulrich . Georg Thieme Verlag, 2014, p. 117 ( limited preview in Google Book search).

[Calvin_L._Stevens,_Carl_R._Johnson,_Don_C._de_Jongh,_Norman_A._Lebel,_Norman_L._Allinger,_Michael_P._Cava-5] Calvin L. Stevens, Carl R. Johnson, Don C. de Jongh, Norman A. Lebel, Norman L. Allinger, Michael P. Cava: Gnichtel, Horst: Organische Chemie. [Main volume] Walter de Gruyter, 1980, p. 641 ( limited preview in Google Book search).

[Dietrich_Henschler-6] Dietrich Henschler: Toxicology of organochlorine compounds . John Wiley & Sons, 2008, ISBN 3-527-62421-X , pp. 34 ( limited preview in Google Book search).