1-chloro-2-butene

Structural formula
	Structural formula of ( E ) -1-chloro-2-butene (= trans form)
General
Surname	1-chloro-2-butene
other names	1-chlorobut-2-ene; Crotyl chloride;
Molecular formula	C 4 H 7 Cl
Brief description	colorless liquid with a pungent odor
External identifiers / databases
EC number	209-739-5
ECHA InfoCard	100,008,855
PubChem	11589
Wikidata	Q14757784
properties
Molar mass	90.55 g mol −1
Physical state	liquid
density	0.93 g cm −3 ; 0.9426 g cm −3 ( cis ); 0.9295 g cm −3 ( trans );
Melting point	−65 ° C
boiling point	84 ° C ( cis ); 85 ° C ( trans );
Vapor pressure	494 mbar (20 ° C)
solubility	slightly soluble in water (14 g l −1 at 20 ° C); soluble in ethanol and acetone;
Refractive index	1.430 (20 ° C); 1.439 ( cis ); 1.435 ( trans );
safety instructions
H and P phrases	H: 225-302-332-314-317-412
	P: 210-280-305 + 351 + 338-310
	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-chloro-2-butene (also called crotyl chloride ) is a chemical compound from the group of unsaturated aliphatic organic chlorinated hydrocarbons .

Isomers

1-Chloro-2-butene occurs in two isomeric forms, the ( E ) form (= trans form) and the ( Z ) form (= cis form).

Isomers of 1-chloro-2-butene
Surname	(2 E ) -1-chloro-2-butene	(2 Z ) -1-chloro-2-butene
other names	trans -1-chloro-2-butene	cis -1-chloro-2-butene
Structural formula
CAS number	4894-61-5	4628-21-1
	591-97-9 (unspec.)
EC number	225-516-5	225-041-3
	209-739-5 (unspec.)
ECHA info card	100.023.196	100.022.765
	100.008.855 (unspec.)
PubChem	637923	5463237
	11589 (unspec.)
Wikidata	Q22829214	Q27276414
	Q14757784 (unspec.)

Extraction and presentation

1-Chloro-2-butene can be obtained by reacting methylallyl alcohol with thionyl chloride . The pure isomers can be prepared by chlorine rearrangement of the corresponding alcohols via Ph ₃ P in various solvents. The compound can also be obtained by reacting crotyl alcohol with phosphorus trichloride in the presence of pyridine .

properties

1-chloro-2-butene is a very volatile, easily flammable, colorless liquid with a pungent odor that is sparingly soluble in water.

use

1-Chloro-2-butene is used to study the reactions of atomic chlorine with a number of unsaturated aldehydes and ketones and to make ( E ) -crotyltrichlorosilanes.

safety instructions

The vapors of 1-chloro-2-butene can form an explosive mixture with air ( flash point –12 ° C, ignition temperature 510 ° C).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 1-chloro-2-butene in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f ^g William M. Haynes: CRC Handbook of Chemistry and Physics, 94th Edition . CRC Press, 2013, ISBN 978-1-4665-7115-0 , pp. 102 ( limited preview in Google Book search).
↑ ^a ^b Data sheet Crotyl chloride, technical from Sigma-Aldrich , accessed on September 19, 2015 ( PDF ).
↑ Gurdeep Raj: Organic Name Reactions Reagents and Molecular Rearrangements . Krishna Prakashan Media, 2013, ISBN 978-81-8283-672-3 , pp. A-18 ( limited preview in Google Book search).
↑ Crotyl Chloride In: e-EROS Encyclopedia of Reagents for Organic Synthesis - D'Angelo - Wiley Online Library, doi: 10.1002 / 047084289X.rc254 .
^ Lewis F. Hatch, Stuart S. Nesbitt: Allylic Chlorides. IX. Preparation of cis and trans Crotyl Chloride. In: Journal of the American Chemical Society . 72, 1950, p. 727, doi: 10.1021 / ja01158a021 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 1-chloro-2-butene in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

[William_M._Haynes-2] ↑ ^a ^b ^c ^d ^e ^f ^g William M. Haynes: CRC Handbook of Chemistry and Physics, 94th Edition . CRC Press, 2013, ISBN 978-1-4665-7115-0 , pp. 102 ( limited preview in Google Book search).

[Sigma-3] Data sheet Crotyl chloride, technical from Sigma-Aldrich , accessed on September 19, 2015 ( PDF ).

[Gurdeep_Raj-4] Gurdeep Raj: Organic Name Reactions Reagents and Molecular Rearrangements . Krishna Prakashan Media, 2013, ISBN 978-81-8283-672-3 , pp. A-18 ( limited preview in Google Book search).

[wiley.com-5] Crotyl Chloride In: e-EROS Encyclopedia of Reagents for Organic Synthesis - D'Angelo - Wiley Online Library, doi: 10.1002 / 047084289X.rc254 .

[DOI10.1021/ja01158a021-6] Lewis F. Hatch, Stuart S. Nesbitt: Allylic Chlorides. IX. Preparation of cis and trans Crotyl Chloride. In: Journal of the American Chemical Society . 72, 1950, p. 727, doi: 10.1021 / ja01158a021 .