Crotonic acid methyl ester

Structural formula
General
Surname	Crotonic acid methyl ester
other names	Methyl crotonate
Molecular formula	C 5 H 8 O 2
Brief description	colorless liquid with a pungent odor
External identifiers / databases
EC number	210-793-7
ECHA InfoCard	100.009.813
PubChem	638132
Wikidata	Q1141622
properties
Molar mass	100.12 g mol −1
Physical state	liquid
density	0.94 g cm −3
Melting point	−42 ° C
boiling point	118-120 ° C
solubility	practically insoluble in water
Refractive index	1.423 (20 ° C)
safety instructions
H and P phrases	H: 225-319
	P: 210-305 + 351 + 338-370 + 378-403 + 235
	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

Crotonic acid methyl ester is an unsaturated carboxylic acid ester with a trans -substituted carbon-carbon double bond. The isomeric cis compound is of little importance.

Historical

The scientific investigation of crotonic acid methyl ester was first reported in 1879 by G. Kahlbaum .

presentation

Crotonic acid methyl ester can be prepared by passing hydrogen chloride into a solution of crotonic acid in methanol .

The esterification can also be catalyzed by sulfuric acid.

Reactions

Crotonic acid methyl ester reacts with sodium methoxide to form the methyl ester of 3-methoxybutyric acid.

Individual evidence

↑ ^a ^b ^c ^d Entry on methyl crotonate in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ ^a ^b ^c Data sheet Methyl crotonate from Sigma-Aldrich , accessed on June 3, 2011 ( PDF ).
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-344.
↑ ^a ^b G. WA Kahlbaum: About some methyl esters from the propionic acid and butyric acid group . In: Reports of the German Chemical Society . 12, 1879, pp. 343-344. ( Digitized on Gallica )
^ Association of authors: Organikum , 19th edition, Johann Ambrosius Barth, Leipzig · Berlin · Heidelberg 1993, ISBN 3-335-00343-8 , pp. 420-421.
^ F. Beilstein: Handbook of organic chemistry , 3rd edition, 1st volume. Verlag Leopold Voss, 1893. P. 561. ( full text )

[GESTIS-1] Entry on methyl crotonate in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[Sigma-2] Data sheet Methyl crotonate from Sigma-Aldrich , accessed on June 3, 2011 ( PDF ).

[CRC90_3_344-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-344.

[Kahlbaum-4] G. WA Kahlbaum: About some methyl esters from the propionic acid and butyric acid group . In: Reports of the German Chemical Society . 12, 1879, pp. 343-344. ( Digitized on Gallica )

[ORGANIKUM_19_420-5] Association of authors: Organikum , 19th edition, Johann Ambrosius Barth, Leipzig · Berlin · Heidelberg 1993, ISBN 3-335-00343-8 , pp. 420-421.

[Beilstein-6] F. Beilstein: Handbook of organic chemistry , 3rd edition, 1st volume. Verlag Leopold Voss, 1893. P. 561. ( full text )