Crotonic acid
Crotonic acid
Names
Preferred IUPAC name
Other names
(E )-But-2-enoic acidE )-2-Butenoic acidtrans -2-Butenoic acid
Identifiers
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.213
UNII
InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2+
Y Key:
LDHQCZJRKDOVOX-NSCUHMNNSA-N
Y InChI=1/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2+
Key: LDHQCZJRKDOVOX-NSCUHMNNBH
Properties
C 4 H 6 O 2
Molar mass g·mol−1
Density 1.02 g/cm3
Melting point 70 to 73 °C (158 to 163 °F; 343 to 346 K)
Boiling point 185 to 189 °C (365 to 372 °F; 458 to 462 K)
Acidity (pK a )4.69 [ 1]
Hazards
Safety data sheet (SDS)SIRI.org
Related compounds
crotonate
propionic acid acrylic acid butyric acid succinic acid malic acid tartaric acid fumaric acid pentanoic acid tetrolic acid
Related compounds
butanol butyraldehyde crotonaldehyde 2-butanone 3-Butenoic acid
Except where otherwise noted, data are given for materials in their
standard state (at 25
°C [77
°F], 100
kPa).
Chemical compound
Crotonic acid ((2E )-but-2-enoic acid ) is a short-chain unsaturated carboxylic acid described by the formula CH3 CH=CHCO2 H. The name crotonic acid was given because it was erroneously thought to be a saponification product of croton oil .[ 2] cis -alkeneIsocrotonic acid is an isomer of crotonic acid. Crotonic acid is soluble in water and many organic solvents. Its odor is similar to that of butyric acid .
Use
Crotonic acid is mainly used as a comonomer with vinyl acetate.[ 14] adhesives .[ 4]
Crotonyl chloride reacts with N -ethyl-2-methylaniline (N -ethyl-o -toluidine) to provide crotamiton , which is used as an agent against scabies .[ 15]
Crotamiton synthesis Safety
Its LD50 is 1 g/kg (oral, rats).[ 4] [ 14]
References
↑ Dawson, R. M. C.; et al. (1959). Data for Biochemical Research . Oxford: Clarendon Press. ↑ Chisholm, Hugh , ed. (1911). "Crotonic Acid" Encyclopædia Britannica 7 (11th ed.). Cambridge University Press. p. 511.1 2 Beyer, Hans; Walter, Wolfgang (1984). Organische Chemie (in German). Stuttgart: S. Hirzel Verlag. ISBN 3-7776-0406-2 1 2 3 Schulz, R. P.; Blumenstein, J.; Kohlpaintner, C. (2005). "Crotonaldehyde and Crotonic Acid". Ullmann's Encyclopedia of Industrial Chemistry doi :10.1002/14356007.a08_083 . ISBN 978-3-527-30673-2 ↑ Rinne, A.; Tollens, B. (1871). "Ueber das Allylcyanür oder Crotonitril" [ On allyl cyanide or crotononitrile] . Justus Liebigs Annalen der Chemie 159 (1): 105– 109. doi :10.1002/jlac.18711590110 . ↑ Pomeranz, C. (1906). "Ueber Allylcyanid und Allylsenföl" [ On allyl cyanide and allylic mustard oil] . Justus Liebigs Annalen der Chemie 351 (1– 3): 354– 362. doi :10.1002/jlac.19073510127 . ↑ Beilstein, F. (1893). Handbuch der organischen Chemie 1 (3rd ed.). Verlag Leopold Voss. p. 506. ↑ Shimizu, S.; Kekka, S.; Kashino, S.; Haisa, M. (1974). "Topochemical Studies. III. The Crystal and Molecular Structures of Crotonic Acid, CH3 CH=CHCO2 H, and Crotonamide, CH3 CH=CHCONH2 " . Bulletin of the Chemical Society of Japan . 47 (7): 1627– 1631. doi :10.1246/bcsj.47.1627 1 2 3 4 Heilbron (1953). "Crotonic acid" . Dictionary of Organic Compounds . 1 : 615. ↑ Lovén, J. M.; Johansson, H. (1915). "Einige schwefelhaltige β-Substitutionsderivate der Buttersäure" [ Some sulfur-containing β-substitution derivatives of butyric acid] . Berichte der deutschen chemischen Gesellschaft 48 (2): 1254– 1262. doi :10.1002/cber.19150480205 . ↑ Clover, A. M.; Richmond, G. F. (1903). "The Hydrolysis of Organic Peroxides and Peracids" . American Chemical Journal 29 (3): 179– 203. ↑ Beilstein, F. (1893). Handbuch der organischen Chemie 1 (3rd ed.). Verlag Leopold Voss. p. 562. ↑ Carter, H. E.; West, H. D. (1955). "dl -Threonine" . Organic Syntheses ; Collected Volumes , vol. 3, p. 813. 1 2 Entry on Butensäuren . at: Römpp Online . Georg Thieme Verlag, retrieved January 7, 2020. ↑ Kleemann, A.; Engel, J. Pharmazeutische Wirkstoffe: Synthesen, Patente, Anwendungen . Vol. 5 (2nd rev. and updated ed.). Stuttgart & New York: Georg Thieme Verlag. p. 251. ISBN 3-13-558402-X
