Isocrotonic Acid
Title: Isocrotonic Acid
CAS Registry Number: 503-64-0
CAS Name: (2Z)-2-Butenoic acid
Additional Names: cis-2-butenoic acid; cis-crotonic acid
Molecular Formula: C4H6O2
Molecular Weight: 86.09
Percent Composition: C 55.81%, H 7.02%, O 37.17%
Line Formula: CH3CH=CHCOOH
Literature References: Prepd by reacting acetaldehyde with malonic acid in the presence of pyridine: v. Auwers et al., Ann. 432, 46 (1923); from ethyl acetoacetate: Hatch, Nesbitt, J. Am. Chem. Soc. 72, 727 (1950); from but-2-ynoic acid: Allan et al., J. Chem. Soc. 1955, 1862; from CH3CH=CHMgBr + CO2: Normant, Maitte, Bull. Soc. Chim. Fr. 1956, 1439. Structure: v. Auwers, Wissebach, Ber. 56, 715 (1923); Plisov, Bogatskii, Zh. Obshch. Khim. 27, 360 (1957), C.A. 51, 15401c (1957). Review: W. Blau et al., in Ullmann's Encyclopedia of Industrial Chemistry vol. A8 (VCH, Weinheim, 5th ed., 1987) pp 83-89.
Properties: Liquid. bp5 55-56°; bp10 62-64°; bp760 168-169°. mp 15°; crystallized from pentane. d420 1.0267. nD14 1.4483. nD20 1.4450. uv max (95% ethanol): 205.5 nm (e 13500).
Melting point: mp 15°
Boiling point: bp5 55-56°; bp10 62-64°; bp760 168-169°
Index of refraction: nD14 1.4483; nD20 1.4450
Absorption maximum: uv max (95% ethanol): 205.5 nm (e 13500)
Density: d420 1.0267
 
Derivative Type: Methyl ester
Molecular Formula: C5H8O2
Molecular Weight: 100.12
Percent Composition: C 59.98%, H 8.05%, O 31.96%
Properties: Liquid. bp 118°. nD20 1.4175. uv max (95% ethanol): 205.5 nm (e 14000).
Boiling point: bp 118°
Index of refraction: nD20 1.4175
Absorption maximum: uv max (95% ethanol): 205.5 nm (e 14000)
 
Derivative Type: Benzyl ester
Molecular Formula: C11H12O2
Molecular Weight: 176.21
Percent Composition: C 74.98%, H 6.86%, O 18.16%
Properties: Liquid. bp10 121-122°. nD20 1.5110.
Boiling point: bp10 121-122°
Index of refraction: nD20 1.5110
 
CAUTION: Can cause severe irritation of skin, mucous membranes.

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