m-Nitrocinnamic Acid
Title: m-Nitrocinnamic Acid
CAS Registry Number: 555-68-0
CAS Name: 3-(3-Nitrophenyl)-2-propenoic acid
Molecular Formula: C9H7NO4
Molecular Weight: 193.16
Percent Composition: C 55.96%, H 3.65%, N 7.25%, O 33.13%
Line Formula: NO2C6H4CH=CHCOOH
Literature References: Prepd by heating a mixture of m-nitrobenzaldehyde, sodium acetate and acetic anhydride: Thayer, Org. Synth. 5, 83 (1925). From m-nitrobenzaldehyde and malonic acid in the presence of glycine in a little water at 100°: Dakin, J. Biol. Chem. 7, 54 (1909-1910).
Derivative Type: trans-Form
Properties: Prepd by the above methods. White needles from benzene or alcohol. mp 200-201°. Can be sublimed or distilled at atmospheric press. with very little decompn. Absorption spectrum: Purvis, J. Chem. Soc. 107, 971 (1906). One gram dissolves in ~100 ml alcohol at 25°.
Melting point: mp 200-201°
Derivative Type: cis-Form
Literature References: Prepd by ultraviolet irradiation of a soln in water-alcohol-ammonia giving a 22% yield: Wollring, Ber. 47, 112 (1914).
Properties: Minute needles from toluene + methanol, mp 158°. By reirradiation of a chloroform soln containing a trace of bromine, the more stable trans-form is regenerated.
Melting point: mp 158°

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