6595. 3-Nitrocinnamic Acid

Nomenclature

CAS number: 555-68-0
3-(3-Nitrophenyl)-2-propenoic acid; 3-nitrobenzenepropenoic acid; 3-(3-nitrophenyl)acrylic acid.
C9H7NO4; mol wt 193.16.
C 55.96%, H 3.65%, N 7.25%, O 33.13%.

Description and 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).

Chemical structure

Derivative

(E)-Form.

Nomenclature

CAS number: 1772-76-5

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°.

Derivative

(Z)-Form.

Nomenclature

CAS number: 5676-61-9

Description and 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.