9353. Thiophene

Nomenclature

CAS number: 110-02-1
Thiofuran; thiofurfuran; thiole; thiotetrole; divinylene sulfide.
C4H4S; mol wt 84.14.
C 57.10%, H 4.79%, S 38.11%.

Description and references

Found in coal tar, in coal gas, and in technical benzene: V. Meyer, Ber. 16, 1471 (1883); 17, 2642 (1884). Made available in commercial quantities by a process utilizing the dehydrogenation of butane with sulfur as the dehydrogenating agent, followed by cyclization with sulfur to form the thiophene ring: Rasmussen, Ray, Chem. Inds. 60, 593, 620 (1947). Laboratory prepn by heating sodium succinate with phosphorus trisulfide: R. Phillips, Org. Synth. coll. vol. II, 578 (1943). Also prepd by passing ethylene or acetylene into boiling sulfur; or by passing acetylene and hydrogen sulfide over hot bauxite or nickel hydroxide: US 1421743 C.A. 16, 3093 (1922). Review: B. Buchholz in Kirk-Othmer Encyclopedia of Chemical Technology vol. 22 (Wiley-Interscience, New York, 3rd ed., 1983) pp 965-973.

Chemical structure

Properties

Liquid. Slight aromatic odor resembling that of benzene. Flammable. d40 1.0873; d425 1.0573; d450 1.0285. mp 38.3°. bp760 84.4°; bp400 64.7°; bp200 46.5°; bp100 30.5°; bp60 20.1°; bp40 12.5°; bp20 0.0°; bp10 10.9°; bp5 20.8°; nD25 1.52684. Absorption spectrum: Purvis, J. Chem. Soc. 97, 1653, 1656 (1910). Insol in water; miscible with most organic solvents. May be heated to 850° without decompn.

Use

Solvent similar to benzene, but suitable for lower and higher temps; manuf of resins from thiophene-phenol mixtures and formaldehyde; manuf of dyes and pharmaceuticals.