n-Butyl Mercaptan
Structural Formula Vector Image
Title: n-Butyl Mercaptan
CAS Registry Number: 109-79-5
CAS Name: 1-Butanethiol
Additional Names: normal butyl thioalcohol; thiobutyl alcohol
Molecular Formula: C4H10S
Molecular Weight: 90.19
Percent Composition: C 53.27%, H 11.18%, S 35.55%
Line Formula: CH3(CH2)2CH2SH
Literature References: Formed by the action of yeast on a product obtained when hydrogen sulfide is made to react with butyraldehyde in alcoholic ammonia: Nord, Ber. 52, 1209 (1919); by passing vapors of butanol and hydrogen sulfide over thorium oxide catalyst: Kramer, Reid, J. Am. Chem. Soc. 43, 880 (1921); together with dibutyl sulfide in distilling an aq soln of sodium butyl sulfate and sodium sulfide: Gray, Gutekunst, J. Am. Chem. Soc. 42, 858 (1920); by slightly warming dithiocarbamic butyl ester with aq KOH: v. Braun, Engelbertz, Ber. 56, 1574 (1923); the sodium salt is formed when dibutyl disulfide is treated with sodium in ether or alcohol: Moses, Reid, J. Am. Chem. Soc. 48, 777 (1926). Physical properties: Mathias, ibid. 72, 1897 (1950); W. E. Haines et al., J. Phys. Chem. 60, 549 (1956). Once cited to occur in "skunk" fluid, see Beckmann, Pharm. Zentralhalle 37, 557 (1896); T. B. Aldrich, J. Exp. Med. 1, 323 (1896); however, recent literature rebuts this: K. K. Anderson, D. T. Bernstein, J. Chem. Ecol. 1, 493 (1975); eidem, J. Chem. Educ. 55, 159 (1978).
Properties: Mobile liquid. Heavy skunk odor. mp -115.9°. bp766 98.2°; bp760 98.4°. Flammable. d425 0.83679. nD25 1.44014. Slightly sol in water. Very sol in alcohol, ether, liquid hydrogen sulfide. Forms azeotropic mixtures with butyl alcohol (bp 97.8°; 85.16% butanethiol) and with butyl alcohol and water.
Melting point: mp -115.9°
Boiling point: bp766 98.2°; bp760 98.4°; Forms azeotropic mixtures with butyl alcohol (bp 97.8°; 85.16% butanethiol)
Index of refraction: nD25 1.44014
Density: d425 0.83679
CAUTION: Potential symptoms of overexposure are irritation of eyes, skin; muscle weakness, malaise, sweating, nausea, vomiting, headache, confusion. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 42.

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