1-Butanethiol

1-Butanethiol[1]
Names
	Preferred IUPAC name Butane-1-thiol
	Other names Butyl mercaptan; n-Butyl mercaptan; Thiobutyl alcohol; Mercaptobutane; n-Butanethiol; 1-Mercaptobutane
Identifiers
CAS Number	109-79-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	7721 ;
ECHA InfoCard	100.003.370
PubChem CID	8012;
UNII	77OY909F30 ;
CompTox Dashboard (EPA)	DTXSID6026824 ;
	InChI InChI=1S/C4H10S/c1-2-3-4-5/h5H,2-4H2,1H3 Key: WQAQPCDUOCURKW-UHFFFAOYSA-N ; InChI=1/C4H10S/c1-2-3-4-5/h5H,2-4H2,1H3 Key: WQAQPCDUOCURKW-UHFFFAOYAG;
	SMILES SCCCC;
Properties
Chemical formula	C4H10S
Molar mass	90.18 g·mol−1
Appearance	Clear liquid
Odor	cabbage-like, skunk-like, garlic-like[2]
Density	0.83679 g/mL
Melting point	−115.8 °C (−176.4 °F; 157.3 K)
Boiling point	98.2 °C (208.8 °F; 371.3 K)
Solubility in water	Slightly soluble (0.06% at 20°C)[2]
Vapor pressure	35 mmHg (20°C)[2]
Hazards
NFPA 704 (fire diamond)	2 3 0
Flash point	2 °C; 35 °F; 275 K[2]
	Lethal dose or concentration (LD, LC):
LC50 (median concentration)	4020 ppm (rat, 4 hr); 2500 ppm (mouse, 4 hr); 770 ppm (dog, 30 min)[3]
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 10 ppm (35 mg/m3)[2]
REL (Recommended)	C 0.5 ppm (1.8 mg/m3) [15-minute][2]
IDLH (Immediate danger)	500 ppm[2]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

1-Butanethiol, also known as butyl mercaptan, is a volatile, clear to yellowish liquid with a fetid (extremely foul-smelling) odor, commonly described as "skunk" odor. In fact, 1-butanethiol is structurally similar to several major constituents of a skunk's defensive spray but is not actually present in the spray.[4] The scent of 1-butanethiol is so strong that the human nose can easily detect it in the air at concentrations as low as 10 parts per billion. The threshold level for 1-butanethiol is reported as 1.4 ppb[5]

Chemistry

1-Butanethiol is chemically classified among the thiols, which are organic compounds with molecular formulas and structural formulas similar to alcohols, except that the sulfur-containing sulfhydryl group (-SH) replaces the oxygen-containing hydroxyl group (-OH) in the molecule. 1-Butanethiol's basic molecular formula is C₄H₉SH, and its structural formula is similar to that of the alcohol n-butanol. 1-Butanethiol is prepared by the free radical catalyzed addition of hydrogen sulfide to 1-butene. Commercially, this is performed using ultraviolet light. 1-Butanethiol is a thiol of low molecular weight, and it is highly flammable.

Uses

1-Butanethiol is used as an industrial solvent, and as an intermediate for cotton defoliants.[6] It is sometimes placed in the "stink bombs" and "stink perfumes" for pranksters.

Safety

1-Butanethiol is a very noxious and caustic chemical compound, and at sufficiently high concentrations, it produces serious health effects in both humans and animals, especially as a result of prolonged exposure. Higher concentrations can lead to unconsciousness and coma after prolonged exposure. Contact with the skin and mucous membranes causes burns, and contact with the eyes can lead to blurred vision or complete blindness.

Inhalation may cause weakness, confusion, cough, dizziness, drowsiness, headache, nausea, vomiting, and shortness of breath. The substance irritates the eyes, the skin, and the respiratory tract. It may cause effects on the thyroid and the nervous system and could cause lowering of consciousness.[7]

Notes

Merck Index, 12th Edition, 1611.
NIOSH Pocket Guide to Chemical Hazards. "#0083". National Institute for Occupational Safety and Health (NIOSH).
"n-Butyl mercaptan". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
Andersen K. K., Bernstein D. T. (1978). "1-Butanethiol and the Striped Skunk". Journal of Chemical Education. 55 (3): 159–160. Bibcode:1978JChEd..55..159A. doi:10.1021/ed055p159.
Devos, M; F. Patte; J. Rouault; P. Lafort; L. J. Van Gemert (1990). Standardized Human Olfactory Thresholds. Oxford: IRL Press. p. 34. ISBN 0199631468.
National Library of Medicine HSDB Database. "Merphos". National Library of Medicine. Retrieved 2012-05-17.
"n-BUTYL MERCAPTAN". International Chemical Safety Cards. National Institute for Occupational Safety and Health. Archived from the original on September 30, 2017. Retrieved January 11, 2012.

References

U.S. Department of Labor Archived 2017-09-30 at the Wayback Machine
The Good Scents Company
HazMap

External links

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[1] Merck Index, 12th Edition, 1611.

[PGCH-2] NIOSH Pocket Guide to Chemical Hazards. "#0083". National Institute for Occupational Safety and Health (NIOSH).

[3] "n-Butyl mercaptan". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[4] Andersen K. K., Bernstein D. T. (1978). "1-Butanethiol and the Striped Skunk". Journal of Chemical Education. 55 (3): 159–160. Bibcode:1978JChEd..55..159A. doi:10.1021/ed055p159.

[5] Devos, M; F. Patte; J. Rouault; P. Lafort; L. J. Van Gemert (1990). Standardized Human Olfactory Thresholds. Oxford: IRL Press. p. 34. ISBN 0199631468.

[6] National Library of Medicine HSDB Database. "Merphos". National Library of Medicine. Retrieved 2012-05-17.

[7] "n-BUTYL MERCAPTAN". International Chemical Safety Cards. National Institute for Occupational Safety and Health. Archived from the original on September 30, 2017. Retrieved January 11, 2012.