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Butane-1-thiol

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Butane-1-thiol
Skeletal formula
Ball-and-stick model
3D-stick model
Names
Preferred IUPAC name Butane-1-thiol
Other names Butyl mercaptan
n-Butyl mercaptan
Thiobutyl alcohol
Mercaptobutane
n-Butanethiol
1-Mercaptobutane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.370 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H10S/c1-2-3-4-5/h5H,2-4H2,1H3Key: WQAQPCDUOCURKW-UHFFFAOYSA-N
  • InChI=1/C4H10S/c1-2-3-4-5/h5H,2-4H2,1H3Key: WQAQPCDUOCURKW-UHFFFAOYAG
SMILES
  • SCCCC
Properties
Chemical formula C4H10S
Molar mass 90.18 g·mol
Appearance Clear liquid
Odor cabbage-like, skunk-like, garlic-like
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)
Vapor pressure 35 mmHg (20°C)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 3 0
Flash point 2 °C; 35 °F; 275 K
Lethal dose or concentration (LD, LC):
LC50 (median concentration) 4020 ppm (rat, 4 hr)
2500 ppm (mouse, 4 hr)
770 ppm (dog, 30 min)
NIOSH (US health exposure limits):
PEL (Permissible) TWA 10 ppm (35 mg/m)
REL (Recommended) C 0.5 ppm (1.8 mg/m)
IDLH (Immediate danger) 500 ppm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Butane-1-thiol, 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. 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

Chemistry

Butane-1-thiol 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

Butane-1-thiol is used as an industrial solvent, and as an intermediate for cotton defoliants. It is sometimes placed in "stink bombs" and "stink perfumes" for pranksters.

Safety

Butane-1-thiol 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.

See also

Notes

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

References

External links

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