Butane-1-thiol
{{Short description|Organosulfur compound (C4H9SH)}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 443492557
| Reference = Merck Index, 12th Edition, 1611.
| ImageFile = 1-Butanethiol.svg
| ImageSize = 180px
| ImageName = Skeletal formula
| ImageFile1 = 1-Butanethiol-3D-balls.png
| ImageName1 = Ball-and-stick model
| ImageFile2 = 1-Butanethiol-3D-sticks-by-AHRLS-2012.png
| ImageName2 = 3D-stick model
| PIN = Butane-1-thiol
| OtherNames = Butyl mercaptan
n-Butyl mercaptan
Thiobutyl alcohol
Mercaptobutane
n-Butanethiol
1-Mercaptobutane
|Section1={{Chembox Identifiers
| Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7721
| InChIKey = WQAQPCDUOCURKW-UHFFFAOYAG
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H10S/c1-2-3-4-5/h5H,2-4H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WQAQPCDUOCURKW-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 109-79-5
| EINECS =
| PubChem = 8012
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 77OY909F30
| SMILES = SCCCC
| InChI = 1/C4H10S/c1-2-3-4-5/h5H,2-4H2,1H3
}}
|Section2={{Chembox Properties
| C=4 | H=10 | S=1
| Appearance = colorless liquid
| Odor = cabbage-like, skunk-like, garlic-like
| Density = 0.83679 g/mL
| MeltingPtC = -115.8
| MeltingPt_notes =
| BoilingPtC = 98.2
| BoilingPt_notes =
| Solubility = Slightly soluble (0.06% at 20°C)
| SolubleOther =
| Solvent =
| pKa =
| VaporPressure = 35 mmHg (20°C)
}}
|Section7={{Chembox Hazards
| MainHazards =
| NFPA-H = 2
| NFPA-F = 3
| NFPA-R = 0
| NFPA-S =
| FlashPtF = 35
| AutoignitionPt =
| ExploLimits =
| PEL = TWA 10 ppm (35 mg/m3){{PGCH|0083}}
| REL = C 0.5 ppm (1.8 mg/m3) [15-minute]
| LC50 = 4020 ppm (rat, 4 hr)
2500 ppm (mouse, 4 hr)
770 ppm (dog, 30 min){{IDLH|109795| n-Butyl mercaptan}}
}}
}}
Butane-1-thiol, also known as butyl mercaptan, is an organosulfur compound with the formula {{chem2|CH3CH2CH2CH2SH}}. It is classified as a thiol. It is a volatile, colorless liquid with a fetid (extremely foul-smelling) odor, commonly described as "skunk" odor. In fact, 1-butanethiol is structurally similar to several constituents of a skunk's defensive spray but is not present in the spray.{{cite journal |journal=Journal of Chemical Education |volume= 55 |issue= 3 |year= 1978 |title=1-Butanethiol and the Striped Skunk |author= Andersen K. K., Bernstein D. T. |doi=10.1021/ed055p159|pages = 159–160 |bibcode= 1978JChEd..55..159A }} 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{{cite book|last=Devos|first=M|title=Standardized Human Olfactory Thresholds|year=1990|publisher=IRL Press|location=Oxford|isbn=0199631468|pages=34|author2=F. Patte |author3=J. Rouault |author4=P. Lafort |author5=L. J. Van Gemert}}
Uses
Butane-1-thiol is used as an industrial solvent,{{Citation needed|date=May 2012}} and as an intermediate for cotton defoliants.{{cite web|last=National Library of Medicine HSDB Database|title=Merphos|url=http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+1777|publisher=National Library of Medicine|accessdate=2012-05-17}} It is sometimes placed in "stink bombs" and "stink perfumes" for pranksters.
Safety
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.{{cite web |url=https://www.cdc.gov/niosh/ipcsneng/neng0018.html |title=n-BUTYL MERCAPTAN |work=International Chemical Safety Cards |publisher=National Institute for Occupational Safety and Health |accessdate=January 11, 2012 |archive-url=https://web.archive.org/web/20170930174754/https://www.cdc.gov/niosh/ipcsneng/neng0018.html |archive-date=September 30, 2017 |url-status=dead}}
See also
- tert-Butylthiol (tert-butyl mercaptan)
Notes
{{Reflist}}
References
- [http://www.osha.gov/dts/chemicalsampling/data/CH_223600.html U.S. Department of Labor] {{Webarchive|url=https://web.archive.org/web/20170930175144/https://www.osha.gov/dts/chemicalsampling/data/CH_223600.html |date=2017-09-30 }}
- [http://www.thegoodscentscompany.com/data/rw1007541.html The Good Scents Company]
- [https://web.archive.org/web/20060929134431/http://hazmap.nlm.nih.gov/cgi-bin/hazmap_generic?tbl=TblAgents&id=184 HazMap]
External links
- [https://web.archive.org/web/20111003071953/http://users.humboldt.edu/wfwood/skunkspray.shtml The Skunk's Defensive Secretion]
- [https://www.cdc.gov/niosh/npg/npgd0083.html CDC - NIOSH Pocket Guide to Chemical Hazards]
{{DEFAULTSORT:Butanethiol1}}