Propanethiol

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Propanethiol[1]
1-Propanethiol.svg
Names
Preferred IUPAC name
Propane-1-thiol
Other names
n-Propylthiol
1-Propanethiol
Propan-1-thiol
Propyl mercaptan
Mercaptan C3
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.142
UNII
Properties
C3H8S
Molar mass 76.16 g·mol−1
Appearance Colorless to pale yellow liquid
Odor cabbage-like[4]
Density 0.84 g/mL
Melting point −113 °C (−171 °F; 160 K)
Boiling point 67 to 68 °C (153 to 154 °F; 340 to 341 K)
Slight[4]
Vapor pressure 155 mmHg[4]
Acidity (pKa) 8[citation needed]
-58.5·10−6 cm3/mol
Hazards
Flash point −21 °C; −5 °F; 253 K[4]
US health exposure limits (NIOSH):
PEL (Permissible)
none[4]
REL (Recommended)
C 0.5 ppm (1.6 mg/m3) [15-minute][4]
IDLH (Immediate danger)
N.D.[4]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Propanethiol is an organic compound with the molecular formula C3H8S. It belongs to the group of thiols, it is a colorless liquid with a strong, offensive odor. It is moderately toxic and is less dense than water and slightly soluble in water, it is used as a feedstock for insecticides.[5] It is highly flammable and it gives off irritating or toxic fumes (or gases) in a fire. Heating it will cause rise in pressure with risk of bursting.[6][7]

Chemistry[edit]

Propanethiol is chemically classified among the thiols, which are organic compounds with molecular formulas and structural formulas similar to alcohols, except that sulfur-containing sulfhydryl group (-SH) replaces the oxygen-containing hydroxyl group in the molecule. Propanethiol's basic molecular formula is C3H7SH, and its structural formula is similar to that of the alcohol n-propanol.

Propanethiol is manufactured commercially by the reaction of propene with hydrogen sulfide with ultraviolet light initiation in an anti-Markovnikov addition.[8] It can also be prepared by the reaction of sodium hydrosulfide with 1-chloropropane.

References[edit]

  1. ^ International Chemical Safety Card 0317
  2. ^ ChEBI 8473
  3. ^ CSID:7560, accessed 19:05, Feb 10, 2013
  4. ^ a b c d e f g "NIOSH Pocket Guide to Chemical Hazards #0526". National Institute for Occupational Safety and Health (NIOSH). 
  5. ^ 1-Propanethiol, chemicalbook.com
  6. ^ 1-Propanethiol, inchem.org
  7. ^ 1-Propanethiol, International Chemical Safety Card
  8. ^ Rector P.Louthan, United States Patent 3,050,452, Aug. 21, 1962, Preparation of Organic Sulfur Compounds