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Ethylene thiourea

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Ethylene thiourea
Names
Preferred IUPAC name Imidazolidine-2-thione
Other names 1,3-Ethylene-2-thiourea, N,N-Ethylenethiourea
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.280 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H6N2S/c6-3-4-1-2-5-3/h1-2H2,(H2,4,5,6)Key: PDQAZBWRQCGBEV-UHFFFAOYSA-N
  • InChI=1/C3H6N2S/c6-3-4-1-2-5-3/h1-2H2,(H2,4,5,6)Key: PDQAZBWRQCGBEV-UHFFFAOYAQ
SMILES
  • C1CNC(=S)N1
Properties
Chemical formula C3H6N2S
Molar mass 102.16 g·mol
Appearance White solid
Odor Faint, amine-like
Melting point 203 °C (397 °F; 476 K)
Boiling point 347.18 °C (656.92 °F; 620.33 K)
Solubility in water 2% (30 °C)
Vapor pressure 16 mmHg (20 °C)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards combustible
Flash point 252.2 °C (486.0 °F; 525.3 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose) 1832 mg/kg (oral, rat)
NIOSH (US health exposure limits):
PEL (Permissible) None
REL (Recommended) Ca Use encapsulated form.
IDLH (Immediate danger) Ca
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Ethylene thiourea (ETU) is an organosulfur compound with the formula C3H6N2S. It is an example of an N,N-disubstituted thiourea. It is a white solid. It is synthesized by treating ethylenediamine with carbon disulfide.

Ethylene thioureas are an excellent accelerant of vulcanization of neoprene rubbers. In commercial use is the N,N'-diphenylethylenethiourea. Due to reproductive toxicity, carcinogenicity, and mutagenicity, alternatives are being sought to the ethylenethioureas. One candidate replacement is N-methyl-2-thiazolidinethione.

Ethylene thiourea can be used as a biomarker of exposure to ethylenebisdithiocarbamates (EBDTCs), which are frequently employed as fungicides in agriculture, mainly on fruits, vegetables and ornamental plants.

EPA classification

EPA (United States Environmental Protection Agency) has classified ethylene thiourea as a Group B2, probable human carcinogen. Ethylene thiourea has been shown to be a potent teratogen (causes birth defects) in rats orally or dermally exposed.

See also

References

  1. ^ NIOSH Pocket Guide to Chemical Hazards. "#0276". National Institute for Occupational Safety and Health (NIOSH).
  2. https://chem.nlm.nih.gov/chemidplus/rn/96-45-7
  3. C. F. H. Allen; C. O. Edens; James VanAllan. "Ethylene Thiourea". Organic Syntheses; Collected Volumes, vol. 3, p. 394.
  4. Rüdiger Schubart (2000). "Dithiocarbamic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_001. ISBN 3527306730.
  5. Martínez Vidal, José L.; Frenich, Antonia Garrido (2005). Pesticide Protocols. Springer Science & Business Media. p. 79. ISBN 9781592599295. ethylene thiourea.
  6. "Ethylene Thiourea" (PDF). Ethylene Thiourea. January 2000 .
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