Ethylene thiourea

Ethylene thiourea
Names
Preferred IUPAC name
Imidazolidine-2-thione
Other names
1,3-Ethylene-2-thiourea, N,N-Ethylenethiourea
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.280 Edit this at Wikidata
UNII
  • 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
  • C1CNC(=S)N1
Properties
C3H6N2S
Molar mass 102.16 g·mol−1
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)
2% (30 °C)[1]
Vapor pressure 16 mmHg (20 °C)[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 combustible[1]
Flash point 252.2 °C (486.0 °F; 525.3 K)
Lethal dose or concentration (LD, LC):
1832 mg/kg (oral, rat)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 None[1]
REL (Recommended)
 Ca Use encapsulated form.[1]
IDLH (Immediate danger)
 Ca [N.D.][1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[3]

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.[4]

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.[5]

EPA classification

EPA (United States Environmental Protection Agency) has classified ethylene thiourea as a Group B2, probable human carcinogen.[6] Ethylene thiourea has been shown to be a potent teratogen (causes birth defects) in rats orally or dermally exposed.

See also

References

  1. ^ a b c d e f 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 [dead link‍]
  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 [April 1992].