Ethylene thiourea

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 thiourea

Names
Preferred IUPAC name Imidazolidine-2-thione
Other names 1,3-Ethylene-2-thiourea, N,N-Ethylenethiourea
Identifiers
CAS Number	96-45-7^Y
3D model (JSmol)	Interactive image
ChemSpider	2005851
ECHA InfoCard	100.002.280
PubChem CID	2723650
UNII	24FOJ4N18S^Y
CompTox Dashboard (EPA)	DTXSID5020601
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^−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)
Solubility in water	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):
LD50 (median dose)	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). Infobox references

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

• Mercaptobenzothiazole - a cyclic dithiocarbamate also used as a vulcanization accelerant

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 ^{[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].