Tetraethyl pyrophosphate

Tetraethyl pyrophosphate

Names
IUPAC name tetraethyl diphosphate
Identifiers
CAS Number	107-49-3 Y
ChEMBL	ChEMBL293787 Y
ChemSpider	7585 Y
Jmol interactive 3D	Image
PubChem	7873
InChI InChI=1S/C8H20O7P2/c1-5-11-16(9,12-6-2)15-17(10,13-7-3)14-8-4/h5-8H2,1-4H3 Y Key: IDCBOTIENDVCBQ-UHFFFAOYSA-N Y InChI=1/C8H20O7P2/c1-5-11-16(9,12-6-2)15-17(10,13-7-3)14-8-4/h5-8H2,1-4H3 Key: IDCBOTIENDVCBQ-UHFFFAOYAI
SMILES O=P(OP(=O)(OCC)OCC)(OCC)OCC
Properties
Chemical formula	C8H20O7P2
Molar mass	290.19 g·mol−1
Appearance	colorless to amber liquid[1]
Odor	faint, fruity[1]
Density	1.19 g/mL (20°C)[1]
Melting point	0 °C; 32 °F; 273 K [1]
Boiling point	decomposes[1]
Solubility in water	miscible[1]
Vapor pressure	0.0002 mmHg (20°C)[1]
Hazards
Lethal dose or concentration (LD, LC):
LDLo (Lowest published)	0.5 mg/kg (rat, oral) 2.3 mg/kg (guinea pig, oral) 3 mg/kg (mouse, oral)[2]
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 0.05 mg/m3 [skin][1]
REL (Recommended)	TWA 0.05 mg/m3 [skin][1]
IDLH (Immediate danger	5 mg/m3[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tetraethyl pyrophosphate, abbreviated TEPP, is an organophosphate compound. It is used as a pesticide.

This compound is a clear, colorless liquid. It is soluble in water, but hydrolyzes rapidly.^[3] It was first synthesized by Philippe de Clermont. This compound may be prepared by two equivalents of diethyl chlorophosphate with one equivalent of water in the presence of pyridine to scavenge the hydrogen chloride formed:^[4]

References

1. 1 2 3 4 5 6 7 8 9 10 "NIOSH Pocket Guide to Chemical Hazards #0590". National Institute for Occupational Safety and Health (NIOSH). 
2. ↑ "TEPP". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH). 
3. ↑ Robert L. Metcalf (2005), "Insect Control", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a14_263 
4. ↑ Toy, A. D. F. (1948). "The Preparation of Tetraethyl Pyrophosphate and Other Tetraalkyl Pyrophosphates". J. Am. Chem. Soc. 70 (11): 3882. doi:10.1021/ja01191a104.