Isobornyl thiocyanoacetate

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Isobornyl thiocyanoacetate Basic information
Product Name:Isobornyl thiocyanoacetate
Synonyms:isoborneol,thiocyanatoacetate;Isobornylester kyseliny thiokyanatooctove;isobornylesterkyselinythiokyanatooctove;isobornylthiocyanatoacetate,technical;Thanisol;thanite(herculespowder);thiocyanato-,1,7,7-trimethylbicyclo(2,2,1)hept-2-ylester,exo-aceticaci;thiocyanato-,1,7,7-trimethylbicyclo(2.2.1)hept-2-ylester,exo-aceticaci
CAS:115-31-1
MF:C13H19NO2S
MW:253.36
EINECS:204-081-5
Product Categories:
Mol File:115-31-1.mol
Isobornyl thiocyanoacetate Structure
Isobornyl thiocyanoacetate Chemical Properties
Boiling point bp0.06 95°
density d425 1.1465
refractive index nD25 1.512
Fp 82°C (180°F)
Henry's Law Constant3.8×101 mol/(m3Pa) at 25℃, HSDB (2015)
EPA Substance Registry SystemIsobornyl thiocyanatoacetate (115-31-1)
Safety Information
Hazard Codes Xn,N
Risk Statements 22-50/53
Safety Statements 24/25-60-61
TSCA TSCA listed
Hazardous Substances Data115-31-1(Hazardous Substances Data)
Toxicityguinea pig,LD50,oral,551mg/kg (551mg/kg),Farm Chemicals Handbook. Vol. -, Pg. C300, 1991.
MSDS Information
Isobornyl thiocyanoacetate Usage And Synthesis
Chemical PropertiesYellow oily liquid; terpene-like odor. Very soluble in alcohol, benzene, chloroform, and ether; practically insoluble in water. Combustible.
OriginatorBornate,Wyeth,US,1946
UsesInsecticide, especially in cattle sprays.
Production MethodsIsobornyl thiocyanoacetate is synthesised through a two-step process starting with camphene, a bicyclic monoterpene. First, camphene is reacted with chloroacetic acid at elevated temperatures for 16 hours, producing isobornyl monochloroacetate. This intermediate is then dissolved in ethyl alcohol, and potassium thiocyanate is added. The mixture is refluxed for approximately 8 hours, during which the chlorine atom is substituted by a thiocyanate group, yielding isobornyl thiocyanoacetate.
DefinitionThe technical grade contains 82% or more of isobornyl thiocyanoacetate, also other terpenes and derivatives.
Manufacturing Process200 g of camphene and 150 g of chloroacetic acid were heated 16 hours at 125°C, cooled to room temperature and the resulting product washed with water. In this way, 177 g of isobornyl monochloroacetate, analyzing 12.8%, by weight, chlorine was recovered. 174 g of the isobornyl monochloroacetate was dissolved in 300 cc of ethyl alcohol, 100 g of potassium thiocyanate added to this solution and the mixture refluxed for a period of 8 hours. 276 g of a product was recovered, which analyzed as follows: chlorine, 0.2% by wt. and sulfur, 10.9% by wt. This analysis shows the product to be principally isobornyl thiocyanoacetate.
Therapeutic FunctionPediculicide
HazardToxic by ingestion, strong irritant.
Pesticide TypeInsecticide; Veterinary substance
Isobornyl thiocyanoacetate Preparation Products And Raw materials
Raw materialsCamphene-->Potassium thiocyanate-->Chloroacetic acid
Tag:Isobornyl thiocyanoacetate(115-31-1) Related Product Information
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