Chemistry:IR3535

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IR3535
IR3535
Names
IUPAC name
Ethyl N-acetyl-N-butyl-β-alaninate
Other names
  • Ethyl N-acetyl-N-butyl-β-alaninate
  • Ethyl butylacetylaminopropionate
  • EBAAP
  • β-alanine, N-acetyl-N-butyl-, ethyl ester
Identifiers
3D model (JSmol)
ChemSpider
Properties
C11H21NO3
Molar mass 215.293 g·mol−1
Appearance Colourless liquid
Odor Almost odorless
Density 0.998 g/cm3 (at 20 °C)
70 g/L (at 20 °C)
Solubility in Acetone, ethyl acetate, dichloromethane, n-heptane, methanol, p-xylene >250 g/L (at RT)
log P 1.7 (at 23 °C)
Hazards
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H319
P280, P305+351+338, P337+313
Flash point 159 °C (318 °F; 432 K)
Lethal dose or concentration (LD, LC):
  • >5000 mg/kg (rat, oral)
  • 10000 mg/kg (rate, dermal)
  • >5.1 mg/L (rat, inhalation)
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
Tracking categories (test):

IR3535 (Insect Repellent 3535), also known by the non-proprietary name ethyl butylacetylaminopropionate, is one of the most common active ingredients in insect repellents. As it is solely a repellent it has no killing action and does not give rise to selection pressure or development of resistance.[1] It is a colourless and almost odourless oil and is intended to be applied to the skin (humans and animals).[1] [2] It has a broad efficacy against various insects like mosquitoes, ticks, lice, and other bugs.[1] [2] [3]In comparison to other insect repellent active ingredients, IR3535 is safe for use even on infants, pregnant and breastfeeding women. It is biodegradable and completely degraded in the environment within a very short time.[1]

IR3535 is a registered trademark of Merck KGaA.[4][5]

Chemistry

IR3535 and beta-alanine

The structure of IR3535 is based on beta-alanine.[6] The EPA has classified IR3535 as a biochemical substance (biopesticide)[7] based on the fact that it is "functionally identical" to beta alanine. [8]

References

  1. 1.0 1.1 1.2 1.3 EU Assessment Report IR3535
  2. 2.0 2.1 EPA Technical Document IR3535
  3. EPA Fact Sheet IR3535
  4. "Insect Repellent IR3535". https://www.merckgroup.com/en/s/insect-repellent.html. 
  5. "EPA, Draft Pesticide Product label for IR3535". https://www3.epa.gov/pesticides/chem_search/ppls/070759-00002-20071030.pdf. 
  6. EPA: Similarity to beta-alanine
  7. EPA: Regulating Biopesticides
  8. EPA: IR3535 technical document

External links