Ethyl butylacetylaminopropionate

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Ethyl butylacetylaminopropionate
IR3535
Names
IUPAC name
Ethyl N-acetyl-N-butyl-β-alaninate
Preferred IUPAC name
Ethyl 3-(N-butylacetamido)propanoate
Other names
  • EBAAP
  • β-alanine, N-acetyl-N-butyl-, ethyl ester
  • IR3535
  • Insect Repellent 3535
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.052.560 Edit this at Wikidata
UNII
  • InChI=1S/C11H21NO3/c1-4-6-8-12(10(3)13)9-7-11(14)15-5-2/h4-9H2,1-3H3 checkY
    Key: VZRKEAFHFMSHCD-UHFFFAOYSA-N checkY
  • CCCCN(CCC(=O)OCC)C(=O)C
Properties
C11H21NO3
Molar mass 215.293 g·mol−1
Appearance Colorless 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 labelling:
GHS07: Exclamation mark
Warning
H319
P280, P305+P351+P338, P337+P313
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).
checkY verify (what is checkY☒N ?)

Ethyl butylacetylaminopropionate (trade name IR3535) is an insect repellent which is applied topically to prevent bites and stings from mosquitos, ticks, and other insects.[1] It is a colorless and almost odorless oil, has efficacy against a broad range of insects, and is reasonably biodegradable.[2][3][4]

Chemistry[edit]

Ethyl butylacetylaminopropionate is a derivative of non-proteinogenic amino acid beta-alanine.[3]

Comparison of ethyl butylacetylaminopropionate and beta-alanine

References[edit]

  1. ^ Lo, Wai Ling; Mok, Ka Leung; Yu Pui Ming, Stephanie Dorothy (2018-09-01). "Which insect repellents should we choose? Implications from results of local market survey and review of current guidelines". Hong Kong Journal of Emergency Medicine. 25 (5): 272–280. doi:10.1177/1024907918773630. ISSN 1024-9079.
  2. ^ Ethyl butylacetylaminopropionate Product-type 19 (insect repellent)
  3. ^ a b 3-(N-Butyl-N-acetyl)-aminopropionic acid, ethyl ester (113509) Technical Document
  4. ^ 3-(N-Butyl-N-acetyl)-aminopropionic acid, ethyl ester (IR3535) (113509) Fact Sheet

External links[edit]