*** Welcome to piglix ***

DEET

DEET
DEET.svg
DEET Ball and Stick.png
Names
Preferred IUPAC name
N,N-Diethyl-3-methylbenzamide
Other names
N,N-Diethyl-m-toluamide
Identifiers
134-62-3 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:7071 N
ChEMBL ChEMBL1453317 N
ChemSpider 4133 YesY
ECHA InfoCard 100.004.682
KEGG D02379 YesY
PubChem 4284
UNII FB0C1XZV4Y YesY
Properties
C12H17NO
Molar mass 191.27 g/mol
Density 0.998 g/mL
Melting point −33 °C (−27 °F; 240 K)
Boiling point 288 to 292 °C (550 to 558 °F; 561 to 565 K)
Pharmacology
P03BX02 (WHO) QP53GX01 (WHO)
Hazards
Safety data sheet External MSDS
Harmful Xn
R-phrases R23 R24 R25
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

N,N-Diethyl-meta-toluamide, also called DEET (/dt/) or diethyltoluamide, is the most common active ingredient in insect repellents. It is a slightly yellow oil intended to be applied to the skin or to clothing, and provides protection against mosquitoes, ticks, fleas, chiggers, leeches, and many biting insects.

DEET was developed in 1944 by Samuel Gertler of the United States Department of Agriculture for use by the United States Army, following its experience of jungle warfare during World War II. It was originally tested as a pesticide on farm fields, and entered military use in 1946 and civilian use in 1957. It was used in Vietnam and Southeast Asia.

In its original form known as "bug juice", the application solution for DEET was composed of 75% DEET and ethanol. Later, a new application of the repellant was developed by U.S. Army and the USDA consisted of DEET and other polymers that extended the release of the DEET and reduced its evaporation rate. This extended release application was registered by the EPA in 1991.

A slightly yellow liquid at room temperature, it can be prepared by converting m-toluic acid (3-methylbenzoic acid) to the corresponding acyl chloride, and allowing it to react with diethylamine:

DEET was historically believed to work by blocking insect olfactory receptors for 1-octen-3-ol, a volatile substance that is contained in human sweat and breath. The prevailing theory was that DEET effectively "blinds" the insect's senses so that the biting/feeding instinct is not triggered by humans or other animals which produce these chemicals. DEET does not appear to affect the insect's ability to smell carbon dioxide, as had been suspected earlier.


...
Wikipedia

...