DEET

DEET

Names
Preferred IUPAC name N,N-Diethyl-3-methylbenzamide
Other names N,N-Diethyl-m-toluamide
Identifiers
CAS Number	134-62-3 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:7071 N
ChEMBL	ChEMBL1453317 N
ChemSpider	4133 Y
ECHA InfoCard	100.004.682
KEGG	D02379 Y
PubChem	4284
UNII	FB0C1XZV4Y Y
InChI InChI=1S/C12H17NO/c1-4-13(5-2)12(14)11-8-6-7-10(3)9-11/h6-9H,4-5H2,1-3H3 Y Key: MMOXZBCLCQITDF-UHFFFAOYSA-N Y InChI=1S/C12H17NO/c1-4-13(5-2)12(14)11-8-6-7-10(3)9-11/h6-9H,4-5H2,1-3H3 Key: MMOXZBCLCQITDF-UHFFFAOYAE
SMILES O=C(c1cc(ccc1)C)N(CC)CC
Properties
Chemical formula	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
ATC code	P03BX02 (WHO) QP53GX01 (WHO)
Hazards
Safety data sheet	External MSDS
EU classification (DSD)	Xn
R-phrases	R23 R24 R25
NFPA 704	1 2 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

N,N-Diethyl-meta-toluamide, also called DEET (/diːt/) 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.