N,N-Diethyl-m-toluamid

DEET · DIETHYLTOLUAMIDE · DET · N,N-DIETHYL-3-METHYLBENZAMIDE · muscol · mgk · Detamide · Diethyl-m-toluamide

Identifikatoren & physikalische Daten

CAS No.	134-62-3
Summenformel	C12H17NO
Durchschnittliche Molmasse	191,27 g/mol
Monoisotopische Masse	191,13101416 g/mol
SMILES	CCN(CC)C(=O)c1cccc(C)c1
InChIKey	MMOXZBCLCQITDF-UHFFFAOYSA-N
PubChem CID	4284
ChEMBL	CHEMBL1453317
ChEBI	CHEBI:7071
EC No.	205-149-7
DTXSID	DTXSID2021995
Lokaler Name	N,N-Diethyl-m-toluamid

Chemische & physikalische Eigenschaften

XLogP	2
Polarare Oberfläche (TPSA)	20,3
H-Brücken-Donoren	0
H-Brücken-Akzeptoren	1
Frei drehbare Bindungen	3
Schwere Atome	14
Formalladung	0
Komplexität	187
Arzneimittel	Pharmaceuticals -> Listed in ZINC15
Kosmetika	Skin protecting
SpringerMaterials Properties	Boiling point
Pestizide	Pesticides -> Insect RepellentsPesticide (DEET (N,N-diethyl-m-toluamide)) -> USDA PDBPesticide and(or) Waste-water effluent contaminant
LogP (Verteilungskoeffizient)	log Kow = 2.022.34
Geruch	Faint, characteristic odor
Dichte	0.996 at 68 °F (NTP, 1992) - Less dense than waterwill float0.996 g/cu cm at 20 °C0.998 g/mL at 20 °C(lit.)
Viscosity	13.3 cP at 30 °C
Color/Form	Nearly colorless to amberlike liquid
Löslichkeit	less than 1 mg/mL at 68 °F (NTP, 1992)Very soluble in benzene, ethyl ether, ethanolMiscible with ethanol, ether, isopropanol, chloroform, benzene and carbon disulfide. Practically insoluble in glycerinMiscible with 2-propanol, cottonseed oil, propylene glycol19.6 [ug/mL] (The mean of the results at pH 7.4)DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)NEGLIGIBLE
Flammpunkt	311 °F (NTP, 1992)155 °C (open cup)95 °C (203 °F) - closed cup>230 °F
Human Drugs	Breast FeedingLactationInsect RepellentsPharmaceuticals
Schmelzpunkt	-45 °C
Siedepunkt	111 °C1 mm Hg
Dampfdichte	6.7 (vs air)
Dampfdruck	<0.01 mm Hg ( 25 °C)
Brechungsindex	n20/D 1.523(lit.)
Lagerbedingungen	room temp
pKa (Säurekonstante)	-1.37±0.70(Predicted)
Aggregatzustand	Liquid
Farbe	Clear
Wichte	0.996
Geruch	mild bland odor
Merck	14,2856
BRN	2046711
Henry-Konstante	4.7×102 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität	Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, strong bases. Hydrolyzes slowly in water.
Hauptanwendungen	agricultureenvironmental
Kosmetik-Inhaltsstoffe Funktionen	SKIN PROTECTING
InChI	1S/C12H17NO/c1-4-13(5-2)12(14)11-8-6-7-10(3)9-11/h6-9H,4-5H2,1-3H3
InChIKey	CXVBTGKUSLNJQZ-UHFFFAOYSA-N
SMILES	CCN(CC)C(=O)c1cccc(C)c1
CAS Datenbank	134-62-3(CAS DataBase Reference)
NIST chemische Informationen	Diethyltoluamide(134-62-3)
EPA chemische Informationen	N,N-Diethyl-m-toluamide (134-62-3)

Sicherheit & Vorschriften

GHS-Einstufung	WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Regulatorische Informationen	Chemical: Benzamide, N,N-diethyl-3-methyl-Hazard Traits - DermatotoxicityNeurotoxicityDiethyl toluamide: Does not have an individual approval but may be used under an appropriate group standard
Brandgefahren	This chemical is combustible. (NTP, 1992)
Gesundheitsgefahren	SYMPTOMS: Symptoms of exposure to this compound may include eye and mucous membrane irritation. It can cause contact dermatitis, conjunctivitis, exacerbation of seborrhea and acne vulgaris. Eye contact may result in a smarting sensation. Ingestion of this material can cause central nervous system disturbances. Symptoms resulting from exposure to this compound include disorientation, staggering gait, slurred speech, crying out, episodes consisting of stiffening into a sitting position, extending of extremities, flexing of the fingers and dorsiflexing the toes. It may also cause jaundice, aplastic anemia, bleeding, convulsive seizure or death. It may irritate tender areas of the skin. It may also cause severe eye injury. Other symptoms are desquamation about the nose, dryness of face, a slight tingling sensation and a bullous eruption in the antecubital fossae. Irritation of the gastro-intestinal tract and coma are possible. It may cause purpuric or ecchymotic areas.
Gefahrenübersicht	DEET is a chemical (N,N-diethyl-meta-toluamide) used as the active ingredient in many insect repellent products. DEET was developed by the U.S. Army in 1946 and was registered for use by the general public in 1957. It is now widely used, with approximately 30% of the U.S. population using DEET repellents each year. DEET products are currently available in a variety of forms: liquids, lotions, sprays, and even impregnated materials, such as wristbands. Formulations registered for direct application to human skin contain from 4% to 100% DEET. Approximately 230 products containing DEET are currently registered with the U.S. Environmental Protection Agency (EPA).

Anwendungen & Verwendung

Beschreibung

DEET was first developed and patented by the US Army in 1946. It was approved for general public use by the US Environmental Protection Agency (EPA) in 1957 and was reregistered in 1998. It has been estimated that more than 1.8 million kg (～4 million pounds) of DEET are used in the United States every year in more than 225 registered products. DEET is often sold and used in lotions or sprays with concentrations up to 100%. However, the Center for Disease Control recommends only 30–50% DEET to reduce the incidence of vector-borne disease transmission. Registered products must contain at least 95% of the meta-isomer, but small amounts of the more toxic ortho-isomer and the less toxic para-isomer are permitted.

History

Formulations registered for direct human application contain from 4% to 100% DEET. DEET was developed as a joint effort by the Department of Defense and U.S. Department of Agriculture (USDA). After examining hundreds of compounds for their repellent capabilities in the 1940s, DEET was selected and patented by the U.S. Army in 1946.the USDA did not announce DEET’s discovery until 1954, and it was registered for public use in 1957. DEET is prepared from m-toluoyl chloride and diethylamine in benzene or ether.