Identification and Related Records
- 【Name】
- N,N-Diethyl-3-methylbenzamide
- 【Registry number】
- 134-62-3 (CAS DataBase Reference)
- 【Synonyms】
-
DETA
DEET
N,N-Diethyl-m-toluamide
m-Toluic acid diethylamide
3-methyl-2-deutero-N,N-diethylbenzamide
3-Methyl-N,N-diethylbenzamide
A.I. 3-22542
AI 3-22542
ai3-22542
amincenec-em
Autan
Baker'S antifol
DEET
N,N-diethyl-3-methyl-Benzamide
n,n-diethyl-m-toluamid
- 【EINECS(EC#)】
- 205-149-7
- 【Molecular Formula】
- C12H17NO (Products with the same molecular formula)
- 【Molecular Weight】
- 191.27
- 【Inchi】
- InChI=1/C12H17NO/c1-4-13(5-2)12(14)11-8-6-7-10(3)9-11/h6-9H,4-5H2,1-3H3
- 【InChIKey】
- MMOXZBCLCQITDF-UHFFFAOYSA-N
- 【Canonical SMILES】
- CCN(CC)C(=O)C1=CC(=CC=C1)C
134-62-3.mol
Chemical and Physical Properties
- 【Appearance】
- Colorless to Amberlike Liquid
- 【Density】
- 0.9955
- 【Melting Point】
- -45
- 【Boiling Point】
- 111℃ (1 mmHg)
- 【Vapour】
- 0.0075mmHg at 25°C
- 【Refractive Index】
- 1.52-1.524
- 【Flash Point】
- 155℃
- 【Water】
- NEGLIGIBLE
- 【Solubilities】
- negligible
- 【Color/Form】
- Liquid
WATER WHITE TO AMBER
- 【Stability】
- Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, strong bases. Hydrolyzes slowly in water.
- 【HS Code】
- 29242995
- 【Storage temp】
- Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
- 【Spectral properties】
- Index of refraction: 1.5212 @ 20 deg C/D
Intense mass spectral peaks: 119 m/z (100%), 190 m/z (46%), 91 m/z (41%), 191 m/z (17%)
IR: 2:942F (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI)
MS: NIST 7113 (NIST/EPA/MCDC Mass Spectral Database 1990 version)
NMR: 7:74C (Aldrich Library of Mass Spectra, Aldrich Chemical Co, Milwaukee, WI)
- 【Computed Properties】
- Molecular Weight:191.26948 [g/mol]
Molecular Formula:C12H17NO
XLogP3:2
H-Bond Donor:0
H-Bond Acceptor:1
Rotatable Bond Count:3
Exact Mass:191.131014
MonoIsotopic Mass:191.131014
Topological Polar Surface Area:20.3
Heavy Atom Count:14
Formal Charge:0
Complexity:187
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Ring Count:1
Effective Rotor Count:4
Conformer Sampling RMSD:0.6
CID Conformer Count:16
Safety and Handling
- 【Hazard Codes】
- Xn:Harmful
- 【Risk Statements】
- R22;R36/38;R52/53
- 【Safety Statements 】
- S61
- 【HazardClass】
- 6.1(b)
- 【Safety】
-
Safety Information about N,N-Diethyl-m-toluamide (CAS NO.134-62-3):
Hazard Codes:?
Xn
Risk Statements: 22-36/38-52/53
R22: Harmful if swallowed.?
R36/38: Irritating to eyes and skin.?
R52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 61
S21:When using do not smoke.
RIDADR: 2810
WGK Germany: 2
RTECS: XS3675000
HazardClass: 6.1(b)
PackingGroup: III
HS Code: 29242995
Poison by intravenous route. Moderately toxic by ingestion and skin contact. Human systemic effects: coma, convulsions, dermatitis, mydriasis (pupillary dilation), nausea or vomiting, stiffness. An eye and skin irritant. Experimental reproductive effects by skin contact. Mutation data reported. Can cause central nervous system disturbances. A pesticide. DEET is the active ingredient in most commercial insect repellents. When heated to decomposition DIETHYL-m-TOLUAMIDE?(134-62-3) emits toxic fumes of NOx.
- 【PackingGroup 】
- III
- 【Skin, Eye, and Respiratory Irritations】
- IRRITANT TO ... MUCOUS MEMBRANES ...
Undiluted material is a moderate-to-severe irritant in the eye. Dermal application of undiluted material and 50% solutions caused no primary irritation in man ...
THE UNDILUTED COMPD MAY IRRITATE MUCOUS MEMBRANES ...
- 【Transport】
- 2810
- 【Formulations/Preparations】
- USEPA/OPP Pesticide Code 080301; Trade Names: Deet, Delphene, MGK diethyltoluamide, pyrocide intermediate 5734 (080301+057001+043302+047201), Detamide, Metadelphene, Chigger-Wash, Skeeter skat (080301+067212).
Aerosol bombs, creams, stick, and soln in isopropanol.
WITH ETHYL OR ISOPROPYL ALCOHOL, WITH OTHER REPELLENTS.
LIQUID REPELLENT "OFF" IS COMPOSED OF EQUAL PARTS OF /N,N-DIETHYL-M-TOLUAMIDE/ AND AN INERT LIQUID; PRESSURIZED SPRAY IS 15% SOLN IN DENATURED ALCOHOL WITH FREON GAS.
Emulsifiable concentrate; Emulsion, water in oil
Contains a minimum of 95% meta isomer as technical active ingredient; manufacturing products - 17.5% to 88.89%
Impregnated material, 7.15-82.0%; liquid - RTU, 7.00-100%; pressurized liquid, 3.99-80.00%; sunscreen/DEET, 7.13-20.00%
- 【Other Preventative Measures】
- SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Avoid skin and eye contact with the concentrate.
- 【Protective Equipment and Clothing】
- IRRITANT TO ... MUCOUS MEMBRANES ...
Undiluted material is a moderate-to-severe irritant in the eye. Dermal application of undiluted material and 50% solutions caused no primary irritation in man ...
THE UNDILUTED COMPD MAY IRRITATE MUCOUS MEMBRANES ...
- 【Specification】
-
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.?
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a cool, dry place. Store in a tightly closed container.
- 【Octanol/Water Partition Coefficient】
- log Kow = 2.02
- 【Report】
-
Reported in EPA TSCA Inventory.
- 【Disposal Methods】
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Use and Manufacturing
- 【Use and Manufacturing】
- Methods of Manufacturing
Prepn from m-toluoyl chloride and diethylamine in benzene or ether: Maxim, Bull Soc Chim Romania 11, 29 (1929); Chem Zentr, 1929, II, 2324, C.A. 24,94 (1930); Beilstein 9, II, 325; McCabe et al., J Org Chem 19, 493, 496 (1954).Consumption Patterns
(1990) 4X10+6 lbs active ingredient
30% of US population uses DEET annually as an insect repellent. Approx 21% households use DEET annually; 19% of households use it on household members; about 4% of households that have cats and/or dogs use it on those pets.
- 【Usage】
-
Insect repellent
Biomedical Effects and Toxicity
- 【Pharmacological Action】
- - Substances causing insects to turn away from them or reject them as food.
- 【Biomedical Effects and Toxicity】
- (14)C-DEET IN 0.3% SOLN OF 20% ETHANOL WAS APPLIED TO BACKS OF MICE. HIGH CONCN OF RADIOACTIVITY FOUND IN LACRIMAL GLAND, LIVER, BILE, INTESTINAL CONTENTS, KIDNEY, URINE, & NASAL MUCOSA. RESULTS WERE SIMILAR TO THOSE OBTAINED AFTER IV ADMIN. A 25% SOLN OF (14)C-DEET IN ABSOLUTE ALC WAS APPLIED TO HUMAN VOLUNTEERS, & URINARY EXCRETION WAS MEASURED. URINARY CONCN REACHED A PEAK AFTER SEVERAL HOURS.
(14)C-DEET WAS RAPIDLY RESORBED IN LARGE AMT BY SKIN OF MICE & PENETRATED INTO BLOOD WITH MAX CONCN IN 1 HR. EXCRETION WAS ALMOST COMPLETE FROM BLOOD WITHIN 1-3 DAYS & MOST WAS EXCRETED IN URINE. RESIDUAL AMT DETECTED FOR 1-3 MO IN SKIN, FATTY TISSUE, & MUSCLES.
AT AN APPLICATION DOSE OF 0.25 UG/SQ CM, 9.6% IN VIVO & 9.7% IN VITRO /OF THE ADMINISTERED DOSE/ EVAPORATED FROM THE SKIN OF HUMANS IN THE FIRST HR AFTER APPLICATION. [SPENCER TS ET AL; J INVEST DERMATOL 72 (6): 317-9 (1979)] PubMed Abstract
After intravenous injection, DET is rapidly distributed through the body /of mice/ and quickly recovered in urine within the first 8 hr. The cmpd is selectively concentrated within the lacrimal glands, nasal mucosa, and mouse yolk sac.
Deet is absorbed and distributed rather rapidly following movement through the skin. ... Topically applied radioactive deet reached a maximum concentration in the blood by 1 hr postapplication; it was almost completely eliminated from the blood within 1-3 days. Deet is rapidly eliminated mainly in the urine and to a lesser extent in the feces.
DEET is efficiently absorbed across the skin and by the gut. Blood concentrations of about 3 mg/l have been reported several hours after dermal application in the prescribed fashion.
Using radioautography following iv injection of (14)C-deet, high tissue levels were found at first in the liver, kidney, lacrimal gland, and nasal mucosa. Very soon, concentrations higher than that in the blood were found in the thyroid and brown fat. Concentrations were highest and most persistent in the lacrimal gland. Concentrations in the fetus remained lower than those in the mother. Excretion was rapid and mainly by way of the kidney. By 4 hours after injection, very little radioactivity remained in any tissue, except the lacrimal gland ... An essentially similar picture was seen following dermal application. However, low levels of excretion continued during the entire 1 month period of observation. Direct measurement of the skin indicated that persistent excretion depended mainly on continuing absorption from the skin ... .
... 7 to 13% of a topical treatment of about 1 mg/sq cm & from 9% of a dose of 1.86 mg/sq cm to 56% of a dose of 0.077 mg/sq cm penetrated the skin of volunteers. ... Only 16% of a topical application to the forearm at 4 micrograms/sq cm penetrated during a 96 hr interval. ... The penetration of deet into & through human abdominal skin was 29.8% (29.6% remained in skin, 0.2% penetrated) at 1 hr after application of the lower concn & 36.3% (29.7% remained in skin, 6.6% penetrated) at 12 hr following application of the higher concn.
About 10 to 15% of each dose can be recovered unchanged from the urine. Volume of distribution is 2.1 L/kg. Plasma half-life is 2.5 hr. DEET is eliminated by hepatic oxidative metabolism through the P450 enzyme system. About 10 to 14% is excreted in the urine unchanged. Urinary half-life is 4 hr. DEET and its metabolites can be detected in the urine for 2 weeks and from the skin and adipose tissues for 1 to 3 months after dermal application. It exhibits an enterohepatic recirculation.
Environmental Fate and Exposure Potential
- 【Environmental Fate/Exposure Summary】
- TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 300(SRC), determined from a log Kow of 2.02(2) and a regression-derived equation(3), indicates that DEET is expected to have moderate mobility in soil(SRC). Volatilization of DEET from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(4). DEET is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.6X10-3 mm Hg(5). Biodegradation in soil may not be an important fate process based on limited biodegradation data; DEET, at 100 mg/l, did not biodegrade under aerobic conditions over a period of 4 weeks with a sewage inoculum and the Japanese MITI test(6). Biodegradation using an anaerobic aquifer slurry from a municipal landfill was negligible(7).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 300(SRC), determined from a log Kow of 2.02(2) and a regression-derived equation(3), indicates that DEET is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.1X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), BCF values of 0.8-2.4(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation in water may not be an important fate process based on limited biodegradation data; DEET, at 100 mg/l, did not biodegrade under aerobic conditions over a period of 4 weeks with a sewage inoculum and the Japanese MITI test(6). Biodegradation using an anaerobic aquifer slurry from a municipal landfill was negligible(7).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), DEET, which has a vapor pressure of 5.6X10-3 mm Hg at 20 deg C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase DEET is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 15(SRC), calculated from its rate constant of 2.5X10-11 cu cm/molecule-sec at 25 deg C(SRC), determined using a structure estimation method(3).
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