Diethyltoluamide

Base Information

• Chemical Name: Diethyltoluamide
• CAS No.: 134-62-3
• Deprecated CAS: 94271-03-1
• Molecular Formula: C12H17NO
• Molecular Weight: 191.273
• Hs Code.: 29242995
• European Community (EC) Number: 205-149-7
• NSC Number: 759564,33840
• UNII: FB0C1XZV4Y
• DSSTox Substance ID: DTXSID2021995
• Nikkaji Number: J5.598K
• Wikipedia: DEET
• Wikidata: Q408389
• NCI Thesaurus Code: C80601
• Metabolomics Workbench ID: 50010
• ChEMBL ID: CHEMBL1453317
• Mol file: 134-62-3.mol

Synonyms:DEET;DEET, 2,5-di-Me-Analog;DET;DETA;N,N Diethyl 3 methylbenzamide;N,N Diethyl m toluamide;N,N Diethyltoluamide;N,N-Diethyl-2,5-dimethylbenzamide;N,N-Diethyl-3-methylbenzamide;N,N-Diethyl-m-toluamide;N,N-Diethyltoluamide;R 209;R-209;R209

Chemical Property of Diethyltoluamide

Chemical Property:

• Appearance/Colour: Colorless to Amberlike Liquid
• Vapor Pressure: <0.01 mm Hg ( 25 °C)
• Melting Point: -45oC
• Refractive Index: n20/D 1.523(lit.)
• Boiling Point: 297.5 °C at 760 mmHg
• PKA: -1.37±0.70(Predicted)
• Flash Point: 141.7 °C
• PSA: 20.31000
• Density: 0.985 g/cm³
• LogP: 2.47700
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: NEGLIGIBLE
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 191.131014166
• Heavy Atom Count: 14
• Complexity: 187

Purity/Quality:

98.00% ^*data from raw suppliers

DEET ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/38-52/53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Insect Repellents
• Canonical SMILES: CCN(CC)C(=O)C1=CC=CC(=C1)C
• Recent ClinicalTrials: A Health Service Research Study to Investigate Survival of Metastatic Pancreatic Cancer Patients After Sequential Chemotherapy
• Uses: 1. As major components for a variety of solid, liquid mosquito repellent series. 2. Insect repellent, having unique effects for mosquito controlling . Formulation: 70%, 95% liquid. DEET is an Insect repellent.This compound is a contaminant of emerging concern (CECs). Insect repellent DEET is used as an insect repellent.
• production method: By the Inter-toluene chloride and diethyl amine reaction. Industrial products containing 5%-15% isomer.
• Description: 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.
• Indications: DEET is an organic liquid that is an excellent mosquito repellent; stronger preparations of DEET are also effective against stable flies, although little protection is provided against ticks. Commercial preparations are available in aerosol, cream, or lotion form and vary in concentration from 6% to 100%. Because DEET is absorbed into the bloodstream, it should be applied sparingly. Lesser concentrations of DEET should be used whenever possible, with additional applications to the skin if needed. Reports of a toxic encephalopathy and brief seizures have been documented in children after overzealous use. Less serious neurologic side effects include confusion, irritability, and insomnia. Contact dermatitis has been observed with preparations containing higher concentrations of DEET. Use preparations with <20% DEET in children. Avoid mucous membranes, broken skin, and hands of children, because they are often in contact with the mouth. Spray clothing instead of skin whenever possible, but avoid contact with rayon, acetate, or spandex, because these materials may be damaged by DEET.

Technology Process of Diethyltoluamide

There total 31 articles about Diethyltoluamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

→ N,N-Diethyl-3-methylbenzamide (134-62-3,94271-03-1)

Guidance literature:

Reference yield: 97.5%

N,N-diethylcarbamyl chloride (88-10-8) + m-Toluic acid (99-04-7) → N,N-Diethyl-3-methylbenzamide (134-62-3,94271-03-1)

Guidance literature:

With triethylamine; at 20 ℃; for 0.333333h;

Reference yield: 96.0%

diethylamine (109-89-7) + m-Toluic acid (99-04-7) → N,N-Diethyl-3-methylbenzamide (134-62-3,94271-03-1)

Guidance literature:

With Zn-MCM-22 catalyst; at 100 - 280 ℃; for 6h; under 15001.5 Torr; Inert atmosphere; Large scale;

upstream raw materials:

diethylamine

3-Methylbenzoyl chloride

m-Toluic acid

N,N-Diethyl-3-methyl-2-(2-methyl-propane-2-sulfonyl)-benzamide

Downstream raw materials:

3-Methylacetophenone

3-methylbenzyl alcohol

N-ethyl-N-(3-methylbenzyl)ethanamine

2-(3-methylphenyl)-4,5-dihydro-oxazole

Refernces

• 1、 Lei, Yizhu,Zhang, Xuefeng,Gu, Yanlong,Hu, Jianglin,Li, Guangxing,Shi, Kaiyi. "Palladium supported on triphenylphosphine-functionalized porous organic polymer: An efficient heterogeneous catalyst for aminocarbonylation". . p. 1 - 7. Retrieved 2016.
• 2、 Kar, Sayan,Xie, Yinjun,Zhou, Quan Quan,Diskin-Posner, Yael,Ben-David, Yehoshoa,Milstein, David. "Near-Ambient-Temperature Dehydrogenative Synthesis of the Amide Bond: Mechanistic Insight and Applications". . p. 7383 - 7393. Retrieved 2021/06/30.
• 3、 Nielsen, John,Tung, Truong Thanh. "Amide bond formation in aqueous solution: Direct coupling of metal carboxylate salts with ammonium salts at room temperature". supporting information. p. 10073 - 10080. Retrieved 2021/12/10.