54333-75-4

Basic information

• Product Name: N,N-Diethyl-2-chloropropionamide
• Synonyms: 2-chloro-N,N-diethylpropionamide;N,N-Diethyl-2-chloropropionamide
• CAS NO: 54333-75-4
• Molecular Formula: C₇H₁₄ClNO
• Molecular Weight: 163.65
• EINECS: 259-107-8
• Mol File: 54333-75-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 217 °C
• Flash Point: 85 °C
• Appearance: /
• Density: 1.021
• Vapor Pressure: 0.137mmHg at 25°C
• Refractive Index: 1.449
• PKA: -0.89±0.70(Predicted)
• CAS DataBase Reference: N,N-Diethyl-2-chloropropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Diethyl-2-chloropropionamide(54333-75-4)
• EPA Substance Registry System: N,N-Diethyl-2-chloropropionamide(54333-75-4)

Safety Data

• Hazardous Substances Data: 54333-75-4(Hazardous Substances Data)

Usage

General Description

N,N-Diethyl-2-chloropropionamide, also known as DEET, is a common active ingredient in insect repellents. It works by interfering with the insect's ability to detect human skin and blood, thus preventing them from biting and transmitting diseases. DEET has been shown to be effective at repelling a wide range of insects, including mosquitoes, ticks, fleas, and biting flies. While it is generally considered safe for use on human skin, some individuals may experience skin irritation or allergic reactions. It is important to follow the instructions on the product label when using DEET-based insect repellents, and to wash it off after returning indoors.

InChI:InChI=1/C7H14ClNO/c1-4-9(5-2)7(10)6(3)8/h6H,4-5H2,1-3H3

Upstream product

• 1114-51-8 N,N-diethylpropanamide 
• 109-89-7 diethylamine 
• 7623-09-8 2-chloropropionyl chloride 

Downstream Products

• 98110-07-7 N-(2,6-dimethyl-phenyl)-alanine diethylamide 
• 118247-09-9 2-[(2'-Acetoxybenzoyl)oxy]-2'-methyl-N,N-diethylacetamide 
• 368425-37-0 2-chloro-N,N-diethyl-3-hydroxy-2-methyl-3-phenylpropanamide 
• 368425-51-8 2-Chloro-N,N-diethyl-3-hydroxy-2-methyl-3-phenylpentanamide 
• 368425-52-9 2-Chloro-N,N-diethyl-3-hydroxy-2,3-dimethyl-4-phenylbutanamide 
• 368425-42-7 2-Chloro-N,N-diethyl-3-cyclohexyl-3-hydroxy-2-methylpropanamide 
• 600734-09-6 2,3-epoxy-N,N-diethyl-2-methyl-3-phenylpropanamide 
• 600734-14-3 2,3-epoxy-N,N-diethyl-2-methyl-3-phenylbutanamide 
• 600734-15-4 2,3-epoxy-N,N-diethyl-2-methyl-3-phenylpentanamide 
• 600734-28-9 2,3-epoxy-N,N-diethyl-2-methyl-4-phenylpentanamide 
• 733046-05-4 2,3-epoxy-N,N,3-triethyl-2-methylpentanamide 
• 1253101-17-5 diethylcarbamoylmethyl phenylpropiolate 
• 59843-81-1 4-chloro-N,N-diethyl-α-methyl-3-phenylpyrazole-1-acetamide 
• 59843-82-2 2-(4-chloro-5-phenyl-pyrazol-1-yl)-N,N-diethyl-propionamide 

Relevant articles and documents

Efficient α-chlorination of carbonyl containing compounds under basic conditions using methyl chlorosulfate

An efficient method for the α-chlorination of ketones under basic conditions is described using methyl chlorosulfate. Its applicability for the chlorination of other functional groups has also been studied and it is equally useful for the synthesis of α-chloroesters and amides. Methyl chlorosulfate is described for the first time as a positive chlorine source. Some aldol reactions which occur during the chlorination of some substrates are also reported.

Evaluation of glycolamide esters and various other esters of aspirin as true aspirin prodrugs

A series of glycolamide, glycolate, (acyloxy)methyl, alkyl, and aryl esters of acetylsalicylic acid (aspirin) were synthesized and evaluated as potential prodrug forms of aspirin. N,N-Disubstituted glycolamide esters were found to be rapidly hydrolized in human plasma, resulting in the formation of aspirin as well as the corresponding salicylate esters. These in turn hydrolyzed rapidly to salicylic acid. The largest amount of aspirin formed from the esters were 50 and 55% in case of the N,N-dimethyl- and N,N-diethylglycolamide esters, respectively. Similar results were obtained in blood with the N,N-dimethyl- and N,N-diethylglycolamide esters. Unsubstituted and monosubstituted glycolamide esters as well as most other esters previously suggested to be aspirin prodrugs were shown to hydrolyze exclusively to the corresponding salicylic acid esters. Lipophilicity parameters and water solubilities of the esters were determined, and structural factors favoring ester prodrug hydrolysis at the expense of deacetylation to yield salicylate ester are discussed. The properties of some N,N-disubstituted glycolamide esters of aspirin are highlighted with respect to their use as potential aspirin prodrugs.