2431-96-1 Usage
Description
N,N-DIETHYL-2-PHENYLACETAMIDE is a low-cost and broad-spectrum repellent that is safe and effective for personal protection against hematophagous arthropods. It is known for its repellent activity against a variety of hematophagous insects and other pests, making it a valuable compound in the field of insect repellents.
Uses
Used in Insect Repellent Applications:
N,N-DIETHYL-2-PHENYLACETAMIDE is used as a personal protection agent against hematophagous arthropods such as mosquitoes, black flies, horse flies, muscoid flies, rat fleas, and ticks, as well as land leeches and cockroaches. It exerts its repellent effects through interactions with odorant receptors (Ors) and gustatory receptor neurons (GRN) in mosquitoes, although the detailed mechanism of action is still inconclusive.
Used in Pest Control Industry:
N,N-DIETHYL-2-PHENYLACETAMIDE is used as a repellent in the pest control industry to protect against a wide range of hematophagous insects and other pests. Its broad-spectrum activity and low cost make it an attractive option for various applications, including outdoor events, agricultural settings, and residential areas.
Referrence
Kalyanasundaram, Muthuswami, and N. Mathew. "N,N-Diethyl Phenylacetamide (DEPA): A Safe and Effective Repellent for Personal Protection Against Hematophagous Arthropods." Journal of Medical Entomology 43.3(2013):518-25.
Rao, S. S., and K. M. Rao. "Insect Repellent N, N-diethylphenylacetamide: An Update." Journal of Medical Entomology 8.3(1991):303.
Dickens, Joseph C., and J. D. Bohbot. "Mini review: Mode of action of mosquito repellents." Pesticide Biochemistry & Physiology 106.3(2013):149-155.
Synthesis Reference(s)
The Journal of Organic Chemistry, 46, p. 1215, 1981 DOI: 10.1021/jo00319a037
Metabolic pathway
When rats are exposed to whole-body attack by
diethylphenylacetamide (DEPA), DEPA enters the
systemic circulation when it is inhaled, and crosses
air ? lung and lung ? blood barriers to be biodegraded
and excreted. DEPA is converted by dealkylation and
hydrolysis to the two acetamides,
ethylphenylacetamide (EPA) and phenylacetamide
(PA), and to phenylacetic acid (PhAA) which are
excreted and identified as urinary metabolites.
Check Digit Verification of cas no
The CAS Registry Mumber 2431-96-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,4,3 and 1 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 2431-96:
(6*2)+(5*4)+(4*3)+(3*1)+(2*9)+(1*6)=71
71 % 10 = 1
So 2431-96-1 is a valid CAS Registry Number.
InChI:InChI=1/C12H17NO/c1-3-13(4-2)12(14)10-11-8-6-5-7-9-11/h5-9H,3-4,10H2,1-2H3
2431-96-1Relevant articles and documents
An Efficient Palladium-Catalysed Aminocarbonylation of Benzyl Chlorides
Oram, Niall,Richardson, Jeffery,Rilvin-Derrick, Eloise
, p. 369 - 372 (2020/02/27)
An improved procedure for the aminocarbonylation of benzyl chloride derivatives using carbon monoxide and either primary or secondary amines has been developed. Studying the competing background alkylation reaction allowed the solvent and base to be selected for a simple catalyst screen, which, in turn, enabled the discovery of a method for the preparation of 2-arylacetamides under mild conditions, with minimal side-products using an inexpensive phosphine ligand. This non-traditional optimisation strategy allowed us to overcome the background alkylation, which has been cited as justification for the development of more complex and less atom-economical approaches.
Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters: Via C-N bond activation
Yu, Weijie,Yang, Shuwu,Xiong, Fei,Fan, Tianxiang,Feng, Yan,Huang, Yuanyuan,Fu, Junkai,Wang, Tao
supporting information, p. 3099 - 3103 (2018/05/22)
An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C-N bond cleavage. This protocol features mild reaction conditions under atmospheric pressure of CO, a redox-neutral process without an additional oxidant, and a broad substrate scope for various kinds of amines, alcohols and phenols.
Phototriggered Dehydration Condensation Using an Aminocyclopropenone
Mishiro, Kenji,Yushima, Yuki,Kunishima, Munetaka
supporting information, p. 4912 - 4915 (2017/09/23)
A phototriggered dehydration condensation using an aminocyclopropenone has been developed. The UV irradiation of an aminocyclopropenone generated a highly reactive ynamine in situ and the dehydration condensation of a carboxylic acid and an amine coexisting in the reaction solution smoothly proceeded to afford an amide. This reaction is completely controllable by the ON/OFF states of a UV lamp.