2431-96-1

Basic information

• Product Name: N,N-DIETHYL-2-PHENYLACETAMIDE
• Synonyms: N,N-DIETHYL-2-PHENYLACETAMIDE;n,n-diethyl-2-phenyl-acetamid;n,n-diethyl-benzeneacetamid;n,n-diethylbenzeneacetamide;n,n-diethylphenylacetamide;phenyl-n,n-diethylacetamide;DEPA;DEPA(N,N-Diethyl-2-phenylacetamide)
• CAS NO: 2431-96-1
• Molecular Formula: C₁₂H₁₇NO
• Molecular Weight: 191.27
• EINECS: 219-400-3
• Product Categories: Amides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 2431-96-1.mol
• Article Data: 53

Chemical Properties

• Melting Point: 84-86 °C
• Boiling Point: 169-171 °C18 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.004 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000691mmHg at 25°C
• Refractive Index: n20/D 1.522(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -0.44±0.70(Predicted)
• CAS DataBase Reference: N,N-DIETHYL-2-PHENYLACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIETHYL-2-PHENYLACETAMIDE(2431-96-1)
• EPA Substance Registry System: N,N-DIETHYL-2-PHENYLACETAMIDE(2431-96-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• WGK Germany: 3
• RTECS: AB7410000
• Hazardous Substances Data: 2431-96-1(Hazardous Substances Data)

Usage

Description

N, N-DIETHYL-2-PHENYLACETAMIDE is a safe and effective, low-cost and broad-spectrum repellent for personal protection against Hematophagous arthropods1. It has repellent activity against hematophagous insects including mosquitoes, black flies, horse flies, muscoid flies, rat fleas, and ticks, as well as land leeches and cockroaches.As an Insect repellents, it exert its effects through interactions with Ors (odorant receptors) and GRs (gustatory receptor neuron (GRN)) in mosquitoes. However, the detailed mechanism of action remains inconclusive.

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.

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

Upstream product

• 109-89-7 diethylamine 
• 103-80-0 phenylacetyl chloride 
• 103-82-2 phenylacetic acid 
• 33641-61-1 N,N,N′,N′-tetraethylthionylamide 
• 21954-69-8 diethyl-amidosulfurous acid methyl ester 
• 4696-96-2 N,N-diethyl-2-phenylethanethioamide 
• 100-39-0 benzyl bromide 
• 112081-91-1 Diethylamino-methylsulfanyl-acetonitrile 
• 5330-97-2 N-hydroxy-2-phenylacetamide 
• 74-96-4 ethyl bromide 
• 5465-00-9 N-ethylphenylacetamide 
• 38042-52-3 2-chloro-2-(phenylsulfinyl)-1-phenyl-1-ethanone 
• 660-68-4 diethyl amine hydrochloride 
• 3496-32-0 phenylketene 

Downstream Products

• 451-40-1 phenyl benzyl ketone 
• 5300-21-0 N,N-diethylphenethylamine 
• 93990-67-1 N,N-diethyl-4-morpholin-4-yl-4-oxo-2-phenyl-butyramide 
• 106438-10-2 α-(ω-N-methylacetanilido)-phenylessigsaeure-diaethylamid 
• 955-10-2 3-phenylcumarin 
• 23000-32-0 8-methoxy-3-phenyl-2H-chromen-2-one 
• 19698-34-1 N_.N-Diethyl-1-chlor-2-chlorcarbonyl-styrylamin 
• 2019-69-4 N,N-diethyl-2-(2-hydroxyphenyl)acetamide 
• 101-97-3 Ethyl 2-phenylethanoate 
• 82489-29-0 (E)-N,N-diethyl-2-phenylethen-1-amine 
• 1422748-00-2 2-(2,6-dibenzoylphenyl)-N,N-diethylacetamide 
• 1422748-01-3 2-(2-benzoylphenyl)-N,N-diethylacetamide 
• 1449216-42-5 2-(4-(tert-butyl)phenyl)-N,N-diethyl-2-phenylacetamide 
• 1449216-43-6 N,N-diethyl-2-phenyl-2-(m-tolyl)acetamide 

Relevant articles and documents

Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization

Herein, we report a metal-free synthesis of cyclic amidines, oxazines, and an oxazinone under mild conditions by electrophilic amide activation. This strategy features an unusual Umpolung cyclization mode and enables the smooth union of α-aryl amides and diverse alkylazides, effectively rerouting our previously reported α-amination transform.

Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters: Via C-N bond activation

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

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.