2728-05-4

Basic information

• Product Name: N,N-Diethyl-p-toluamide
• Synonyms: N,N-Diethyl-p-toluamide;N,N-Diethyl-p-methylbenzamide;p-DETA;BenzaMide, N,N-diethyl-4-Methyl-;DiethyltoluaMide Related CoMpound A
• CAS NO: 2728-05-4
• Molecular Formula: C₁₂H₁₇NO
• Molecular Weight: 191.26948
• Mol File: 2728-05-4.mol
• Article Data: 46

Chemical Properties

• Melting Point: 53-54 °C
• Boiling Point: 318.3°Cat760mmHg
• Flash Point: 140.8°C
• Appearance: /
• Density: 0.985g/cm³
• Vapor Pressure: 0.000365mmHg at 25°C
• Refractive Index: 1.517
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -0.93±0.70(Predicted)
• CAS DataBase Reference: N,N-Diethyl-p-toluamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Diethyl-p-toluamide(2728-05-4)
• EPA Substance Registry System: N,N-Diethyl-p-toluamide(2728-05-4)

Safety Data

• RTECS: XS4025000
• Hazardous Substances Data: 2728-05-4(Hazardous Substances Data)

Usage

Uses

N,N-Diethyl-p-toluamide, is a buildig block used in the synthesis of phthalocyanines. It can also be used in preparation of new insect repellents.

InChI:InChI=1/C12H17NO/c1-4-13(5-2)12(14)11-8-6-10(3)7-9-11/h6-9H,4-5H2,1-3H3

Synthetic route

4-methyl-benzoyl chloride (874-60-2) + diethylamine (109-89-7) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
	98%
In dichloromethane at 0℃; for 24h; Inert atmosphere;	71%
With benzene

p-Toluic acid (99-94-5) + diethylamine (109-89-7) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane at 0℃; for 0.5h;	97%
With n-butyl-sec-butylmagnesium 1.) n-heptane, 1h, reflux, 2.) methylene chloride, 65 deg C, 12 h; Yield given. Multistep reaction;

4-tolyl iodide (624-31-7) + potassium 2-(diethylamino)-2-oxoacetate → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions

Yield

With tris-(dibenzylideneacetone)dipalladium(0); potassium dihydrogenphosphate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl acetamide at 25℃; for 20h; Schlenk technique; Inert atmosphere; Irradiation; chemoselective reaction;

97%

carbon monoxide (201230-82-2) + 4-tolyl iodide (624-31-7) + triethylamine (121-44-8) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With palladium 10% on activated carbon; oxygen In acetonitrile at 100℃; under 4560.31 Torr; for 8h; Autoclave; Green chemistry;	96%

carbon monoxide (201230-82-2) + 4-tolyl iodide (624-31-7) + diethylamine (109-89-7) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With [Bmim][PdI2](PPh3); potassium carbonate In 1,4-dioxane at 90℃; under 15001.5 Torr; for 5h; Reagent/catalyst; Autoclave;	95%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; under 750.075 Torr; for 2h; Autoclave; chemoselective reaction;	91%
With triethylamine In N,N-dimethyl acetamide at 130℃; under 15001.5 Torr; for 1.5h; Autoclave; Green chemistry;	90%

(4-methylphenyl)acetonitrile (2947-61-7) + triethylamine (121-44-8) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With oxygen; copper dichloride In toluene at 110℃; under 760.051 Torr; for 48h; Schlenk technique;	87%

carbon monoxide (201230-82-2) + 4-methylphenylboronic acid (5720-05-8) + triethylamine (121-44-8) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With copper(l) iodide; oxygen; palladium dichloride In acetonitrile at 100℃; under 1520.1 Torr; for 12h; Autoclave; High pressure;	86%

carbon monoxide (201230-82-2) + 4-tolyl iodide (624-31-7) + diethylamine (109-89-7) → N,N-Diethyl-p-toluamid (2728-05-4) + N,N-diethyl-4-methyl-α-oxo-benzeneacetamide (80120-40-7)

Conditions	Yield
With [bmim]PF6; triethylamine; Pd carbene at 80℃; under 15200 Torr; for 0.566667h;	A 5% B 85%
With caesium carbonate In toluene at 80℃; under 760.051 Torr; for 20h; Microwave irradiation; Sealed tube;	A n/a B 40%
PdCl2(PMePh2)2 In neat (no solvent) at 80℃; under 50 Torr; for 2h; Product distribution; Mechanism;	A 4 % Chromat. B 96 % Chromat.

2-(diethylamino)-2-oxoacetic acid (55441-26-4) + potassium (4-methylphenyl)trifluoroborate → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With dipotassium peroxodisulfate; palladium diacetate In water; dimethyl sulfoxide; acetonitrile at 20℃;	85%

para-bromotoluene (106-38-7) + potassium 2-(diethylamino)-2-oxoacetate → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With bis(benzonitrile)palladium(ll) chloride; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; sodium acetate; nixantphos In N,N-dimethyl acetamide at 25℃; for 20h; Schlenk technique; Inert atmosphere; Irradiation; chemoselective reaction;	85%

carbon monoxide (201230-82-2) + para-bromotoluene (106-38-7) + diethylamine (109-89-7) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With palladium diacetate; caesium carbonate; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In N,N-dimethyl-formamide at 80℃; under 2068.65 Torr; Inert atmosphere;	83%
With palladium diacetate; caesium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In N,N-dimethyl-formamide at 80℃; under 2327.23 Torr;	83%
With triethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate at 60℃; under 760.051 Torr;	81%
With triethylamine; Pd-bis(1-methylbenzothiazole-2-carbene) In N,N-dimethyl acetamide at 130℃; for 7h;	91 % Chromat.

p-Toluic acid (99-94-5) + triethylamine (121-44-8) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With trifuran-2-yl-phosphane; palladium diacetate; 2,2-dimethylpropanoic anhydride In toluene at 120℃; for 15h; Inert atmosphere;	79%
With tetrachloromethane; potassium carbonate In dichloromethane for 24h; Inert atmosphere; Irradiation;	63%

C32H28GaO4S4(1-)*(x)H2O*K(1+) + diethylamine (109-89-7) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
In tetrahydrofuran at 25℃; for 1h;	77%

C32H28InO4S4(1-)*(x)H2O*K(1+) + diethylamine (109-89-7) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
In tetrahydrofuran at 25℃; for 1h;	73%

4-Methylbenzyl alcohol (589-18-4) + diethylamine (109-89-7) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With 1-methyl-1H-imidazole; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 4,4'-Dimethoxy-2,2'-bipyridin; 9-azabicyclo<3.3.1>nonane-N-oxyl; oxygen In dichloromethane at 20℃; under 760.051 Torr; for 2h; Molecular sieve;	71%

N-formyldiethylamine (617-84-5) + p-Toluic acid (99-94-5) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With tert.-butylhydroperoxide; copper(II) perchlorate hexahydrate at 100℃; for 15h;	69%

furfural (98-01-1) + 4-tolyl iodide (624-31-7) + triethylamine (121-44-8) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With Wilkinson’s catalyst; 1,3-bis-(diphenylphosphino)propane; water In tetrahydrofuran at 140℃; for 12h; Inert atmosphere; Sealed tube;	67%

diethyl amine hydrochloride (660-68-4) + 4-methyl-benzaldehyde (104-87-0) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With tert.-butylhydroperoxide; calcium carbonate In water at 60℃; for 16h; Inert atmosphere; Green chemistry;	58%

C32H28InO4S4(1-)*(x)H2O*K(1+) + 1-amino-2-propene (107-11-9) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
In tetrahydrofuran at 25℃; for 1h;	47%

diethylamine (109-89-7) + p-toluoyl-1H-1,2,3-benzotriazole (59046-28-5) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
In tetrahydrofuran at 20℃; for 4h;	44%

1,2-di(4-methylphenyl)-1,2-ethanedione (3457-48-5) + diethylamine (109-89-7) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With tert.-butylhydroperoxide; potassium carbonate In tetrahydrofuran at 80℃; for 12h; Sealed tube;	37%

N-formyldiethylamine (617-84-5) + 4-tolyl iodide (624-31-7) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
Stage #1: N-formyldiethylamine; 4-tolyl iodide With palladium diacetate at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With trichlorophosphate at 140℃; for 5h; Inert atmosphere;	26%

p-Toluic acid (99-94-5) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With tetrachlorosilane; benzene Behandeln des von SiCl4 befreiten Reaktionsgemisches mit Diaethylamin;
Multi-step reaction with 2 steps 1: thionyl chloride / Reflux; Inert atmosphere 2: triethylamine / Inert atmosphere View Scheme

carbon monoxide (201230-82-2) + para-bromotoluene (106-38-7) + diethylamine (109-89-7) → N,N-Diethyl-p-toluamid (2728-05-4) + N,N-diethyl-4-methyl-α-oxo-benzeneacetamide (80120-40-7)

Conditions	Yield
PdCl2(PMePh2)2 In neat (no solvent) at 100℃; under 7600 Torr; for 24h;	A 16 % Chromat. B 84 % Chromat.
PdCl2(PMePh2)2 In neat (no solvent) at 100℃; under 10 Torr; for 24h; Product distribution; Mechanism;	A 16 % Chromat. B 84 % Chromat.
PdCl2(PMePh2)2 at 100℃; under 7600 Torr; for 45h; Yield given. Yields of byproduct given;

diethylamine (109-89-7) + p-toluic pivalic anhydride (78823-38-8) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
In acetonitrile for 2h; Ambient temperature; Yield given;

para-chlorotoluene (106-43-4) + dimethyl amine (124-40-3) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
With pyridine In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran

4-Methylbenzyl alcohol (589-18-4) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 2 h / 20 °C / Inert atmosphere; Green chemistry 2: tert.-butylhydroperoxide; calcium carbonate / water / 16 h / 60 °C / Inert atmosphere; Green chemistry View Scheme

ethyl N,N-diethyloxamate (5411-58-5) → N,N-Diethyl-p-toluamid (2728-05-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate / ethanol / 10 h / 60 °C / Schlenk technique; Inert atmosphere 2: [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; potassium dihydrogenphosphate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / N,N-dimethyl acetamide / 20 h / 25 °C / Schlenk technique; Inert atmosphere; Irradiation View Scheme
Multi-step reaction with 2 steps 1: potassium tert-butylate / ethanol / 10 h / 60 °C / Schlenk technique; Inert atmosphere 2: [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; bis(benzonitrile)palladium(ll) chloride; nixantphos; sodium acetate / N,N-dimethyl acetamide / 20 h / 25 °C / Schlenk technique; Inert atmosphere; Irradiation View Scheme

4-Methylbenzyl alcohol (589-18-4) + diethylamine (109-89-7) → N,N-Diethyl-p-toluamid (2728-05-4) + 4-methyl-benzaldehyde (104-87-0)

Conditions	Yield
With 1-methyl-1H-imidazole; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 4,4'-Dimethoxy-2,2'-bipyridin; 9-azabicyclo<3.3.1>nonane-N-oxyl; oxygen In dichloromethane at 20℃; under 760.051 Torr; for 2h; Molecular sieve;	A 38 %Spectr. B 56 %Spectr.

styrene (292638-84-7) + N,N-Diethyl-p-toluamid (2728-05-4) → N,N-diethyl-4-methyl-2-(1-phenylethyl)benzamide (1620210-45-8)

Conditions	Yield
With bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; 1,4-bis[bis(pentafluorophenyl)phosphino]butane In 1,4-dioxane at 100℃; for 48h; Sealed tube; Inert atmosphere;	97%

N,N-Diethyl-p-toluamid (2728-05-4) → N-ethyl-N-(4-methylbenzyl)ethanamine (34306-01-9)

Conditions	Yield
With triethyl borane; phenylsilane; sodium hydroxide In tetrahydrofuran; tert-butyl methyl ether at 80℃; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;	94%
With triethyl borane; phenylsilane; sodium hydroxide In tetrahydrofuran; tert-butyl methyl ether at 80℃; for 48h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;	94%

N,N-Diethyl-p-toluamid (2728-05-4) → C12H17(2)H2N

Conditions	Yield
With triethyl borane; phenylsilane-d3; sodium hydroxide In tetrahydrofuran; tert-butyl methyl ether at 80℃; for 48h; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;	92%

N,N-Diethyl-p-toluamid (2728-05-4) → C12H19N*ClH

Conditions	Yield
Stage #1: N,N-Diethyl-p-toluamid With [κ2-{Ph2P(Se)NC9H6N}Al(Me)2]; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 20℃; for 12h; Schlenk technique; Glovebox; Stage #2: With hydrogenchloride In water chemoselective reaction;	90%

N,N-Diethyl-p-toluamid (2728-05-4) + phosphonic acid diethyl ester (762-04-9) → diethyl (2-(diethylcarbamoyl)-5-methylphenyl)phosphonate (1450829-67-0)

Conditions	Yield
With dipotassium peroxodisulfate; silver sulfate In water; acetonitrile at 90℃; for 1h; regioselective reaction;	80%

N,N-Diethyl-p-toluamid (2728-05-4) + N-tosyl-1,2-oxazetidine → C21H28N2O4S

Conditions	Yield
Stage #1: N,N-Diethyl-p-toluamid With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tetrahydrofuran; hexane; cyclohexane at -78℃; for 1h; Inert atmosphere; Stage #2: N-tosyl-1,2-oxazetidine In tetrahydrofuran; hexane; cyclohexane at -78℃; for 1.5h; Inert atmosphere;	79%

Dimethyldisulphide (624-92-0) + N,N-Diethyl-p-toluamid (2728-05-4) → N,N-diethyl-2-methylsulfanyl-4-methylbenzamide (596805-23-1)

Conditions	Yield
Stage #1: N,N-Diethyl-p-toluamid With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.5h; Stage #2: Dimethyldisulphide In tetrahydrofuran; cyclohexane at -78 - 20℃;	71%

N,N-Diethyl-p-toluamid (2728-05-4) + toluene-4-sulfonic acid hydrazide (1576-35-8) → N,N-diethyl-4-methyl-N'-tosylbenzohydrazonamide

Conditions	Yield
Stage #1: N,N-Diethyl-p-toluamid With 2-methoxypyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0℃; Inert atmosphere; Stage #2: toluene-4-sulfonic acid hydrazide In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	69%

N,N-Diethyl-p-toluamid (2728-05-4) + 4-methoxy-benzaldehyde (123-11-5) → N,N-diethyl-2-(4-methoxybenzoyl)-4-methylbenzamide (1321616-92-5)

Conditions	Yield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In tetrahydrofuran at 110℃; for 20h; Inert atmosphere; regioselective reaction;	67%

N,N-Diethyl-p-toluamid (2728-05-4) → N,N-diethyl-4-methylselenobenzamide (160594-72-9)

Conditions	Yield
Stage #1: N,N-Diethyl-p-toluamid With oxalyl dichloride In diethyl ether at 0 - 20℃; for 4h; Stage #2: With LiAlHSeH In tetrahydrofuran at 20℃; for 3h;	61%
Stage #1: N,N-Diethyl-p-toluamid With oxalyl dichloride In diethyl ether at 0 - 20℃; for 4h; Stage #2: With LiAlHSeH In tetrahydrofuran; diethyl ether at 20℃; for 3h;	61%

Triethoxyvinylsilane (78-08-0) + N,N-Diethyl-p-toluamid (2728-05-4) → C14H19NO

Conditions	Yield
With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; lithium fluoride In 1,2-dichloro-ethane at 120℃; for 20h; Schlenk technique;	56%

iodobenzene (591-50-4) + N,N-Diethyl-p-toluamid (2728-05-4) → N,N-diethyl-5-methyl[1,1'-biphenyl]-2-carboxamide (312955-15-0)

Conditions

Yield

Stage #1: N,N-Diethyl-p-toluamid With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.5h; Ullmann-Ziegler cross-coupling; Inert atmosphere; Stage #2: In tetrahydrofuran; cyclohexane for 0.25h; Ullmann-Ziegler cross-coupling; Inert atmosphere; Stage #3: iodobenzene With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; cyclohexane at 60℃; for 12h; Ullmann-Ziegler cross-coupling; Inert atmosphere;

53%

Upstream product

• 99-94-5 p-Toluic acid 
• 109-89-7 diethylamine 
• 106-42-3 para-xylene 
• 121-44-8 triethylamine 
• 589-18-4 4-Methylbenzyl alcohol 
• 201230-82-2 carbon monoxide 
• 624-31-7 4-tolyl iodide 
• 106-38-7 para-bromotoluene 
• 5411-58-5 ethyl N,N-diethyloxamate 
• 2947-61-7 (4-methylphenyl)acetonitrile 
• 3457-48-5 1,2-di(4-methylphenyl)-1,2-ethanedione 
• 660-68-4 diethyl amine hydrochloride 
• 104-87-0 4-methyl-benzaldehyde 
• 617-84-5 N-formyldiethylamine 

Downstream Products

• 34306-01-9 N-ethyl-N-(4-methylbenzyl)ethanamine 
• 1620210-45-8 N,N-diethyl-4-methyl-2-(1-phenylethyl)benzamide 
• 1450829-67-0 diethyl (2-(diethylcarbamoyl)-5-methylphenyl)phosphonate 
• 1321616-92-5 N,N-diethyl-2-(4-methoxybenzoyl)-4-methylbenzamide 
• 1019852-96-0 C₁₂H₁₅⁽²⁾H₂NO 
• 16587-47-6 6-methylbenzo[b]thiophene 
• 596805-23-1 N,N-diethyl-2-methylsulfanyl-4-methylbenzamide 
• 160594-72-9 N,N-diethyl-4-methylselenobenzamide 
• 88733-51-1 2-Amino-N,N-diethyl-4-methyl-benzamide 
• 71888-40-9 C₁₂H₁₆⁽²⁾HNO 
• 1218-89-9 4,4'-dimethylbenzoin 
• 104-87-0 4-methyl-benzaldehyde 
• 122-00-9 para-methylacetophenone 
• 105259-46-9 6-methyl-2-thiophenyl-1,4-naphthoquinone 

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