24544-08-9

Basic information

• Product Name: 2,6-Diethyl-4-methylaniline
• Synonyms: 2,6-DIETHYL-4-METHYLANILINE;2,6-diethyl-4-methylbenzenamine;2,6-Diethyl-4-methylanilin;2,6-Diethyl-p-toluidine (NH2=1);2,6-DIETHYL-4-METHYLANILINE(DEMA),DEMA:=98.5%(CAPILLARY GC);(2,6-diethyl-4-methyl-phenyl)amine;Benzenamine,2,6-diethyl-4-methyl-;DEMA
• CAS NO: 24544-08-9
• Molecular Formula: C₁₁H₁₇N
• Molecular Weight: 163.26
• EINECS: 246-307-5
• Product Categories: Intermediates of Dyes and Pigments;o-alkylated Anilines;Aniline Derivatives
• Mol File: 24544-08-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 259.058 °C at 760 mmHg
• Flash Point: 111.736 °C
• Appearance: Colourless to yellowish liquid
• Density: 0.94 g/cm³
• Vapor Pressure: 0.0132mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 4.56±0.10(Predicted)
• Water Solubility: 570mg/L at 20℃
• CAS DataBase Reference: 2,6-Diethyl-4-methylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Diethyl-4-methylaniline(24544-08-9)
• EPA Substance Registry System: 2,6-Diethyl-4-methylaniline(24544-08-9)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 24544-08-9(Hazardous Substances Data)

Usage

Chemical Properties

Colourless to yellowish liquid

Uses

2,6-Diethyl-4-methylaniline (DEMA) is used as intermediate for chemical synthesis. WWW Link

InChI:InChI=1/C11H17N/c1-4-9-6-8(3)7-10(5-2)11(9)12/h6-7H,4-5,12H2,1-3H3

Synthetic route

ethanol (64-17-5) + p-toluidine hydrochloride (540-23-8) → 2,6-diethyl-4-methylaniline (24544-08-9)

Conditions	Yield
at 300℃;

p-toluidine (106-49-0) + aluminium (7429-90-5) → 2,6-diethyl-4-methylaniline (24544-08-9)

Conditions	Yield
aluminium trichloride In water

2,6-diethyl-4-methylaniline (24544-08-9) + (S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid (26250-84-0) → C22H34N2O3 (1526920-89-7)

Conditions	Yield
Stage #1: (S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid With triethylamine; isobutyl chloroformate In dichloromethane at 0℃; for 0.5h; Stage #2: 2,6-diethyl-4-methylaniline In dichloromethane at 0 - 20℃; for 24h;	99%

2,6-diethyl-4-methylaniline (24544-08-9) → 1-bromo-2,6-diethyl-4-methylbenzene (314084-61-2)

Conditions	Yield
Stage #1: 2,6-diethyl-4-methylaniline With hydrogen bromide at 10℃; for 0.5h; Stage #2: With sodium nitrite at -5 - 0℃; for 2.5h; Stage #3: With ferrous(II) sulfate heptahydrate; hydrogen bromide; sodium bromide In water at 65 - 75℃; for 0.5h; Reagent/catalyst;	95%
Stage #1: 2,6-diethyl-4-methylaniline With hydrogen bromide In water at 80℃; for 1.5h; Stage #2: With sodium nitrite In water at -10 - -5℃; for 2h; Stage #3: With ferrous(II) sulfate heptahydrate; hydrogen bromide In water at 80℃; for 2h;	94.66%
Stage #1: 2,6-diethyl-4-methylaniline With hydrogen bromide; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: With copper(I) bromide at 5 - 60℃; for 4h;	89.2%

2,6-diethyl-4-methylaniline (24544-08-9) + diethyl malonate (105-53-3) → 2-(2,6-diethyl-4-methylphenyl)malonic acid diethyl ester (328932-70-3)

Conditions	Yield
Stage #1: 2,6-diethyl-4-methylaniline With copper(l) iodide; isopentyl nitrite In tetrahydrofuran at 5 - 10℃; for 2h; Stage #2: diethyl malonate With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 2.5h; Reagent/catalyst;	92%

2,6-diethyl-4-methylaniline (24544-08-9) → 2-chloro-1,3-diethyl-5-methylbenzene

Conditions	Yield
Stage #1: 2,6-diethyl-4-methylaniline With hydrogenchloride In 1,2-dichloro-benzene at 45 - 70℃; Stage #2: With hydrogenchloride; isopentyl nitrite In 1,2-dichloro-benzene at 45 - 50℃; for 2h;	90%
Stage #1: 2,6-diethyl-4-methylaniline With hydrogenchloride In water at 50℃; Sandmeyer Reaction; Stage #2: With sodium nitrite In water at -10 - -5℃; for 1h; Sandmeyer Reaction; Stage #3: With hydrogenchloride; iron(III) chloride In water at -10 - 65℃; for 1.5h; Product distribution / selectivity; Sandmeyer Reaction;

cobalt(II) chloride hexahydrate + 2,6-diethyl-4-methylaniline (24544-08-9) + α,α′-dioxo-2,3:5,6-bis(hexamethylene)pyridine (96413-30-8) → C39H51Cl2CoN3

Conditions	Yield
With acetic acid for 12h; Reflux;	90%
With acetic anhydride at 130℃; for 12h;	90%

2,6-diethyl-4-methylaniline (24544-08-9) + C11H16NO3S(1-)*Na(1+) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C41H41N2O7S2(1-)*Na(1+)

Conditions	Yield
Stage #1: C11H16NO3S(1-)*Na(1+); 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide In ethylene glycol at 120℃; for 2h; Stage #2: 2,6-diethyl-4-methylaniline In ethylene glycol at 180℃; for 18h; Reagent/catalyst;	88%

iron(II) chloride tetrahydrate + 2,6-diethyl-4-methylaniline (24544-08-9) + α,α′-dioxo-2,3:5,6-bis(hexamethylene)pyridine (96413-30-8) → [2,3:5,6-{C5H10C(N-4-Me-2,6-Et2C6H2)}2C5HN]FeCl2

Conditions	Yield
With acetic anhydride at 130℃; for 12h;	87%
In acetic acid for 12h; Inert atmosphere; Schlenk technique; Reflux;	75%

6-(2,4,6-triisopropylphenyl)-2-pyridinecarboxaldehyde (1433897-26-7) + 2,6-diethyl-4-methylaniline (24544-08-9) → (E)-N-(2,6-diethyl-4-methylphenyl)-1-(6-(2,4,6-triisopropylphenyl)pyridin-2-yl)methanimine

Conditions	Yield
With formic acid In methanol at 60℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;	87%

1,1-Dichloroethylene (75-35-4) + 2,6-diethyl-4-methylaniline (24544-08-9) → C13H17Cl3

Conditions	Yield
With tert.-butylnitrite; copper dichloride In acetonitrile at 10 - 20℃; for 16h; Reagent/catalyst;	85.1%

2,6-diethyl-4-methylaniline (24544-08-9) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) + 3,5-diisopropyl sulfanilic acid sodium salt → C42H43N2O7S2(1-)*Na(1+)

Conditions	Yield
Stage #1: 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide; 3,5-diisopropyl sulfanilic acid sodium salt With 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide In ethylene glycol at 120℃; for 2h; Stage #2: 2,6-diethyl-4-methylaniline In ethylene glycol at 180℃; for 18h;	85%

2,6-diethyl-4-methylaniline (24544-08-9) → 2,6-diethyl-4-methyliodobenzene

Conditions	Yield
Stage #1: 2,6-diethyl-4-methylaniline With hydrogenchloride In water at 80 - 90℃; Stage #2: With sodium nitrite In water at -10 - 0℃; Stage #3: With hydrogenchloride; sodium iodide In water at 80 - 90℃; for 16h;	83%
Stage #1: 2,6-diethyl-4-methylaniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1h; Stage #2: With potassium iodide In water at 5 - 20℃; Reagent/catalyst;

1,4-dihydroxy-9,10-anthracenedione (81-64-1) + 2,6-diethyl-4-methylaniline (24544-08-9) → C.I. Solvent Blue 97 (32724-62-2)

Conditions	Yield
With LACTIC ACID; Trimethyl borate; 2,3-dihydro-1,4-dihydroxyanthraquinone at 115 - 145℃; for 11.5h;	82%

1-Nitronaphthalene (86-57-7) + 2,6-diethyl-4-methylaniline (24544-08-9) → C21H23N

Conditions	Yield
With potassium phosphate tribasic trihydrate; 2-(2,6-diethyl-4-methylphenyl)-5-(2,4,6-triisopropylphenyl)imidazo[1,5-a]pyridin-2-ium chloride; palladium(II) acetylacetonate In 1,4-dioxane at 130℃; for 24h; Sealed tube; Inert atmosphere;	80%
With bis(acetylacetonato)palladium(II); potassium phosphate tribasic trihydrate; 2-(2,6-diethyl-4-methylphenyl)-5-(2,4,6-triisopropylphenyl)imidazo[1,5-a]pyridin-2-ium chloride In 1,4-dioxane at 130℃; for 24h; Inert atmosphere;	80%

2-acetyl-cycloheptapyridine + 2,6-diethyl-4-methylaniline (24544-08-9) → 2-(1-(2,6-diethyl-4-methylphenylimino)ethyl)cycloheptapyridine

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 6h; Inert atmosphere; Schlenk technique; Reflux;	78%

nickel(II) chloride hexahydrate + 2,6-diethyl-4-methylaniline (24544-08-9) + 2-(hydroxymethyl)-6,7-dihydroquinolin-8(5H)-one → C21H26Cl2N2NiO

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 8h; Reflux;	78%

cobalt(II) chloride hexahydrate + 2,6-diethyl-4-methylaniline (24544-08-9) + 1,2,3,7,8,9,10-heptahydrocyclohepta[b]-quinoline-4,6-dione → N4,N6-bis(2,6-diethyl-4-methylphenyl)-2,3,7,8,9,10-hexahydro-1H-cycloheptaquinoline-4,6-diimine cobalt dichloride

Conditions	Yield
In acetic acid for 12h; Inert atmosphere; Schlenk technique; Reflux;	77%
With acetic acid at 130℃; for 12h; Inert atmosphere;	77%

iron(II) chloride tetrahydrate + 2,6-diethyl-4-methylaniline (24544-08-9) + 1,2,3,7,8,9,10-heptahydrocyclohepta[b]-quinoline-4,6-dione → N4,N6-bis(2,6-diethyl-4-methylphenyl)-2,3,7,8,9,10-hexahydro-1H-cycloheptaquinoline-4,6-diimine ferric dichloride

Conditions	Yield
With acetic acid at 130℃; for 12h; Inert atmosphere;	74%

4-oxo-1,2,3,4-tetrahydroacridine (49568-10-7) + nickel(II) chloride hexahydrate + 2,6-diethyl-4-methylaniline (24544-08-9) → 4-(2,6-diethyl-4-methylphenylimino)-1,2,3-trihydroacridylnickel(II) dichloride

Conditions	Yield
In acetic acid for 3h; Reflux;	72.9%

nickel(II) chloride hexahydrate + 2-isopropyl-5,6,7-trihydroquinolin-8-one (1369217-33-3) + 2,6-diethyl-4-methylaniline (24544-08-9) → 2,6-diethyl-4-methyl-N-(2-isopropyl-5,6,7-trihydroquinolin-8-ylidene)phenylaminonickel(II) dichloride

Conditions	Yield
In acetic acid under N2, Schlenk technique; quinoline deriv., amine, NiCl2*6H2O and acetic acid placed in round bottom flask; stirred at reflux for 5 h; acid removed under reduced pressure; residue dissolved in MeOH; pptd. with Et2O; filtered, washed with Et2O, dried under vac.; elem. anal.;	72%

nickel(II) chloride hexahydrate + 2,6-diethyl-4-methylaniline (24544-08-9) + 2-chloro-5,6,7,8-tetrahydroquinolin-8-one (129337-86-6) → [2,6-diethyl-4-methyl-N-(2-chloro-5,6,7-trihydroquinolin-8-ylidene)phenylamino]nickel(II) dichloride (1263563-92-3)

Conditions	Yield
In acetic acid (N2); quinolinone, aniline and NiCl2*6H2O were refluxed in AcOH for 3 h; evapd. in vac., dissolved in MeOH, filtered, precipitated with Et2O, filtered, washed with Et2O, dried in vac., elem. anal.;	71%

4-oxo-1,2,3,4-tetrahydroacridine (49568-10-7) + iron(II) chloride tetrahydrate + 2,6-diethyl-4-methylaniline (24544-08-9) → C24H26Cl2FeN2

Conditions	Yield
With acetic acid for 3h; Inert atmosphere; Reflux;	70.3%
With acetic acid for 3h; Inert atmosphere; Reflux;	70.3%

nickel(II) chloride hexahydrate + 2,6-diethyl-4-methylaniline (24544-08-9) + 2-propyl-2,3-dihydroacridine-4-one → 4-(2,6-diethyl-4-methylphenylimino)-2-propyl-1,3-dihydroacridine nickel dichloride

Conditions	Yield
With acetic acid for 5h; Reflux;	70%

chromium(III) chloride hexahydrate + 2,6-diethyl-4-methylaniline (24544-08-9) + α,α’-dioxo-2,3 : 5,6-bis(pentamethylene)pyridine (96413-29-5) → C37H47Cl3CrN3

Conditions	Yield
In acetic acid for 3h; Reflux; Inert atmosphere; Schlenk technique;	70%

2-((2,6-dibenzhydryl-4-chlorophenyl)imino)acenaphthylen-1-one (1396115-05-1) + 2,6-diethyl-4-methylaniline (24544-08-9) → 2,6-dibenzhydryl-N-(2-(2,6-diethyl-4-methylphenylimino)acenaphthylenylidne)-4-chlorobenzenamine

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 120℃;	69%

2,6-diethyl-4-methylaniline (24544-08-9) + 2-benzoyl-5,6,7,8-tetrahydro cyclohepta[b]pyridin-9-one + iron(II) chloride → C39H45Cl2FeN3

Conditions	Yield
With acetic acid for 6h; Inert atmosphere; Reflux;	68.4%

1-quinolin-2-yl-ethanone (1011-47-8) + 2,6-diethyl-4-methylaniline (24544-08-9) → 2,6-diethyl-4-methyl-N-(1-(quinolin-2-yl)ethylidene) benzenamine (1319733-82-8)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 12h; Reflux;	68%

iron(II) chloride tetrahydrate + 2,6-diethyl-4-methylaniline (24544-08-9) + α,α’-dioxo-2,3 : 5,6-bis(pentamethylene)pyridine (96413-29-5) → C37H47Cl2FeN3

Conditions	Yield
With acetic acid In acetic acid at 120℃; for 4h; Inert atmosphere;	67.5%

Upstream product

• 64-17-5 ethanol 
• 540-23-8 p-toluidine hydrochloride 
• 106-49-0 p-toluidine 
• 7429-90-5 aluminium 

Downstream Products

• 71757-51-2 1-(2,6-Diethyl-4-methyl-cyclohexyl)-3-(1-methyl-butyl)-thiourea 
• 71757-52-3 1-(2,6-Diethyl-4-methyl-cyclohexyl)-3-methyl-thiourea 
• 32724-62-2 C_.I_. Solvent Blue 97 
• 1227404-38-7 C₁₂H₇N₂C(CH₂CH₃)NC₆H₂(CH₂CH₃)2(CH₃) 
• 1263563-92-3 [2,6-diethyl-4-methyl-N-(2-chloro-5,6,7-trihydroquinolin-8-ylidene)phenylamino]nickel(II) dichloride 
• 1263564-03-9 [2,6-diethyl-4-methyl-N-(2-phenyl-5,6,7-trihydroquinolin-8-ylidene)phenylamino]nickel(II) dichloride 
• 1352916-91-6 C₁₃H₁₈BrNO 
• 1352916-93-8 C₂₃H₃₄N₂O 
• 1352916-96-1 C₂₃H₃₆N₂ 
• 1369217-27-5 2,6-diethyl-4-methyl-N-(2-methyl-5,6,7-trihydroquinolin-8-ylidene)phenylaminonickel(II) dichloride 
• 1373619-06-7 2-[1-(2,6-dibenzhydryl-4-chlorophenylimino)ethyl]-6-[1-(2,6-diethyl-4-methylphenylimino)ethyl]pyridine 
• 1401439-36-8 C₃₂H₃₃NO 
• 1429044-96-1 2,4-bis{6-[1-(2,6-diethyl-4-methylphenylimino)ethyl]pyridin-2-yl}-3H-benzazepine 
• 1596368-93-2 C₄₇H₄₁ClF₄N₂ 

Relevant articles and documents

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