• Name

  4,4'-Methylenebis(2,6-diethylaniline)

• EINECS 237-185-4
• CAS No. 13680-35-8
• Article Data3
• CAS DataBase
• Density 1.019 g/cm³
• Solubility 440μg/L at 20℃
• Melting Point 88-90 °C(lit.)
• Formula C₂₁H₃₀N₂
• Boiling Point 463.5 °C at 760 mmHg
• Molecular Weight 310.483
• Flash Point 281 °C
• Transport Information
• Appearance Crystalline powder
• Safety 26-36
• Risk Codes 22-36/37/38
• Molecular Structure
• Hazard Symbols Xn
• Synonyms Ethacure 208;4-[(4-amino-3,5-diethyl-phenyl)methyl]-2,6-diethyl-aniline;4,4-Methylenebis(2,6-diethylaniline);4,4’-Methylene-Bis(2,6-Diethylaniline) (MDEA);4,4'-Methylene-Bis(2,6-Diethylaniline);4,4'-Methylene-bis-(2,6-diethylaniline);Kayabond C 300;Benzenamine,4,4'-methylenebis[2,6-diethyl-;Lonzacure M-DEA;Kayabond C 300S;
• PSA 52.04000
• LogP 5.85380

Synthetic route

50-00-0

formaldehyd

579-66-8

2,6-diethylaniline

5266-85-3

2-isopropyl-6-methylaniline

A

M-MIPADEA

B

16298-38-7

methylene-1,1-bis(2-isopropyl-6-methylaniline)

C

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

Conditions

Conditions	Yield
With sulfuric acid In water; isopropyl alcohol at 60℃; for 5.5h; Product distribution / selectivity;
With sulfuric acid In water; isopropyl alcohol at 60℃; for 5.5h; Product distribution / selectivity;

...Expand

50-00-0

formaldehyd

579-66-8

2,6-diethylaniline

5266-85-3

2-isopropyl-6-methylaniline

A

M-MIPADEA

B

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

Conditions

Conditions	Yield
With sulfuric acid In water; isopropyl alcohol at 60℃; for 5.5h; Product distribution / selectivity;

...Expand

50-00-0

formaldehyd

579-66-8

2,6-diethylaniline

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

Conditions

Conditions	Yield
Stage #1: 2,6-diethylaniline With hydrogenchloride In water at 50 - 55℃; for 0.5h; Inert atmosphere; Stage #2: formaldehyd In water at 90 - 95℃; for 2h; Temperature;

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

106246-33-7

4,4'-methylene-bis-(3-chloro-2,6-diethylaniline)

Conditions

Conditions	Yield
Stage #1: 4,4′-methylenebis(2,6-diethylaniline) With hydrogenchloride In water at 20℃; for 0.25h; Stage #2: With dihydrogen peroxide In water at 45 - 65℃; for 3h;	99.3%
With chlorine; acetic acid at 50 - 55℃; Reagent/catalyst; Temperature;	92.8%

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

60469-05-8

bis-(3,5-diethyl-4-aminocyclohexyl)-methane

Conditions

Conditions	Yield
With Ru/Al2O3; hydrogen In cyclohexane at 110℃; under 15001.5 Torr;

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

90-02-8

salicylaldehyde

849704-38-7

[(HOC6H4-o-C(H)=N-2,6-(CH3CH2)2(4-C6H2))2-4-CH2]

Conditions

Conditions	Yield
toluene-4-sulfonic acid In methanol for 12h; Heating / reflux;	95%

24623-65-2

3-tert-butyl-2-hydroxybenzaldehyde

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

937721-14-7

[(HO-(3-tert-butyl)C6H3-o-C(H)=N-2,6-(ethyl)2C6H2)2-4-CH2]

Conditions

Conditions	Yield
toluene-4-sulfonic acid In methanol for 12h; Heating / reflux;	95%

108-31-6

maleic anhydride

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

105357-12-8

di(3,5-diethyl-4-maleimido-phenyl)methane

Conditions

Conditions	Yield
Stage #1: maleic anhydride; 4,4′-methylenebis(2,6-diethylaniline) In toluene Stage #2: With methanesulfonic acid In toluene for 1.5h; Reflux;	96%

50-00-0

formaldehyd

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

C66H90N6

Conditions

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 100 - 150℃; for 12h;	99%

5470-96-2

quinoline 2-carbaldehyde

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

C41H40N4

Conditions

Conditions	Yield
In ethanol at 20℃; for 24h;	50%

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

78-93-3

butanone

910915-05-8

N,N'-di-sec-butyl-4,4'-methylenebis(2,6-diethylbenzeneamine)

Conditions

Conditions	Yield
With amberlyst-15; hydrogen; Pt(S)/C at 22 - 95℃; under 7224.57 Torr; for 3h; sulfonated divinylbenzene/styrene copolymer H ion form; Product distribution / selectivity; Autoclave;	94 %Chromat.
With amberlyst-15; hydrogen; Pt(S)/C In tetrahydrofuran at 22 - 120℃; under 5414.51 - 7224.57 Torr; for 5h; sulfonated divinylbenzene/styrene copolymer H ion form; Product distribution / selectivity; Autoclave;	86 %Chromat.

950-81-2

4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

1296869-06-1

CH2[C6H2(C2H5)2NCHC3N2(CH3)2(C6H5)O]2

Conditions

Conditions	Yield
With formic acid In methanol for 4h; Reflux; Inert atmosphere;	41.4%

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

78-93-3

butanone

A

C25H36N2

B

910915-11-6

N,N'-di-sec-butylidene-4,4'-methylenebis(2,6-diethylbenzeneamine)

Conditions

Conditions	Yield
With Amberlist-15 In hexanes at 40℃; for 49h; sulfonated divinylbenzene/styrene copolymer H ion form; Heating / reflux;	A n/a B 94.7 %Chromat.

...Expand

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

78-93-3

butanone

A

N-sec-butyl-4,4'-methylenebis(2,6-diethylbenzeneamine)

B

910915-05-8

N,N'-di-sec-butyl-4,4'-methylenebis(2,6-diethylbenzeneamine)

Conditions

Conditions	Yield
With hydrogen; Pt(S)/C In toluene at 22 - 130℃; under 6448.83 Torr; for 19.5h; Product distribution / selectivity; Autoclave;	A 4 %Chromat. B 96 %Chromat.

...Expand

39621-11-9

6-(hydroxymethyl)picolinaldehyde

64443-05-6

tetrakis(actonitrile)copper(I) hexafluorophosphate

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

2C35H40N4O2*2Cu(1+)*2F6P(1-)

Conditions

Conditions	Yield
Stage #1: 6-(hydroxymethyl)picolinaldehyde; 4,4′-methylenebis(2,6-diethylaniline) In methanol at 20℃; for 0.5h; Stage #2: tetrakis(actonitrile)copper(I) hexafluorophosphate In methanol at 20℃; for 15h;	36%

...Expand

1121-60-4

pyridine-2-carbaldehyde

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

4,4'-methylene-N,N'-(2-pyridinylmethylene)-bis(2,6-diethylanil)

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 20℃; for 48h;	61%
In methanol

91-02-1

phenyl(pyridin-2-yl)methanone

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

4,4'-methylene-N,N'-(phenyl-2-pyridinylmethlene)-bis(2,6-diethyl-anil)

Conditions

Conditions	Yield
With tetraethoxy orthosilicate; sulfuric acid at 150℃; for 10h;	73%

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

67-64-1

acetone

A

N-isopropylidene-4,4'-methylenebis(2,6-diethylbenzeneamine)

B

910915-14-9

N,N'-diisopropylidene-4,4'-methylenebis(2,6-diethylbenzeneamine)

Conditions

Conditions	Yield
With amberlyst-15 for 24h; sulfonated divinylbenzene/styrene copolymer H ion form; Molecular sieve; Heating / reflux;

...Expand

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

86-52-2

1-Chloromethylnaphthalene

4′-methylenebis(2,6-diethyl-N-(naphthalen-1-ylmethyl)aniline)

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 83℃; for 24h;

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

122-60-1

Phenyl glycidyl ether

1-{4-[3,5-diethyl-4-(2-hydroxy-3-phenoxy-propylamino)-benzyl]-2,6-diethyl-phenylamino}-3-phenoxy-propan-2-ol

Conditions

Conditions	Yield
at 100℃; for 5h;

39621-11-9

6-(hydroxymethyl)picolinaldehyde

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

(6-{[(E)-4-(3,5-Diethyl-4-{[1-(6-hydroxymethyl-pyridin-2-yl)-meth-(E)-ylidene]-amino}-benzyl)-2,6-diethyl-phenylimino]-methyl}-pyridin-2-yl)-methanol

12107-56-1

dichloro(1,5-cyclooctadiene)palladium(II)

950-81-2

4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one

13680-35-8

4,4’-methylenebis(2,6-diethylaniline)

1296869-09-4

CH2[C6H2(C2H5)2NCHC3N2(CH3)2(C6H5)OPdCl2]2

Conditions

Conditions	Yield
In acetic acid under N2, Schlenk techniques; proper 4,4'-methylene bis-(2,6-dialkylaniline), antipyrine-4-carboxaldehyde, PdCl2(COD) added to glacial CH3COOH, reflux (12 h), cooled to room temp.; pptd. (Et2O), solid washed (MeOH, ether); elem. anal.;

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4,4'-METHYLENEBIS(2,6-DIETHYLANILINE) Chemical Properties

4,4'-Methylenebis(2,6-diethylaniline)(13680-35-8) exists as white to brown crystaline powder, insoluble in water.
Molecular Structure:
Molecular Formula:C₂₁H₃₀N₂.
Molecular Weight:310.49.
Density:1.019 g/cm³.
Melting Point:88 ℃.
Boiling Point:463.5 ℃ at 760 mmHg.
Flash Point:281 ℃.

4,4'-METHYLENEBIS(2,6-DIETHYLANILINE) Uses

4,4'-METHYLENEBIS(2,6-DIETHYLANILINE) Toxicity Data With Reference

4,4'-METHYLENEBIS(2,6-DIETHYLANILINE) Safety Profile

Irritating to eyes, respiratory system and skin. Harmful if swallowed. Wear suitable protective clothing.
Hazard Codes: Xn
Risk Statements: 22-36/37/38
22:  Harmful if swallowed 
36/37/38:  Irritating to eyes, respiratory system and skin  
Safety Statements: 26-36
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing 
WGK Germany: 3