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Cas Database

Name	4,4'-METHYLENEBIS(2,6-DIETHYLANILINE)	EINECS	237-185-4
CAS No.	13680-35-8	Density	1.019 g/cm³
PSA	52.04000	LogP	5.85380
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	N/A	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;	Article Data	3

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

: 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%

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)(13680-35-8) provides improved mechanical and dynamic properties, so it is an excellent chain extender for polyurethanes and a curing agent for epoxides. 4,4'-Methylenebis(2,6-diethylaniline)(13680-35-8) is used as a precursor for polyimides and as an intermediate for organic syntheses. 4,4'-Methylenebis(2,6-diethylaniline)(13680-35-8) is available for cast elastomers, RIM elastomers, coatings and chemical resistant coatings.

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

1.rat LD50 oral > 1.901gm/kg (1901mg/kg)
National Technical Information Service. Vol. OTS0533525

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

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