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Basic Information
| CAS No.: | 13680-35-8 |
|---|---|
| Name: | 4,4'-Methylenebis(2,6-diethylaniline) |
| Molecular Structure: | |
|
|
|
| Formula: | C21H30N2 |
| Molecular Weight: | 310.483 |
| 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; |
| EINECS: | 237-185-4 |
| Density: | 1.019 g/cm3 |
| Melting Point: | 88-90 °C(lit.) |
| Boiling Point: | 463.5 °C at 760 mmHg |
| Flash Point: | 281 °C |
| Solubility: | 440μg/L at 20℃ |
| Appearance: | Crystalline powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22-36/37/38 |
| Safety: | 26-36 |
| PSA: | 52.04000 |
| LogP: | 5.85380 |
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Synthetic route
- 50-00-0
formaldehyd
- 579-66-8
2,6-diethylaniline
- 5266-85-3
2-isopropyl-6-methylaniline
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
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
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% |
Conditions
| Conditions | Yield |
|---|---|
| In 1-methyl-pyrrolidin-2-one at 100 - 150℃; for 12h; | 99% |
Conditions
| Conditions | Yield |
|---|---|
| In ethanol at 20℃; for 24h; | 50% |
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4,4'-Methylenebis(2,6-diethylaniline)
Chemistry
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 ℃.
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 ℃.
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.
Toxicity Data With Reference
1.rat LD50 oral > 1.901gm/kg (1901mg/kg)
National Technical Information Service. Vol. OTS0533525
National Technical Information Service. Vol. OTS0533525
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
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