Product Name

  • Name

    4,4'-Methylenebis(N,N-diglycidylaniline)

  • EINECS 249-204-3
  • CAS No. 28768-32-3
  • Article Data6
  • CAS DataBase
  • Density 1.15 g/cm3
  • Solubility 9.2mg/L at 20℃
  • Melting Point
  • Formula C25H30N2O4
  • Boiling Point 619.3 °C at 760 mmHg
  • Molecular Weight 422.524
  • Flash Point 113 °C
  • Transport Information
  • Appearance
  • Safety 36/37
  • Risk Codes 43
  • Molecular Structure Molecular Structure of 28768-32-3 (4,4'-Methylenebis(N,N-diglycidylaniline))
  • Hazard Symbols IrritantXi
  • Synonyms Aniline,4,4'-methylenebis[N,N-bis(2,3-epoxypropyl)- (6CI,8CI);Oxiranemethanamine,N,N'-(methylenedi-4,1-phenylene)bis[N-(oxiranylmethyl)- (9CI);4,4'-Methylenebis[N,N-diglycidylaniline];Bis[4-(diglycidylamino)phenyl]methane;N,N,N',N'-Tetraglycidyl-4,4'-diaminodiphenylmethane;N,N,N',N'-Tetraglycidyl-4,4'-methylenebisbenzenamine;N,N,N',N'-Tetraglycidylbis(p-aminophenyl)methane;Tetraglycidyl 4,4'-diaminodiphenylmethane;Tetraglycidyl methylenedianiline;
  • PSA 56.60000
  • LogP 2.48540

Synthetic route

C25H34Cl4N2O4

C25H34Cl4N2O4

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

Conditions
ConditionsYield
With sodium hydroxide In water at 50℃; for 1.5h; Temperature;96%
With sodium hydroxide at 45℃; under 760.051 Torr; for 2.5h; Temperature;91%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water at 30℃; for 2h; Flow reactor;88.4%
4,4'-diamino diphenyl methane
101-77-9

4,4'-diamino diphenyl methane

epichlorohydrin
106-89-8

epichlorohydrin

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

Conditions
ConditionsYield
Stage #1: 4,4'-diamino diphenyl methane; epichlorohydrin With lanthanum nitrate In toluene at 60 - 85℃; under 150.015 - 300.03 Torr;
Stage #2: With benzyltrimethylammonium chloride; sodium hydroxide In water; toluene at 60 - 70℃; under 150.015 - 375.038 Torr; Pressure; Reagent/catalyst;		91%
4,4'-diamino diphenyl methane
101-77-9

4,4'-diamino diphenyl methane

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid / 80 °C / Flow reactor
2: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water / 2 h / 30 °C / Flow reactor
View Scheme
piperazine
110-85-0

piperazine

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

4,4'-methylene-bis(N,N-di-2-hydroxypropyl-3-piperazinylaniline)

4,4'-methylene-bis(N,N-di-2-hydroxypropyl-3-piperazinylaniline)

Conditions
ConditionsYield
In methanol; diethylene glycol dimethyl ether at 60℃; for 65h;94%
N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

Diethyl iminodiacetate
6290-05-7

Diethyl iminodiacetate

C57H90N6O20

C57H90N6O20

Conditions
ConditionsYield
In methanol; dichloromethane at 20 - 40℃; for 130.5h;78%
N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

N-methylaniline
100-61-8

N-methylaniline

C53H66N6O4

C53H66N6O4

Conditions
ConditionsYield
at 110℃; for 24h; Inert atmosphere;52%
N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

1,1'-(methylenedi-4,1-phenylene)bismaleimide
13676-54-5

1,1'-(methylenedi-4,1-phenylene)bismaleimide

dapsone
80-08-0

dapsone

polymer; monomer(s): N,N,N\,,N\-tetraglycidyl-4,4\-diaminodiphenylmethane; 4,4\-diaminodiphenyl sulfone; 4,4\-bis(maleimido)diphenylmethane

polymer; monomer(s): N,N,N\,,N\-tetraglycidyl-4,4\-diaminodiphenylmethane; 4,4\-diaminodiphenyl sulfone; 4,4\-bis(maleimido)diphenylmethane

Conditions
ConditionsYield
Stage #1: N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane; 1,1'-(methylenedi-4,1-phenylene)bismaleimide; dapsone at 140℃; for 16h;
Stage #2: at 200℃; for 4h;
...Expand
N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

dapsone
80-08-0

dapsone

polymer; monomer(s): N,N,N\,,N\-tetraglycidyl-4,4\-diaminodiphenylmethane; 4,4\-diaminodiphenyl sulfone

polymer; monomer(s): N,N,N\,,N\-tetraglycidyl-4,4\-diaminodiphenylmethane; 4,4\-diaminodiphenyl sulfone

Conditions
ConditionsYield
Stage #1: N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane; dapsone at 140℃; for 16h;
Stage #2: at 200℃; for 4h;
styrene
292638-84-7

styrene

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

polymer, Mw/Mn = 1.27; monomer(s): styrene; 4,4\-methylene-bis(N,N\-diglycidylaniline)

polymer, Mw/Mn = 1.27; monomer(s): styrene; 4,4\-methylene-bis(N,N\-diglycidylaniline)

Conditions
ConditionsYield
With bis(cyclopentadienyl)titanium (III) chloride In 1,4-dioxane at 90℃; Kinetics;
With bis(cyclopentadienyl)titanium (III) chloride In 1,4-dioxane at 90℃;
styrene
292638-84-7

styrene

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

polymer, Mn,GPC = 7496, Mw/Mn = 1.09; monomer(s): styrene; 4,4\-methylene-bis(N,N\-diglycidylaniline)

polymer, Mn,GPC = 7496, Mw/Mn = 1.09; monomer(s): styrene; 4,4\-methylene-bis(N,N\-diglycidylaniline)

Conditions
ConditionsYield
With bis(cyclopentadienyl)titanium (III) chloride In 1,4-dioxane at 90℃; for 7h;
N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

2-amino-2-hydroxymethyl-1,3-propanediol
77-86-1

2-amino-2-hydroxymethyl-1,3-propanediol

A

C29H41N3O7

C29H41N3O7

B

C33H52N4O10

C33H52N4O10

C

C37H63N5O13

C37H63N5O13

D

C41H74N6O16

C41H74N6O16

Conditions
ConditionsYield
In methanol; dichloromethane at 40 - 60℃; for 72h; Product distribution / selectivity;
...Expand
N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

2,2'-iminobis[ethanol]
111-42-2

2,2'-iminobis[ethanol]

A

C37H63N5O10

C37H63N5O10

B

C41H74N6O12

C41H74N6O12

Conditions
ConditionsYield
In methanol at 20 - 60℃; for 48h;
...Expand
N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

Diethyl iminodiacetate
6290-05-7

Diethyl iminodiacetate

A

C33H45N3O8

C33H45N3O8

B

C41H60N4O12

C41H60N4O12

Conditions
ConditionsYield
In methanol; dichloromethane at 20℃; for 48.5h;
...Expand
N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

C37H42N4O6S
103443-52-3

C37H42N4O6S

C62H72N6O10S

C62H72N6O10S

Conditions
ConditionsYield
Activation energy; Heating;
N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

dapsone
80-08-0

dapsone

C37H42N4O6S
103443-52-3

C37H42N4O6S

Conditions
ConditionsYield
Activation energy; Heating;
N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

dapsone
80-08-0

dapsone

C62H72N6O10S

C62H72N6O10S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Heating
2: Heating
View Scheme
N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

allyl alcohol
107-18-6

allyl alcohol

C31H42N2O6

C31H42N2O6

Conditions
ConditionsYield
With tetraethylammonium bromide; sodium hydroxide In tetrahydrofuran; acetonitrile at 20℃; for 6h;
N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

C51H84N4O14Si2

C51H84N4O14Si2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide; tetraethylammonium bromide / acetonitrile; tetrahydrofuran / 6 h / 20 °C
2: N-ethyl-N,N-diisopropylamine / acetonitrile / 30 h / 65 °C
View Scheme
N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

C43H74N2O12Si2

C43H74N2O12Si2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide; tetraethylammonium bromide / acetonitrile; tetrahydrofuran / 6 h / 20 °C
2: platinum(IV) oxide / toluene / 24 h / 80 °C
View Scheme
N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane
28768-32-3

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane

ethanol
64-17-5

ethanol

C29H42N2O6

C29H42N2O6

Conditions
ConditionsYield
With tetraethylammonium bromide; sodium hydroxide In tetrahydrofuran; acetonitrile at 26℃; for 2.5h;

4,4'-Methylenebis(N,N-diglycidylaniline) Specification

The 4,4'-Methylenebis(N,N-diglycidylaniline), with the CAS registry number 28768-32-3, is also known as 4,4'-Methylenebis[N,N-bis(2,3-epoxypropyl)aniline]. It belongs to the product categories of Organics; Epoxide Monomers; Monomers; Polymer Science. Its EINECS number is 249-204-3. This chemical's molecular formula is C25H30N2O4 and formula weight is 422.52. What's more, its IUPAC name and systematic name are the same which is called 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-N,N-bis(oxiran-2-ylmethyl)aniline.

Physical properties of 4,4'-Methylenebis(N,N-diglycidylaniline): (1)ACD/LogP: 3.92; (2)ACD/LogD (pH 5.5): 3.87; (3)ACD/LogD (pH 7.4): 3.92; (4)ACD/BCF (pH 5.5): 502.87; (5)ACD/BCF (pH 7.4): 564.01; (6)ACD/KOC (pH 5.5): 2890.35; (7)ACD/KOC (pH 7.4): 3241.82; (8)#H bond acceptors: 6; (9)#Freely Rotating Bonds: 12; (10)Index of Refraction: 1.654; (11)Molar Refractivity: 119.55 cm3; (12)Molar Volume: 326 cm3; (13)Surface Tension: 66.4 dyne/cm; (14)Density: 1.295 g/cm3; (15)Flash Point: 177.1 °C; (16)Enthalpy of Vaporization: 91.8 kJ/mol; (17)Boiling Point: 619.3 °C at 760 mmHg; (18)Vapour Pressure: 2.9E-15 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. In addition, it may cause sensitisation by skin contact. Wheneve you will contact it, please wear suitable protective clothing and gloves.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1C(O1)CN(CC2CO2)C3=CC=C(C=C3)CC4=CC=C(C=C4)N(CC5CO5)CC6CO6
(2)InChI: InChI=1S/C25H30N2O4/c1-5-20(26(10-22-14-28-22)11-23-15-29-23)6-2-18(1)9-19-3-7-21(8-4-19)27(12-24-16-30-24)13-25-17-31-25/h1-8,22-25H,9-17H2
(3)InChIKey: FAUAZXVRLVIARB-UHFFFAOYSA-N

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