5026-74-4

Basic information

• Product Name: N,N-DIGLYCIDYL-4-GLYCIDYLOXYANILINE
• Synonyms: N,N-DIGLYCIDYL-4-GLYCIDYLOXYANILINE;-(diglycidylamino)phenylglycidylether;4-(2-Oxiranylmethoxy)-N,N-bis(2-oxiranylmethyl)aniline;4-(Diglycidylamino)phenyl glycidyl ether;Aniline, p-(2,3-epoxypropoxy)-N,N-bis(2,3-epoxypropyl)-;Aniline,p-(2,3-epoxypropoxy)-N,N-bis(2,3-epoxypropyl);ERL 0500;ERL-0510(Triglycidyl-p-Aminophenol)
• CAS NO: 5026-74-4
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.32
• EINECS: 225-716-2
• Product Categories: Epoxide Monomers;Monomers;Polymer Science
• Mol File: 5026-74-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 420.18°C (rough estimate)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.22 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.06E-08mmHg at 25°C
• Refractive Index: n20/D 1.567(lit.)
• Storage Temp.: 2-8°C
• PKA: 4.78±0.50(Predicted)
• Water Solubility: 3.34g/L at 20℃
• CAS DataBase Reference: N,N-DIGLYCIDYL-4-GLYCIDYLOXYANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIGLYCIDYL-4-GLYCIDYLOXYANILINE(5026-74-4)
• EPA Substance Registry System: N,N-DIGLYCIDYL-4-GLYCIDYLOXYANILINE(5026-74-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-40-43
• Safety Statements: 23-26-36
• WGK Germany: 2
• RTECS: RR0504000
• Hazardous Substances Data: 5026-74-4(Hazardous Substances Data)

Usage

Chemical Properties

Brown viscous liquid

Safety Profile

Moderately toxic ingestion. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOxí.

InChI:InChI=1/C15H19NO4/c1-3-12(17-9-15-10-20-15)4-2-11(1)16(5-13-7-18-13)6-14-8-19-14/h1-4,13-15H,5-10H2

Synthetic route

4-amino-phenol (123-30-8) + epichlorohydrin (106-89-8) → p-(diglycidylamino)phenyl glycidyl ether (5026-74-4)

Conditions	Yield
Stage #1: 4-amino-phenol; epichlorohydrin In water at 40℃; for 5h; Inert atmosphere; Green chemistry; Stage #2: With sodium hydroxide In water at 55℃; under 135.014 Torr; Solvent; Temperature; Pressure; Green chemistry;	95%

4-ethoxycarbonylpiperazine (120-43-4) + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → C36H61N7O10

Conditions	Yield
In methanol at 20℃; for 48h;	92%

poly(β-vinyloxyethylamine); monomer(s): β-vinyloxyethylamine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, curing time 4 h; monomer(s): β-vinyloxyethylamine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol for 4h;

poly(β-vinyloxyethylamine); monomer(s): β-vinyloxyethylamine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, curing time 6 h; monomer(s): β-vinyloxyethylamine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol for 6h;

poly(β-vinyloxyethylamine); monomer(s): β-vinyloxyethylamine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, curing time 8 h; monomer(s): β-vinyloxyethylamine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol for 8h;

poly(β-vinyloxyethylamine); monomer(s): β-vinyloxyethylamine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, curing time 10 h; monomer(s): β-vinyloxyethylamine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol for 10h;

poly(β-vinyloxyethylamine); monomer(s): β-vinyloxyethylamine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, poly(β-vinyloxyethylamine) to N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline feed ratio 1:1; monomer(s): β-vinyloxyethylamine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol Heating;

poly(β-vinyloxyethylamine); monomer(s): β-vinyloxyethylamine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, poly(β-vinyloxyethylamine) to N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline feed ratio 2:1; monomer(s): β-vinyloxyethylamine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol Heating;

poly(β-vinyloxyethylamine); monomer(s): β-vinyloxyethylamine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, poly(β-vinyloxyethylamine) to N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline feed ratio 3:1; monomer(s): β-vinyloxyethylamine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol Heating;

poly(β-vinyloxyethylamine); monomer(s): β-vinyloxyethylamine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, poly(β-vinyloxyethylamine) to N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline feed ratio 4:1; monomer(s): β-vinyloxyethylamine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol Heating;

poly(β-vinyloxyethylamine); monomer(s): β-vinyloxyethylamine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, prepared at 60 deg C; monomer(s): β-vinyloxyethylamine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol at 60℃;

poly(β-vinyloxyethylamine); monomer(s): β-vinyloxyethylamine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, prepared at 80 deg C; monomer(s): β-vinyloxyethylamine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol at 80℃;

poly(β-vinyloxyethylamine); monomer(s): β-vinyloxyethylamine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, prepared at 100 deg C; monomer(s): β-vinyloxyethylamine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol at 100℃;

poly(β-vinyloxyethylamine); monomer(s): β-vinyloxyethylamine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, prepared at 120 deg C; monomer(s): β-vinyloxyethylamine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol at 120℃;

poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)], β-vinyloxyethylamine to 2-methyl-5-vinylpyridine feed ratio 25:75; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, prepared at 120 deg C; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol at 120℃;

poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)], β-vinyloxyethylamine to 2-methyl-5-vinylpyridine feed ratio 25:75; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, curing time 4 h; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol for 4h;

poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)], β-vinyloxyethylamine to 2-methyl-5-vinylpyridine feed ratio 25:75; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, curing time 6 h; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol for 6h;

poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)], β-vinyloxyethylamine to 2-methyl-5-vinylpyridine feed ratio 25:75; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, curing time 8 h; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol for 8h;

poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)], β-vinyloxyethylamine to 2-methyl-5-vinylpyridine feed ratio 25:75; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, curing time 10 h; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol for 10h;

poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)], β-vinyloxyethylamine to 2-methyl-5-vinylpyridine feed ratio 25:75; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)] to N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline feed ratio 1:1

Conditions	Yield
In 2-methyl-propan-1-ol Heating;

poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)], β-vinyloxyethylamine to 2-methyl-5-vinylpyridine feed ratio 25:75; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)] to N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline feed ratio 2:1

Conditions	Yield
In 2-methyl-propan-1-ol Heating;

poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)], β-vinyloxyethylamine to 2-methyl-5-vinylpyridine feed ratio 25:75; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)] to N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline feed ratio 3:1

Conditions	Yield
In 2-methyl-propan-1-ol Heating;

poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)], β-vinyloxyethylamine to 2-methyl-5-vinylpyridine feed ratio 25:75; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)] to N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline feed ratio 4:1

Conditions	Yield
In 2-methyl-propan-1-ol Heating;

poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)], β-vinyloxyethylamine to 2-methyl-5-vinylpyridine feed ratio 25:75; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, prepared at 60 deg C; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol at 60℃;

poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)], β-vinyloxyethylamine to 2-methyl-5-vinylpyridine feed ratio 25:75; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, prepared at 80 deg C; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol at 80℃;

poly[(β-vinyloxyethylamine)-co-(2-methyl-5-vinylpyridine)], β-vinyloxyethylamine to 2-methyl-5-vinylpyridine feed ratio 25:75; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, prepared at 100 deg C; monomer(s): β-vinyloxyethylamine; 2-methyl-5-vinylpyridine; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol at 100℃;

poly[(β-vinyloxyethylamine)-co-(N-vinylpyrrolidone)]; monomer(s): β-vinyloxyethylamine; N-vinylpyrrolidone + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, prepared at 60 deg C; monomer(s): β-vinyloxyethylamine; N-vinylpyrrolidone; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol at 60℃;

poly[(β-vinyloxyethylamine)-co-(N-vinylpyrrolidone)]; monomer(s): β-vinyloxyethylamine; N-vinylpyrrolidone + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, prepared at 80 deg C; monomer(s): β-vinyloxyethylamine; N-vinylpyrrolidone; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol at 80℃;

poly[(β-vinyloxyethylamine)-co-(N-vinylpyrrolidone)]; monomer(s): β-vinyloxyethylamine; N-vinylpyrrolidone + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, prepared at 100 deg C; monomer(s): β-vinyloxyethylamine; N-vinylpyrrolidone; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol at 100℃;

poly[(β-vinyloxyethylamine)-co-(N-vinylpyrrolidone)]; monomer(s): β-vinyloxyethylamine; N-vinylpyrrolidone + p-(diglycidylamino)phenyl glycidyl ether (5026-74-4) → polymer, cross-linked, prepared at 120 deg C; monomer(s): β-vinyloxyethylamine; N-vinylpyrrolidone; N,N-di(2,3-epoxypropyl)-4-(2,3-epoxypropyloxy)aniline

Conditions	Yield
In 2-methyl-propan-1-ol at 120℃;

Upstream product

• 123-30-8 4-amino-phenol 
• 106-89-8 epichlorohydrin 

Relevant articles and documents

[0001] ENERGY EFFICIENT MANUFACTURING PROCESS FOR PREPARING N,0- TRIGLYCIDYL AMINOPHENOLS

The invention relates to an improved process for making monomelic triglycidyl compounds, wherein the triglycidyl compounds include N, O-triglycidyl compounds containing at least one primary aromatic amine and one phenolic functional group attached to the same or a different aromatic ring. The methods of the present invention result in the production of N, O-triglycidyl compounds, such as those of formula I and II. The improved process is energy efficient, environment friendly, and results in increased yields of product. The methods of the present invention can be performed in the absence of protic organic co-solvents during the reaction of an epihalohyrdrin with an aminophenol, such as compounds of fonnula III and IV, which provides an intermediate halohydiin compound. The methods of the present invention may also be performed in the absence of a phase transfer catalyst.