136-84-5

Basic information

• Product Name: DIMETHYLOL ETHYLENE UREA
• Synonyms: N,N-DIMETHYLOL ETHYLENE UREA;1,3-bis(hydroxymethyl)-2-imidazolidinon;1,3-bis(hydroxymethyl)-2-Imidazolidinone;1,3-Dihydroxymethyl-2-imidazolidone;1,3-Dimethylol-2-imidazolidinone;1,3-Dimethylolethyleneurea;2-Imidazolidinone, 1,3-bis(hydroxymethyl)-;Aerotex Reactant No. 100
• CAS NO: 136-84-5
• Molecular Formula: C₅H₁₀N₂O₃
• Molecular Weight: 146.14
• EINECS: 205-264-2
• Mol File: 136-84-5.mol
• Article Data: 0

Chemical Properties

• Melting Point: 99 °C
• Boiling Point: 342.6 °C at 760 mmHg
• Flash Point: 161 °C
• Appearance: /
• Density: 1.398 g/cm³
• Vapor Pressure: 4.81E-06mmHg at 25°C
• Refractive Index: 1.555
• PKA: 14.20±0.10(Predicted)
• CAS DataBase Reference: DIMETHYLOL ETHYLENE UREA(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYLOL ETHYLENE UREA(136-84-5)
• EPA Substance Registry System: DIMETHYLOL ETHYLENE UREA(136-84-5)

Safety Data

• Hazardous Substances Data: 136-84-5(Hazardous Substances Data)

Usage

General Description

Dimethylol ethylene urea is a compound that acts as a crosslinking agent and intermediate in the production of resins. It is a white, crystalline solid that is soluble in water and has a variety of industrial uses, such as in the production of adhesives, coatings, and textiles. It is commonly used as a formaldehyde scavenger in the textile industry to improve fabric crease resistance and to enhance the durability of finished products. Additionally, dimethylol ethylene urea is used in the production of wood adhesives and in the manufacture of paper and cardboard products. However, it is important to note that dimethylol ethylene urea is classified as a skin and eye irritant and may cause allergic reactions in some individuals. Therefore, proper safety measures and protective equipment must be used when handling this chemical.

InChI:InChI=1/C5H10N2O3/c8-3-6-1-2-7(4-9)5(6)10/h8-9H,1-4H2

Synthetic route

imidazolidone (120-93-4) + formaldehyd (50-00-0) → 1,3-bis(hydroxymethyl)-imidazolidin-2-one (136-84-5)

Conditions	Yield
With methanol; sodium hydroxide

2,4-imidazolidinedione (461-72-3) + 1,3-bis(hydroxymethyl)-imidazolidin-2-one (136-84-5) → 1,3-bis(2,4-dioxoimidazolidin-1-ylmethyl)imidazolidin-2-one (1107610-58-1)

Conditions	Yield
With hydrogenchloride In methanol for 1h; Heating;	71%

1,3-bis(hydroxymethyl)-imidazolidin-2-one (136-84-5) + toluene-4-sulfonamide (70-55-3) → 1,3-bis(p-toluenesulfonylaminomethyl)imidazolidin-2-one (924850-84-0)

Conditions	Yield
With hydrogenchloride In methanol for 1h; Heating;	65%

acetamide (60-35-5) + 1,3-bis(hydroxymethyl)-imidazolidin-2-one (136-84-5) → 1,3-bis(acetylaminomethyl)imidazolidin-2-one (25538-42-5)

Conditions	Yield
With hydrogenchloride In methanol for 1h; Heating;	64%

1,3-bis(hydroxymethyl)-imidazolidin-2-one (136-84-5) → 1,3-dimethyl-2-imidazolidinone (80-73-9)

Conditions	Yield
With sodium formate; potassium carbonate In formic acid	63%

1,3-bis(hydroxymethyl)-imidazolidin-2-one (136-84-5) + N-carbamoylglycine (462-60-2) → C7H12N4O6 (1107610-61-6)

Conditions	Yield
With hydrogenchloride In methanol for 1h; Heating;	63%

1,3-bis(hydroxymethyl)-imidazolidin-2-one (136-84-5) + phenyl carbamate (64-10-8) → 1,1'-methylene-bis(3-phenylurea) (18872-98-5)

Conditions	Yield
With hydrogenchloride In methanol for 1h; Heating;	53%

1,3-bis(hydroxymethyl)-imidazolidin-2-one (136-84-5) + benzamide (55-21-0) → 1,3-bis(benzoylaminomethyl)imidazolidin-2-one (1107610-59-2)

Conditions	Yield
With hydrogenchloride In methanol for 1h; Heating;	50%

benzenesulfonamide (98-10-2) + 1,3-bis(hydroxymethyl)-imidazolidin-2-one (136-84-5) → 1,3-bis(phenylsulfonylaminomethyl)imidazolidin-2-one (1107610-60-5)

Conditions	Yield
With hydrogenchloride In methanol for 1h; Heating;	42%

1,3-bis(hydroxymethyl)-imidazolidin-2-one (136-84-5) + urethane (51-79-6) → N,N'-methanediyl-bis-carbamic acid diethyl ester (3693-53-6)

Conditions	Yield
With hydrogenchloride In methanol for 1h; Heating;	17%

1,3-bis(hydroxymethyl)-imidazolidin-2-one (136-84-5) + N-butylsulfamide (42731-63-5) → N',N'''-dibutyl-N,N''-methanediyl-bis-sulfamide (63845-59-0)

Conditions	Yield
With hydrogenchloride In methanol for 1h; Heating;	9%

1,3-bis(hydroxymethyl)-imidazolidin-2-one (136-84-5) + 4-hydroxy-3,5-di-tert-butylthiophenol (950-59-4) → 1,3-bis(3,5-di-tert.-butyl-4-hydroxyphenylthiomethyl)-2-imidazolidone (94343-98-3)

Conditions	Yield
In methanol

Upstream product

• 120-93-4 imidazolidone 
• 50-00-0 formaldehyd 

Downstream Products

• 94343-98-3 1,3-bis(3,5-di-tert.-butyl-4-hydroxyphenylthiomethyl)-2-imidazolidone 
• 3693-53-6 N,N'-methanediyl-bis-carbamic acid diethyl ester 
• 924850-84-0 1,3-bis(p-toluenesulfonylaminomethyl)imidazolidin-2-one 
• 1107610-59-2 1,3-bis(benzoylaminomethyl)imidazolidin-2-one 
• 18872-98-5 1,1'-methylene-bis(3-phenylurea) 
• 1107610-60-5 1,3-bis(phenylsulfonylaminomethyl)imidazolidin-2-one 
• 80-73-9 1,3-dimethyl-2-imidazolidinone