141-07-1

Usage

Uses

Used in Polymer Production:
1,3-BIS(METHOXYMETHYL)UREA is used as a crosslinking agent for improving the strength, durability, and heat resistance of polymers, particularly in the manufacturing of resins and adhesives. Its crosslinking properties allow for the creation of materials with enhanced structural integrity and performance characteristics.
Used in Polyurethane Foam Industry:
In the polyurethane foam industry, 1,3-BIS(METHOXYMETHYL)UREA serves as a stabilizer, ensuring the uniformity and quality of the foam produced. Its stabilizing effect contributes to the production of consistent, high-quality polyurethane foams used in various applications, including insulation, cushioning, and upholstery.
Used in Epoxy Resin Industry:
As a curing agent for epoxy resins, 1,3-BIS(METHOXYMETHYL)UREA plays a crucial role in the hardening process of these resins. Its use results in the formation of a solid, thermosetting polymer with high mechanical strength and chemical resistance, suitable for applications in coatings, adhesives, and electrical insulation.
Used as a Flame Retardant:
In certain applications, 1,3-BIS(METHOXYMETHYL)UREA can function as a flame retardant, providing an additional layer of safety in materials that are prone to ignition. Its flame retardant properties make it a valuable component in the production of materials intended for environments with increased fire risk.
Environmental Considerations:
1,3-BIS(METHOXYMETHYL)UREA is noted for its low acute toxicity, positioning it as an environmentally friendly option in the chemical industry. This characteristic is particularly important in applications where the health and safety of both workers and end-users are paramount, as well as in the context of ecological sustainability.

InChI:InChI=1/C5H12N2O3/c1-9-3-6-5(8)7-4-10-2/h3-4H2,1-2H3,(H2,6,7,8)

Synthetic route

methanol (67-56-1) + 1,3-bis(hydroxymethyl)urea (140-95-4) → N,N'-bis(methoxymethyl)urea (141-07-1)

Conditions	Yield
With hydrogenchloride
With phosphoric acid at 55 - 60℃;
With sulfuric acid at 45 - 48℃;

methanol (67-56-1) + formaldehyd (50-00-0) + urea (57-13-6) → N,N'-bis(methoxymethyl)urea (141-07-1)

Conditions	Yield
With sodium hydroxide

methanol (67-56-1) + tris(hydroxymethyl)urea (13329-70-9) → N,N'-bis(methoxymethyl)urea (141-07-1) + tris(methoxymethyl)urea (13822-64-5)

Conditions	Yield
With hydrogenchloride at 0 - 5℃; for 0.166667h; Yield given;

formaldehyd (50-00-0) + bis-(N'-hydroxymethyl-ureidomethyl)-ether (1910-86-7) + barium hydroxide → 3,5-bis(methoxymethyl)perhydro-1,3,5-oxadiazin-4-one (7388-44-5) + N,N'-bis(methoxymethyl)urea (141-07-1)

Conditions	Yield
beim Behandeln des Reaktionsprodukts mit Chlorwasserstoff enthaltendem Methanol;

N-methoxymethyl-N,N'-dimethylurea (21115-51-5) + N,N'-bis(methoxymethyl)urea (141-07-1) → 5,5'-carbonylbis<1,3-dimethyl-3,4,5,6-tetrahydro-1,3,5-triazin-2(1H)-one> (120482-18-0)

Conditions	Yield
toluene-4-sulfonic acid In N,N-dimethyl-formamide at 110℃; for 0.5h;	76%

1-octadecanol (112-92-5) + N,N'-bis(methoxymethyl)urea (141-07-1) → N-methoxymethyl-N'-octadecyloxymethyl-urea

Conditions	Yield
With benzene-1,2-dicarboxylic acid at 70℃; unter Abdestillieren des abgespaltenen Methanols;

n-hexan-2-ol (626-93-7) + N,N'-bis(methoxymethyl)urea (141-07-1) → N,N'-bis-(1-methyl-pentyloxymethyl)-urea

Conditions	Yield
With phthalic anhydride; benzene unter Abdestillieren von Methanol und Benzol;

thioacetic acid (507-09-5) + N,N'-bis(methoxymethyl)urea (141-07-1) → N,N'-bis-(acetylsulfanyl-methyl)-urea

Conditions	Yield
With 1,4-dioxane; hydrogenchloride

1-Decanol (112-30-1) + N,N'-bis(methoxymethyl)urea (141-07-1) → N,N'-bis-decyloxymethyl-urea

Conditions	Yield
With sodium; benzene untrer Abdestillieren von Methanol+Benzol;

1,4-dioxane (123-91-1) + hydrogenchloride (7647-01-0) + thioacetic acid (507-09-5) + N,N'-bis(methoxymethyl)urea (141-07-1) → N,N'-bis-(acetylsulfanyl-methyl)-urea

Conditions	Yield
reagiert analog mit N-Methoxymethyl-carbonsaeureamiden;
reagiert analog mit N-Methoxymethyl-carbonsaeureamiden;

N,N'-bis(methoxymethyl)urea (141-07-1) + dodecyl alcohol (1 mol) → N-dodecyloxymethyl-N'-methoxymethyl-urea

Conditions	Yield
With benzene-1,2-dicarboxylic acid at 85 - 100℃; unter Abdestillieren des abgespaltenen Methanols;

N,N'-bis(methoxymethyl)urea (141-07-1) + dodecyl alcohol (2 mol) → N,N'-bis-dodecyloxymethyl-urea

Conditions	Yield
With phthalic anhydride; benzene unter Abdestillieren von Methanol+Benzol;

Upstream product

• 67-56-1 methanol 
• 140-95-4 1,3-bis(hydroxymethyl)urea 
• 50-00-0 formaldehyd 
• 57-13-6 urea 
• 13329-70-9 tris(hydroxymethyl)urea 
• 1910-86-7 bis-(N'-hydroxymethyl-ureidomethyl)-ether 

Downstream Products

• 96-31-1 N,N'-Dimethylurea 
• 67-56-1 methanol 
• 17741-86-5 N-methoxymethyl-N'-hydroxymethylurea 
• 50-00-0 formaldehyd 
• 4981-47-9 N,N'-bis-butoxymethyl-urea 

Relevant academic research and scientific papers

The Formation Pathway of 3,5-Bis(methoxymethyl)perhydro-1,3,5-oxadiazin-4-one

The investigation of the reactions of urea and its methyl derivatives with formaldehyde elucidated the formation pathway of 3,5-bis(methoxymethyl)perhydro-1,3,5-oxadiazin-4-one. 1) The addition of formaldehyde to urea became increasingly difficult according to the increase of the number of added formaldehyde molecules, probably because of the steric hindrance of the hydroxymethyl groups. 2) 3,5-Bis(methoxymethyl)perhydro-1,3,5-oxadiazin-4-one was concluded to be derived from urea via tris(hydroxymethyl)urea and 3-(hydroxymethyl)perhydro-1,3,5-oxadiazin-4-one but not via tetrakis(hydroxymethyl)urea or perhydro-1,3,5-oxadiazin-4-one.