3089-11-0

Basic information

• Product Name: 2,4,6-TRIS[BIS(METHOXYMETHYL)AMINO]-1,3,5-TRIAZINE
• Synonyms: 2,4,6-TRIS[BIS(METHOXYMETHYL)AMINO]- 1,3,5-TRIAZINE (EP);HMMM;Metazine;1,3,5-Triazine-2,4,6-triamine, N,N,N,N,N,N-hexakis(methoxymethyl)-;N,N,N'',N'',N ,N -HEXAKIS(METHOXYMETHYL)-1,3,5-TRIAZINE-2,4,6- TRIAMINE);Hexa(methoxymethyl)malamine;Hexamethylolmelaminehexamethyl ether;N,N,N',N',N'',N''-Hexa(methoxymethyl)-1,3,5-triazine-2,4,6-triamine
• CAS NO: 3089-11-0
• Molecular Formula: C₁₅H₃₀N₆O₆
• Molecular Weight: 390.44
• EINECS: 221-422-3
• Product Categories: Organics
• Mol File: 3089-11-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 49°C
• Boiling Point: 0°C
• Flash Point: 0°C
• Appearance: /
• Density: 1.1513 (rough estimate)
• Vapor Pressure: 1.23E-09mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly),
• PKA: 2.20±0.10(Predicted)
• Stability: Stability
• CAS DataBase Reference: 2,4,6-TRIS[BIS(METHOXYMETHYL)AMINO]-1,3,5-TRIAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRIS[BIS(METHOXYMETHYL)AMINO]-1,3,5-TRIAZINE(3089-11-0)
• EPA Substance Registry System: 2,4,6-TRIS[BIS(METHOXYMETHYL)AMINO]-1,3,5-TRIAZINE(3089-11-0)

Safety Data

• RTECS: XZ1065000
• Hazardous Substances Data: 3089-11-0(Hazardous Substances Data)

Usage

Uses

ross-linking agent for alkyds, epoxies, cellulosics, and vinyls.

InChI:InChI=1/C15H30N6O6/c1-22-7-19(8-23-2)13-16-14(20(9-24-3)10-25-4)18-15(17-13)21(11-26-5)12-27-6/h7-12H2,1-6H3

Synthetic route

methanol (67-56-1) + hexa(hydroxymethyl)melamine (531-18-0) → N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0)

Conditions	Yield
With hydrogenchloride
With nitric acid In water at 45 - 55℃; for 1.5h; pH=1.5 - 3.8; Product distribution / selectivity;
With hydrogenchloride In water at 35℃; for 2h; pH=2.5; pH-value; Temperature;

N,N-bis(2-hydroxylethyl)aminomethylphosphonic acid diethyl ester (2781-11-5) + N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) → C63H138N12O30P6

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 130℃; for 11h; Inert atmosphere;	98%

N,N-bis(2-hydroxylethyl)aminomethylphosphonic acid diethyl ester (2781-11-5) + N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) + ethylene glycol (107-21-1) → C45H96N9O22P3

Conditions	Yield
Stage #1: N,N-bis(2-hydroxylethyl)aminomethylphosphonic acid diethyl ester; hexakis-N-methoxymethyl-[1,3,5]triazine-2,4,6-triamine With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 125℃; for 4h; Inert atmosphere; Stage #2: ethylene glycol In N,N-dimethyl-formamide at 95℃; for 4h; Inert atmosphere;	97%

N,N-bis(2-hydroxylethyl)aminomethylphosphonic acid diethyl ester (2781-11-5) + N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) → C47H102N10O22P4

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 125℃; for 7h; Inert atmosphere;	97%

Butane-1,4-diol (110-63-4) + N,N-bis(2-hydroxylethyl)aminomethylphosphonic acid diethyl ester (2781-11-5) + N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) → C29H60N7O12P

Conditions	Yield
Stage #1: N,N-bis(2-hydroxylethyl)aminomethylphosphonic acid diethyl ester; hexakis-N-methoxymethyl-[1,3,5]triazine-2,4,6-triamine With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere; Stage #2: Butane-1,4-diol In N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere;	95%

N,N-bis(2-hydroxylethyl)aminomethylphosphonic acid diethyl ester (2781-11-5) + N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) → C31H66N8O14P2

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 120℃; for 3h; Inert atmosphere;	95%

N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → N,N,N',N',N'',N''-Hexakis-(10-oxo-10H-9-oxa-10λ5-phospha-phenanthren-10-ylmethyl)-[1,3,5]triazine-2,4,6-triamine (66499-32-9)

Conditions	Yield
With benzenesulfonic acid at 170 - 235℃; Temperature;	89%

N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) → N2,N2,N4,N4,N6,N6-hexakis((nitrooxy)methyl)-1,3,5-triazine-2,4,6-triamine + N2,N2,N4,N4,N6-pentakis((nitrooxy)methyl)-N6-nitro-1,3,5-triazine-2,4,6-triamine

Conditions	Yield
With nitric acid; acetic anhydride; acetic acid at 25℃; for 72h; Reagent/catalyst;	A 27.3% B 41.2%

BPA (80-05-7) + N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) → methanol (67-56-1) + C41H60N12O10

divinylcarbinol (922-65-6) + N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) → C39H54N6O6

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 110℃; Inert atmosphere;

3-ethyl-3-(hydroxymethyl)oxetane (3047-32-3) + N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) + oxiranyl-methanol (556-52-5) + 2-hydroxyethyl acrylate (818-61-1) → C35H56N6O13

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 80℃; for 3h;

3-ethyl-3-(hydroxymethyl)oxetane (3047-32-3) + N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) → C45H78N6O12

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 80℃; for 3h;

3-ethyl-3-(hydroxymethyl)oxetane (3047-32-3) + N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) → C35H62N6O10

Conditions	Yield
With propylene glycol methyl ether acetate; toluene-4-sulfonic acid at 80℃; for 1h;

sodium molybdate dihydrate (7631-95-0) + N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) → C28H54MoN12O14

Conditions	Yield
at 105℃; for 1.5h;

disodium octaborate tetrahydrate + N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) → C13H25BN6O7

Conditions	Yield
In water at 100℃; for 2h;

sodium molybdate dihydrate (7631-95-0) + N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) → C13H24MoN6O8

Conditions	Yield
at 108℃; for 1h;

borax + N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) → C28H55BN12O13

Conditions	Yield
In water at 108℃; for 1h;

antimony(III) trioxide + N2,N2,N4,N4,N6,N6-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine (3089-11-0) → C13H25N6O7Sb

Conditions	Yield
In water at 110℃; for 0.5h;

Upstream product

• 67-56-1 methanol 
• 531-18-0 hexa(hydroxymethyl)melamine 

Relevant articles and documents

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Continuous process for production of methylol melamines and use thereof for production of highly etherified melamine resins

The object of the present invention is a novel continuous process for the production of methylol melamines, especially of hexamethylol melamine and of a mixture of higher methylol melamines, wherein a continuous synthesis from a formaldehyde solution and melamine is combined with a continuous drying of the resulting product mixture, whereby a product in the form of a powdery material with a low content of free formaldehyde and water is obtained. Simultaneously, the invention also relates to a process for the production of highly etherified melamine resins based on hexamethylol melamine produced by a process according to the present invention and to the use of hexamethylol melamine produced by a process according to the present invention in a process of the production of highly etherified melamine resins. Particularly, the invention relates to a process of the production of hexamethoxymethylol melamine (HMMM), hexabutoxymethylol melamine (HBMM) and mixed ethers of C1-C5 alkohols on the basis of hexamethylol melamine produced by a process according to the invention.