90-72-2

Basic information

• Product Name: Tris(dimethylaminomethyl)phenol
• Synonyms: Tris(dimethylaminomethyl)phenol, 2,4,6-;2,4,6-TRI(DIMETHYLAMINOETHYL)PHENOL;2,4,6-Tris(dimethylaminomethyl)phenol, DMP-30TM, Epon(R) DMP 30 substitute;DMP-30TM;a,a',a''-Tris(dimethylamino)mesitol;Protex NX 3;TAP (aminophenol);Versamine EH 30
• CAS NO: 90-72-2
• Molecular Formula: C₁₅H₂₇N₃O
• Molecular Weight: 265.39
• EINECS: 202-013-9
• Product Categories: Phenyls & Phenyl-Het;Phenyls & Phenyl-Het;It is typically used in combination with other standard amine catalysts such as ZX DMCHA.;Dye
• Mol File: 90-72-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 316℃
• Boiling Point: 130-135 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colorless or light yellow transparent liquid
• Density: 0.969 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: <0.01 mm Hg ( 21 °C)
• Refractive Index: n20/D 1.516(lit.)
• Storage Temp.: 2-8°C
• Solubility: Soluble in water
• PKA: 6.27±0.50(Predicted)
• Water Solubility: 850g/L at 20℃
• BRN: 795751
• CAS DataBase Reference: Tris(dimethylaminomethyl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: Tris(dimethylaminomethyl)phenol(90-72-2)
• EPA Substance Registry System: Tris(dimethylaminomethyl)phenol(90-72-2)

Safety Data

• Hazard Codes: Xn,Xi,C
• Statements: 22-36/38-52/53-34
• Safety Statements: 26-28-2-61-45-36/37/39
• RIDADR: UN 2735 8/PG 3
• WGK Germany: 1
• RTECS: SN3500000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 90-72-2(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow liquid. Combustible.

Uses

Different sources of media describe the Uses of 90-72-2 differently. You can refer to the following data:
1. tris(dimethylaminomethyl)phenol be used for is used as a curing accelerator to promote a relatively short time in the epoxy resin is fully cured. High temperature curing epoxy resin system have significant role in promoting, but also appropriate to improve the bonding strength.
2. 2,4,6-Tris(dimethylaminomethyl)phenol can be used:In the synthesis of water-soluble metal phthalocyanines bearing twelve dimethylamino groups.To prepare phenolate anion-based branched/cross-linked anion exchange membranes (AEMs).As a curing agent in the production of epoxy membranes.

InChI:InChI=1/C15H27N3O/c1-13(2,16)9-7-10(14(3,4)17)12(19)11(8-9)15(5,6)18/h7-8,19H,16-18H2,1-6H3

Synthetic route

triethylsiloxymethyl-N,N-dimethylamine (1353053-97-0) + 2,6-bis-<(dimethyamino)methyl>phenol (15827-34-6) → 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2)

Conditions	Yield
Sealed tube; Heating;	90%

formaldehyd (50-00-0) + dimethyl amine (124-40-3) + phenol (108-95-2) → 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2)

Conditions	Yield
In water for 2.5h;	80%
In water at 25 - 100℃; for 3h; Mannich reaction;	80%
With water
Stage #1: formaldehyd; dimethyl amine In water at 60℃; under 3000.3 Torr; for 5h; Large scale; Stage #2: phenol In water at 90℃; for 3.5h; Temperature; Large scale;

3-chloro-2,4,6-tris-dimethylaminomethyl-phenol; trihydrochloride (131253-33-3) → 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2)

Conditions	Yield
With water; platinum Hydrogenation;

formaldehyd (50-00-0) + dimethyl amine (124-40-3) + 4-hydroxy-benzoic acid (99-96-7) → 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2)

Conditions	Yield
With water

formaldehyd (50-00-0) + water (7732-18-5) + dimethyl amine (124-40-3) + phenol (108-95-2) → 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2)

Conditions	Yield
at 90 - 95℃;

bis(diethylamino)dihydrosilane (27804-64-4) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → bis[2,4,6-tris((dimethylamino)methyl)phenoxy]dihydrosilane

Conditions	Yield
In chloroform at 20℃; for 0.25h;	96%

lead(II) bis(trimethylsilyl)amide (55147-59-6, 65455-92-7) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → bis[2,4,6-tris(dimethylaminomethyl)phenoxy]-plumbylene

Conditions	Yield
In pentane N2 or Ar-atmosphere; stirring (room temp., 2 h); evapn. (reduced pressure), recrystn. (pentane, -30°C); elem. anal.;	96%
In benzene byproducts: HN(SiMe3)2; 2 equiv. ligand;

bis[bis(trimethylsilyl)amino]germanium(II) (59863-12-6) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → bis[2,4,6-tris((dimethylamino)methyl)phenoxy]germanium(II)

Conditions	Yield
In pentane N2 or Ar-atmosphere; stirring (room temp., 2 h); evapn. (vac.), extg. (pentane), pptn. (-30°C, 48 h), filtering, drying (vac.); elem. anal.;	96%
In benzene byproducts: HN(SiMe3)2; 2 equiv. ligand;
In benzene byproducts: (Me3Si)2NH; N2 or Ar-atmosphere, 20°C;

bis(bis(trimethylsilyl)amido)tin(II) (55147-78-9) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → bis[2,4,6-tris(dimethylaminomethyl)phenoxy]-stannylene (524960-14-3)

Conditions	Yield
In pentane N2 or Ar-atmosphere; stirring (room temp., 2 h); concg. (vac.), filtering, drying (vac.); elem. anal.;	96%
In benzene byproducts: HN(SiMe3)2; 2 equiv. ligand;
In benzene byproducts: (Me3Si)2NH; N2 or Ar-atmosphere, 20°C;

2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) + bis(dimethylamino)bis(trimethylsilyl)silane → bis[2,4,6-tris((dimethylamino)methyl)phenoxy]bis(trimethylsilyl)silane (394739-08-3)

Conditions	Yield
In toluene for 2h; Heating;	95%

N,N-Dimethyltrimethylsilylamine (2083-91-2) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → [2,4,6-tris((dimethylamino)methyl)phenoxy]trimethylsilane (161787-77-5)

Conditions	Yield
In pentane	94%

2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) + [2,4,6-tris(((dimethylamino)methyl)phenoxy)phenyl]silane → bis[(2,4,6-tris((dimethylamino)methyl)phenoxy)phenyl]silane

Conditions	Yield
In pentane at 20℃; for 3h;	94%

2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) + bis[(2,4,6-tris((dimethylamino)methyl)phenoxy)phenyl]silane → C51H83N9O3Si

Conditions	Yield
In pentane at 20℃;	94%

tri(dimethylamino)silane (15112-89-7) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → tris[2,4,6-tris((dimethylamino)methyl)phenoxy]hydrosilane

Conditions	Yield
With ammonium sulfate at 110℃; for 48h;	92%

bis(diethylamino)dimethylsilane (4669-59-4) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → bis[2,4,6-tris((dimethylamino)methyl)phenoxy]dimethylsilane (394739-06-1)

Conditions	Yield
In pentane for 2h; Heating;	91%

bis(bis(trimethylsilyl)amido)tin(II) (55147-78-9) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → [bis(trimethylsilyl)amino][2,4,6-tris(dimethylaminomethyl)phenoxy]tin(II) (211423-73-3, 175855-63-7)

Conditions	Yield
In pentane inert atmosphere; dropwise addn. of ligand to equimolar amt. of Sn-compd., stirring (room temp., 2 h); solvent removal (vac.), dissoln. in pentane, crystn. (-30°C); elem. anal.;	91%

2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → lithium 2,4,6-tris((dimethylamino)methyl)phenoxide

Conditions	Yield
With n-butyllithium In diethyl ether at 20℃; for 2h;	90%

2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) + bis[2,4,6-tris((dimethylamino)methyl)phenoxy]dihydrosilane → tris[2,4,6-tris((dimethylamino)methyl)phenoxy]hydrosilane

Conditions	Yield
In chloroform at 20℃; for 24h;	90%

bis[bis(trimethylsilyl)amino]germanium(II) (59863-12-6) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → [bis(trimethylsilyl)amino][2,4,6-tris(dimethylaminomethyl)phenoxy]germanium(II) (211423-72-2)

Conditions	Yield
In pentane inert atmosphere; dropwise addn. of ligand to equimolar amt. of Ge-compd., stirring (room temp., 2 h); solvent removal (vac.), dissoln. in pentane, crystn. (-30°C);	89%

2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) + (dimethylamino)tris(trimethylsilyl)silane → [2,4,6-tris((dimethylamino)methyl)phenoxy]tris(trimethylsilyl)silane

Conditions	Yield
In pentane for 2h; Heating;	83%

lead(II) bis(trimethylsilyl)amide (55147-59-6, 65455-92-7) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → [bis(trimethylsilyl)amino][2,4,6-tris(dimethylaminomethyl)phenoxy]lead(II) (211423-74-4)

Conditions	Yield
In pentane inert atmosphere; dropwise addn. of ligand to Pb-compd., stirring (room temp., 2 h); solvent removal (vac.), dissoln. in pentane, crystn. (-30°C); elem. anal.;	82%

germanium(II) chloride dioxane + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → tris(dimesitylgermylenecarbodiimide) (202127-98-8)

Conditions	Yield
In tetrahydrofuran byproducts: LiCl; N2-atmosphere; stirring (room temp.); C6H6 addn., filtering, evapn.;	78%

triphenylphosphine (603-35-0) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) + silver(l) oxide (20667-12-3) → [2,4,6-tris(dimethylaminomethyl)phenolato]bis(triphenylphosphine)silver(I) (616880-27-4)

Conditions	Yield
In toluene Ag2O, PPh3, and 2,4,6-tris(dimethylaminomethyl)phenol in toluene were stirred overnight at room temp.; react. mixt. was filtered, filtrate was left to stand at room temp., ppt. was filtered, washed with toluene and dried in vacuo; elem. anal.;	66%

3-nitrobenzene-1,2-dicarbonitrile (51762-67-5) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → 3-[2,4,6-tris-(N,N-dimethylaminomethyl)phenoxy]phthalonitrile

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 0 - 60℃; Inert atmosphere;	64%
With potassium carbonate In dimethyl sulfoxide at 20 - 60℃; Inert atmosphere;	64%
With potassium carbonate In N,N-dimethyl-formamide at 45℃; for 24h; Inert atmosphere;
With potassium carbonate In N,N-dimethyl-formamide at 45℃; for 24h; Inert atmosphere;

trimethylaluminum (75-24-1) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → [Me2AlOC6H2(CH2NMe2)3-2,4,6](AlMe3)2

Conditions	Yield
In toluene byproducts: CH4; all manipulations under dry O2-free N2 atm.; soln. of org. compd. added dropwise to cooled (-10°C) soln. of Me3Al with vigorous stirring,react. mixt. stirred for 12 h at room temp.; solvent removed in vac., residue recrystd. from hexane/toluene (1/3); elem. anal.;	62%

phenylsilanyl trifluoromethanesulfonate (127808-36-0) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → [2,4,6-tris(((dimethylamino)methyl)phenoxy)phenyl]silane + bis[(2,4,6-tris((dimethylamino)methyl)phenoxy)phenyl]silane

Conditions	Yield
With triethylamine In toluene at 20℃; for 3h;	A 60% B n/a

cadmium bis(trimethylsilyl)amide + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → [Cd(μ-2,4,6-tris(dimethylamino-methylphenolate)(bis(trimethylsilyl)amide)]2 (847906-04-1)

Conditions	Yield
In toluene under inert atm. alcohol was slowly added to Cd complex in toluene, stirred for 12 h, pyridine was added, mixt. was warmed until clear; elem. anal.;	59.4%

tris(bis(trimethylsilyl)amido)praseodymium(III) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → Pr(3+)*3((CH3)2NCH2)3C6H2O(1-)=[Pr(((CH3)2NCH2)3C6H2O)3] + Pr(((CH3)2NCH2)3C6H2O)3(H2O)2

Conditions	Yield
In hexane 25°C; filtn., crystn. of second product after solvent redn.; elem. anal.;	A 59% B 23%

trimethylaluminum (75-24-1) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → Me2AlOC6H2(CH2NMe2)3-2,4,6

Conditions	Yield
In toluene byproducts: CH4; all manipulations under dry O2-free N2 atm.; soln. of org. compd. added dropwise to cooled (-10°C) soln. of Me3Al with vigorous stirring,react. mixt. stirred for 12 h at room temp.; solvent removed in vac., residue washed with hexane, sublimed in vac.; elem. anal.;	55%

4-Nitrophthalonitrile (31643-49-9) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → 4-(2,4,6-tris((dimethylamino)methyl)phenoxy)phthalonitrile

Conditions	Yield
Stage #1: 2,4,6-tris(dimethylaminomethyl)phenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4-Nitrophthalonitrile In N,N-dimethyl-formamide at 20℃; for 10.25h;	50.8%
With potassium carbonate In N,N-dimethyl-formamide

2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) + phthalocyanine silicon(IV) dichloride (19333-10-9) → bis(2,4,6-tris(N,N-dimethylaminomethyl)phenoxy)[phtalocyaninato]silicon (1415224-02-0)

Conditions	Yield
With sodium hydride In toluene for 6h; Inert atmosphere; Reflux;	35.6%

phenylsilane (694-53-1) + 2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → C51H83N9O3Si

Conditions	Yield
	31%

2,4,6-tris(dimethylaminomethyl)phenol (90-72-2) → bis[2,4,6-tris((dimethylamino)methyl)phenoxy]dichlorosilane

Conditions	Yield
With bis(N,N-dimethylamino)dichlorosilane In toluene at 110℃; for 6h; slow distillation;	23%
Multi-step reaction with 2 steps 1: 91 percent / pentane / 2 h / Heating 2: 80 percent / SiCl4 / 80 °C View Scheme
Multi-step reaction with 3 steps 1: 90 percent / nBuLi / diethyl ether / 2 h / 20 °C 2: 28 percent / diethyl ether / 48 h / 20 °C 3: 80 percent / SiCl4 / 80 °C View Scheme
Multi-step reaction with 2 steps 1: 90 percent / nBuLi / diethyl ether / 2 h / 20 °C 2: 23 percent / SiCl4 / diethyl ether / 48 h / 20 °C View Scheme

Upstream product

• 131253-33-3 3-chloro-2,4,6-tris-dimethylaminomethyl-phenol; trihydrochloride 
• 50-00-0 formaldehyd 
• 124-40-3 dimethyl amine 
• 108-95-2 phenol 
• 99-96-7 4-hydroxy-benzoic acid 
• 7732-18-5 water 
• 1353053-97-0 triethylsiloxymethyl-N,N-dimethylamine 
• 15827-34-6 2,6-bis-<(dimethyamino)methyl>phenol 

Downstream Products

• 2219-90-1 2,4,6-triacetoxymethylphenyl acetate 
• 16102-19-5 2-Hydroxy-benzene-1,3,5-tricarbothioic acid tris-dimethylamide 
• 202127-98-8 tris(dimesitylgermylenecarbodiimide) 
• 175855-63-7 Sn(OC₆H₂(CH₂N(CH₃)2)3)(N(Si(CH₃)3)2) 
• 175855-62-6 Ge(OC₆H₂(CH₂N(CH₃)2)3)(N(Si(CH₃)3)2) 
• 616880-27-4 [2,4,6-tris(dimethylaminomethyl)phenolato]bis(triphenylphosphine)silver(I) 
• 1415224-02-0 bis(2,4,6-tris(N,N-dimethylaminomethyl)phenoxy)[phtalocyaninato]silicon 
• 335-26-2 1,3,5-tris-[(bis-trifluoromethyl-amino)-difluoro-methyl]-nonafluoro-cyclohexane 
• 202190-00-9 (((CH₃)2NCH₂)3C₆H₂O)2Ge((OC₆H₂O(C(CH₃)3)2)2) 
• 202189-96-6 Sn[2,4,6-tris(dimethylaminomethyl)phenoxy]2((t-Bu)2C₆H₂O₂) 
• 202189-97-7 (((CH₃)2NCH₂)3C₆H₂O)2Sn(O₂C₂(C₆H₅)2) 
• 202190-02-1 (((CH₃)2NCH₂)3C₆H₂O)2Ge((NC(O))2NCH₃) 
• 202190-03-2 (((CH₃)2NCH₂)3C₆H₂O)2Sn((NC(O))2NCH₃) 

Relevant articles and documents

Production method of 2, 4, 6-tri (dimethylaminomethyl) phenol

The invention discloses a production method of 2, 4, 6-tri (dimethylaminomethyl) phenol. The production method comprises the following steps: (1) adding formaldehyde into dimethylamine, heating to 50-60 DEG C, and reacting for 1-3 hours to obtain a solution system; (2) adding phenol into the solution system obtained in the step (1), heating to 80-90 DEG C, reacting for 1.5-4 hours, standing for layering, and carrying out oil-water separation to obtain a target product at the upper layer and a water phase at the lower layer; and (3) feeding the water phase obtained in the step (2) into double towers for rectification, extracting dimethylamine aqueous solution from the tower top of the first rectifying tower, returning to the step (1) as a raw material, feeding the aqueous solution discharged from the tower bottom of the first rectifying tower into a second rectifying tower, feeding the aqueous solution extracted from the tower top of the second rectifying tower into a biochemical device, and feeding materials discharged from the tower kettle of the second rectifying tower into the step (2) as a raw material. The production method has the advantages of high yield, few by-products andless sewage.

Phenolic structure and colour in Mannich reaction products

Mannich reactions have been carried out with a variety of model alkylphenols and dimethylamine, methylamine, and diethylenetriamine to trace the origin of persistent coloured products occurring in related reactions with pentadeca(e)nylphenol and 4-tert-alkylphenols. It was found to be attributable to the presence of resorcinolic impurities.